Oxanamide - Misplaced Pages

Chemical compound Pharmaceutical compound

Oxanamide
Clinical data

ATC code	none
Identifiers
IUPAC name 2-ethyl-3-propyloxirane-2-carboxamide
CAS Number	126-93-2
PubChem CID	31365
ChemSpider	29098
UNII	050271194T
CompTox Dashboard (EPA)	DTXSID50925350
Chemical and physical data
Formula	C₈H₁₅NO₂
Molar mass	157.213 g·mol
3D model (JSmol)	Interactive image
SMILES CCCC1C(O1)(CC)C(=O)N
InChI InChI=1S/C8H15NO2/c1-3-5-6-8(4-2,11-6)7(9)10/h6H,3-5H2,1-2H3,(H2,9,10) Key:WBLPIVIXQOFTPQ-UHFFFAOYSA-N
(verify)

Oxanamide (Quiactin) is an anxiolytic and muscle relaxant which can produce sedative and hypnotic effects in sufficiently high doses. An uncontrolled trial on patients treated in a clinical gynecology practice published in 1959 found that oxanamide was efficacious in the treatment of anxiety resulting from premenstrual syndrome, menopause, and various other causes, with minimal sedation or other side effects.

References

Kuhn WL, Ketteler HJ, Van Maanen EF (January 1960). "Effects of oxanamide on the central nervous system". Proceedings of the Society for Experimental Biology and Medicine. 103: 101–3. doi:10.3181/00379727-103-25425. PMID 14412594. S2CID 40927309.
Woodhull RB (April 1959). "Oxanamide; adjunctive use of a new tranquilizer in gynecology". California Medicine. 90 (4): 275–7. PMC 1577644. PMID 13638840.

v t e Anxiolytics (N05B)
5-HT_1ARTooltip 5-HT1A receptor agonists	Buspirone Gepirone Tandospirone
GABA_ARTooltip GABAA receptor PAMsTooltip positive allosteric modulators	Benzodiazepines: Adinazolam Alprazolam Bromazepam Camazepam Chlordiazepoxide Clobazam Clonazepam Clorazepate Clotiazepam Cloxazolam Diazepam Ethyl loflazepate Etizolam Fludiazepam Halazepam Ketazolam Lorazepam Medazepam Nordazepam Oxazepam Pinazepam Prazepam; Others: Alpidem Barbiturates (e.g., phenobarbital) Carbamates (e.g., meprobamate) Carisoprodol Chlormezanone Ethanol (alcohol) Etifoxine
Hypnotics	Zopiclone
Gabapentinoids (α₂δ VDCC blockers)	Gabapentin Gabapentin enacarbil Phenibut Pregabalin
Antidepressants	SSRIsTooltip Selective serotonin reuptake inhibitors (e.g., escitalopram) SNRIsTooltip Serotonin-norepinephrine reuptake inhibitors (e.g., duloxetine) SARIsTooltip Serotonin antagonist and reuptake inhibitors (e.g., trazodone) TCAsTooltip Tricyclic antidepressants (e.g., clomipramine) TeCAsTooltip Tetracyclic antidepressants (e.g., mirtazapine) MAOIsTooltip Monoamine oxidase inhibitors (e.g., phenelzine); Others: Agomelatine Bupropion Tianeptine Vilazodone Vortioxetine
Antipsychotics	Quetiapine Flupentixol
Sympatholytics (Antiadrenergics)	Alpha-1 blockers (e.g., prazosin) Alpha-2 agonists (e.g., clonidine, dexmedetomidine, guanfacine) Beta blockers (e.g., propranolol)
Others	Benzoctamine Cycloserine Fabomotizole Hydroxyzine Lorpiprazole Mebicar Mepiprazole Nicotine Opipramol Oxaflozane Phenaglycodol Phenibut Picamilon Selank Tiagabine Tofisopam Validolum
WHO-EM Withdrawn from market Clinical trials: Phase III Never to phase III

Hypnotics/sedatives (N05C)

GABA_A

Alcohols	2M2B Chloralodol Ethanol (alcohol) Diethylpropanediol Ethchlorvynol Methylpentynol Trichloroethanol
Barbiturates	Allobarbital Amobarbital Aprobarbital Barbital Butabarbital Butobarbital Cyclobarbital Ethallobarbital Heptabarb Hexobarbital Mephobarbital Methohexital Narcobarbital Pentobarbital Phenallymal Phenobarbital Propylbarbital Proxibarbal Reposal Secobarbital Talbutal Thiamylal Thiopental Thiotetrabarbital Vinbarbital Vinylbital
Benzodiazepines	Brotizolam Cinolazepam Climazolam Clonazolam Doxefazepam Estazolam Flubromazolam Flunitrazolam Flunitrazepam Flurazepam Flutemazepam Flutoprazepam Loprazolam Lormetazepam Midazolam Nimetazepam Nitemazepam Nitrazepam Nitrazolam Quazepam Temazepam Triazolam
Carbamates	Carisoprodol Emylcamate Ethinamate Hexapropymate Meprobamate Methocarbamol Phenprobamate Procymate Tybamate
Imidazoles	Etomidate Metomidate Propoxate
Monoureides	Acecarbromal Apronal (apronalide) Bromisoval Capuride Carbromal Ectylurea
Neuroactive steroids	Acebrochol Allopregnanolone Alphadolone Alphaxolone Eltanolone Hydroxydione Minaxolone Progesterone
Nonbenzodiazepines	Eszopiclone Indiplon Lirequinil Necopidem Pazinaclone Saripidem Suproclone Suriclone Zaleplon Zolpidem Zopiclone
Phenols	Propofol
Piperidinediones	Glutethimide Methyprylon Pyrithyldione Piperidione
Quinazolinones	Afloqualone Cloroqualone Diproqualone Etaqualone Mebroqualone Mecloqualone Methaqualone Methylmethaqualone Nitromethaqualone SL-164
Others	Acetophenone Acetylglycinamide chloral hydrate Bromide compounds Lithium bromide Potassium bromide Sodium bromide Centalun Chloral betaine Chloral hydrate Chloralose Clomethiazole Dichloralphenazone Gaboxadol Kavalactones Loreclezole Paraldehyde Petrichloral Sulfonylalkanes Sulfonmethane (sulfonal) Tetronal Trional Triclofos Sesquiterpene Isovaleramide Isovaleric acid Valerenic acid

GABA_B

H₁

Antihistamines	Captodiame Cyproheptadine Diphenhydramine Doxylamine Hydroxyzine Methapyrilene Perlapine Pheniramine Promethazine Propiomazine
Antidepressants	Serotonin antagonists and reuptake inhibitors Etoperidone Nefazodone Trazodone Tricyclic antidepressants Amitriptyline Doxepin Trimipramine, etc. Tetracyclic antidepressants Mianserin Mirtazapine, etc.
Antipsychotics	Typical antipsychotics Chlorpromazine Thioridazine, etc. Atypical antipsychotics Olanzapine Quetiapine Risperidone, etc.

α₂-Adrenergic

5-HT_2A

Antidepressants	Trazodone Tricyclic antidepressants Amitriptyline Doxepin Trimipramine, etc. Tetracyclic antidepressants Mianserin Mirtazapine, etc.
Antipsychotics	Typical antipsychotics Chlorpromazine Thioridazine, etc. Atypical antipsychotics Olanzapine Quetiapine Risperidone, etc.
Others	Niaprazine

Melatonin

Orexin

α₂δ VDCC

Others

Skeletal muscle relaxants (M03)

Peripherally acting
(primarily antinicotinic,
NMJ block)

Non-depolarizing

Curare alkaloids

4° ammonium agents

ultra-short duration: Gantacurium

short duration: Rapacuronium
Mivacurium
Chandonium

unsorted: Hexafluronium (Hexafluorenium)

Depolarizing

Choline derivatives: Suxamethonium (Succinylcholine)

Polyalkylene derivatives: Hexamethonium

ACh release inhibitors

Botulinum toxin

Centrally acting

Carbamic acid esters	Carisoprodol Cyclarbamate Difebarbamate Febarbamate Meprobamate Phenprobamate Styramate Tybamate
Benzodiazepines	Bromazepam Diazepam Clonazepam Flunitrazepam Lorazepam Nitrazepam Temazepam Tetrazepam
Nonbenzodiazepines	Eszopiclone
Thienodiazepines	Etizolam
Quinazolines	Methaqualone
Anticholinergics (Antimuscarinics)	Cyclobenzaprine Orphenadrine
Other	Arbaclofen placarbil Baclofen Chlormezanone Chlorphenesin Chlorzoxazone Eperisone Fenyramidol Flopropione Gabapentin GHB Inaperisone Lanperisone Mephenesin Mephenoxalone Metaxalone Methocarbamol Phenibut Pregabalin Pridinol Promoxolane Quinine Silperisone Thiocolchicoside Tizanidine Tolperisone Zoxazolamine

Directly acting

Dantrolene

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