SB-272183

SB-272183
Clinical data
Other namesSB272183
Drug classSerotonin 5-HT1A receptor antagonist; Serotonin 5-HT1B receptor antagonist; Serotonin 5-HT1D receptor antagonist
Identifiers
  • 5-chloro-6-(4-methylpiperazin-1-yl)-N-(4-pyridin-4-ylnaphthalen-1-yl)-2,3-dihydroindole-1-carboxamide
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
ChEMBL
Chemical and physical data
FormulaC29H28ClN5O
Molar mass498.03 g·mol−1
3D model (JSmol)
  • CN1CCN(CC1)C2=C(C=C3CCN(C3=C2)C(=O)NC4=CC=C(C5=CC=CC=C54)C6=CC=NC=C6)Cl
  • InChI=1S/C29H28ClN5O/c1-33-14-16-34(17-15-33)28-19-27-21(18-25(28)30)10-13-35(27)29(36)32-26-7-6-22(20-8-11-31-12-9-20)23-4-2-3-5-24(23)26/h2-9,11-12,18-19H,10,13-17H2,1H3,(H,32,36)
  • Key:DAPBIPAGJXKFCI-UHFFFAOYSA-N

SB-272183 is a selective serotonin 5-HT1A, 5-HT1B, and 5-HT1D receptor antagonist.[1][2][3] It shows high affinity for these receptors, with Ki values of 10 nM, 7.9 nM, and 2.0 nM, respectively, and with at least 30-fold selectivity over various other receptors.[1][2][4][3] The drug was a partial agonist of the serotonin 5-HT1A, 5-HT1B, and 5-HT1D receptors in vitro, but showed only antagonistic activity ex vivo in native tissue.[1][2][3] SB-272183 was first described in the scientific literature in 2001.[3][5] It is said to have been the first selective serotonin 5-HT1A, 5-HT1B, and 5-HT1D receptor antagonist to be described.[2]

References

  1. ^ a b c Slassi A (June 2002). "Recent advances in 5-HT1B/1D receptor antagonists and agonists and their potential therapeutic applications". Current Topics in Medicinal Chemistry. 2 (6): 559–574. doi:10.2174/1568026023393903. PMID 12052194.
  2. ^ a b c d Dawson LA, Bromidge SM (2008). "5-HT1 receptor augmentation strategies as enhanced efficacy: therapeutics for psychiatric disorders". Current Topics in Medicinal Chemistry. 8 (12): 1008–1023. doi:10.2174/156802608785161439. PMID 18691129.
  3. ^ a b c d Watson J, Roberts C, Scott C, Kendall I, Collin L, Day NC, et al. (July 2001). "SB-272183, a selective 5-HT(1A), 5-HT(1B) and 5-HT(1D) receptor antagonist in native tissue". British Journal of Pharmacology. 133 (6): 797–806. doi:10.1038/sj.bjp.0704133. PMC 1572841. PMID 11454652.
  4. ^ Roberts C, Price GW, Middlemiss DN (November 2001). "Ligands for the investigation of 5-HT autoreceptor function". Brain Research Bulletin. 56 (5): 463–469. doi:10.1016/s0361-9230(01)00628-1. PMID 11750791.
  5. ^ Langmead CJ, Watson J, Herdon HJ, Scott CM, Price GW (November 2001). "Effects of 5-HT, fenfluramine, ketanserin and the 5-HT autoreceptor antagonist, SB-272183, on basal [H-3] 5-HT release from guinea-pig cortical slices in the presence and absence of paroxetine". British Journal of Pharmacology. 134.
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