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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H24N2O7S
Molecular Weight 460.5
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of APREMILAST

SMILES

CCOC1=CC(=CC=C1OC)[C@@H](CS(C)(=O)=O)N2C(=O)C3=CC=CC(NC(C)=O)=C3C2=O

InChI

InChIKey=IMOZEMNVLZVGJZ-QGZVFWFLSA-N
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

HIDE SMILES / InChI

Description

Apremilast (brand name Otezla) selective inhibitor of phosphodiesterase 4 is used for the treatment of patients with moderate to severe plaque psoriasis. OTEZLA is the first and only PDE4 inhibitor approved for the treatment of plaque psoriasis, a chronic inflammatory disease of the skin resulting from an uncontrolled immune response. Apremilast also inhibits spontaneous production of TNF-alpha from human rheumatoid synovial cells. It has anti-inflammatory activity. By inhibiting PDE-4, apremilast increases intracellular levels of cAMP and thereby inhibits the production of multiple proinflammatory mediators including PDE-4, TNF-alpha, interleukin-2 (IL-2), interferon-gamma, leukotrienes, and nitric oxide synthase.

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
74.0 nM [IC50]
0.074 µM [IC50]
Conditions
PubMed

PubMed

TitleDatePubMed
The effects of selective cytokine inhibitory drugs (CC-10004 and CC-1088) on VEGF and IL-6 expression and apoptosis in myeloma and endothelial cell co-cultures.
2004 Feb
CC-10004 .
2005 May
Discovery of (S)-N-[2-[1-(3-ethoxy-4-methoxyphenyl)-2-methanesulfonylethyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl] acetamide (apremilast), a potent and orally active phosphodiesterase 4 and tumor necrosis factor-alpha inhibitor.
2009 Mar 26
Disposition, metabolism and mass balance of [(14)C]apremilast following oral administration.
2011 Dec
Novel systemic drugs under investigation for the treatment of psoriasis.
2012 Jul
Novel systemic drugs for psoriasis: mechanism of action for apremilast, a specific inhibitor of PDE4.
2013 Jun
Apremilast: a PDE4 inhibitor for the treatment of psoriatic arthritis.
2015 May
Patents

Sample Use Guides

In Vivo Use Guide
The recommended initial dosage titration of OTEZLA (apremilast) from Day 1 to Day 5 is from 10 mg till 30 mg corresponding. Following the 5-day titration, the recommended maintenance dosage is 30 mg twice daily taken orally starting on Day 6. This titration is intended to reduce the gastrointestinal symptoms associated with initial therapy.
Route of Administration: Oral
In Vitro Use Guide
LPS-stimulated human monocytes were treated with concentrations of apremilast ranging from 6.25 nM to 100 nM.
Name Type Language
APREMILAST
DASH   INN   MI   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
CC-10004
Code English
APREMILAST [INN]
Common Name English
APREMILAST [WHO-DD]
Common Name English
(+)-N-(2-((1S)-1-(3-ETHOXY-4-METHOXYPHENYL)-2-(METHYLSULFONYL)ETHYL)-1,3-DIOXO- 2,3-DIHYDRO-1H-ISOINDOL-4-YL)ACETAMIDE
Systematic Name English
APREMILAST [USAN]
Common Name English
APREMILAST [MI]
Common Name English
APREMILAST [VANDF]
Common Name English
OTEZLA
Brand Name English
ACETAMIDE, N-(2-((1S)-1-(3-ETHOXY-4-METHOXYPHENYL)-2-(METHYLSULFONYL)ETHYL)-2,3-DIHYDRO-1,3-DIOXO-1H-ISOINDOL-4-YL)-
Systematic Name English
APREMILAST [JAN]
Common Name English
CC10004
Code English
Classification Tree Code System Code
NDF-RT N0000182961
Created by admin on Tue Mar 06 10:33:25 UTC 2018 , Edited by admin on Tue Mar 06 10:33:25 UTC 2018
WHO-ATC L04AA32
Created by admin on Tue Mar 06 10:33:25 UTC 2018 , Edited by admin on Tue Mar 06 10:33:25 UTC 2018
EMA ASSESSMENT REPORTS OTEZLA (AUTHORIZED: ARTHRITIS, PSORIATIC)
Created by admin on Tue Mar 06 10:33:25 UTC 2018 , Edited by admin on Tue Mar 06 10:33:25 UTC 2018
WHO-VATC QL04AA32
Created by admin on Tue Mar 06 10:33:25 UTC 2018 , Edited by admin on Tue Mar 06 10:33:25 UTC 2018
Code System Code Type Description
IUPHAR
7372
Created by admin on Tue Mar 06 10:33:25 UTC 2018 , Edited by admin on Tue Mar 06 10:33:25 UTC 2018
PRIMARY
NDF-RT
N0000182960
Created by admin on Tue Mar 06 10:33:25 UTC 2018 , Edited by admin on Tue Mar 06 10:33:25 UTC 2018
PRIMARY Phosphodiesterase 4 Inhibitors [MoA]
INN
8872
Created by admin on Tue Mar 06 10:33:25 UTC 2018 , Edited by admin on Tue Mar 06 10:33:25 UTC 2018
PRIMARY
HSDB
608141-41-9
Created by admin on Tue Mar 06 10:33:25 UTC 2018 , Edited by admin on Tue Mar 06 10:33:25 UTC 2018
PRIMARY
MERCK INDEX
M2010
Created by admin on Tue Mar 06 10:33:25 UTC 2018 , Edited by admin on Tue Mar 06 10:33:25 UTC 2018
PRIMARY Merck Index
MESH
C505730
Created by admin on Tue Mar 06 10:33:25 UTC 2018 , Edited by admin on Tue Mar 06 10:33:25 UTC 2018
PRIMARY
PUBCHEM
11561674
Created by admin on Tue Mar 06 10:33:25 UTC 2018 , Edited by admin on Tue Mar 06 10:33:25 UTC 2018
PRIMARY
EVMPD
SUB130837
Created by admin on Tue Mar 06 10:33:25 UTC 2018 , Edited by admin on Tue Mar 06 10:33:25 UTC 2018
PRIMARY
ChEMBL
CHEMBL514800
Created by admin on Tue Mar 06 10:33:25 UTC 2018 , Edited by admin on Tue Mar 06 10:33:25 UTC 2018
PRIMARY
RXCUI
1492727
Created by admin on Tue Mar 06 10:33:25 UTC 2018 , Edited by admin on Tue Mar 06 10:33:25 UTC 2018
PRIMARY RxNorm
CAS
608141-41-9
Created by admin on Tue Mar 06 10:33:25 UTC 2018 , Edited by admin on Tue Mar 06 10:33:25 UTC 2018
PRIMARY