List of benzodiazepines

(Redirected from Benzodiazepine equivalent) A list

Benzodiazepines
The core structure of benzodiazepines. "R" labels denote common locations of side chains, which give different benzodiazepines their unique properties.
Pronunciation: /ˌbɛnzoʊdaɪˈæzəpiːn/ Benzodiazepine List of benzodiazepines Benzodiazepine overdose Benzodiazepine dependence Benzodiazepine misuse Benzodiazepine withdrawal syndrome Effects of long-term benzodiazepine use
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The tables below contain a sample list of benzodiazepines and benzodiazepine analogs that are commonly prescribed, with their basic pharmacological characteristics, such as half-life and equivalent doses to other benzodiazepines, also listed, along with their trade names and primary uses. The elimination half-life is how long it takes for half of the drug to be eliminated by the body. "Time to peak" refers to when maximum levels of the drug in the blood occur after a given dose. Benzodiazepines generally share the same pharmacological properties, such as anxiolytic, sedative, hypnotic, skeletal muscle relaxant, amnesic, and anticonvulsant effects. Variation in potency of certain effects may exist amongst individual benzodiazepines. Some benzodiazepines produce active metabolites. Active metabolites are produced when a person's body metabolizes the drug into compounds that share a similar pharmacological profile to the parent compound and thus are relevant when calculating how long the pharmacological effects of a drug will last. Long-acting benzodiazepines with long-acting active metabolites, such as diazepam and chlordiazepoxide, are often prescribed for benzodiazepine or alcohol withdrawal as well as for anxiety if constant dose levels are required throughout the day. Shorter-acting benzodiazepines are often preferred for insomnia due to their lesser hangover effect.

It is fairly important to note that elimination half-life of diazepam and chlordiazepoxide, as well as other long half-life benzodiazepines, is twice as long in the elderly compared to younger individuals. Due to increased sensitivity and potentially dangerous adverse events among elderly patients, it is recommended to avoid prescribing them as specified by the 2015 American Geriatrics Society Beers Criteria. Individuals with an impaired liver also metabolize benzodiazepines more slowly. Thus, the approximate equivalent of doses below may need to be adjusted accordingly in individuals on short acting benzodiazepines who metabolize long-acting benzodiazepines more slowly and vice versa. The changes are most notable with long acting benzodiazepines as these are prone to significant accumulation in such individuals and can lead to withdrawal symptoms. For example, the equivalent dose of diazepam in an elderly individual on lorazepam may be half of what would be expected in a younger individual. Equivalent doses of benzodiazepines differ as much as 20 fold.

Pharmacokinetic properties of various benzodiazepines

Equivalency data in the table below is taken from the Ashton "Benzodiazepine Equivalence Table".

Drug Name	Common Trade Names	Year Approved (US FDA)	Typical Oral Dosage Formulations (mg)	Approx. Equivalent Oral Dose to 10 mg Diazepam (mg)	Peak Onset of Action (hours)	Elimination Half-life of Active Metabolite (hours)	Primary Therapeutic Use
Adinazolam	Deracyn	Research chemical			1–2	3	anxiolytic, antidepressant
Alprazolam	Xanax, Helex, Xanor, Trankimazin, Onax, Alprox, Misar, Restyl, Solanax, Tafil, Neurol, Frontin, Kalma, Ksalol, Farmapram	1981	0.25, 0.5, 1, 2	0.5	1–3	11-13	anxiolytic, antidepressant
Bentazepam	Thiadipona		25		1–3	2–4	anxiolytic
Bretazenil						2.5	anxiolytic, anticonvulsant
Bromazepam	Lexotanil, Lexotan, Lexilium, Lectopam, Lexaurin, Lexatin, Bromam	1981	1.5, 3, 6	6	1–5	20–40	anxiolytic, hypnotic, muscle relaxant
Bromazolam		Research chemical	2 , 4	2			anxiolytic
Brotizolam	Lendormin, Dormex, Sintonal, Noctilan		0.25	0.5	0.5–2	4–5	hypnotic
Camazepam	Albego, Limpidon			40	1–3	6–11	anxiolytic
Chlordiazepoxide	Librium, Risolid, Elenium	1960	5, 10, 25	25	1.5–6	36–200	anxiolytic
Cinazepam	Levana		0.5, 1, 2		2–4	60	hypnotic, anxiolytic
Cinolazepam	Gerodorm		40		0.5–2	9	hypnotic
Clobazam	Onfi, Frisium, Urbanol	2011	5, 10, 20	20	1–5	8–60	anxiolytic, anticonvulsant
Clonazepam	Rivatril, Rivotril, Klonopin, Iktorivil, Paxam	1975	0.5, 1, 2	0.5-1	1–5	19.5–50	anticonvulsant, anxiolytic
Clonazolam		Research chemical	0.25, 0.5	0.2	0.5-1	3-4	hypnotic, anticonvulsant
Clorazepate	Tranxene, Tranxilium	1972	3.75, 5, 7.5	15	Variable	32–152	anxiolytic, anticonvulsant
Clotiazepam	Veratran, Clozan, Rize		5, 10	10	1–3	4	anxiolytic
Cloxazolam	Cloxam, Sepazon, Olcadil		1, 2, 4	1.5	2–5	55–77	anxiolytic, anticonvulsant
Delorazepam	Dadumir		0.5, 1, 2	1-1.5	1–2	79<	anxiolytic, amnesic
Deschloroetizolam		Research chemical	1, 2	4			anxiolytic
Diazepam	Antenex, Apaurin, Apzepam, Apozepam, Diazepan, Hexalid, Normabel, Pax, Stesolid, Stedon, Tranquirit, Valium, Vival, Valaxona	1963	2, 5, 10	10	1–1.5	32–205	anxiolytic, anticonvulsant, muscle relaxant, amnesic
Diclazepam		Research chemical	1, 2	2	1.5–3	42	anxiolytic, muscle relaxant
Estazolam	ProSom, Nuctalon	1990	1, 2	2	3–5	10–24	hypnotic, anxiolytic
Ethyl carfluzepate		Not approved		2	1–5	11–24	hypnotic
Etizolam	Etilaam, Etizest, Pasaden, Depas	Often sold as a research chemical, but is approved for human use in many countries. Controlled substance in some US states, Canada, Germany, Austria, and others.	1	2	1–3	5-7	anxiolytic, muscle relaxant, anticonvulsant
Ethyl loflazepate	Victan, Meilax, Ronlax			2	2.5–3	73–119	anxiolytic
Flualprazolam		Research chemical	0.5, 1	0.25	1-2	12-22	anxiolytic, hypnotic
Flubromazepam	Templex	Research chemical	4, 8, 12	4	1.5–8	100–220	anxiolytic, hypnotic, amnesic, muscle relaxant, anticonvulsant
Flubromazolam	Remnon	Research chemical	0.25, 0.5	0.075	0.5-5	10-20	hypnotic
Fluclotizolam		Research chemical		0.25-0.5			anxiolytic
Flunitrazepam	Rohypnol, Hipnosedon, Vulbegal, Fluscand, Flunipam, Ronal, Rohydorm, Hypnodorm	1972	1, 2	1.5	0.5–3	18–200	hypnotic
Flunitrazolam		Research chemical	0.25, 0.5	0.1	0.5-1	5-13	hypnotic
Flurazepam	Dalmadorm, Dalmane, Fluzepam	1970	30	20-25	1–1.5	40–250	hypnotic
Flutazolam	Coreminal		4	10	1-3	47-100	hypnotic
Flutemazepam		Research chemical		1	0.5-5	8-20	hypnotic, anxiolytic, anticonvulsant, muscle relaxant
Flutoprazepam	Restas	1984	1, 2	2.5	0.5–9	87	hypnotic, anticonvulsant, muscle relaxant
Halazepam	Alapryl, Paxipam	1981	20, 40	40	3–6	15-35	anxiolytic
Ketazolam	Anxon, Sedotime	1980	15, 30, 45	20	2.5–6	30-100	anxiolytic
Loprazolam	Dormonoct, Havlane	1983	1, 2	1.5	2–5	6–20	hypnotic
Lorazepam	Ativan, Orfidal, Lorenin, Lorsilan, Temesta, Tavor, Lorabenz	1977	0.5, 1, 2, 2.5	1	2–4	10–20	anxiolytic, anticonvulsant, hypnotic, muscle relaxant
Lormetazepam	Loramet, Noctamid, Pronoctan	1984	1, 2	1.5	0.5–2	10-12	hypnotic, anxiolytic
Meclonazepam		Research chemical	6				anxiolytic
Medazepam	Nobrium, Ansilan, Mezapam, Rudotel, Raporan		10	10	4-8	36–200	anxiolytic
Metizolam		Research chemical	1, 2, 4	2–4		12	anxiolytic
Mexazolam	Melex, Sedoxil		0.5, 1		1–2		anxiolytic
Midazolam	Dormicum, Flormidal, Versed, Hypnovel, Dormonid	1985	7.5, 15	10 (oral) 4 (IV)	0.5–1	1.8-6	hypnotic, anticonvulsant
Nifoxipam		Research chemical	0.5, 1, 2				hypnotic
Nimetazepam	Erimin, Lavol	1984	5	2.5-5	0.5–3	14–30	hypnotic
Nitemazepam		Research chemical		2	0.5-5	10-27	hypnotic, anticonvulsant
Nitrazepam	Mogadon, Alodorm, Pacisyn, Dumolid, Nitrazadon	1965	5, 10	5	0.5–7	17–48	hypnotic, anticonvulsant
Nitrazolam		Research chemical	0.5, 1				hypnotic
Nordazepam	Madar, Stilny		5, 7.5, 15	10-15		30–150	anxiolytic
Norflurazepam		Research chemical		5		47-100	hypnotic
Oxazepam	Seresta, Serax, Serenid, Serepax, Sobril, Oxabenz, Oxapax, Oxascand, Ox-Pam, Opamox, Alepam, Medopam, Murelax, Noripam, Purata	1965	10, 15, 30, 50	30	3–4	4–11	anxiolytic
Phenazepam	Phenazepam, Phenzitat	Research chemical			1.5–4	60	anxiolytic, anticonvulsant
Pinazepam	Domar, Duna		5, 10			40–100	anxiolytic
Prazepam	Demetrin, Lysanxia, Prazene, Centrax	1976	10, 20, 30	15-20	2–6	36–200	anxiolytic
Premazepam		Not approved		15	2–6	10–13	anxiolytic
Pyrazolam		Research chemical	0.25, 0.5, 1		1–1.5	16–18	anxiolytic, amnesic
Quazepam	Doral, Quiedorm	1985	15	20	1–5	39–120	hypnotic
Rilmazafone	Rhythmy					11	hypnotic
Temazepam	Restoril, Normison, Euhypnos, Temaze, Tenox	1981	10, 20	15-20	0.5–3	4–11	hypnotic, anxiolytic, muscle relaxant
Tetrazepam	Myolastan, Clinoxam, Epsipam, Musaril		50		1–3	3–26	muscle relaxant, anxiolytic
Triazolam	Halcion, Rilamir, Notison, Somese	1980	0.125, 0.25	0.5	0.5–2	2	hypnotic
Drug Name	Common Trade Names	Year Approved	Typical Dosages of Oral Tablets (mg)	Approx. Equivalent Oral Dose to 10mg Diazepam (mg)	Peak onset of action (hours)	Elimination Half-life of Active Metabolite (hours)	Primary Therapeutic Use

Atypical benzodiazepine receptor ligands

Drug Name	Common Trade Names	Year approved (US FDA)	Elimination Half-life of Active Metabolite (hours)	Primary Therapeutic Use
DMCM				anxiogenic, convulsant
Flumazenil	Anexate, Lanexat, Mazicon, Romazicon		1	antidote
Eszopiclone	Lunesta	2004	6	hypnotic
Zaleplon	Sonata, Starnoc	1999	1	hypnotic
Zolpidem	Ambien, Nytamel, Sanval, Stilnoct, Stilnox, Sublinox (Canada), Xolnox, Zoldem, Zolnod	1992	2.6	hypnotic
Zopiclone	Imovane, Rhovane, Ximovan; Zileze; Zimoclone; Zimovane; Zopitan; Zorclone, Zopiklone		4–6	hypnotic

Not all trade names are listed.
An alternative table published by the state of South Australia uses equivalent approximate oral dosages to 5 mg diazepam.
^ Technically this is a thienodiazepine, but produces very similar effects as benzodiazepines.
^ Technically this is a thienotriazolodiazepine, but produces very similar effects as benzodiazepines.
Flumazenil is an imidazobenzodiazepine derivative, and in layman's terms, it is a benzodiazepine overdose antidote that is given intravenously in Intensive Care Units (ICUs) to reverse the effects of benzodiazepine overdoses, as well for overdoses of the non-benzodiazepine "Z-drugs" such as zolpidem. Flumazenil is contraindicated for benzodiazepine-tolerant patients in overdose cases. In such cases, the benefits are far outweighed by the risks, which include potential and severe seizures. The method by which flumazenil acts to prevent non-benzodiazepine tolerant overdose from causing potential harm is via preventing the benzodiazepines and Z-drugs from binding to the GABA_A receptors via competitive inhibition which the flumazenil creates. Clinical observation notating the patient's oxygen levels, respiratory, heart and blood pressure rates are used, as they are much safer than the potential seizure effects from flumazenil. Supportive care to mediate any problems resulting from abnormal rates of the pulmonary, respiratory, and cardiovascular systems is typically the only treatment that is required in benzodiazepine-only overdoses. In most cases, activated charcoal/carbon is often used to prevent benzodiazepines from being absorbed by the gastrointestinal tract, and the use of stomach-pumping/gastric lavage is no longer commonly used nor suggested by some toxicologists. Even in cases where other central nervous system (CNS) depressants (such as in combined benzodiazepine and tricyclic antidepressant/TCA overdoses) are detected and/or suspected, endotrachial intubation for the airway path and supportive oxygen are typically implemented and are much safer than flumazenil.

Controversy

In 2015 the UK's House of Commons attempted to get a two to four week limit mandate for prescribing benzodiazepines to replace the two to four week benzodiazepine prescribing guidelines, which are merely recommended.

Binding data and structure-activity relationship

A large number of benzodiazepine derivatives have been synthesised and their structure-activity relationships explored in detail. This chart contains binding data for benzodiazepines and related drugs investigated by Roche up to the late 1990s (though in some cases the compounds were originally synthesised by other companies such as Takeda or Upjohn). Other benzodiazepines are also listed for comparison purposes, but it does not however include binding data for;

Benzodiazepines developed in the former Soviet Union (e.g. phenazepam, gidazepam etc.)
Benzodiazepines predominantly used only in Japan (e.g. nimetazepam, flutoprazepam etc.)
4,5-cyclised benzodiazepines (e.g. ketazolam, cloxazolam etc.), and other compounds not researched by Roche
Benzodiazepines developed more recently (e.g. remimazolam, QH-ii-066, Ro48-6791 etc.)
"Designer" benzodiazepines for which in vitro binding data are unavailable (e.g. flubromazolam, pyrazolam etc.)

While binding or activity data are available for most of these compounds also, the assay conditions vary between sources, meaning that in many cases the values are not suitable for a direct comparison. Many older sources used animal measures of activity (i.e. sedation or anticonvulsant activity) but did not measure in vitro binding to benzodiazepine receptors. See for instance Table 2 vs Table 11 in the Chem Rev paper, Table 2 lists in vitro pIC₅₀ values matching those below, while Table 11 has pEC₅₀ values derived from in vivo assays in mice, which show the same activity trends but cannot be compared directly, and includes data for compounds such as diclazepam and flubromazepam which are not available in the main data set.

Also note;

IC₅₀ / pIC₅₀ values represent binding affinity only and do not reflect efficacy or pharmacokinetics, and some compounds listed are GABA_A antagonists rather than agonists (e.g. flumazenil).
Low IC₅₀ or high pIC₅₀ values indicate tighter binding (pIC₅₀ of 8.0 = IC₅₀ of 10nM, pIC₅₀ of 9.0 = IC₅₀ of 1nM, etc.)
These are non subtype selective IC₅₀ values averaged across all GABA_A receptor subtypes, so subtype selective compounds with strong binding at one subtype but weak at others will appear unusually weak due to averaging of binding values (see e.g. CL-218,872)
indicates a predicted value from in silico modelling.
Finally, note that the benzodiazepine core is a privileged scaffold, which has been used to derive drugs with diverse activity that is not limited to the GABA_A modulatory action of the classical benzodiazepines, such as devazepide and tifluadom, however these have not been included in the list below. 2,3-benzodiazepines such as tofisopam are also not listed, as these act primarily as AMPA receptor modulators, and are inactive at GABA_A receptors.

Table

Table of benzodiazepines

Code	pIC₅₀ / IC₅₀	Chemical name	PubChem	CAS number
Ro05-3061	7.3979 / 40nM	7-fluoro-5-phenyl-1H-benzo diazepin-2(3H)-one	75849	2648-00-2
Ro05-4865	7.7696 / 17nM	7-fluoro-5-phenyl-1-methyl-1H-benzo diazepin-2(3H)-one	44366179
Ro05-6820	8.1308 / 7.4nM	7-fluoro-5-(2-fluorophenyl)-1H-benzo diazepin-2(3H)-one	44366116
Ro05-6822	8.2924 / 5.1nM	7-fluoro-5-(2-fluorophenyl)-1-methyl-1H-benzo diazepin-2(3H)-one	23275675	2024-34-2
Iso-flubromazepam		7-fluoro-5-(2-bromophenyl)-1H-benzo diazepin-2(3H)-one	15292433	153873-96-2
Nordazepam	8.0269 / 9.4nM	7-chloro-5-phenyl-1H-benzo diazepin-2(3H)-one	2997	1088-11-5
Diazepam	8.0915 / 8.1nM	7-chloro-5-phenyl-1-methyl-1H-benzo diazepin-2(3H)-one	3016	439-14-5
Norflurazepam (Ro05-3367)	8.699	7-chloro-5-(2-fluorophenyl)-1H-benzo diazepin-2(3H)-one	4540	2886-65-9
Fludiazepam		7-chloro-5-(2-fluorophenyl)-1-methyl-1H-benzo diazepin-2(3H)-one	3369	3900-31-0
Ro07-3953	8.7959 / 1.6nM	7-chloro-5-(2,6-difluorophenyl)-1H-benzo diazepin-2(3H)-one	23275763
Difludiazepam (Ro07-4065)	8.3872 / 4.1nM	7-chloro-5-(2,6-difluorophenyl)-1-methyl-1H-benzo diazepin-2(3H)-one	44366236	39080-67-6
Delorazepam	8.7447 / 1.8nM	7-chloro-5-(2-chlorophenyl)-1H-benzo diazepin-2(3H)-one	17925	2894-67-9
Diclazepam (Ro05-3448)	7.8	7-chloro-5-(2-chlorophenyl)-1-methyl-1H-benzo diazepin-2(3H)-one	76168	2894-68-0
Ro05-4864	TSPO ligand	7-chloro-5-(4-chlorophenyl)-1-methyl-1H-benzo diazepin-2(3H)-one	1688	14439-61-3
Ro07-5193	8.5229	7-chloro-5-(2-chloro-6-fluorophenyl)-1H-benzo diazepin-2(3H)-one	44366219
Ro22-3294	8.1549	7-chloro-5-(2,6-dichlorophenyl)-1H-benzo diazepin-2(3H)-one	12790028
Ro07-5220	8.2596	7-chloro-5-(2,6-dichlorophenyl)-1-methyl-1H-benzo diazepin-2(3H)-one	9975396	30144-88-8
7-BPDBD	7.8	7-bromo-5-phenyl-1H-benzo diazepin-2(3H)-one	76167	2894-61-3
QH-II-063		7-bromo-5-phenyl-1-methyl-1H-benzo diazepin-2(3H)-one	627432	28611-28-1
Phenazepam	8.4	7-bromo-5-(2-chlorophenyl)-1H-benzo diazepin-2(3H)-one	40113	51753-57-2
Flubromazepam (JYI-42)	7.6	7-bromo-5-(2-fluorophenyl)-1H-benzo diazepin-2(3H)-one	12947024	2647-50-9
Flubrometazepam		7-bromo-5-(2-fluorophenyl)-1-methyl-1H-benzo diazepin-2(3H)-one	135809	86890-79-1
SH-I-048A		(3S)-7-bromo-5-(2-fluorophenyl)-3-methyl-1H-benzo diazepin-2(3H)-one	49850464	872874-11-8
Gidazepam	6.4	2-(7-bromo-2-oxo-5-phenyl-2,3-dihydro-1H-benzo diazepin-1-yl)acetohydrazide	121919	129186-29-4
Ro13-3780	8.6198	7-bromo-5-(2,6-difluorophenyl)-1-methyl-1H-benzo diazepin-2(3H)-one	9975396	103380-73-0
Ro07-9749		7-iodo-5-(2-fluorophenyl)-1H-benzo diazepin-2(3H)-one	3082318	30843-56-2
Ro07-9957	8.5376	7-iodo-5-(2-fluorophenyl)-1-methyl-1H-benzo diazepin-2(3H)-one	118749
Ro05-2904	7.8861 / 13nM	7-trifluoromethyl-5-phenyl-1H-benzo diazepin-2(3H)-one	16795	2285-16-7
Ro14-3074	8.2757 / 5.3nM	7-azido-5-(2-fluorophenyl)-1H-benzo diazepin-2(3H)-one
Nitrazepam	8.0 / 10nM	7-nitro-5-phenyl-1H-benzo diazepin-2(3H)-one	4506	146-22-5
Nimetazepam		7-nitro-5-phenyl-1-methyl-1H-benzo diazepin-2(3H)-one	4496	2011-67-8
Ro05-4435	8.829 / 1.5nM	7-nitro-5-(2-fluorophenyl)-1H-benzo diazepin-2(3H)-one	520217	2558-30-7
Flunitrazepam	8.4202 / 3.8nM	7-nitro-5-(2-fluorophenyl)-1-methyl-1H-benzo diazepin-2(3H)-one	3380	1622-62-4
Clonazepam	8.7447 / 1.8nM	7-nitro-5-(2-chlorophenyl)-1H-benzo diazepin-2(3H)-one	2802	1622-61-3
Ro05-4082	8.6576	7-nitro-5-(2-chlorophenyl)-1-methyl-1H-benzo diazepin-2(3H)-one	528222	5527-71-9
Ro05-3590	8.4559 / 3.5nM	7-nitro-5--1H-benzo diazepin-2(3H)-one	15024	1427-45-8
QH-146		7-nitro-5-(2-nitrophenyl)-1-methyl-1H-benzo diazepin-2(3H)-one	44383992
Ro20-7736	7.0177 / 96nM	7-hydroxyamino-5-(2-fluorophenyl)-1-methyl-1H-benzo diazepin-2(3H)-one
Ro05-3072	6.4134 / 386nM	7-amino-5-phenyl-1H-benzo diazepin-2(3H)-one	78641	4928-02-3
Ro05-4318	6.3372 / 460nM	7-amino-5-phenyl-1-methyl-1H-benzo diazepin-2(3H)-one	23275339	4959-16-4
Ro20-1815	7.1871 / 65nM	7-amino-5-(2-fluorophenyl)-1-methyl-1H-benzo diazepin-2(3H)-one	92294	34084-50-9
Ro05-4619	7.1249 / 75nM	7-amino-5-(2-chlorophenyl)-1H-benzo diazepin-2(3H)-one	188298	4959-17-5
Ro05-3308	IC₅₀ >1000nM	N-(2-oxo-5-phenyl-2,3-dihydro-1H-benzo diazepin-7-yl)acetamide
Ro12-6377	7.1249 / 455nM	1-(5-(2-fluorophenyl)-1-methyl-2-oxo-2,5-dihydro-1H-benzo diazepin-7-yl)-3-methylurea
Ro05-9090	IC₅₀ >1000nM	7-(aminomethyl)-1-methyl-5-phenyl-1H-benzo diazepin-2(3H)-one
Ro05-3343	IC₅₀ >1000nM	N,N-dimethyl-2-oxo-5-phenyl-2,3-dihydro-1H-benzo diazepine-7-sulfonamide	214460	12037-79-5
Ro05-4528	6.4202 / 380nM	7-cyano-5-phenyl-1-methyl-1H-benzo diazepin-2(3H)-one
Ro20-2541	7.5229 / 30nM	7-cyano-5-(2-fluorophenyl)-1-methyl-1H-benzo diazepin-2(3H)-one
Ro20-2533	7.4437 / 36nM	7-ethyl-5-phenyl-1H-benzo diazepin-2(3H)-one	10264786
Ro20-5747	7.6198 / 24nM	7-vinyl-5-phenyl-1H-benzo diazepin-2(3H)-one	44366036
QH-ii-066	7.4	7-ethynyl-5-phenyl-1-methyl-1H-benzo diazepin-2(3H)-one	9838431	183239-39-6
OMB-18		7-ethynyl-5-(2-fluorophenyl)-1-methyl-1H-benzo diazepin-2(3H)-one	89276170
XLI-352		7-ethynyl-5-(2-chlorophenyl)-1-methyl-1H-benzo diazepin-2(3H)-one	21065236
Ro20-5397	7.3665 / 43nM	7-formyl-5-phenyl-1H-benzo diazepin-2(3H)-one
Ro20-3053	7.7447 / 18nM	7-acetyl-5-phenyl-1H-benzo diazepin-2(3H)-one	21828109
Ro05-2921	6.4559 / 350nM	5-phenyl-1H-benzo diazepin-2(3H)-one	76175	2898-08-0
Ro05-3663	IC₅₀ >1000nM	5-methyl-1H-benzo diazepin-2(3H)-one	5080	70656-87-0
Ro05-4336	7.6778 / 21nM	5-(2-fluorophenyl)-1H-benzo diazepin-2(3H)-one	13292074
Ro07-4419	7.7212 / 19nM	5-(2,6-difluorophenyl)-1H-benzo diazepin-2(3H)-one	44366255
Ro05-4520	7.8539 / 14nM	5-(2-fluorophenyl)-1-methyl-1H-benzo diazepin-2(3H)-one	193319	844-11-1
Ro05-4608	8.4202	5-(2-chlorophenyl)-1-methyl-1H-benzo diazepin-2(3H)-one	10469149
Ro05-3546	6.4949 / 320nM	6-chloro-5-phenyl-1H-benzo diazepin-2(3H)-one	14590445
Ro13-0699	6.8239 / 150nM	6-chloro-5-(2-fluorophenyl)-1-methyl-1H-benzo diazepin-2(3H)-one	44377764
Ro07-6198	7.5528 / 28nM	8-chloro-5-(2,6-difluorophenyl)-1H-benzo diazepin-2(3H)-one	23275762
Ro20-8895	7.7212 / 19nM	8-methyl-5-(2-fluorophenyl)-1H-benzo diazepin-2(3H)-one	44366169
Ro13-0593	7.1427 / 72nM	9-chloro-5-(2-fluorophenyl)-1-methyl-1H-benzo diazepin-2(3H)-one
Ro13-0882	IC₅₀ 300nM	6,8-dichloro-5-(2-fluorophenyl)-1-methyl-1H-benzo diazepin-2(3H)-one
Ro22-6762	7.3979 / 40nM	7,8-dichloro-5-phenyl-1-methyl-1H-benzo diazepin-2(3H)-one	44366089
Ro20-8065	8.4437 / 3.6nM	7,8-dichloro-5-(2-fluorophenyl)-1H-benzo diazepin-2(3H)-one	10358803	88695-06-1
Ro20-8552	7.8539 / 14nM	7-methyl-8-chloro-5-(2-fluorophenyl)-1H-benzo diazepin-2(3H)-one	44366138
Ro05-2750	7.4318 / 37nM	6,8-dichloro-5-phenyl-1H-benzo diazepin-2(3H)-one
Ro14-2312	IC₅₀ >1000nM	6-amino-8-chloro-5-(2-fluorophenyl)-1-methyl-1H-benzo diazepin-2(3H)-one
Ro07-3609	7.284
Ro11-8125	7.4318 / 37nM	5-(2-chlorophenyl)-1H-thieno diazepin-2(3H)-one
Ro08-6739	IC₅₀ 70nM	7-chloro-5-phenyl-1H-thieno diazepin-2(3H)-one
Ro09-9212	8.4089 / 3.9nM	7-chloro-5-(2-chlorophenyl)-1H-thieno diazepin-2(3H)-one	135721042
Ro10-2643	IC₅₀ 9.4nM	7-chloro-5-(2-chlorophenyl)-1H-thieno diazepin-2(3H)-one
Clotiazepam		7-ethyl-5-(2-chlorophenyl)-1-methyl-1H-thieno diazepin-2(3H)-one	2811	33671-46-4
Bentazepam	8.5	5-phenyl-3,5a,6,7,8,9-hexahydro-2H-benzothieno diazepin-2(3H)-one	34592	29462-18-8
Lopirazepam		7-chloro-5-(2-chlorophenyl)-3-hydroxy-1,3-dihydro-2H-pyrido diazepin-2-one	68672	42863-81-0
Premazepam	6.7696 / 170nM	6,7-dimethyl-5-phenyl-3,7-dihydropyrrolo diazepin-2(1H)-one	72104	57435-86-6
Ripazepam		1-ethyl-3-methyl-8-phenyl-4,6-dihydropyrazolo diazepin-5(1H)-one	33474	26308-28-1
Zolazepam		1,3,8-trimethyl-4-(2-fluorophenyl)-6,8-dihydropyrazolo diazepin-7(1H)-one	35775	31352-82-6
Zomebazam	8.1	1,3,8-trimethyl-4-phenyl-6,8-dihydropyrazolo diazepine-5,7(1H,4H)-dione	132677	78466-70-3
Ro17-2221	6.585 / 260nM	1-(2-aminoethyl)-5-phenyl-1H-benzo diazepin-2(3H)-one
Ro07-5096	IC₅₀ >1000nM	2-(7-chloro-5-(2-fluorophenyl)-2-oxo-2,3-dihydro-1H-benzo diazepin-1-yl)acetic acid
Ro08-3026	7.2007
Halazepam	7.0362 / 92nM	7-chloro-5-phenyl-1-(2,2,2-trifluoroethyl)-1H-benzo diazepin-2(3H)-one	31640	23092-17-3
Quazepam		7-chloro-5-(2-fluorophenyl)-1-(2,2,2-trifluoroethyl)-1H-benzo diazepin-2(3H)-thione	4999	36735-22-5
Fletazepam		7-chloro-5-(2-fluorophenyl)-1-(2,2,2-trifluoroethyl)-1H-benzo diazepine	36834	34482-99-0
Pinazepam	7.0339 / 92.5nM	7-chloro-5-phenyl-1-(prop-2-yn-1-yl)-1H-benzo diazepin-2(3H)-one	40391	52463-83-9
Prazepam	IC₅₀ 110nM	7-chloro-5-phenyl-1-cyclopropylmethyl-1H-benzo diazepin-2(3H)-one	4890	2955-38-6
Flutoprazepam	6.6	7-chloro-5-(2-fluorophenyl)-1-cyclopropylmethyl-1H-benzo diazepin-2(3H)-one	3400	25967-29-7
Cloniprazepam	7.8	7-nitro-5-(2-chlorophenyl)-1-cyclopropylmethyl-1H-benzo diazepin-2(3H)-one
Ro20-1310	6.2076 / 620nM	7-chloro-5-phenyl-1-(t-butyl)-1H-benzo diazepin-2(3H)-one
Fosazepam		7-chloro-5-phenyl-1-(dimethylphosphorylmethyl)-1H-benzo diazepin-2(3H)-one	37114	35322-07-7
Iclazepam		7-chloro-5-phenyl-1--1H-benzo diazepin-2(3H)-one	68777	57916-70-8
Tolufazepam		7-chloro-5-(2-chlorophenyl)-1--1H-benzo diazepin-2(3H)-one	65647	86273-92-9
Elfazepam	6.9	7-chloro-5-(2-fluorophenyl)-1-(2-ethylsulfonylethyl)-1H-benzo diazepin-2(3H)-one	65445	52042-01-0
Reclazepam		2--1,3-oxazol-4(5H)-one	3052777	76053-16-2
Ro07-1986	8.0809 / 8.3nM	1-(2-aminoethyl)-7-chloro-5-(2-fluorophenyl)-1H-benzo diazepin-2(3H)-one
Flurazepam	7.8297	7-chloro-1--5-(2-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one	3393	17617-23-1
Ro07-2750	7.6108 / 24.5nM	7-chloro-5-(2-fluorophenyl)-1-(2-hydroxyethyl)-1H-benzo diazepin-2(3H)-one
Motrazepam	IC₅₀ 430nM	1-(methoxymethyl)-7-nitro-5-phenyl-1H-benzo diazepin-2(3H)-one	65764	29442-58-8
Ro08-9013	7.3716
Proflazepam	6.8539 / 140nM	7-chloro-1-(2,3-dihydroxypropyl)-5-(2-fluorophenyl)-1H-benzo diazepin-2(3H)-one	3050433	52829-30-8
Ro22-4683	6.5229 / 300nM	7-nitro-5-(2-fluorophenyl)-1-(t-butyl)-1H-benzo diazepin-2(3H)-one
Ro15-8852	6.1391 / 726nM	5-(2-chlorophenyl)-4-methyl-7-nitro-4,5-dihydro-1H-benzo diazepin-2(3H)-one
Chlorodiazepoxide	6.4535 / 352nM	7-chloro-2-methylamino-5-phenyl-3H-benzo diazepine-4-oxide	2712	58-25-3
Cyprazepam		7-chloro-N-(cyclopropylmethyl)-4-hydroxy-5-phenyl-3H-benzo diazepin-2-imine	27452	15687-07-7
Uldazepam	7.6	7-chloro-5-(2-chlorophenyl)-N-prop-2-enoxy-3H-benzo diazepin-2-amine	34274	28546-58-9
Demoxepam	6.5086 / 310nM	7-chloro-1,3-dihydro-5-phenyl-2H-benzo diazepin-2-one-4-oxide	13756	963-39-3
Medazepam	IC₅₀ 870nM	7-chloro-5-phenyl-1-methyl-1H-benzo diazepine	4041	2898-12-6
Tuclazepam	7.7	7-chloro-5-(2-chlorophenyl)-2-(hydroxymethyl)-1-methyl-2,3-dihydro-1H-benzo diazepine	3050405	51037-88-8
Metaclazepam		7-bromo-5-(2-chlorophenyl)-2-(methoxymethyl)-1-methyl-2,3-dihydro-1H-benzo diazepine	71272	84031-17-4
Sulazepam	7.7	7-chloro-5-phenyl-1-methyl-1H-benzo diazepin-2(3H)-thione	17931	2898-13-7
Tetrazepam	7.4685 / 34nM	7-chloro-5-(cyclohexen-1-yl)-1-methyl-1H-benzo diazepin-2(3H)-one	25215	10379-14-3
Nortetrazepam	IC₅₀ 34nM	7-chloro-5-(cyclohexen-1-yl)-1H-benzo diazepin-2(3H)-one	166581	10379-11-0
Menitrazepam		7-nitro-5-(cyclohexen-1-yl)-1-methyl-1H-benzo diazepin-2(3H)-one	189875	28781-64-8
Ro05-3328	7.0605 / 87nM	7-chloro-5-cyclohexyl-1H-benzo diazepin-2(3H)-one
Clazolam	8.1	2-chloro-5-methyl-5,9,10,14b-tetrahydroisoquino benzodiazepin-6(7H)-one	24107	7492-29-7
Bromazepam	7.7447 / 18nM	7-bromo-5-(pyridin-2-yl)-1H-benzo diazepin-2(3H)-one	2441	1812-30-2
Methylbromazepam		7-bromo-5-(pyridin-2-yl)-1-methyl-1H-benzo diazepin-2(3H)-one	630183	1812-33-5
Pyridazino-diazepam		7-chloro-5-(pyridazin-3-yl)-1-methyl-1H-benzo diazepin-2(3H)-one
SCHEMBL9684958		7-chloro-5-(1H-pyrazol-5-yl)-1H-benzo diazepin-2(3H)-one	21738192
Compound 6a	9.5	7-chloro-5-(3,5-dimethyl-4H-1,2,4-triazol-4-yl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one
JC-184		7-bromo-5-(2-thienyl)-1H-benzo diazepin-2(3H)-one	21065240
BDBM50083903		7-chloro-5-(2-furanyl)-1-methyl-1H-benzo diazepin-2(3H)-one	10423506
Ro05-5605	6.5376
Ro11-3129	8.1871	(+)-2-amino-N-propanamide	21413751	65607-70-7
Ro03-7355	6.3768
Ro11-4878	8.4559 / 3.5nM	7-chloro-5-(2-fluorophenyl)-3-methyl-1H-benzo diazepin-2(3H)-one
Meclonazepam	8.9208 / 1.2nM	(3S)-7-nitro-5-(2-chlorophenyl)-3-methyl-1H-benzo diazepin-2(3H)-one	3033985	58662-84-3
Ro11-6896	8.1549 / 7nM	7-nitro-5-(2-fluorophenyl)-1,3-dimethyl-1H-benzo diazepin-2(3H)-one
Ro06-7263	7.3098 / 49nM	1,7-dichloro-5-phenyl-3-methyl-1H-benzo diazepin-2(3H)-one
Oxazepam	7.7447 / 18nM	7-chloro-3-hydroxy-5-phenyl-1H-benzo diazepin-2(3H)-one	4616	604-75-1
Temazepam	7.7959 / 16nM	7-chloro-3-hydroxy-5-phenyl-1-methyl-1H-benzo diazepin-2(3H)-one	5391	846-50-4
Lorazepam	8.4559 / 3.5nM	7-chloro-3-hydroxy-5-(2-chlorophenyl)-1H-benzo diazepin-2(3H)-one	3958	846-49-1
Lormetazepam		7-chloro-3-hydroxy-5-(2-chlorophenyl)-1-methyl-1H-benzo diazepin-2(3H)-one	13314	848-75-9
Flutemazepam	8.1	7-chloro-3-hydroxy-5-(2-fluorophenyl)-1-methyl-1H-benzo diazepin-2(3H)-one	40344	52391-89-6
Cinolazepam		7-chloro-3-hydroxy-5-(2-fluorophenyl)-1-(2-cyanoethyl)-1H-benzo diazepin-2(3H)-one	3033621	75696-02-5
Doxefazepam		7-chloro-3-hydroxy-5-(2-fluorophenyl)-1-(2-hydroxyethyl)-1H-benzo diazepin-2(3H)-one	38668	40762-15-0
Nifoxipam	8.5	7-nitro-3-hydroxy-5-(2-fluorophenyl)-1H-benzo diazepin-2(3H)-one	3058221	74723-10-7
Nitemazepam		7-nitro-3-hydroxy-5-phenyl-1-methyl-1H-benzo diazepin-2(3H)-one	12362353	40762-03-6
3-Hydroxyphenazepam	8.7	7-bromo-3-hydroxy-5-(2-chlorophenyl)-1H-benzo diazepin-2(3H)-one	125820	70030-11-4
Cinazepam		7-bromo-3-succinyloxy-5-(2-chlorophenyl)-1H-benzo diazepin-2(3H)-one	629281	172986-25-3
Pivoxazepam		7-chloro-3-pivalyloxy-5-phenyl-1H-benzo diazepin-2(3H)-one	68722	55299-10-0
Camazepam	6.0458	7-chloro-1-methyl-2-oxo-5-phenyl-2,3-dihydro-1H-benzo diazepin-3-yl N,N-dimethylcarbamate	37367	36104-80-0
Clorazepate	IC₅₀ 59nM	7-chloro-2-oxo-5-phenyl-1H-benzo diazepine-3-carboxylic acid	2809	23887-31-2
Nitrazepate		7-nitro-2-oxo-5-phenyl-1H-benzo diazepine-3-carboxylic acid	21740	5571-84-6
Ethyl carfluzepate	8.0	ethyl 7-chloro-5-(2-fluorophenyl)-1-(methylcarbamoyl)-2-oxo-3H-benzo diazepine-3-carboxylate	68856	65400-85-3
Ethyl dirazepate	7.5	ethyl 7-chloro-5-(2-chlorophenyl)-2-oxo-3H-benzo diazepine-3-carboxylate	208941	23980-14-5
Ethyl loflazepate		ethyl 7-chloro-5-(2-fluorophenyl)-2-oxo-3H-benzo diazepine-3-carboxylate	3299	29177-84-2
Carburazepam	7.9	7-chloro-1-methyl-2-oxo-5-phenyl-1,2,3,5-tetrahydro-4H-benzo diazepine-4-carboxamide	68787	59009-93-7
Ro20-7078	8.2757 / 5.3nM	3,7-dichloro-5-(2-fluorophenyl)-1H-benzo diazepin-2(3H)-one
Clobazam	6.8861 / 130nM	7-chloro-1-methyl-5-phenyl-1H-1,5-benzodiazepine-2,4(3H,5H)-dione	2789	22316-47-8
Desmethylclobazam	6.6778 / 210nM	7-chloro-5-phenyl-1H-1,5-benzodiazepine-2,4(3H,5H)-dione
Triflubazam	8.4	7-trifluoromethyl-1-methyl-5-phenyl-1H-1,5-benzodiazepine-2,4(3H,5H)-dione	2789	22316-47-8
Lofendazam		7-chloro-5-phenyl-1,3,4,5-tetrahydro-4H-1,5-benzodiazepin-4-one	71709	29176-29-2
Arfendazam	8.3	ethyl 7-chloro-4-oxo-5-phenyl-2,3-dihydro-1,5-benzodiazepine-1-carboxylate	65803	37669-57-1
CP-1414S	7.9	8-nitro-1-phenyl-4-amino-3H-1,5-benzodiazepin-2-one	37594	36975-99-2
Compound 6i	8.6	9-chloro-11-phenyl-6,11-dihydro-5H-pyrimidobenzodiazepin-5-one
Oxazolam		10-chloro-2-methyl-11b-phenyl-2,3,7,11b-tetrahydrobenzooxazolo diazepin-6(5H)-one	62779	24143-17-7
Cloxazolam		10-chloro-11b-(2-chlorophenyl)-2,3,5,7-tetrahydro-oxazolo benzodiazepin-6(5H)-one	2816	24166-13-0
Mexazolam		10-chloro-11b-(2-chlorophenyl)-3-methyl-2,3,7,11b-tetrahydrooxazolo benzodiazepin-6(5H)-one	4177	31868-18-5
Flutazolam		10-chloro-11b-(2-fluorophenyl)-7-(2-hydroxyethyl)-3,5-dihydro-2H-oxazolo benzodiazepin-6(5H)-one	3398	27060-91-9
Haloxazolam		10-bromo-11b-(2-fluorophenyl)-2,3,5,7-tetrahydro-oxazolo benzodiazepin-6(5H)-one	3563	59128-97-1
Ketazolam		11-chloro-8,12b-dihydro-2,8-dimethyl-12b-phenyl-4H-oxazino benzodiazepine-4,7(6H)-dione	33746	27223-35-4
U-35005	8.3665 / 4.3nM	6-(2-chlorophenyl)-1-methyl-4H-benzo triazolo diazepine	21680194
4'-Chlorodeschloroalprazolam		6-(4-chlorophenyl)-1-methyl-4H-triazolobenzodiazepine	142641556	92262-72-1
Estazolam	8.0706 / 8.5nM	8-chloro-6-phenyl-4H-benzo triazolo diazepine	3261	29975-16-4
Alprazolam	7.699 / 20nM	8-chloro-6-phenyl-1-methyl-4H-benzo triazolo diazepine	2118	28981-97-7
Triazolam	8.3979 / 4nM	8-chloro-6-(2-chlorophenyl)-1-methyl-4H-benzo triazolo diazepine	5556	28911-01-5
alpha-Hydroxytriazolam	8.3768 / 4.2nM	8-chloro-6-(2-chlorophenyl)-1-hydroxymethyl-4H-benzo triazolo diazepine	1963	37115-45-0
Flualprazolam	8.3	8-chloro-6-(2-fluorophenyl)-1-methyl-4H-benzo triazolo diazepine	10359044	28910-91-0
Iso-flualprazolam		8-fluoro-6-(2-chlorophenyl)-1-methyl-4H-benzo triazolo diazepine
Desmethyltriazolam	8.3	8-chloro-6-(2-chlorophenyl)-4H-benzo triazolo diazepine	826660	42292-42-2
Nitrazolam	8.5	8-nitro-6-phenyl-1-methyl-4H-benzo triazolo diazepine	20317278	28910-99-8
Desmethylnitrazolam	8.8	8-nitro-6-phenyl-4H-benzo triazolo diazepine	20317280	30858-58-3
Clonazolam	9.5	8-nitro-6-(2-chlorophenyl)-1-methyl-4H-benzo triazolo diazepine	12317881	33887-02-4
Flunitrazolam	8.8	8-nitro-6-(2-fluorophenyl)-1-methyl-4H-benzo triazolo diazepine	137700379	2243815-18-9
Flubromazolam (JYI-73)	8.8	8-bromo-6-(2-fluorophenyl)-1-methyl-4H-benzo triazolo diazepine	21930924	612526-40-6
Fluiodomazolam (BDBM50011621)		8-iodo-6-(2-fluorophenyl)-1-methyl-4H-benzo triazolo diazepine	14851835
Triflumazolam (SCHEMBL7327294)		8-trifluoromethyl-6-phenyl-1-methyl-4H-benzo triazolo diazepine	19010444	28910-98-7
JYI-70		8-ethynyl-6-(2-fluorophenyl)-1-methyl-4H-benzo triazolo diazepine	14851900
XLI-296		8-ethynyl-6-(2-chlorophenyl)-1-methyl-4H-benzo triazolo diazepine	14851901
Clobromazolam (DM-II-90)	8.2	8-bromo-6-(2-chlorophenyl)-1-methyl-4H-benzo triazolo diazepine	1032830	87213-50-1
Bromazolam (XLI-268)	8.5	8-bromo-6-phenyl-1-methyl-4H-benzo triazolo diazepine	12562546	71368-80-4
Pyrazolam (SH-I-04)	8.1	8-bromo-6-(pyridin-2-yl)-1-methyl-4H-benzo triazolo diazepine	12562545	39243-02-2
Pyclazolam	8.2	8-chloro-6-(pyridin-2-yl)-1-methyl-4H-benzo triazolo diazepine	20368150
Pynazolam	9.4	8-nitro-6-(pyridin-2-yl)-1-methyl-4H-benzo triazolo diazepine	20368157	2034366-97-5
Pyeazolam (SH-TRI-108)	7.9	8-ethynyl-6-(pyridin-2-yl)-1-methyl-4H-benzo triazolo diazepine	71811108	1349115-59-8
Adinazolam	6.8697 / 135nM	8-chloro-6-phenyl-1-(N,N-dimethylaminomethyl)-4H-benzo triazolo diazepine	37632	37115-32-5
U-42352		8-chloro-6-phenyl-1-(N-methylaminomethyl)-4H-benzo triazolo diazepine	119094	37115-33-6
Fluadinazolam	7.1	8-chloro-6-(2-fluorophenyl)-1-(N,N-dimethylaminomethyl)-4H-benzo triazolo diazepine	21537253	37391-59-6
U-43465 F	7.9431	8-chloro-1--6-phenyl-4H-s-triazolobenzodiazepine	134388	83983-74-8
Ro11-5073	8.4815 / 3.3nM	(4S)-8-chloro-6-(2-fluorophenyl)-1,4-dimethyl-4H-benzo triazolo diazepine	101637147
Ro11-6679	8.3979 / 4nM	8-nitro-6-(2-fluorophenyl)-1,4-dimethyl-4H-benzo triazolo diazepine
Ro17-4582	8.4559 / 3.5nM	4-(2-chlorophenyl)-9-methyl-6H-thieno triazolo diazepine
Etizolam	8.5086 / 3.1nM	2-ethyl-4-(2-chlorophenyl)-9-methyl-6H-thieno triazolo diazepine	3307	40054-69-1
Deschloroetizolam	8.5	2-ethyl-4-phenyl-9-methyl-6H-thieno triazolo diazepine	827322	40054-73-7
Desmethyletizolam		2-ethyl-4-(2-chlorophenyl)-6H-thieno triazolo diazepine	12434325	40054-68-0
Fluetizolam	8.8	2-ethyl-4-(2-fluorophenyl)-9-methyl-6H-thieno triazolo diazepine	12434320	40054-88-4
Nitizolam		2-nitro-4-(2-chlorophenyl)-9-methyl-6H-thieno triazolo diazepine	70600959
Iprotizolam		2-isopropyl-4-(2-chlorophenyl)-9-methyl-6H-thieno triazolo diazepine	67727941
Clotizolam (Ro11-1465)	8.8539 / 1.4nM	2-chloro-4-(2-chlorophenyl)-9-methyl-4H-thieno triazolo diazepine	3041455	54123-06-7
Deschloroclotizolam		2-chloro-4-phenyl-9-methyl-4H-thieno triazolo diazepine	157010678	1629324-97-5
Fluclotizolam	9.1	2-chloro-4-(2-fluorophenyl)-9-methyl-4H-thieno triazolo diazepine	21317700	54123-15-8
Difluclotizolam		2-chloro-4-(2,6-difluorophenyl)-9-methyl-4H-thieno triazolo diazepine	21317683
Brotizolam	8.9208	2-bromo-4-(2-chlorophenyl)-9-methyl-6H-thieno triazolo diazepine	2451	57801-81-7
Flubrotizolam (LS-152,574)	9.6	2-bromo-4-(2-fluorophenyl)-9-methyl-6H-thieno triazolo diazepine	3044878	57801-95-3
Ro14-1636	8.8239	2-iodo-4-(2-chlorophenyl)-9-methyl-6H-thieno triazolo diazepine	14851924
Ciclotizolam	8.0	2-bromo-4-(2-chlorophenyl)-9-cyclohexyl-6H-thieno triazolo diazepine	71949	58765-21-2
Ro11-7800	8.5376 / 2.9nM	(2-chloro-4-(2-chlorophenyl)-6H-thieno triazolo diazepin-9-yl)methanamine
Zapizolam	8.8	8-chloro-6-(2-chlorophenyl)-4H-pyrido triazolo diazepine	68832	64098-32-4
Rilmazolam (LS-188,599)	7.3	8-chloro-6-(2-chlorophenyl)-N,N-dimethyl-4H-1,2,4-triazolo benzodiazepine-2-carboxamide	148494	50330-59-1
Midazolam	8.3188 / 4.8nM	8-chloro-6-(2-fluorophenyl)-1-methyl-4H-imidazo benzodiazepine	4192	59467-70-8
alpha-Hydroxymidazolam	8.3468 / 4.5nM	8-chloro-6-(2-fluorophenyl)-1-hydroxymethyl-4H-imidazo benzodiazepine	107917	59468-90-5
Ro22-0284		8-chloro-6-(2-fluorophenyl)-1-hydroxymethyl-4-hydroxy-4H-imidazo benzodiazepine	10316307	64740-68-7
Climazolam	8.1	8-chloro-6-(2-chlorophenyl)-1-methyl-4H-imidazo benzodiazepine	68790	59467-77-5
Remimazolam	8.3	methyl 3- benzodiazepin-4-yl]propanoate	9824461	308242-62-8
Ro15-8670	7.8239 / 15nM	ethyl 8-chloro-6-phenyl-4H-benzoimidazo diazepine-3-carboxylate	14907889
JYI-32		ethyl 8-bromo-6-(2-fluorophenyl)-4H-benzoimidazo diazepine-3-carboxylate	21930922
JY-XHE-057		ethyl 8-ethynyl-6-(2-fluorophenyl)-4H-benzoimidazo diazepine-3-carboxylate	21065283
Ro16-0529	7.8539 / 14nM	tert-butyl 7-chloro-6-phenyl-4H-benzoimidazo diazepine-3-carboxylate
Ro21-5205	8.1308 / 7.4nM	methyl 8-chloro-6-(2-fluorophenyl)-4H-benzoimidazo diazepine-3-carboxylate	12801973
SH-053-R-CH3-2'F	7.9	ethyl (4R)-8-ethynyl-6-(2-fluorophenyl)-4-methyl-4H-benzoimidazo diazepine-3-carboxylate	11574585	872874-14-1
HZ-166		ethyl 8-ethynyl-6-(pyridin-2-yl)-4H-benzoimidazo diazepine-3-carboxylate	10309028	612527-56-7
MP-III-022	9.1	(4R)-8-ethynyl-6-(2-fluorophenyl)-N,4-dimethyl-4H-benzoimidazo diazepine-3-carboxamide	130439777
GL-II-73		(4R)-8-ethynyl-6-(2-fluorophenyl)-N,N,4-trimethyl-4H-benzoimidazo diazepine-3-carboxamide	130439778
YT-III-31		8-ethynyl-6-phenyl-N-methyl-4H-benzoimidazo diazepine-3-carboxamide	49848318
Ro22-1892	7.9208 / 12nM	8-chloro-6-(2-fluorophenyl)-3-(isopropoxycarbonyl)-4H-benzoimidazo diazepine 5-oxide
Ro22-0992	7.8861 / 13nM	8-chloro-6-(2-chlorophenyl)-4H-benzoimidazo diazepine-3-carboxylic acid
Ro21-8137	8.4559 / 3.5nM	8-chloro-6-(2-fluorophenyl)-4H-benzoimidazo diazepine-3-carboxamide
Ro21-8384	8.4202	8-chloro-6-(2-chlorophenyl)-4H-benzoimidazo diazepine-3-carboxamide	162997	63176-94-3
Imidazenil	8.8	8-fluoro-6-(2-bromophenyl)-4H-benzoimidazo diazepine-3-carboxamide	119194	151271-08-8
Ro23-0364		6-(2-chlorophenyl)-4H-benzoimidazo diazepine-3-carboxamide	194998	113066-25-4
Ro21-8482	7.585 / 26nM	8-chloro-6-(2-chlorophenyl)-1--4H-benzoimidazo diazepine-3-carboxamide
Loprazolam	8.2007	(2Z)-6-(2-chlorophenyl)-2--8-nitro-2,4-dihydro-1H-imidazo benzodiazepin-1-one	3033860	61197-73-7
Fluloprazolam	8.0	(2Z)-6-(2-fluorophenyl)-2--8-nitro-2,4-dihydro-1H-imidazo benzodiazepin-1-one	12371485
PS-I-35		(2Z)-6-phenyl-2--8-bromo-2,4-dihydro-1H-imidazo benzodiazepin-1-one	72660859
Ro14-1359	7.1549 / 70nM	7-chloro-5-(2-fluorophenyl)-1H-benzoazepin-2(3H)-one
Ro15-8867	7.6021 / 25nM	7-nitro-5-(2-chlorophenyl)-1H-benzoazepin-2(3H)-one
Ro14-7187	6.3872 / 410nM	1-methyl-6-phenyl-4H-benzo triazoloazepine	85687871
Ro13-9868	7.3768 / 42nM	8-chloro-1-methyl-6-phenyl-4H-benzo triazoloazepine
Ro14-5921	7.7212 / 19nM	8-chloro-6-(2-fluorophenyl)-4H-benzo triazoloazepine	20449965
Ro14-0304	8.1871 / 6.5nM	8-chloro-6-(2-fluorophenyl)-1-methyl-4H-benzo triazoloazepine	20449964
Ro14-2652	8.2518 / 5.6nM	(8-chloro-6-(2-fluorophenyl)-4H-benzo triazoloazepin-1-yl)methanamine
Ro15-9270	8.301 / 5nM	6-(2-chlorophenyl)-1-methyl-8-nitro-4H-benzo triazoloazepine	20450010
Ro14-0609	7.6126 / 24.4nM	8-chloro-6-(2-fluorophenyl)-5,6-dihydro-4H-benzo triazoloazepine
Ro15-2201	8.8239 / 1.5nM	methyl 6-phenyl-4H-benzoimidazoazepine-3-carboxylate
Ro15-0791	8.6021 / 2.5nM	ethyl 6-phenyl-4H-benzoimidazoazepine-3-carboxylate
Ro15-2200	8.3768 / 4.2nM	ethyl 6-(2-fluorophenyl)-4H-benzoimidazoazepine-3-carboxylate
Ro14-3929	7.7959 / 16nM	ethyl 8-chloro-6-(2-fluorophenyl)-4H-benzoimidazoazepine-3-carboxylate
Ro14-3930	7.8239 / 15nM	8-chloro-6-(2-fluorophenyl)-4H-benzoimidazoazepine-3-carboxamide
Ro14-5568	6.6383 / 230nM	8-chloro-6-(2-fluorophenyl)-4H-benzoimidazoazepine
Ro22-1274	7.1249 / 75nM	8-chloro-1-(2-fluorophenyl)-3H-benzoazepine	13271760	89376-31-8
Ro22-1251	7.9586 / 11nM	9-chloro-2-methyl-7-phenyl-5H-benzopyrimidoazepine
Ro22-1366	8.3979 / 4nM	9-chloro-7-(2-fluorophenyl)-2-methyl-5H-benzopyrimidoazepine
Ro22-2038	8.5528 / 2.8nM	9-chloro-7-(2-fluorophenyl)-5H-benzopyrimidoazepin-2-amine
Ro22-3245	8.5528 / 2.8nM	9-chloro-7-(2-chlorophenyl)-5H-benzopyrimidoazepine
Ro22-3148	6.3768 / 420nM	6-phenyl-2,4-dihydrobenzo triazoloazepine
Ro22-3147	8.284 / 5.2nM	6-(2-chlorophenyl)-2,4-dihydrobenzo triazoloazepine
Ro22-0780	7.9586 / 11nM	8-chloro-6-phenyl-2,4-dihydrobenzo triazoloazepine
Ro22-2466	8.7212 / 1.9nM	8-chloro-6-(2-fluorophenyl)-2,4-dihydrobenzo triazoloazepine
Ro22-2468	8.6021
Ro22-8515		8-chloro-6-(2-chlorophenyl)-1,4-dihydropyrrolo benzazepin-3(2H)-one	145981
Ro14-5974	8.1938 / 6.4nM	(S)-ethyl 9-oxo-11,12,13,13a-tetrahydro-9H-benzoimidazopyrrolo diazepine-1-carboxylate	10041121	88552-32-3
Ro15-4941	8.7696 / 1.7nM	(S)-ethyl 8-chloro-9-oxo-11,12,13,13a-tetrahydro-9H-benzoimidazopyrrolo diazepine-1-carboxylate
Ro14-5975	7.2076 / 62nM	(S)-ethyl 7-chloro-9-oxo-11,12,13,13a-tetrahydro-9H-benzoimidazopyrrolo diazepine-1-carboxylate
Ro16-3607	7.3372 / 46nM	(S)-tert-butyl 8-methoxy-9-oxo-11,12,13,13a-tetrahydro-9H-benzoimidazopyrrolo diazepine-1-carboxylate
Ro16-6624	8 / 10nM	(S)-tert-butyl 8-ethyl-9-oxo-11,12,13,13a-tetrahydro-9H-benzoimidazopyrrolo diazepine-1-carboxylate
Ro16-3774	8.4949 / 3.2nM	(S)-tert-butyl 8-methyl-9-oxo-11,12,13,13a-tetrahydro-9H-benzoimidazopyrrolo diazepine-1-carboxylate
Ro16-0071	8.4949 / 3.2nM	(S)-tert-butyl 9-oxo-11,12,13,13a-tetrahydro-9H-benzoimidazopyrrolo diazepine-1-carboxylate
Ro16-5824	8.4685 / 3.4nM	(S)-tert-butyl 8-(methylthio)-9-oxo-11,12,13,13a-tetrahydro-9H-benzoimidazopyrrolo diazepine-1-carboxylate
Ro16-8912	8.2076 / 6.2nM	(S)-tert-butyl 8-fluoro-9-oxo-11,12,13,13a-tetrahydro-9H-benzoimidazopyrrolo diazepine-1-carboxylate
Ro16-4261	8.1135 / 7.7nM	(S)-tert-butyl 7-fluoro-9-oxo-11,12,13,13a-tetrahydro-9H-benzoimidazopyrrolo diazepine-1-carboxylate
Ro16-0075	8.6021
Ro16-6127	8.5086 / 3.1nM	(S)-tert-butyl 8-chloro-7-fluoro-9-oxo-11,12,13,13a-tetrahydro-9H-benzoimidazopyrrolo diazepine-1-carboxylate
Ro16-3058	7.0458
Bretazenil	8.6576	(S)-tert-butyl 8-bromo-9-oxo-11,12,13,13a-tetrahydro-9H-imidazopyrrolo benzodiazepine-1-carboxylate	107926	84379-13-5
EVT-201		7-chloro-3-(5--1,2,4-oxadiazol-3-yl)-5-methyl-4,5-dihydro-6H-imidazo benzodiazepin-6-one	9885841	308239-86-3
FG-8205		7-chloro-5-methyl-3-(5-propan-2-yl-1,2,4-oxadiazol-3-yl)-4H-imidazo benzodiazepin-6-one	129710	122384-14-9
L-655,708		ethyl (13aS)-7-methoxy-9-oxo-11,12,13,13a-tetrahydro-9H-imidazopyrrolo benzodiazepine-1-carboxylate	5311203	130477-52-0
PWZ-029		8-chloro-3-(methoxymethyl)-5-methyl-4H-imidazo benzodiazepin-6-one	9971547
Ro48-6791		8-fluoro-5-methyl-3-(5--1,2,4-oxadiazol-3-yl)-4H-imidazo benzodiazepin-6-one	9953485	172407-17-9
Ro48-8684		8-fluoro-5-methyl-3-(5--1,3-oxazol-2-yl)-4H-imidazo benzodiazepin-6-one	9866317
Ro4882224		3,10-dichloro-9H-benzoimidazo triazolo diazepine	11673720
Ro4938581		3-bromo-10-(difluoromethyl)-9H-benzoimidazo triazolo diazepine	11624499	883093-10-5
Ro16-6605	8.6778
Ro16-6048	8.4815 / 3.3nM	(S)-tert-butyl 9-oxo-8-(trifluoromethyl)-11,12,13,13a-tetrahydro-9H-benzoimidazopyrrolo diazepine-1-carboxylate
Ro16-6950	8.5528 / 2.8nM	(S)-tert-butyl 8-nitro-9-oxo-11,12,13,13a-tetrahydro-9H-benzoimidazopyrrolo diazepine-1-carboxylate
Ro16-4019	8.8539 / 1.4nM	(S)-propyl 8-chloro-9-oxo-11,12,13,13a-tetrahydro-9H-benzoimidazopyrrolo diazepine-1-carboxylate
Ro16-3031	8.6021 / 2.5nM	(S)-isopropyl 8-chloro-9-oxo-11,12,13,13a-tetrahydro-9H-benzoimidazopyrrolo diazepine-1-carboxylate
Ro16-9906	8.7696 / 1.7nM	(S)-allyl 8-chloro-9-oxo-11,12,13,13a-tetrahydro-9H-benzoimidazopyrrolo diazepine-1-carboxylate
Ro16-7081	8.585
Ro16-7082	8.2007 / 6.3nM	(S)-isobutyl 8-chloro-9-oxo-11,12,13,13a-tetrahydro-9H-benzoimidazopyrrolo diazepine-1-carboxylate
Ro16-7083	8.5376 / 2.9nM	(13aS)-sec-butyl 8-chloro-9-oxo-11,12,13,13a-tetrahydro-9H-benzoimidazopyrrolo diazepine-1-carboxylate
Ro16-9918	8.6383 / 2.3nM	(S)-cyclopropylmethyl 8-chloro-9-oxo-11,12,13,13a-tetrahydro-9H-benzoimidazopyrrolo diazepine-1-carboxylate
Ro16-4020	8.585
Ro16-6654	8.3979 / 4nM	(S)-cyclohexyl 8-chloro-9-oxo-11,12,13,13a-tetrahydro-9H-benzoimidazopyrrolo diazepine-1-carboxylate
Ro17-3206	8.4685
Ro17-3207	8.284
Ro16-4021	8.8239
Ro17-1302	8.2757 / 5.3nM	(S)-phenyl 8-chloro-9-oxo-11,12,13,13a-tetrahydro-9H-benzoimidazopyrrolo diazepine-1-carboxylate
Ro15-2427	IC₅₀ >1000nM	5-methyl-6-oxo-5,6-dihydro-4H-benzoimidazo diazepine-3-carboxamide
Ro14-7437	8.5229 / 3nM	ethyl 5-methyl-6-oxo-4H-imidazo benzodiazepine-3-carboxylate	127597	83210-63-3
Sarmazenil (Ro15-3505)	8.5686 / 2.7nM	ethyl 7-chloro-5-methyl-6-oxo-5,6-dihydro-4H-benzoimidazo diazepine-3-carboxylate	71231	78771-13-8
Ro15-1310	8.1675 / 6.8nM	ethyl 8-chloro-5-methyl-6-oxo-5,6-dihydro-4H-benzoimidazo diazepine-3-carboxylate	114888	78756-33-9
Ro15-1746	IC₅₀ >1000nM	ethyl 9-chloro-5-methyl-6-oxo-5,6-dihydro-4H-benzoimidazo diazepine-3-carboxylate
Ro15-3237	IC₅₀ >1000nM	ethyl 10-chloro-5-methyl-6-oxo-5,6-dihydro-4H-benzoimidazo diazepine-3-carboxylate
Ro15-5623	8.699
Flumazenil	8.6021	ethyl 8-fluoro-5-methyl-6-oxo-5,6-dihydro-4H-benzoimidazo diazepine-3-carboxylate	3373	78755-81-4
Ro15-4513		ethyl 8-azido-5-methyl-6-oxo-5,6-dihydro-4H-benzoimidazo diazepine-3-carboxylate	5081	91917-65-6
RY-031		ethyl 8-ethyl-5-methyl-6-oxo-5,6-dihydro-4H-benzoimidazo diazepine-3-carboxylate	10245056
TG-4-29		ethyl 8-vinyl-5-methyl-6-oxo-5,6-dihydro-4H-benzoimidazo diazepine-3-carboxylate	10591116
RY-080		ethyl 8-ethynyl-5-methyl-6-oxo-5,6-dihydro-4H-benzoimidazo diazepine-3-carboxylate	5311418
YT-II-76		ethyl 8-cyclopropyl-5-methyl-6-oxo-5,6-dihydro-4H-benzoimidazo diazepine-3-carboxylate	46214569
SVO-8-14		ethyl 8-allyl-5-methyl-6-oxo-5,6-dihydro-4H-benzoimidazo diazepine-3-carboxylate	15316982
SVO-8-30		ethyl 8-(furan-2-yl)-5-methyl-6-oxo-5,6-dihydro-4H-benzoimidazo diazepine-3-carboxylate	15316986
SVO-8-67		ethyl 8-phenyl-5-methyl-6-oxo-5,6-dihydro-4H-benzoimidazo diazepine-3-carboxylate	15316984
TG-4-39		ethyl 8-(thiophen-2-yl)-5-methyl-6-oxo-5,6-dihydro-4H-benzoimidazo diazepine-3-carboxylate	15316985
CD-214		cyclopropyl 8-chloro-5-methyl-6-oxo-5,6-dihydro-4H-benzoimidazo diazepine-3-carboxylate	101652266
DM-139		t-butyl 8-(pyrrolidin-1-yl)-5-methyl-6-oxo-5,6-dihydro-4H-benzoimidazo diazepine-3-carboxylate	10547937
DM-146		t-butyl 8-(piperidin-1-yl)-5-methyl-6-oxo-5,6-dihydro-4H-benzoimidazo diazepine-3-carboxylate	10834569
DM-173		t-butyl 8-(dimethylamino)-5-methyl-6-oxo-5,6-dihydro-4H-benzoimidazo diazepine-3-carboxylate	10808192
DM-215		t-butyl 8-methoxy-5-methyl-6-oxo-5,6-dihydro-4H-benzoimidazo diazepine-3-carboxylate	10807310
Ro19-4603		t-butyl 5,6-dihydro-5-methyl-6-oxo-4H-imidazothienodiazepine-3-carboxylate	127382	99632-94-7
Iomazenil		ethyl 7-iodo-5-methyl-6-oxo-5,6-dihydro-4H-benzoimidazo diazepine-3-carboxylate	10251042	127985-21-1
Ro17-9741	8.6198 / 2.4nM	(S)-methyl 8-chloro-9-oxo-9,11,12,12a-tetrahydroazetobenzoimidazo diazepine-1-carboxylate
Ro16-0858	8.8861	ethyl 8-chloro-9-oxo-12,12a-dihydro-9H,11H-azetobenzoimidazo diazepine-1-carboxylate
Ro16-0153	8.2757	tert-butyl 8-chloro-9-oxo-12,12a-dihydro-9H,11H-azetobenzoimidazo diazepine-1-carboxylate
Ro17-1812	8.8861	(S)-cyclopropylmethyl 8-chloro-9-oxo-9,11,12,12a-tetrahydroazetobenzoimidazo diazepine-1-carboxylate	146197	90450-01-4
Ro17-3211	8.62
Ro17-3401	9.0458
Ro17-3620	8.2924
Ro16-9351	8.4318
Ro16-9905	8.9208
Ro17-1338	9
Zopiclone	7.5086	6-(5-chloropyridin-2-yl)-7-oxo-6,7-dihydro-5H-pyrrolopyrazin-5-yl 4-methylpiperazine-1-carboxylate	5735	43200-80-2
Suriclone	8.6778	dithiinopyrrol- 7-yl]4-methylpiperazine- 1-carboxylate	40903	53813-83-5
CL-218,872	6.9208	3-methyl-6--triazolopyridazine	107950	66548-69-4
GBLD-345	9	2-(4-aminophenyl)-3-methoxy-N-imidazopyridazin-6-amine	4602899	122479-08-7

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v t e Benzodiazepines
1,4-Benzodiazepines	2-Oxoquazepam 3-Hydroxyphenazepam Bromazepam BMS-906024* Camazepam Carburazepam Chlordiazepoxide Cinazepam Cinolazepam Clonazepam Cloniprazepam Clorazepate Cyprazepam Delorazepam Demoxepam Desmethylflunitrazepam Devazepide* Diazepam Diclazepam Difludiazepam Doxefazepam Elfazepam Ethyl carfluzepate Ethyl dirazepate Ethyl loflazepate Flubromazepam Fletazepam Fludiazepam Flunitrazepam Flurazepam Flutemazepam Flutoprazepam Fosazepam Gidazepam Halazepam Iclazepam Irazepine* Kenazepine Ketazolam Lorazepam Lormetazepam Lufuradom* Meclonazepam Medazepam Menitrazepam Metaclazepam Motrazepam N-Desalkylflurazepam Nifoxipam Nimetazepam Nitemazepam Nitrazepam Nitrazepate Nordazepam Nortetrazepam Oxazepam Phenazepam Pinazepam Pivoxazepam Prazepam Proflazepam Quazepam QH-II-66 Reclazepam RO4491533* Ro05-4082 Ro5-4864* Ro07-5220 Ro07-9749 Ro20-8065 Ro20-8552 SH-I-048A Sulazepam Temazepam Tetrazepam Tifluadom* Timelotem* Tolufazepam Triflunordazepam Tuclazepam Uldazepam
1,5-Benzodiazepines	Arfendazam Clobazam CP-1414S Lofendazam Triflubazam
2,3-Benzodiazepines*	Girisopam GYKI-52466 GYKI-52895 Nerisopam Talampanel Tofisopam
Triazolobenzodiazepines	Adinazolam Alprazolam Balovaptan* Bromazolam Clonazolam Estazolam Fluadinazolam Flualprazolam Flubromazolam Flunitrazolam Nitrazolam Phenazolam Pyrazolam Rilmazolam (active metabolite of Rilmazafone) Triazolam
Imidazobenzodiazepines	Bretazenil Climazolam EVT-201 FG-8205 Flumazenil GL-II-73 Imidazenil I-Iomazenil L-655,708 Loprazolam Midazolam PWZ-029 Remimazolam Ro15-4513 Ro48-6791 Ro48-8684 Ro4938581 Sarmazenil SH-053-R-CH3-2′F
Oxazolobenzodiazepines	Cloxazolam Flutazolam Haloxazolam Mexazolam Oxazolam
Thienodiazepines	Bentazepam Clotiazepam Ro09-9212
Thienotriazolodiazepines	α-Hydroxyetizolam Apafant* Brotizolam Ciclotizolam Clotizolam Deschloroclotizolam Deschloroetizolam Etizolam Flubrotizolam Fluclotizolam Fluetizolam Israpafant* JQ1* Metizolam
Thienobenzodiazepines*	Olanzapine Telenzepine
Pyridodiazepines	Lopirazepam
Pyridotriazolodiazepines	Zapizolam
Pyrazolodiazepines	Razobazam* Ripazepam Zolazepam Zomebazam Zometapine*
Pyrrolodiazepines	Premazepam
Tetrahydroisoquinobenzodiazepines	Clazolam
Pyrrolobenzodiazepines*	Anthramycin
Benzodiazepine prodrugs	Alprazolam triazolobenzophenone Avizafone Rilmazafone
* atypical activity profile (not GABA_A receptor ligands)

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