Apremilast

Apremilast

Clinical data
Pronunciation	/əˈprɛmᵻlæst/ ə-PREM-i-last
Trade names	Otezla
AHFS/Drugs.com	Otezla
MedlinePlus	a614022
License data	EU EMA: Otezla US FDA: Apremilast
Pregnancy category	AU: B3 US: C (Risk not ruled out)
Routes of administration	by mouth (tablets)
ATC code	L04AA32 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	73%;Tmax = ~2.5 hours
Protein binding	~68%
Metabolism	Liver (CYP3A4, with minor contributions from CYP2A6, CYP1A2)
Metabolites	O-desmethylapremilast glucuronide (and others)
Biological half-life	6–9 hours
Excretion	Urine (58%), faeces (39%)
Identifiers
IUPAC name N-{2-[(1S)-1-(3-Ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl}acetamide
Synonyms	CC-10004
CAS Number	608141-41-9
PubChem CID	11561674
DrugBank	DB05676
ChemSpider	9736448
UNII	UP7QBP99PN
KEGG	D08860
ChEBI	CHEBI:78540
ChEMBL	CHEMBL514800
ECHA InfoCard	100.234.786
Chemical and physical data
Formula	C22H24N2O7S
Molar mass	460.500 g/mol
3D model (Jmol)	Interactive image
SMILES O=S(=O)(C)C[C@H](c1ccc(OC)c(OCC)c1)N3C(=O)c2cccc(c2C3=O)NC(=O)C
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 Key:IMOZEMNVLZVGJZ-QGZVFWFLSA-N

Apremilast (brand name Otezla) is a medication for the treatment of certain types of psoriasis and psoriatic arthritis. It may also be useful for other immune system related inflammatory diseases. 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 was approved by the United States Food and Drug Administration in 2014 for treatment of adults with active psoriatic arthritis and moderate to severe plaque psoriasis. Apremilast, similar to methotrexate, is taken by mouth.

In Europe, the drug is contraindicated during pregnancy because mice and monkeys receiving very high doses of apremilast have been observed to suffer miscarriages and other pregnancy problems. In the U.S., it may be used for pregnant women "if the potential benefit justifies the potential risk to the fetus".

Common, usually mild to moderate adverse effects associated with apremilast include headache, back pain, nausea, diarrhea, fatigue, nasopharyngitis and upper respiratory tract infections.

Other side effects include:

Concurrent use of strong enzyme inducers has been shown to decrease exposure of apremilast and can result in reduced or loss of efficacy of apremilast. It is not recommended to use simultaneously with strong P450 enzyme inducers, including rifampicin, phenobarbital, carbamazepine, phenytoin, and St. John's Wort.