CHEBI:61918 - (S)-thalidomide

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ChEBI Name (S)-thalidomide
ChEBI ASCII Name (S)-thalidomide
Definition A 2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione that has S-configuration at the chiral centre.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C13H10N2O4
Net Charge 0
Average Mass 258.22950
Monoisotopic Mass 258.064
InChI InChI=1S/C13H10N2O4/c16-10-6-5-9(11(17)14-10)15-12(18)7-3-1-2-4-8(7)13(15)19/h1-4,9H,5-6H2,(H,14,16,17)/t9-/m0/s1
SMILES O=C1CC[C@H](N2C(=O)c3ccccc3C2=O)C(=O)N1
Roles Classification
Biological Role(s): teratogenic agent
A role played by a chemical compound in biological systems with adverse consequences in embryo developments, leading to birth defects, embryo death or altered development, growth retardation and functional defect.
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ChEBI Ontology
Outgoing (S)-thalidomide (CHEBI:61918) has role teratogenic agent (CHEBI:50905)
(S)-thalidomide (CHEBI:61918) is a 2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione (CHEBI:74947)
(S)-thalidomide (CHEBI:61918) is enantiomer of (R)-thalidomide (CHEBI:61917)
Incoming thalidomide (CHEBI:9513) has part (S)-thalidomide (CHEBI:61918)
(R)-thalidomide (CHEBI:61917) is enantiomer of (S)-thalidomide (CHEBI:61918)
Synonyms Sources
(−)-thalidomide ChemIDplus
(S)-(−)-thalidomide ChEBI
l-thalidomide ChemIDplus
L-thalidomide ChemIDplus
S-(−)-thalidomide ChemIDplus
Registry Numbers Types Sources
5756816 Reaxys Registry Number Reaxys
841-67-8 CAS Registry Number ChemIDplus
Last Modified
26 July 2013
General Comment
2011-04-19 Racemic thalidomide was originally introduced as a sedative and hypnotic for treatment of morning sickness in 1957, but was withdrawn from use in the early 1960s after it was shown to produce severe teratogenic effects. It was subsequently found that the (R)-enantiomer is effective against morning sickness, whereas the (S)-enantiomer is teratogenic. However, as the enantiomers can interconvert in vivo, administering only the (R)-enantomer would not prevent the teratogenic effect.