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CHEBI:78540 - apremilast

ChEBI IDCHEBI:78540
ChEBI Nameapremilast
Stars
DefinitionA 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.
Last Modified22 February 2017
Submittertmorrison
DownloadsMolfile
FormulaC22H24N2O7S
Net Charge0
Average Mass460.508
Monoisotopic Mass460.13042
SMILESCCOc1cc([C@@H](CS(C)(=O)=O)N2C(=O)c3cccc(NC(C)=O)c3C2=O)ccc1OC
InChIInChI=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
InChIKeyIMOZEMNVLZVGJZ-QGZVFWFLSA-N
Wikipedia
Roles Classification
Biological Role:
phosphodiesterase IV inhibitor  An EC 3.1.4.53 (3',5'-cyclic-AMP phosphodiesterase) inhibitor that specifically blocks the action of phosphodiesterase IV.
Application:
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.
ChEBI Ontology
Outgoing Relation(s)
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  Source
apremilastChemIDplus
apremilastWHO MedNet
apremilastumWHO MedNet
aprémilastWHO MedNet
Synonyms  Source
CC-10004ChemIDplus
CC10004ChemIDplus
CC 10004ChemIDplus
Brand Name  Source
OTEZLAKEGG DRUG
Manual XrefsDatabases
D08860KEGG DRUG
ApremilastWikipedia
4829DrugCentral
Registry NumbersSources
Reaxys:12446985Reaxys
CAS:608141-41-9KEGG DRUG
CAS:608141-41-9ChemIDplus
Citations