SB-206553

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]

SB-206553
Identifiers
IUPAC name
  • 5-methyl-1-(3-pyridylcarbamoyl)-1,2,3,5-tetrahydropyrrolo[2,3-f]indole
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC17H16N4O
Molar mass292.342 g·mol−1
3D model (JSmol)
SMILES
  • Cn2ccc(c2c3)cc1c3CCN1C(=O)Nc4cccnc4
InChI
  • 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

References
  1. 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.
  2. Kennett GA, Wood MD, Bright F, Cilia J, Piper DC, Gager T, et al. (February 1996). "In vitro and in vivo profile of SB 206553, a potent 5-HT2C/5-HT2B receptor antagonist with anxiolytic-like properties". British Journal of Pharmacology. 117 (3): 427–434. doi:10.1111/j.1476-5381.1996.tb15208.x. PMC 1909304. PMID 8821530.
  3. 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.
  4. 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.
  5. Di Matteo V, Di Giovanni G, Di Mascio M, Esposito E (1998). "Selective blockade of serotonin2C/2B receptors enhances dopamine release in the rat nucleus accumbens". Neuropharmacology. 37 (2): 265–72. doi:10.1016/S0028-3908(98)00014-8. PMID 9680252.
  6. McCreary AC, Cunningham KA (June 1999). "Effects of the 5-HT2C/2B antagonist SB 206553 on hyperactivity induced by cocaine". Neuropsychopharmacology. 20 (6): 556–64. doi:10.1016/S0893-133X(98)00087-6. PMID 10327425.
  7. 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.
  8. Takahashi RN, Berton O, Mormède P, Chaouloff F (May 2001). "Strain-dependent effects of diazepam and the 5-HT2B/2C receptor antagonist SB 206553 in spontaneously hypertensive and Lewis rats tested in the elevated plus-maze". Brazilian Journal of Medical and Biological Research. 34 (5): 675–82. doi:10.1590/s0100-879x2001000500017. PMID 11323756.
  9. Porras G, Di Matteo V, Fracasso C, Lucas G, De Deurwaerdère P, Caccia S, et al. (March 2002). "5-HT2A and 5-HT2C/2B receptor subtypes modulate dopamine release induced in vivo by amphetamine and morphine in both the rat nucleus accumbens and striatum". Neuropsychopharmacology. 26 (3): 311–24. doi:10.1016/S0893-133X(01)00333-5. PMID 11850146.
  10. Navailles S, De Deurwaerdère P, Porras G, Spampinato U (February 2004). "In vivo evidence that 5-HT2C receptor antagonist but not agonist modulates cocaine-induced dopamine outflow in the rat nucleus accumbens and striatum". Neuropsychopharmacology. 29 (2): 319–26. doi:10.1038/sj.npp.1300329. PMID 14560323.
  11. Canal CE, Olaghere da Silva UB, Gresch PJ, Watt EE, Sanders-Bush E, Airey DC (April 2010). "The serotonin 2C receptor potently modulates the head-twitch response in mice induced by a phenethylamine hallucinogen". Psychopharmacology. 209 (2): 163–74. doi:10.1007/s00213-010-1784-0. PMC 2868321. PMID 20165943.
  12. Graves SM, Napier TC (June 2012). "SB 206553, a putative 5-HT2C inverse agonist, attenuates methamphetamine-seeking in rats". BMC Neuroscience. 13: 65. doi:10.1186/1471-2202-13-65. PMC 3441362. PMID 22697313.
  13. 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.
  14. Kim SK, Li Y, Abrol R, Heo J, Goddard III WA (February 2011). "Predicted structures and dynamics for agonists and antagonists bound to serotonin 5-HT2B and 5-HT2C receptors". Journal of Chemical Information and Modeling. 51 (2): 420–33. doi:10.1021/ci100375b. PMC 3070210. PMID 21299232.


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