Ro 19-4603

Ro 19-4603^[1]
Names
	IUPAC name tert-Butyl 8-methyl-7-oxo-5-thia-1,8,12-triazatricyclo[8.3.0.02,6]trideca-2(6),3,10,12-tetraene-11-carboxylate
Identifiers
CAS Number	99632-94-7;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:34952;
ChEMBL	ChEMBL269366;
ChemSpider	113034;
IUPHAR/BPS	4297;
KEGG	C13716;
PubChem CID	127382;
	InChI InChI=1S/C15H17N3O3S/c1-15(2,3)21-14(20)11-10-7-17(4)13(19)12-9(5-6-22-12)18(10)8-16-11/h5-6,8H,7H2,1-4H3 Key: ZIGMMUKDYCABPW-UHFFFAOYSA-N;
	SMILES CC(C)(C)OC(=O)C1=C2CN(C(=O)C3=C(N2C=N1)C=CS3)C;
Properties
Chemical formula	C15H17N3O3S
Molar mass	319.38 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Ro 19-4603 is an inverse agonist of the benzodiazepine binding site. It has effects antagonistic to those of benzodiazepines.

Chemistry[edit]

Despite acting at the benzodiazepine site, it does not possess the benzodiazepine struture. It is an Imidazothienodiazepine: a thiophene ring, an imidazole ring and a diazepine ring fused together.

Effects & Pharmacodynamics[edit]

Ro 19-4603 is an inverse agonist at the benzodiazepine binding site. Due to this, it has effects similar to other benzodiazepine inverse agonists, notably: anxiogenesis,^[2] convulsions.^[3]

Administration of this compound was able to decrease voluntary alcohol consumption. This was also observed in rats selected for high alcohol preference.^[4] In addition to decreasing its consumption, Ro 19-4603 is able to antagonize the intoxicating effects of alcohol.^[5]

References[edit]

^ "Tert-butyl 5-methyl-6-oxo-5,6-dihydro-4h-imidazo[1,5-a]thieno[2,3-f][1,4]diazepine-3-carboxylate".
^ Belzung, C.; Misslin, R.; Vogel, E. (July 1990). "Anxiogenic effects of a benzodiazepine receptor partial inverse agonist, RO 19-4603, in a light/dark choice situation". Pharmacology, Biochemistry, and Behavior. 36 (3): 593–596. doi:10.1016/0091-3057(90)90260-o. ISSN 0091-3057. PMID 2165618. S2CID 9881393.
^ Kubová, H.; Mares, P. (October 1994). "Convulsant action of a benzodiazepine receptor agonist/inverse agonist Ro 19-4603 in developing rats". Naunyn-Schmiedeberg's Archives of Pharmacology. 350 (4): 393–397. doi:10.1007/BF00178957. ISSN 0028-1298. PMID 7845475. S2CID 1751486.
^ Balakleevsky, A.; Colombo, G.; Fadda, F.; Gessa, G. L. (1990). "Ro 19-4603, a benzodiazepine receptor inverse agonist, attenuates voluntary ethanol consumption in rats selectively bred for high ethanol preference". Alcohol and Alcoholism (Oxford, Oxfordshire). 25 (5): 449–452. ISSN 0735-0414. PMID 1965120.
^ Lister, R. G.; Durcan, M. J. (1989-03-13). "Antagonism of the intoxicating effects of ethanol by the potent benzodiazepine receptor ligand Ro 19-4603". Brain Research. 482 (1): 141–144. doi:10.1016/0006-8993(89)90551-9. ISSN 0006-8993. PMID 2539880. S2CID 22770686.

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[1] "Tert-butyl 5-methyl-6-oxo-5,6-dihydro-4h-imidazo[1,5-a]thieno[2,3-f][1,4]diazepine-3-carboxylate".

[2] Belzung, C.; Misslin, R.; Vogel, E. (July 1990). "Anxiogenic effects of a benzodiazepine receptor partial inverse agonist, RO 19-4603, in a light/dark choice situation". Pharmacology, Biochemistry, and Behavior. 36 (3): 593–596. doi:10.1016/0091-3057(90)90260-o. ISSN 0091-3057. PMID 2165618. S2CID 9881393.

[3] Kubová, H.; Mares, P. (October 1994). "Convulsant action of a benzodiazepine receptor agonist/inverse agonist Ro 19-4603 in developing rats". Naunyn-Schmiedeberg's Archives of Pharmacology. 350 (4): 393–397. doi:10.1007/BF00178957. ISSN 0028-1298. PMID 7845475. S2CID 1751486.

[4] Balakleevsky, A.; Colombo, G.; Fadda, F.; Gessa, G. L. (1990). "Ro 19-4603, a benzodiazepine receptor inverse agonist, attenuates voluntary ethanol consumption in rats selectively bred for high ethanol preference". Alcohol and Alcoholism (Oxford, Oxfordshire). 25 (5): 449–452. ISSN 0735-0414. PMID 1965120.

[5] Lister, R. G.; Durcan, M. J. (1989-03-13). "Antagonism of the intoxicating effects of ethanol by the potent benzodiazepine receptor ligand Ro 19-4603". Brain Research. 482 (1): 141–144. doi:10.1016/0006-8993(89)90551-9. ISSN 0006-8993. PMID 2539880. S2CID 22770686.

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Names

IUPAC name tert-Butyl 8-methyl-7-oxo-5-thia-1,8,12-triazatricyclo[8.3.0.0^2,6]trideca-2(6),3,10,12-tetraene-11-carboxylate
Identifiers
CAS Number	99632-94-7
3D model (JSmol)	Interactive image
ChEBI	CHEBI:34952
ChEMBL	ChEMBL269366
ChemSpider	113034
IUPHAR/BPS	4297
KEGG	C13716
PubChem CID	127382
InChI InChI=1S/C15H17N3O3S/c1-15(2,3)21-14(20)11-10-7-17(4)13(19)12-9(5-6-22-12)18(10)8-16-11/h5-6,8H,7H2,1-4H3 Key: ZIGMMUKDYCABPW-UHFFFAOYSA-N
SMILES CC(C)(C)OC(=O)C1=C2CN(C(=O)C3=C(N2C=N1)C=CS3)C
Properties
Chemical formula	C₁₅H₁₇N₃O₃S
Molar mass	319.38 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references