Apremilast

Apremilast
Clinical data
Pronunciation	/əˈprɛmɪlæst/ ə-PREM-i-last
Trade names	Otezla, others
Other names	CC-10004
AHFS/Drugs.com	Monograph
MedlinePlus	a614022
License data	US DailyMed: Apremilast;
Pregnancy; category	AU: B3;
Routes of; administration	By mouth
ATC code	L04AA32 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); UK: POM (Prescription only); US: ℞-only; EU: Rx-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	73%; Tmax = ~2.5 hours
Protein binding	c. 68%
Metabolism	Liver (CYP3A4, with minor contributions from CYP2A6, CYP1A2)
Metabolites	O-desmethylapremilast glucuronide (and others)
Elimination 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;
CAS Number	608141-41-9;
PubChem CID	11561674;
DrugBank	DB05676;
ChemSpider	9736448;
UNII	UP7QBP99PN;
KEGG	D08860;
ChEBI	CHEBI:78540;
ChEMBL	ChEMBL514800;
CompTox Dashboard (EPA)	DTXSID30976289 ;
ECHA InfoCard	100.234.786
Chemical and physical data
Formula	C22H24N2O7S
Molar mass	460.50 g·mol−1
3D model (JSmol)	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, 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). It is taken by mouth.

Clinical data


Pronunciation	/əˈprɛmɪlæst/ ə-PREM-i-last
Trade names	Otezla, others
Other names	CC-10004
AHFS/Drugs.com	Monograph
MedlinePlus	a614022
License data	US DailyMed: Apremilast
Pregnancy category	AU: B3
Routes of administration	By mouth
ATC code	L04AA32 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) UK: POM (Prescription only) US: ℞-only EU: Rx-only In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	73%; T_max = ~2.5 hours
Protein binding	c. 68%
Metabolism	Liver (CYP3A4, with minor contributions from CYP2A6, CYP1A2)
Metabolites	O-desmethylapremilast glucuronide (and others)
Elimination 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
CAS Number	608141-41-9
PubChem CID	11561674
DrugBank	DB05676
ChemSpider	9736448
UNII	UP7QBP99PN
KEGG	D08860
ChEBI	CHEBI:78540
ChEMBL	ChEMBL514800
CompTox Dashboard (EPA)	DTXSID30976289
ECHA InfoCard	100.234.786
Chemical and physical data
Formula	C₂₂H₂₄N₂O₇S
Molar mass	460.50 g·mol⁻¹
3D model (JSmol)	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