SB-206553 is a drug which acts as a mixed antagonist for the 5-HT2B and 5-HT2C serotonin receptors.[1][2][3] It has anxiolytic properties in animal studies and interacts with a range of other drugs.[4][5][6][7][8][9][10][11][12] It has also been shown to act as a positive allosteric modulator of α7 nicotinic acetylcholine receptors.[13] Modified derivatives of SB-206553 have been used to probe the structure of the 5-HT2B receptor.[14]
Quick Facts Identifiers, CAS Number ...
SB-206553 |
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5-methyl-1-(3-pyridylcarbamoyl)-1,2,3,5-tetrahydropyrrolo[2,3-f]indole
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Formula | C17H16N4O |
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Molar mass | 292.342 g·mol−1 |
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Cn2ccc(c2c3)cc1c3CCN1C(=O)Nc4cccnc4
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InChI=1S/C17H16N4O/c1-20-7-4-12-10-16-13(9-15(12)20)5-8-21(16)17(22)19-14-3-2-6-18-11-14/h2-4,6-7,9-11H,5,8H2,1H3,(H,19,22) Key:QJQORSLQNXDVGE-UHFFFAOYSA-N
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Forbes IT, Ham P, Booth DH, Martin RT, Thompson M, Baxter GS, et al. (July 1995). "5-Methyl-1-(3-pyridylcarbamoyl)-1,2,3,5-tetrahydropyrrolo[2,3-f]indole: a novel 5-HT2C/5-HT2B receptor antagonist with improved affinity, selectivity, and oral activity". Journal of Medicinal Chemistry. 38 (14): 2524–30. doi:10.1021/jm00014a004. PMID 7629791.
Forbes IT, Dabbs S, Duckworth DM, Ham P, Jones GE, King FD, et al. (December 1996). "Synthesis, biological activity, and molecular modeling of selective 5-HT(2C/2B) receptor antagonists". Journal of Medicinal Chemistry. 39 (25): 4966–77. doi:10.1021/jm960571v. PMID 8960557.
Bromidge SM, Dabbs S, Davies DT, Duckworth DM, Forbes IT, Ham P, et al. (May 1998). "Novel and selective 5-HT2C/2B receptor antagonists as potential anxiolytic agents: synthesis, quantitative structure-activity relationships, and molecular modeling of substituted 1-(3-pyridylcarbamoyl)indolines". Journal of Medicinal Chemistry. 41 (10): 1598–612. doi:10.1021/jm970741j. PMID 9572885.
Di Giovanni G, De Deurwaerdére P, Di Mascio M, Di Matteo V, Esposito E, Spampinato U (1999). "Selective blockade of serotonin-2C/2B receptors enhances mesolimbic and mesostriatal dopaminergic function: a combined in vivo electrophysiological and microdialysis study". Neuroscience. 91 (2): 587–97. doi:10.1016/S0306-4522(98)00655-1. PMID 10366016. S2CID 23080031.
Dunlop J, Lock T, Jow B, Sitzia F, Grauer S, Jow F, et al. (March 2009). "Old and new pharmacology: positive allosteric modulation of the alpha7 nicotinic acetylcholine receptor by the 5-hydroxytryptamine(2B/C) receptor antagonist SB-206553 (3,5-dihydro-5-methyl-N-3-pyridinylbenzo[1,2-b:4,5-b']di pyrrole-1(2H)-carboxamide)". The Journal of Pharmacology and Experimental Therapeutics. 328 (3): 766–76. doi:10.1124/jpet.108.146514. PMID 19050173. S2CID 206500076.