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Ro 19-4603

From Wikipedia, the free encyclopedia

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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
  • 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
  • CC(C)(C)OC(=O)C1=C2CN(C(=O)C3=C(N2C=N1)C=CS3)C
Properties
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).

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 struture. 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

  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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This page was last edited on 30 March 2024, at 16:16
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