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Details

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

SHOW SMILES / InChI
Structure of APREMILAST

SMILES

CCOC1=C(OC)C=CC(=C1)[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
Molecular Formula C22H24N2O7S
Molecular Weight 460.5
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

Unknown
86413
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:56:23 UTC 2023
Edited
by admin
on Fri Dec 15 15:56:23 UTC 2023
Record UNII
UP7QBP99PN
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
APREMILAST
DASH   INN   MI   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
CC-10004
Code English
Apremilast [WHO-DD]
Common Name English
apremilast [INN]
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
N-[2-[(1S)-1-(3-Ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]-2,3-dihydro-1,3-dioxo-1H-isoindol-4-yl]acetamide
Systematic Name English
APREMILAST [MI]
Common Name English
APREMILAST [VANDF]
Common Name English
OTEZLA
Brand Name English
APREMILAST [ORANGE BOOK]
Common 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 Fri Dec 15 15:56:23 UTC 2023 , Edited by admin on Fri Dec 15 15:56:23 UTC 2023
WHO-ATC L04AA32
Created by admin on Fri Dec 15 15:56:23 UTC 2023 , Edited by admin on Fri Dec 15 15:56:23 UTC 2023
EMA ASSESSMENT REPORTS OTEZLA (AUTHORIZED: ARTHRITIS, PSORIATIC)
Created by admin on Fri Dec 15 15:56:23 UTC 2023 , Edited by admin on Fri Dec 15 15:56:23 UTC 2023
NCI_THESAURUS C744
Created by admin on Fri Dec 15 15:56:23 UTC 2023 , Edited by admin on Fri Dec 15 15:56:23 UTC 2023
EU-Orphan Drug EU/3/13/1180
Created by admin on Fri Dec 15 15:56:23 UTC 2023 , Edited by admin on Fri Dec 15 15:56:23 UTC 2023
WHO-VATC QL04AA32
Created by admin on Fri Dec 15 15:56:23 UTC 2023 , Edited by admin on Fri Dec 15 15:56:23 UTC 2023
Code System Code Type Description
EPA CompTox
DTXSID30976289
Created by admin on Fri Dec 15 15:56:23 UTC 2023 , Edited by admin on Fri Dec 15 15:56:23 UTC 2023
PRIMARY
USAN
SS-114
Created by admin on Fri Dec 15 15:56:23 UTC 2023 , Edited by admin on Fri Dec 15 15:56:23 UTC 2023
PRIMARY
IUPHAR
7372
Created by admin on Fri Dec 15 15:56:23 UTC 2023 , Edited by admin on Fri Dec 15 15:56:23 UTC 2023
PRIMARY
NDF-RT
N0000182960
Created by admin on Fri Dec 15 15:56:23 UTC 2023 , Edited by admin on Fri Dec 15 15:56:23 UTC 2023
PRIMARY Phosphodiesterase 4 Inhibitors [MoA]
INN
8872
Created by admin on Fri Dec 15 15:56:23 UTC 2023 , Edited by admin on Fri Dec 15 15:56:23 UTC 2023
PRIMARY
HSDB
8221
Created by admin on Fri Dec 15 15:56:23 UTC 2023 , Edited by admin on Fri Dec 15 15:56:23 UTC 2023
PRIMARY
MERCK INDEX
m2010
Created by admin on Fri Dec 15 15:56:23 UTC 2023 , Edited by admin on Fri Dec 15 15:56:23 UTC 2023
PRIMARY Merck Index
MESH
C505730
Created by admin on Fri Dec 15 15:56:23 UTC 2023 , Edited by admin on Fri Dec 15 15:56:23 UTC 2023
PRIMARY
PUBCHEM
11561674
Created by admin on Fri Dec 15 15:56:23 UTC 2023 , Edited by admin on Fri Dec 15 15:56:23 UTC 2023
PRIMARY
LACTMED
Apremilast
Created by admin on Fri Dec 15 15:56:23 UTC 2023 , Edited by admin on Fri Dec 15 15:56:23 UTC 2023
PRIMARY
EVMPD
SUB130837
Created by admin on Fri Dec 15 15:56:23 UTC 2023 , Edited by admin on Fri Dec 15 15:56:23 UTC 2023
PRIMARY
ChEMBL
CHEMBL514800
Created by admin on Fri Dec 15 15:56:23 UTC 2023 , Edited by admin on Fri Dec 15 15:56:23 UTC 2023
PRIMARY
RXCUI
1492727
Created by admin on Fri Dec 15 15:56:23 UTC 2023 , Edited by admin on Fri Dec 15 15:56:23 UTC 2023
PRIMARY RxNorm
CHEBI
78540
Created by admin on Fri Dec 15 15:56:23 UTC 2023 , Edited by admin on Fri Dec 15 15:56:23 UTC 2023
PRIMARY
CAS
608141-41-9
Created by admin on Fri Dec 15 15:56:23 UTC 2023 , Edited by admin on Fri Dec 15 15:56:23 UTC 2023
PRIMARY
DRUG BANK
DB05676
Created by admin on Fri Dec 15 15:56:23 UTC 2023 , Edited by admin on Fri Dec 15 15:56:23 UTC 2023
PRIMARY
FDA UNII
UP7QBP99PN
Created by admin on Fri Dec 15 15:56:23 UTC 2023 , Edited by admin on Fri Dec 15 15:56:23 UTC 2023
PRIMARY
DAILYMED
UP7QBP99PN
Created by admin on Fri Dec 15 15:56:23 UTC 2023 , Edited by admin on Fri Dec 15 15:56:23 UTC 2023
PRIMARY
SMS_ID
100000156798
Created by admin on Fri Dec 15 15:56:23 UTC 2023 , Edited by admin on Fri Dec 15 15:56:23 UTC 2023
PRIMARY
DRUG CENTRAL
4829
Created by admin on Fri Dec 15 15:56:23 UTC 2023 , Edited by admin on Fri Dec 15 15:56:23 UTC 2023
PRIMARY
NCI_THESAURUS
C147044
Created by admin on Fri Dec 15 15:56:23 UTC 2023 , Edited by admin on Fri Dec 15 15:56:23 UTC 2023
PRIMARY
Related Record Type Details
Structure of APREMILAST
EXCRETED UNCHANGED
URINE
CAMP-SPECIFIC 3',5'-CYCLIC PHOSPHODIESTERASE PDE4B1
TARGET -> INHIBITOR
IC50
CAMP-SPECIFIC 3',5'-CYCLIC PHOSPHODIESTERASE PDE4D2
TARGET -> INHIBITOR
IC50
CAMP-SPECIFIC 3',5'-CYCLIC PHOSPHODIESTERASE PDE4C1
TARGET -> INHIBITOR
IC50
CAMP-SPECIFIC 3',5'-CYCLIC PHOSPHODIESTERASE PDE4B2
TARGET -> INHIBITOR
IC50
Structure of APREMILAST, (±)-
RACEMATE -> ENANTIOMER
CAMP-SPECIFIC 3',5'-CYCLIC PHOSPHODIESTERASE PDE4A1
TARGET -> INHIBITOR
Apremilast is a selective inhibitor of PDE4 that regulates inflammatory mediators.
COMPETITIVE INHIBITOR
IC50
TUMOR NECROSIS FACTOR-.ALPHA. HUMAN (PLASMA DERIVED, SOLUBLE FORM)
TARGET -> INHIBITOR
INHIBITS PDE4 AND INCREASES cAMP CONCENTRATION
INDIRECT
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
Related Record Type Details
Structure of N-DEACETYL-N-HYDROXYACETYL APREMILAST-O-GLUCURONIDE
METABOLITE -> PARENT
MINOR
PLASMA; URINE
Structure of N-DEACETYL APREMILAST
METABOLITE -> PARENT
Metabolites M7 and M17,which were present at trace levels in plasma, did retain some PDE4 and TNF-.alpha. inhibition activity, with IC 50 values similar to those of apremilast.
FECAL
Structure of O-DEMETHYL APREMILAST GLUCURONIDE
METABOLITE INACTIVE -> PARENT
MAJOR
PLASMA; URINE
Structure of 3-ACETAMIDOPHTHALIC ACID
METABOLITE -> PARENT
MINOR
FECAL
Structure of O-DEMETHYL-N-DEACETYL APREMILAST
METABOLITE -> PARENT
MINOR
FECAL
Structure of O-DEMETHYL-N-DEACETYL-N-HYDROXYACETYL APREMILAST
METABOLITE -> PARENT
MINOR
FECAL
Structure of N-DEACETYL-N-HYDROXYACETYL APREMILAST
METABOLITE -> PARENT
Metabolites M7 and M17,which were present at trace levels in plasma, did retain some PDE4 and TNF-.alpha. inhibition activity, with IC 50 values similar to those of apremilast.
FECAL; URINE
Structure of 2-(ACETYLAMINO)-6-((((1S)-1-(3-ETHOXY-4-HYDROXYPHENYL)-2-(METHYLSULFONYL)ETHYL)AMINO)CARBONYL)BENZOIC ACID
METABOLITE -> PARENT
Major fecal
MAJOR
FECAL
Structure of O-DEETHYL APREMILAST-O-GLUCURONIDE
METABOLITE -> PARENT
MINOR
PLASMA; URINE
Structure of O-DEMETHYL APREMILAST GLUCURONIDE
METABOLITE INACTIVE -> PARENT
Structure of 4-((1S)-1-((3-(ACETYLAMINO)-2-CARBOXYBENZOYL)AMINO)-2-(METHYLSULFONYL)ETHYL)-2-ETHOXYPHENYL-.BETA.-D-GLUCOPYRANOSIDURONIC ACID
METABOLITE -> PARENT
MINOR
URINE
Structure of 3-(2-HYDROXYACETAMIDO)PHTHALIC ACID
METABOLITE -> PARENT
MINOR
FECAL
Structure of O-DEMETHYL-N-DEACETYL APREMILAST-O-GLUCURONIDE
METABOLITE -> PARENT
MINOR
PLASMA; URINE
Structure of O-DEMETHYL APREMILAST
METABOLITE -> PARENT
MINOR
FECAL
Related Record Type Details
Structure of APREMILAST
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC
NIH
NCATS
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