DOV-102,677 - Misplaced Pages

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DOV-102,677
Legal status

Legal status	US: Investigational New Drug
Identifiers
IUPAC name (1S,5R)-1-(3,4-dichlorophenyl)-3-azabicyclohexane
CAS Number	410074-75-8
PubChem CID	11637190
ChemSpider	9811932
UNII	NS8NWQ6NF4
ChEMBL	ChEMBL488638
CompTox Dashboard (EPA)	DTXSID50469820
Chemical and physical data
Formula	C₁₁H₁₁Cl₂N
Molar mass	228.12 g·mol
3D model (JSmol)	Interactive image
SMILES C121(CNC2)C3=CC(=C(C=C3)Cl)Cl
InChI InChI=1S/C11H11Cl2N/c12-9-2-1-7(3-10(9)13)11-4-8(11)5-14-6-11/h1-3,8,14H,4-6H2/t8-,11+/m0/s1 Key:BSMNRYCSBFHEMQ-GZMMTYOYSA-N
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DOV-102,677 is a psychoactive drug being developed by Merck and is currently in clinical trials. It is a triple reuptake inhibitor (TRI), or serotonin-norepinephrine-dopamine reuptake inhibitor (SNDRI). It is the (−)-enantiomer of DOV-216,303, and its (+)-enantiomer is DOV-21,947 (amitifadine).

Instead of being developed for depression, DOV-102,677 is being developed for the treatment of alcoholism.

IC₅₀ values for the SERT, NET and DAT are 129 nM, 103 nM, and 133 nM.

Compound	Uptake			Binding
Compound	5-HT	NE	DA	SERT	NET	DAT
DOV-216,303	14	20	78	190	380	190
Amitifadine	12	23	96	100	260	210
DOV-102,677	130	100	130	740	1000	220

DOV-102,677 (20 mg/kg IP) increased extracellular levels of dopamine and serotonin in the prefrontal cortex to 320 and 280% above baseline 100 min after administration. Dopamine levels were stably increased for the duration (240 min) of the study, but serotonin levels declined to baseline by 200 min after administration. Norepinephrine levels increased linearly to a maximum of 348% at 240 min post-dosing.

References

^ Popik P, Krawczyk M, Golembiowska K, Nowak G, Janowsky A, Skolnick P, et al. (2006). "Pharmacological profile of the "triple" monoamine neurotransmitter uptake inhibitor, DOV 102,677". Cellular and Molecular Neurobiology. 26 (4–6): 857–73. doi:10.1007/s10571-006-9012-5. PMID 16636898. S2CID 34989472.
McMillen BA, Shank JE, Jordan KB, Williams HL, Basile AS (November 2007). "Effect of DOV 102,677 on the volitional consumption of ethanol by Myers' high ethanol-preferring rat". Alcoholism: Clinical and Experimental Research. 31 (11): 1866–71. doi:10.1111/j.1530-0277.2007.00513.x. PMID 17908267.

v t e Treatment of drug dependence (N07B)
Nicotine dependence	Bupropion Cytisine Lobeline Mecamylamine Varenicline AATooltip Adrenergic agonist (Clonidine)
Alcohol dependence	AD inhibitor Disulfiram Acamprosate Calcium carbimide Hydrogen cyanamide General anesthetics Nitrous oxide Opioid antagonists Naltrexone Nalmefene Topiramate AATooltip Adrenergic agonist (Clonidine) Baclofen Phenibut
Opioid dependence	AATooltip Adrenergic agonist (Clonidine Lofexidine) Ibogaine Opioids Buprenorphine (+naloxone) Levacetylmethadol Methadone Dihydrocodeine Dihydroetorphine Hydromorphone (extended-release) Morphine (extended-release) Opioid antagonists (Naltrexone Nalmefene)
Benzodiazepine dependence	AATooltip Adrenergic agonist (Clonidine) Benzodiazepines (Diazepam Lorazepam Chlordiazepoxide Oxazepam) Barbiturates (Phenobarbital)

Monoamine reuptake inhibitors

DATTooltip Dopamine transporter
(DRIsTooltip Dopamine reuptake inhibitors)

Piperazines: DBL-583 GBR-12783 GBR-12935 GBR-13069 GBR-13098 JJC8-088 Nefazodone Vanoxerine
Piperidines: 4-Fluoropethidine Benocyclidine (BTCP) Desoxypipradrol Dexmethylphenidate Difemetorex Ethylphenidate HDMP-28 Methylphenidate Pethidine (meperidine) Phencyclidine Pipradrol Serdexmethylphenidate Tenocyclidine
Pyrrolidines: Diphenylprolinol MDPV Naphyrone Prolintane Pyrovalerone
Tropanes: Altropane Benzatropine (benztropine) Brasofensine CFT Cocaine Dichloropane Difluoropine Etybenzatropine (ethybenztropine) FE-β-CPPIT FP-β-CPPIT Ioflupane (I) RTI-55 RTI-112 RTI-113 RTI-121 RTI-126 RTI-150 RTI-177 RTI-229 RTI-336 Tesofensine Troparil Tropoxane WF-11 WF-23 WF-31 WF-33
Others: Adrafinil Amifitadine Armodafinil Amfonelic acid Amineptine Ansofaxine BTQ BTS 74,398 Bupropion Chaenomeles speciosa Ciclazindol Dasotraline Desmethylsertraline Desmethylsibutramine (BTS-54354) Diclofensine Didesmethylsibutramine (BTS-54505) Dimethocaine Diphenylpyraline Dizocilpine (MK-801) DOV-102,677 DOV-216,303 Efavirenz Ephenidine Esketamine EXP-561 Fencamfamin Fezolamine Fluorenol GYKI-52895 Hydroxybupropion Indatraline Ketamine Lefetamine Levophacetoperane Liafensine LR-5182 Manifaxine Mazindol Medifoxamine Mesocarb Metaphit MIN-117 (WF-516) Modafinil Nefopam Nomifensine NS-2359 O-2172 Oroxylin A Perafensine Pridefine Radafaxine Rimcazole Sertraline Sibutramine Solriamfetol Tametraline Tedatioxetine Threohydrobupropion Tripelennamine Venlafaxine

NETTooltip Norepinephrine transporter
(NRIsTooltip Norepinephrine reuptake inhibitors)

Selective norepinephrine reuptake inhibitors: Amedalin Alseroxylon Ciclazindol Daledalin Edivoxetine Esreboxetine Lortalamine Mazindol Nisoxetine Reboxetine Talopram Talsupram Tandamine Teniloxazine Viloxazine
Norepinephrine–dopamine reuptake inhibitors: Amineptine Bupropion Fencamine Fencamfamin Hydroxybupropion Lefetamine Levophacetoperane LR-5182 Manifaxine Methylphenidate Nomifensine O-2172 Radafaxine Serdexmethylphenidate Solriamfetol
Serotonin–norepinephrine reuptake inhibitors: Atomoxetine (tomoxetine) CP-39,332 Desvenlafaxine Duloxetine Eclanamine Levomilnacipran McN5652 Milnacipran N-Methyl-PPPA Nafenodone PPPA Tofenacin Venlafaxine
Serotonin–norepinephrine–dopamine reuptake inhibitors: 3,3-Diphenylcyclobutanamine Amifitadine Ansofaxine Bicifadine Brasofensine Centanafadine Cocaine Dasotraline Desmethylsertraline Desmethylsibutramine (BTS-54354) Diclofensine Didesmethylsibutramine (BTS-54505) DOV-102677 DOV-216303 EXP-561 Fezolamine HDMP-28 HP-505 Indatraline JNJ-7925476 JZ-IV-10 Liafensine Mazindol Naphyrone Nefazodone Nefopam NS-2359 Perafensine PRC200 Pridefine SEP-228431 SEP-228432 Sibutramine Tedatioxetine Tesofensine Threohydrobupropion Tropanes (e.g., cocaine)
Tricyclic antidepressants: Amitriptyline Butriptyline Cianopramine Clomipramine Desipramine Dosulepin (dothiepin) Doxepin Imipramine Lofepramine Melitracen Nortriptyline Protriptyline Trimipramine
Tetracyclic antidepressants: Amoxapine Maprotiline Mianserin Oxaprotiline Setiptiline
Others: Antihistamines (e.g., brompheniramine, chlorphenamine, pheniramine, tripelennamine) Antipsychotics (e.g., loxapine, ziprasidone) Arylcyclohexylamines (e.g., ketamine, phencyclidine) Dopexamine Ephenidine Ginkgo biloba Indeloxazine Nefazodone Opioids (e.g., desmetramadol, methadone, pethidine (meperidine), tapentadol, tramadol, levorphanol)

SERTTooltip Serotonin transporter
(SRIsTooltip Serotonin reuptake inhibitors)

Selective serotonin reuptake inhibitors: 6-Nitroquipazine Alaproclate Centpropazine Cericlamine Citalopram Dapoxetine Desmethylcitalopram Didesmethylcitalopram Escitalopram Femoxetine Fluoxetine Fluvoxamine Indalpine Ifoxetine Norfluoxetine Omiloxetine Panuramine Paroxetine PIM-35 Pirandamine RTI-353 Seproxetine Sertraline Zimelidine Selective serotonin reuptake inhibitors and serotonin receptor modulators: Etoperidone Litoxetine Lubazodone LY-393558 Quipazine SB-649915 TGBA01AD Trazodone Vilazodone Vortioxetine
Serotonin–norepinephrine reuptake inhibitors: Atomoxetine (tomoxetine) Bicifadine CP-39332 Desvenlafaxine Duloxetine Eclanamine Levomilnacipran McN5652 Milnacipran N-Methyl-PPPA PPPA Tofenacin Venlafaxine
Serotonin–norepinephrine–dopamine reuptake inhibitors: 3,3-Diphenylcyclobutanamine Amifitadine Ansofaxine Bicifadine Brasofensine Centanafadine Cocaine Dasotraline Desmethylsertraline Desmethylsibutramine (BTS-54354) Diclofensine Didesmethylsibutramine (BTS-54505) DOV-102677 DOV-216303 EXP-561 Fezolamine HDMP-28 HP-505 Indatraline JNJ-7925476 JZ-IV-10 Liafensine Mazindol Naphyrone Nefazodone Nefopam NS-2359 Perafensine PRC200 Pridefine SEP-228431 SEP-228432 Sibutramine Tedatioxetine Tesofensine Threohydrobupropion Tropanes (e.g., cocaine)
Tricyclic antidepressants: Amitriptyline Cianopramine Clomipramine Cyanodothiepin Desipramine Dosulepin (dothiepin) Doxepin Imipramine Lofepramine Nortriptyline Pipofezine Protriptyline
Others: A-80426 Amoxapine Antihistamines (e.g., brompheniramine, chlorphenamine, dimenhydrinate, diphenhydramine, mepyramine (pyrilamine), pheniramine, tripelennamine) Antipsychotics (e.g., loxapine, ziprasidone) Arylcyclohexylamines (e.g., 3-MeO-PCP, esketamine, ketamine, methoxetamine, phencyclidine) Cyclobenzaprine Delucemine Dextromethorphan Dextrorphan Efavirenz Hypidone Medifoxamine Mesembrine Mifepristone MIN-117 (WF-516) N-Me-5-HT Opioids (e.g., dextropropoxyphene, methadone, pethidine (meperidine), levorphanol, tapentadol, tramadol) Roxindole

VMATsTooltip Vesicular monoamine transporters

Amiodarone
Amphetamines (e.g., amphetamine, methamphetamine, MDMA)
APP
AZIK
Bietaserpine
Deserpidine
Deutetrabenazine
Dihydrotetrabenazine
Efavirenz
GBR-12935
GZ-793A
Ibogaine
Ketanserin
Lobeline
Methoxytetrabenazine
Reserpine
Rose bengal
Tetrabenazine
Valbenazine
Vanoxerine (GBR-12909)

Others

DAT enhancers: Luteolin

DAT modulators: Agonist-like: SoRI-9804
SoRI-20040; Antagonist-like: SoRI-20041

See also: Receptor/signaling modulators • Monoamine releasing agents • Adrenergics • Dopaminergics • Serotonergics • Monoamine metabolism modulators • Monoamine neurotoxins

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