SB-236057

SB-236057
Clinical data
ATC code	none;
Identifiers
	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);
CAS Number	180083-49-2 ;
PubChem CID	5311426;
IUPHAR/BPS	3231;
ChemSpider	4470914;
ChEMBL	ChEMBL1628625;
CompTox Dashboard (EPA)	DTXSID0047321 ;
Chemical and physical data
Formula	C33H34N4O3
Molar mass	534.660 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES n5nc(C)oc5-c(cc2C)ccc2-c6ccc(cc6)C(=O)N(CCc1cc3OC7)c1cc3C7(CC4)CCN4CC;
	InChI 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-HT_1B, acting especially at 5-HT_1B 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 of little use for research into its original applications, yet has made it useful for studying embryonic development instead.[3][4]

References

Middlemiss DN, Göthert M, Schlicker E, Scott CM, Selkirk JV, Watson J, et al. (June 1999). "SB-236057, a selective 5-HT1B receptor inverse agonist, blocks the 5-HT human terminal autoreceptor". European Journal of Pharmacology. 375 (1–3): 359–65. doi:10.1016/s0014-2999(99)00262-9. PMID 10443589.
Roberts C, Watson J, Price GW, Middlemiss DN (2006). "SB-236057-A: a selective 5-HT1B receptor inverse agonist". CNS Drug Reviews. 7 (4): 433–44. doi:10.1111/j.1527-3458.2001.tb00209.x. PMC 6741665. PMID 11830759.
Augustine-Rauch KA, Zhang QJ, Posobiec L, Mirabile R, DeBoer LS, Solomon HM, Wier PJ (October 2004). "SB-236057: Critical window of sensitivity study and embryopathy of a potent musculoskeletal teratogen". Birth Defects Research. Part A, Clinical and Molecular Teratology. 70 (10): 773–88. doi:10.1002/bdra.20079. PMID 15472921.
Augustine-Rauch KA, Zhang QJ, Leonard JL, Chadderton A, Welsh MJ, Rami HK, et al. (October 2004). "Evidence for a molecular mechanism of teratogenicity of SB-236057, a 5-HT1B receptor inverse agonist that alters axial formation". Birth Defects Research. Part A, Clinical and Molecular Teratology. 70 (10): 789–807. doi:10.1002/bdra.20076. PMID 15472891.

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[1] Middlemiss DN, Göthert M, Schlicker E, Scott CM, Selkirk JV, Watson J, et al. (June 1999). "SB-236057, a selective 5-HT1B receptor inverse agonist, blocks the 5-HT human terminal autoreceptor". European Journal of Pharmacology. 375 (1–3): 359–65. doi:10.1016/s0014-2999(99)00262-9. PMID 10443589.

[2] Roberts C, Watson J, Price GW, Middlemiss DN (2006). "SB-236057-A: a selective 5-HT1B receptor inverse agonist". CNS Drug Reviews. 7 (4): 433–44. doi:10.1111/j.1527-3458.2001.tb00209.x. PMC 6741665. PMID 11830759.

[3] Augustine-Rauch KA, Zhang QJ, Posobiec L, Mirabile R, DeBoer LS, Solomon HM, Wier PJ (October 2004). "SB-236057: Critical window of sensitivity study and embryopathy of a potent musculoskeletal teratogen". Birth Defects Research. Part A, Clinical and Molecular Teratology. 70 (10): 773–88. doi:10.1002/bdra.20079. PMID 15472921.

[4] Augustine-Rauch KA, Zhang QJ, Leonard JL, Chadderton A, Welsh MJ, Rami HK, et al. (October 2004). "Evidence for a molecular mechanism of teratogenicity of SB-236057, a 5-HT1B receptor inverse agonist that alters axial formation". Birth Defects Research. Part A, Clinical and Molecular Teratology. 70 (10): 789–807. doi:10.1002/bdra.20076. PMID 15472891.