Apremilast

Apremilast, sold under the brand name Otezla among others, is a medication for the treatment of certain types of psoriasis and psoriatic arthritis. The drug acts as a selective inhibitor of the enzyme phosphodiesterase 4 (PDE4) and inhibits spontaneous production of TNF-alpha from human rheumatoid synovial cells. It is taken by mouth.

Apremilast
Clinical data
Pronunciation/əˈprɛmɪlæst/ ə-PREM-i-last
Trade namesOtezla, Aplex, others
Other namesCC-10004
AHFS/Drugs.comMonograph
MedlinePlusa614022
License data
Pregnancy
category
  • AU: B3
Routes of
administration		By mouth (tablets)
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only)
  • US: ℞-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability73%; Tmax = ~2.5 hours
Protein bindingc. 68%
MetabolismLiver (CYP3A4, with minor contributions from CYP2A6, CYP1A2)
MetabolitesO-desmethylapremilast glucuronide (and others)
Elimination half-life6–9 hours
ExcretionUrine (58%), faeces (39%)
Identifiers
  • N-{2-[(1S)-1-(3-Ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl}acetamide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.234.786
Chemical and physical data
FormulaC22H24N2O7S
Molar mass460.50 g·mol−1
3D model (JSmol)
  • O=S(=O)(C)C[C@H](c1ccc(OC)c(OCC)c1)N3C(=O)c2cccc(c2C3=O)NC(=O)C
  • 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
  • Key:IMOZEMNVLZVGJZ-QGZVFWFLSA-N
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