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;
Chemical and physical data
Formula	C33H34N4O3
Molar mass	534.647 g/mol
3D model (Jmol)	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 little used for research into its original applications, but has made it useful for studying embryonic development instead.^[3]^[4]

References[edit]

^ 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
^ 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
^ 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
^ 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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[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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SB-236057

References[edit]

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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^Y
PubChem CID	5311426
IUPHAR/BPS	3231
ChemSpider	4470914
ChEMBL	CHEMBL1628625
Chemical and physical data
Formula	C₃₃H₃₄N₄O₃
Molar mass	534.647 g/mol
3D model (Jmol)	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