# Suproclone

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Drug

Pharmaceutical compound

Suproclone Clinical data ATC code none Identifiers IUPAC name [6-(7-chloro-1,8-naphthyridin-2-yl)-5-oxo-3,7-dihydro-2H-[1,4]dithiino[2,3-c]pyrrol-7-yl] 4-propanoylpiperazine-1-carboxylate CAS Number 76535-71-2 Y PubChem CID 53696 ChemSpider 48481 Y UNII J4AM5D708G KEGG D05975 Y ChEMBL ChEMBL2105531 CompTox Dashboard (EPA) DTXSID00868445 ECHA InfoCard 100.071.330 Chemical and physical data Formula C22H22ClN5O4S2 Molar mass 520.02 g·mol−1 3D model (JSmol) Interactive image SMILES O=C(N5CCN(C(=O)OC4C=1SCCSC=1C(=O)N4c2nc3nc(Cl)ccc3cc2)CC5)CC InChI InChI=1S/C22H22ClN5O4S2/c1-2-16(29)26-7-9-27(10-8-26)22(31)32-21-18-17(33-11-12-34-18)20(30)28(21)15-6-4-13-3-5-14(23)24-19(13)25-15/h3-6,21H,2,7-12H2,1H3 Y Key:IBAUKGNDWVSETP-UHFFFAOYSA-N Y NY (what is this?) (verify)

**Suproclone** is a [sedative](/source/Sedative) and [anxiolytic](/source/Anxiolytic) drug in the [cyclopyrrolone](/source/Cyclopyrrolone) family of drugs, developed by the French pharmaceutical company Rhône-Poulenc.[1] Other cyclopyrrolone drugs include [zopiclone](/source/Zopiclone), [pagoclone](/source/Pagoclone) and [suriclone](/source/Suriclone).

Suproclone is very similar in structure to the related drug [suriclone](/source/Suriclone), but little information has been published about it specifically. However it can be expected that the mechanism of action by which suproclone produces its sedative and anxiolytic effects is by modulating benzodiazepine receptors (resulting in an increased response to endogenous [GABA](/source/GABA)), in a similar manner to other drugs of this class.[2][3]

## Synthesis

[ChemDrug](https://www.chemdrug.com/article/8/3284/16419747.html) Synthesis:[4] Patent (Ex 1/15):[5]

The condensation between 2,3-Dihydro-1,4-dithiino[2,3-c]furan-5,7-dione [10489-75-5] (1) and 7-Chloro-1,8-naphthyridin-2-amine [15944-33-9] (2) gives PC23343647 (3). Halogenation with phosphoryl chloride leads to PC23343652 (4). Reductino with potassium borohydride afforded [53788-25-3] (5). Treatment with phenyl chloroformate [1885-14-9] (6) resulted in 2-(7-chloro-1,8-naphthyridin-2-yl)-3-phenoxycarbonyloxy-isoindolin-1-one, PC23343637 (7). Reaction with piperazine [110-85-0] (8) afforded (9). Acylation with propionyl chloride completed the synthesis of Suproclone (10).

## References

1. **[^](#cite_ref-1)** Psychotropics.dk. ["suproclone"](http://www.psychotropics.dk/moleculeView/default.aspx?ID=1532&Catalogtype=A&ChapterID=9&Thissortorder=1). Retrieved 24 August 2009.

1. **[^](#cite_ref-2)** Gardner CR (1988). "Pharmacological profiles in vivo of benzodiazepine receptor ligands". *Drug Development Research*. **12** (1): 1–28. [doi](/source/Doi_(identifier)):[10.1002/ddr.430120102](https://doi.org/10.1002%2Fddr.430120102). [S2CID](/source/S2CID_(identifier)) [85573551](https://api.semanticscholar.org/CorpusID:85573551).

1. **[^](#cite_ref-3)** Doble A, Martin I, Nutt D (23 October 2003). *Calming the brain: benzodiazepines and related drugs from laboratory to clinic*. Informa Healthcare. [ISBN](/source/ISBN_(identifier)) [1-84184-052-1](https://en.wikipedia.org/wiki/Special:BookSources/1-84184-052-1).

1. **[^](#cite_ref-4)** Serradell, MN; Castaer, J.; Suproclone. Drugs Fut 1985, 10, 1, 45.

1. **[^](#cite_ref-5)** Claude Cotrel, Claude Jeanmart, Mayer N. Messer, Cornel Crisan, [U.S. patent 4,220,646](https://patents.google.com/patent/US4220646) (1980 to Rhone-Poulenc Industries).

v t e Hypnotics/sedatives (N05C) GABAA 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 Clobazam 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 Neurosteroids Acebrochol Alfadolone Alfaxolone Brexanolone (allopregnanolone) Eltanolone (pregnanolone) Ganaxolone Hydroxydione Minaxolone Progesterone Renanolone Zuranolone Nonbenzodiazepines Eszopiclone Indiplon Lirequinil Necopidem Pagoclone Pazinaclone Saripidem Suproclone Suriclone Zaleplon Zolpidem Zopiclone Phenols Cipepofol (ciprofol) Fospropofol Propofol Propofol hemisuccinate Piperidinediones Glutethimide Methyprylon Piperidione Pyrithyldione 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 (THIP) Ibotenic acid (Amanita muscaria) Kavalactones Loreclezole Muscimol (Amanita muscaria) Paraldehyde Petrichloral Sesquiterpene Isovaleramide Isovaleric acid Valerenic acid Sulfonylalkanes Sulfonmethane (sulfonal) Tetronal Trional Triclofos GABAB 1,4-Butanediol 4-Fluorophenibut Aceburic acid Baclofen GABOB GHB (sodium oxybate) GBL GVL JZP-386 Phenibut Tolibut Valiloxybate (XW-10172) 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 Clonidine Detomidine Dexmedetomidine Lofexidine Medetomidine Romifidine Tasipimidine Tizanidine Xylazine 5-HT2A 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 Agomelatine Melatonin Ramelteon Tasimelteon Orexin Daridorexant Lemborexant Suvorexant α2δ VDCC Atagabalin Baclofen Gabapentin Gabapentin enacarbil Mirogabalin Phenibut Pregabalin Others Cannabinoids (e.g., cannabis, tetrahydrocannabinol/dronabinol, nabilone, cannabidiol, Zenivol) Chlorophenylalkyldiols Fenpentadiol Metaglycodol Phenaglycodol Diethylpropanediol Evoxine Fenadiazole GABA reuptake inhibitors (e.g., tiagabine) Guaifenesin-related muscle relaxants Chlorphenesin Mephenesin Mephenoxalone Metaxalone Methocarbamol Midaflur Opioids (e.g., morphine) Passion flower Phemerazole Scopolamine Serotonin precursors (e.g., tryptophan, 5-hydroxytryptophan (5-HTP; oxitriptan)) Trazodone UMB68 Valnoctamide

v t e GABAA receptor positive modulators Alcohols Brometone Butanol Chloralodol Chlorobutanol (cloretone) Ethanol (alcohol) (alcoholic drink) Ethchlorvynol Isobutanol Isopropanol Menthol Methanol Methylpentynol Pentanol Petrichloral Propanol tert-Butanol (2M2P) tert-Pentanol (2M2B) Tribromoethanol Trichloroethanol Triclofos Trifluoroethanol Barbiturates (-)-DMBB Allobarbital Alphenal Amobarbital Aprobarbital Barbexaclone Barbital Benzobarbital Benzylbutylbarbiturate Brallobarbital Brophebarbital Butabarbital/Secbutabarbital Butalbital Buthalital Butobarbital Butallylonal Carbubarb Crotylbarbital Cyclobarbital Cyclopentobarbital Difebarbamate Enallylpropymal Ethallobarbital Eterobarb Febarbamate Heptabarb Heptobarbital Hexethal Hexobarbital Methallatal Metharbital Methitural Methohexital Methylphenobarbital Narcobarbital Nealbarbital Pentobarbital Phenallymal Phenobarbital Phetharbital Primidone Probarbital Propallylonal Propylbarbital Proxibarbital Reposal Secobarbital Sigmodal Spirobarbital Talbutal Tetrabamate Tetrabarbital Thialbarbital Thiamylal Thiobarbital Thiobutabarbital Thiopental Thiotetrabarbital Valofane Vinbarbital Vinylbital Benzodiazepines 2-Oxoquazepam 3-Hydroxyphenazepam Adinazolam Alprazolam Arfendazam Avizafone Bentazepam Bretazenil Bromazepam Bromazolam Brotizolam Camazepam Carburazepam Chlordiazepoxide Ciclotizolam Cinazepam Cinolazepam Clazolam Climazolam Clobazam Clonazepam Clonazolam Cloniprazepam Clorazepate Clotiazepam Cloxazolam CP-1414S Cyprazepam Delorazepam Demoxepam Diazepam Diclazepam Dimdazenil Doxefazepam Elfazepam Estazolam Ethyl carfluzepate Ethyl dirazepate Ethyl loflazepate Etizolam FG-8205 Fletazepam Flubromazepam Flubromazolam Fludiazepam Flunitrazepam Flunitrazolam Flurazepam Flutazolam Flutemazepam Flutoprazepam Fosazepam Gidazepam Halazepam Haloxazolam Iclazepam Imidazenil Irazepine Ketazolam Lofendazam Lopirazepam Loprazolam Lorazepam Lormetazepam Meclonazepam Medazepam Menitrazepam Metaclazepam Mexazolam Midazolam Motrazepam N-Desalkylflurazepam Nifoxipam Nimetazepam Nitrazepam Nitrazepate Nitrazolam Nordazepam Nortetrazepam Oxazepam Oxazolam Phenazepam Pinazepam Pivoxazepam Prazepam Premazepam Proflazepam Pyrazolam QH-II-66 Quazepam Reclazepam Remimazolam Rilmazafone Ripazepam Ro48-6791 Ro48-8684 SH-053-R-CH3-2′F Sulazepam Temazepam Tetrazepam Tolufazepam Triazolam Triflubazam Triflunordazepam (Ro5-2904) Tuclazepam Uldazepam Zapizolam Zolazepam Zomebazam Carbamates Carisbamate Carisoprodol Clocental Cyclarbamate Difebarbamate Emylcamate Ethinamate Febarbamate Felbamate Hexapropymate Hydroxyphenamate Lorbamate Mebutamate Meprobamate Nisobamate Pentabamate Phenprobamate Procymate Styramate Tetrabamate Tybamate Flavonoids 6-Methylapigenin Ampelopsin (dihydromyricetin) Apigenin Baicalein Baicalin Catechin EGC EGCG Hispidulin Linarin Luteolin Rc-OMe Skullcap constituents (e.g., baicalin) Wogonin Imidazoles Etomidate Metomidate Methoxyetomidate Propoxate Isopropoxate Butomidate Iso-butomidate Sec-butomidate CF2-Etomidate CF3-Etomidate CF3-Propoxate Flutomidate 2,6-Dichloro-3-fluoroetomidate Kava constituents 10-Methoxyyangonin 11-Methoxyyangonin 11-Hydroxyyangonin Desmethoxyyangonin 11-Methoxy-12-hydroxydehydrokavain 7,8-Dihydroyangonin Kavain 5-Hydroxykavain 5,6-Dihydroyangonin 7,8-Dihydrokavain 5,6,7,8-Tetrahydroyangonin 5,6-Dehydromethysticin Methysticin 7,8-Dihydromethysticin Yangonin Monoureides Acecarbromal Apronal (apronalide) Bromisoval Carbromal Capuride Ectylurea Neurosteroids Acebrochol Allopregnanolone (brexanolone) Alfadolone Alfaxalone 3α-Androstanediol Androstenol Androsterone Certain anabolic-androgenic steroids Cholesterol Cortisol (hydrocortisone) DHDOC 3α-DHP 5α-DHP 5β-DHP DHT Etiocholanolone ETX-155 Ganaxolone Hydroxydione LPCN-1154 Minaxolone NORA-520 ORG-20599 ORG-21465 P1-185 Posovolone PRAX-114 Pregnanolone (eltanolone) Progesterone Renanolone SAGE-105 SAGE-324 SAGE-516 SAGE-689 SAGE-872 Testosterone THDOC Zuranolone Nonbenzodiazepines Cyclopyrrolones: Eszopiclone Pagoclone Pazinaclone Suproclone Suriclone Zopiclone Imidazopyridines: Alpidem DS-1 Necopidem Saripidem Zolpidem Pyrazolopyrimidines: Divaplon Fasiplon Indiplon Lorediplon Ocinaplon Panadiplon Taniplon Zaleplon Others: Adipiplon AXS-17 (BAER-101, AZD-7325) CGS-8216 CGS-9896 CGS-13767 CGS-20625 CL-218,872 CP-615,003 CTP-354 ELB-139 GBLD-345 Imepitoin JM-1232 L-838,417 Lirequinil (Ro41-3696) Miltirone (rosmariquinone) NS-2664 NS-2710 NS-11394 NS-11821 Pipequaline ROD-188 RWJ-51204 SB-205,384 SX-3228 TGSC01AA TP-003 TPA-023 TP-13 U-89843A U-90042 Viqualine Y-23684 Phenols Cipepofol Fospropofol Propofol Propofol hemisuccinate Thymol Piperidinediones Glutethimide Methyprylon Piperidione Pyrithyldione Pyrazolopyridines Cartazolate Etazolate ICI-190,622 Tracazolate Quinazolinones Afloqualone Cloroqualone Diproqualone Etaqualone Mebroqualone Mecloqualone Methaqualone Methylmethaqualone Nitromethaqualone SL-164 Volatiles/gases Acetone Acetophenone Acetylglycinamide chloral hydrate Aliflurane Benzene Butane Butylene Centalun Chloral Chloral betaine Chloral hydrate Chloroform Cryofluorane Desflurane Dichloralphenazone Dichloromethane Diethyl ether Enflurane Ethyl chloride Ethylene Fluroxene Gasoline Halopropane Halothane Isoflurane Kerosine Methoxyflurane Methoxypropane Nitric oxide Nitrogen Nitrous oxide Norflurane Paraldehyde Propane Propylene Roflurane Sevoflurane Synthane Teflurane Toluene Trichloroethane (methyl chloroform) Trichloroethylene Vinyl ether Others/unsorted 3-Hydroxybutanal α-EMTBL AA-29504 Alogabat Avermectins (e.g., ivermectin) Bromide compounds (e.g., lithium bromide, potassium bromide, sodium bromide) Carbamazepine Chloralose Chlormezanone Clomethiazole Darigabat DEABL Deuterated etifoxine Dihydroergolines (e.g., dihydroergocryptine, dihydroergosine, dihydroergotamine, ergoloid (dihydroergotoxine)) DS2 Efavirenz Etazepine Etifoxine Fenamates (e.g., flufenamic acid, mefenamic acid, niflumic acid, tolfenamic acid) Fluoxetine Flupirtine Hopantenic acid KRM-II-81 Lanthanum Lavender oil Lignans (e.g., 4-O-methylhonokiol, honokiol, magnolol, obovatol) Loreclezole Menthyl isovalerate (validolum) Monastrol Nezavist (DCUK-Oet) Nicotinic acid Nicotinamide NTX-1955 (RO-7308480) Org 25,435 Phenytoin Propanidid Retigabine (ezogabine) Safranal Seproxetine Stiripentol Sulfonylalkanes (e.g., sulfonmethane (sulfonal), tetronal, trional) Terpenoids (e.g., borneol) Topiramate Valerian constituents (e.g., isovaleric acid, isovaleramide, valerenic acid, valerenol) Unsorted benzodiazepine site positive modulators: α-Pinene MRK-409 (MK-0343) TCS-1105 TCS-1205 See also: Receptor/signaling modulators • GABA receptor modulators • GABA metabolism/transport modulators

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Adapted from the Wikipedia article [Suproclone](https://en.wikipedia.org/wiki/Suproclone) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Suproclone?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.