CHEBI:9513 - thalidomide

Main ChEBI Ontology Automatic Xrefs
ChEBI Name thalidomide
ChEBI ID CHEBI:9513
Definition A racemate comprising equimolar amounts of R- and S-thalidomide.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C13H10N2O4
Net Charge 0
Average Mass 258.22950
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)
InChIKey UEJJHQNACJXSKW-UHFFFAOYSA-N
SMILES O=C1CCC(N2C(=O)c3ccccc3C2=O)C(=O)N1
Roles Classification
Biological Role(s): immunosuppressive agent
An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
leprostatic drug
A substance that suppresses Mycobacterium leprae, ameliorates the clinical manifestations of leprosy, and/or reduces the incidence and severity of leprous reactions.
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.
Application(s): immunosuppressive agent
An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
leprostatic drug
A substance that suppresses Mycobacterium leprae, ameliorates the clinical manifestations of leprosy, and/or reduces the incidence and severity of leprous reactions.
angiogenesis inhibitor
An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.
anticonvulsant
A drug used to prevent seizures or reduce their severity.
antiemetic
A drug used to prevent nausea or vomiting. An antiemetic may act by a wide range of mechanisms: it might affect the medullary control centres (the vomiting centre and the chemoreceptive trigger zone) or affect the peripheral receptors.
sedative
A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.
anti-inflammatory drug
A substance that reduces or suppresses inflammation.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing thalidomide (CHEBI:9513) has part (R)-thalidomide (CHEBI:61917)
thalidomide (CHEBI:9513) has part (S)-thalidomide (CHEBI:61918)
thalidomide (CHEBI:9513) has role angiogenesis inhibitor (CHEBI:48422)
thalidomide (CHEBI:9513) has role anti-inflammatory drug (CHEBI:35472)
thalidomide (CHEBI:9513) has role anticonvulsant (CHEBI:35623)
thalidomide (CHEBI:9513) has role antiemetic (CHEBI:50919)
thalidomide (CHEBI:9513) has role antineoplastic agent (CHEBI:35610)
thalidomide (CHEBI:9513) has role immunosuppressive agent (CHEBI:35705)
thalidomide (CHEBI:9513) has role leprostatic drug (CHEBI:35816)
thalidomide (CHEBI:9513) has role sedative (CHEBI:35717)
thalidomide (CHEBI:9513) has role teratogenic agent (CHEBI:50905)
thalidomide (CHEBI:9513) is a racemate (CHEBI:60911)
Incoming 5-(2,2-diferuloylethen-1-yl)thalidomide (CHEBI:74775) has functional parent thalidomide (CHEBI:9513)
5-[2-(feruloyl)ethen-1-yl]thalidomide (CHEBI:74774) has functional parent thalidomide (CHEBI:9513)
pomalidomide (CHEBI:72690) has functional parent thalidomide (CHEBI:9513)
IUPAC Name
rac-2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione
INNs Sources
talidomida ChemIDplus
thalidomide ChemIDplus
thalidomidum ChemIDplus
Synonyms Sources
(±)-N-(2,6-dioxo-3-piperidyl)phthalimide ChemIDplus
(±)-thalidomide ChemIDplus
1,3-dioxo-2-(2,6-dioxopiperidin-3-yl)isoindoline ChemIDplus
2,6-dioxo-3-phthalimidopiperidine ChemIDplus
3-phthalimidoglutarimide ChemIDplus
α-(N-phthalimido)glutarimide ChemIDplus
α-N-phthalylglutaramide ChemIDplus
α-phthalimidoglutarimide ChemIDplus
N-(2,6-dioxo-3-piperidyl)phthalimide ChemIDplus
N-phthaloylglutamimide ChemIDplus
N-Phthalyl-glutaminsaeure-imid ChemIDplus
N-phthalylglutamic acid imide ChemIDplus
Thalidomide KEGG COMPOUND
Brand Names Sources
Distaval ChemIDplus
K-17 ChemIDplus
Sedalis DrugBank
Softenon ChemIDplus
Talimol ChemIDplus
Database Links Databases
C07910 KEGG COMPOUND
D00754 KEGG DRUG
DB01041 DrugBank
GB768821 Patent
HMDB15175 HMDB
Thalidomide Wikipedia
US2012142734 Patent
WO2013100657 Patent
View more database links
Registry Numbers Types Sources
30233 Reaxys Registry Number Reaxys
50-35-1 CAS Registry Number NIST Chemistry WebBook
50-35-1 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
11349879 PubMed citation CiteXplore
11803357 PubMed citation CiteXplore
12724820 PubMed citation CiteXplore
14689682 PubMed citation CiteXplore
17449064 PubMed citation CiteXplore
18925849 PubMed citation CiteXplore
21207098 PubMed citation CiteXplore
2694291 PubMed citation CiteXplore
8469046 PubMed citation CiteXplore
Last Modified
26 July 2013
General Comments
2011-04-19 Originally introduced as a sedative and hypnotic for treatment of morning sickness in 1957, thalidomide 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.
2011-04-19 Thalidomide is widely used in Brazil for the treatment of moderate to severe cases of erythema nodosum leprosum (ENL, a painful complication of leprosy).