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;
CompTox Dashboard (EPA)	DTXSID90244173 ;
	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

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

Effects & Pharmacodynamics

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

^ "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
CompTox Dashboard (EPA)	DTXSID90244173
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