SB-236057

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SB-236057
SB236057 structure.png
Systematic (IUPAC) name
1'-ethyl-5-[2'-methyl-4'-(5-methyl-1,3,4-oxadiazolyl-2-yl)biphenyl-4-carbonyl]-2,3,6,7-tetrahydrospiro(furo[2,3-f]indole-3,4'-piperidine)
Identifiers
CAS Number 180083-49-2 YesY
ATC code none
PubChem CID: 5311426
IUPHAR/BPS 3231
ChemSpider 4470914
ChEMBL CHEMBL1628625
Chemical data
Formula C33H34N4O3
Molecular mass 534.647 g/mol
  • n5nc(C)oc5-c(cc2C)ccc2-c6ccc(cc6)C(=O)N(CCc1cc3OC7)c1cc3C7(CC4)CCN4CC
  • InChI=1S/C33H34N4O3/c1-4-36-15-12-33(13-16-36)20-39-30-18-25-11-14-37(29(25)19-28(30)33)32(38)24-7-5-23(6-8-24)27-10-9-26(17-21(27)2)31-35-34-22(3)40-31/h5-10,17-19H,4,11-16,20H2,1-3H3
  • Key:WXAKEEQOWUHGCI-UHFFFAOYSA-N

SB-236057 is a compound which is a potent and selective inverse agonist for the serotonin receptor 5-HT1B, acting especially at 5-HT1B autoreceptors on nerve terminals. It produces a rapid increase in serotonin levels in the brain, and was originally researched as a potential antidepressant.[1][2] However subsequent research found that SB-236,057 also acts as a potent teratogen, producing severe musculoskeletal birth defects when rodents were exposed to it during pregnancy. This has made it little used for research into its original applications, but has made it useful for studying embryonic development instead.[3][4]

References

  1. ↑ Middlemiss DN, Göthert M, Schlicker E, Scott CM, Selkirk JV, Watson J, Gaster LM, Wyman P, Riley G, Price GW. SB-236057, a selective 5-HT1B receptor inverse agonist, blocks the 5-HT human terminal autoreceptor. European Journal of Pharmacology. 1999;375(1-3):359-65. PMID 10443589
  2. ↑ Roberts C, Watson J, Price GW, Middlemiss DN. SB-236057-A: a selective 5-HT1B receptor inverse agonist. CNS Drug Reviews. 2001;7(4):433-44. PMID 11830759
  3. ↑ Augustine-Rauch KA, Zhang QJ, Posobiec L, Mirabile R, DeBoer LS, Solomon HM, Wier PJ. SB-236057: Critical window of sensitivity study and embryopathy of a potent musculoskeletal teratogen. Birth Defects Research A, Clinical and Molecular Teratology. 2004 Oct;70(10):773-88. PMID 15472921
  4. ↑ Augustine-Rauch KA, Zhang QJ, Leonard JL, Chadderton A, Welsh MJ, Rami HK, Thompson M, Gaster L, Wier PJ. Evidence for a molecular mechanism of teratogenicity of SB-236057, a 5-HT1B receptor inverse agonist that alters axial formation. Birth Defects Research A, Clinical and Molecular Teratology. 2004 Oct;70(10):789-807. PMID 15472891



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