CHEBI:78540 - apremilast

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ChEBI Name apremilast
ChEBI ID CHEBI:78540
Definition A member of the class of isoindoles that is isoindole-1,3-dione substituted at position 4 by an acetamido group and at position 1 by a 1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl group. Used for treatment of psoriatic arthritis.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Toni Morrison
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Formula C22H24N2O7S
Net Charge 0
Average Mass 460.50000
Monoisotopic Mass 460.130
InChI InChI=1S/C22H24N2O7S/c1-5-31-19-11-14(9-10-18(19)30-3)17(12-32(4,28)29)24-21(26)15-7-6-8-16(23-13(2)25)20(15)22(24)27/h6-11,17H,5,12H2,1-4H3,(H,23,25)/t17-/m1/s1
InChIKey IMOZEMNVLZVGJZ-QGZVFWFLSA-N
SMILES CCOc1cc(ccc1OC)[C@@H](CS(C)(=O)=O)N1C(=O)c2cccc(NC(C)=O)c2C1=O
Roles Classification
Biological Role(s): phosphodiesterase IV inhibitor
An EC 3.1.4.53 (3',5'-cyclic-AMP phosphodiesterase) inhibitor that specifically blocks the action of phosphodiesterase IV.
Application(s): non-steroidal anti-inflammatory drug
An anti-inflammatory drug that is not a steroid. In addition to anti-inflammatory actions, non-steroidal anti-inflammatory drugs have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins.
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ChEBI Ontology
Outgoing apremilast (CHEBI:78540) has role non-steroidal anti-inflammatory drug (CHEBI:35475)
apremilast (CHEBI:78540) has role phosphodiesterase IV inhibitor (CHEBI:68844)
apremilast (CHEBI:78540) is a N-acetylarylamine (CHEBI:13790)
apremilast (CHEBI:78540) is a aromatic ether (CHEBI:35618)
apremilast (CHEBI:78540) is a phthalimides (CHEBI:82851)
apremilast (CHEBI:78540) is a sulfone (CHEBI:35850)
IUPAC Name
N-{2-[(1S)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl}acetamide
INNs Sources
apremilast ChemIDplus
apremilast WHO MedNet
aprémilast WHO MedNet
apremilastum WHO MedNet
Synonyms Sources
CC 10004 ChemIDplus
CC-10004 ChemIDplus
CC10004 ChemIDplus
Brand Name Source
OTEZLA KEGG DRUG
Manual Xrefs Databases
4829 DrugCentral
Apremilast Wikipedia
D08860 KEGG DRUG
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Registry Numbers Types Sources
12446985 Reaxys Registry Number Reaxys
608141-41-9 CAS Registry Number KEGG DRUG
608141-41-9 CAS Registry Number ChemIDplus
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Last Modified
22 February 2017