Fominoben

Fominoben
Clinical data
Trade names	Broncomenal, Deronyl, Finaten, Noleptan, Oleptan, Terion, Tosifar, Tussirama
Identifiers
	IUPAC name N-[3-chloro-2-[[methyl-(2-morpholin-4-yl-2-oxoethyl)amino]methyl]phenyl]benzamide;
CAS Number	18053-31-1 ;
PubChem CID	3407;
DrugBank	DB08968;
ChemSpider	3290;
UNII	TJ2KK6NYJS;
KEGG	D07988;
ChEBI	CHEBI:135639;
ChEMBL	ChEMBL1697837;
CompTox Dashboard (EPA)	DTXSID1023075 ;
ECHA InfoCard	100.038.135
Chemical and physical data
Formula	C21H24ClN3O3
Molar mass	401.89 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN(CC1=C(C=CC=C1Cl)NC(=O)C2=CC=CC=C2)CC(=O)N3CCOCC3;
	InChI InChI=1S/C21H24ClN3O3/c1-24(15-20(26)25-10-12-28-13-11-25)14-17-18(22)8-5-9-19(17)23-21(27)16-6-3-2-4-7-16/h2-9H,10-15H2,1H3,(H,23,27); Key:KSNNEUZOAFRTDS-UHFFFAOYSA-N;

Fominoben is an antitussive agent of the benzanilide class, formerly marketed under the name Noleptan.^[2] It binds poorly to the sigma-1 receptor, a receptor activated by many other antitussives.^[3] It is reported to have respiratory stimulant activity.^[4] Other research has indicated it may be an agonist at the benzodiazepine site of the GABA_A receptor.^[5] It was introduced in Germany in 1973, in Italy in 1979, and in Japan in 1983.^[6]

Adverse effects include appetite suppression, nausea, vomiting, insomnia, irritability, and hallucinations. Rarer side effects include somnolence, dizziness, dry mouth, blurred vision, and urticaria.^[7]

References

^ Swiss Pharmaceutial Society, ed. (January 2000). Index Nominum 2000: International Drug Directory. Taylor & Francis. p. 470. ISBN 978-3-88763-075-1.
^ "FOMINOBEN". NCATS Inxight: Drugs. Retrieved March 25, 2021.
^ Musacchio JM, Klein M (June 1988). "Dextromethorphan binding sites in the guinea pig brain". Cellular and Molecular Neurobiology. 8 (2): 149–56. doi:10.1007/BF00711241. PMC 11567495. PMID 3044591. S2CID 33844132.
^ Sasaki T, Sugiyama M, Sasaki H, Suzuki S, Takishima T (1985). "Effects of the antitussive fominoben (PB89) on hypoxia in chronic obstructive lung disease: comparison with dextromethorphan using a double-blind method". The Journal of International Medical Research. 13 (2): 96–101. doi:10.1177/030006058501300204. PMID 3158563. S2CID 30176251.
^ Crawley JN, Blumstein LK, Baldino F (January 1984). "Anxiolytic-like properties of fominoben". European Journal of Pharmacology. 97 (3–4): 277–81. doi:10.1016/0014-2999(84)90460-6. PMID 6142823.
^ William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia. Elsevier. pp. 1705–7. ISBN 978-0-8155-1856-3.
^ Martín AV (2004). "Tratamiento sintomático de la tos y del resfriado común". Farmacología clínica y terapéutica médica. McGraw-Hill/Interamericana. p. 260. ISBN 9788448604271.

[1] Swiss Pharmaceutial Society, ed. (January 2000). Index Nominum 2000: International Drug Directory. Taylor & Francis. p. 470. ISBN 978-3-88763-075-1.

[2] "FOMINOBEN". NCATS Inxight: Drugs. Retrieved March 25, 2021.

[3] Musacchio JM, Klein M (June 1988). "Dextromethorphan binding sites in the guinea pig brain". Cellular and Molecular Neurobiology. 8 (2): 149–56. doi:10.1007/BF00711241. PMC 11567495. PMID 3044591. S2CID 33844132.

[4] Sasaki T, Sugiyama M, Sasaki H, Suzuki S, Takishima T (1985). "Effects of the antitussive fominoben (PB89) on hypoxia in chronic obstructive lung disease: comparison with dextromethorphan using a double-blind method". The Journal of International Medical Research. 13 (2): 96–101. doi:10.1177/030006058501300204. PMID 3158563. S2CID 30176251.

[5] Crawley JN, Blumstein LK, Baldino F (January 1984). "Anxiolytic-like properties of fominoben". European Journal of Pharmacology. 97 (3–4): 277–81. doi:10.1016/0014-2999(84)90460-6. PMID 6142823.

[6] William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia. Elsevier. pp. 1705–7. ISBN 978-0-8155-1856-3.

[7] Martín AV (2004). "Tratamiento sintomático de la tos y del resfriado común". Farmacología clínica y terapéutica médica. McGraw-Hill/Interamericana. p. 260. ISBN 9788448604271.

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v t e GABA_A 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 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 Propoxate
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
Neuroactive steroids	Acebrochol Allopregnanolone (brexanolone) Alfadolone Alfaxalone 3α-Androstanediol Androstenol Androsterone Certain anabolic-androgenic steroids Cholesterol DHDOC 3α-DHP 5α-DHP 5β-DHP DHT Etiocholanolone Ganaxolone Hydroxydione Minaxolone ORG-20599 ORG-21465 P1-185 Posovolone 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 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) NS-2664 NS-2710 NS-11394 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	Fospropofol Propofol 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 Nicotinic acid Nicotinamide 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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