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Details

Stereochemistry ACHIRAL
Molecular Formula C17H14Cl2F2N2O3
Molecular Weight 403.207
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Roflumilast

SMILES

FC(F)OC1=C(OCC2CC2)C=C(C=C1)C(=O)NC3=C(Cl)C=NC=C3Cl

InChI

InChIKey=MNDBXUUTURYVHR-UHFFFAOYSA-N
InChI=1S/C17H14Cl2F2N2O3/c18-11-6-22-7-12(19)15(11)23-16(24)10-3-4-13(26-17(20)21)14(5-10)25-8-9-1-2-9/h3-7,9,17H,1-2,8H2,(H,22,23,24)

HIDE SMILES / InChI
Molecular Formula C17H14Cl2F2N2O3
Molecular Weight 403.207
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Approval Year

Unknown
86413
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:35:09 UTC 2023
Edited
by admin
on Fri Dec 15 16:35:09 UTC 2023
Record UNII
0P6C6ZOP5U
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Roflumilast
DASH   EMA EPAR   INN   JAN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
DAXAS
Brand Name English
3-(Cyclopropylmethoxy)-N-(3,5-dichloro-4-pyridinyl)-4-(difluoromethoxy)benzamide
Systematic Name English
ROFLUMILAST [MART.]
Common Name English
ROFLUMILAST [ORANGE BOOK]
Common Name English
ROFLUMILAST [JAN]
Common Name English
ROFLUMILAST [MI]
Common Name English
ROFLUMILAST [USAN]
Common Name English
Roflumilast [WHO-DD]
Common Name English
B9302-107
Code English
DALIRESP
Brand Name English
ROFLUMILAST [VANDF]
Common Name English
BY-217
Code English
BYK20869
Code English
ROFLUMILAST [EMA EPAR]
Common Name English
roflumilast [INN]
Common Name English
B-9302-107
Code English
ARQ-151
Code English
ARQ-154 (Roflumilast foam)
Code English
BY217
Code English
BYK-20869
Code English
Benzamide, 3-(cyclopropylmethoxy)-N-(3,5-dichloro-4-pyridinyl)-4-(difluoromethoxy)-
Systematic Name English
ZORYVE
Brand Name English
Classification Tree Code System Code
WHO-ATC R03DX07
Created by admin on Fri Dec 15 16:35:09 UTC 2023 , Edited by admin on Fri Dec 15 16:35:09 UTC 2023
LIVERTOX NBK548195
Created by admin on Fri Dec 15 16:35:09 UTC 2023 , Edited by admin on Fri Dec 15 16:35:09 UTC 2023
EMA ASSESSMENT REPORTS DAXAS (AUTHORIZED: PULMONARY DISEASE, CHRONIC OBSTRUCTIVE )
Created by admin on Fri Dec 15 16:35:09 UTC 2023 , Edited by admin on Fri Dec 15 16:35:09 UTC 2023
WHO-VATC QR03DX07
Created by admin on Fri Dec 15 16:35:09 UTC 2023 , Edited by admin on Fri Dec 15 16:35:09 UTC 2023
NDF-RT N0000182961
Created by admin on Fri Dec 15 16:35:09 UTC 2023 , Edited by admin on Fri Dec 15 16:35:09 UTC 2023
NCI_THESAURUS C744
Created by admin on Fri Dec 15 16:35:09 UTC 2023 , Edited by admin on Fri Dec 15 16:35:09 UTC 2023
EMA ASSESSMENT REPORTS DALIRESP (AUTHORIZED: PULMONARY DISEASE, CHRONIC OBSTRUCTIVE )
Created by admin on Fri Dec 15 16:35:09 UTC 2023 , Edited by admin on Fri Dec 15 16:35:09 UTC 2023
EMA ASSESSMENT REPORTS LIBERTEK (AUTHORIZED: PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
Created by admin on Fri Dec 15 16:35:09 UTC 2023 , Edited by admin on Fri Dec 15 16:35:09 UTC 2023
Code System Code Type Description
NCI_THESAURUS
C76890
Created by admin on Fri Dec 15 16:35:09 UTC 2023 , Edited by admin on Fri Dec 15 16:35:09 UTC 2023
PRIMARY
INN
7598
Created by admin on Fri Dec 15 16:35:09 UTC 2023 , Edited by admin on Fri Dec 15 16:35:09 UTC 2023
PRIMARY
IUPHAR
6962
Created by admin on Fri Dec 15 16:35:09 UTC 2023 , Edited by admin on Fri Dec 15 16:35:09 UTC 2023
PRIMARY
CAS
162401-32-3
Created by admin on Fri Dec 15 16:35:09 UTC 2023 , Edited by admin on Fri Dec 15 16:35:09 UTC 2023
PRIMARY
FDA UNII
0P6C6ZOP5U
Created by admin on Fri Dec 15 16:35:09 UTC 2023 , Edited by admin on Fri Dec 15 16:35:09 UTC 2023
PRIMARY
EPA CompTox
DTXSID8044123
Created by admin on Fri Dec 15 16:35:09 UTC 2023 , Edited by admin on Fri Dec 15 16:35:09 UTC 2023
PRIMARY
MESH
C424423
Created by admin on Fri Dec 15 16:35:09 UTC 2023 , Edited by admin on Fri Dec 15 16:35:09 UTC 2023
PRIMARY
USAN
OO-57
Created by admin on Fri Dec 15 16:35:09 UTC 2023 , Edited by admin on Fri Dec 15 16:35:09 UTC 2023
PRIMARY
WIKIPEDIA
ROFLUMILAST
Created by admin on Fri Dec 15 16:35:09 UTC 2023 , Edited by admin on Fri Dec 15 16:35:09 UTC 2023
PRIMARY
MERCK INDEX
m9648
Created by admin on Fri Dec 15 16:35:09 UTC 2023 , Edited by admin on Fri Dec 15 16:35:09 UTC 2023
PRIMARY Merck Index
NDF-RT
N0000182960
Created by admin on Fri Dec 15 16:35:09 UTC 2023 , Edited by admin on Fri Dec 15 16:35:09 UTC 2023
PRIMARY Phosphodiesterase 4 Inhibitors [MoA]
DRUG CENTRAL
3531
Created by admin on Fri Dec 15 16:35:09 UTC 2023 , Edited by admin on Fri Dec 15 16:35:09 UTC 2023
PRIMARY
DRUG BANK
DB01656
Created by admin on Fri Dec 15 16:35:09 UTC 2023 , Edited by admin on Fri Dec 15 16:35:09 UTC 2023
PRIMARY
SMS_ID
100000080252
Created by admin on Fri Dec 15 16:35:09 UTC 2023 , Edited by admin on Fri Dec 15 16:35:09 UTC 2023
PRIMARY
RS_ITEM_NUM
1605012
Created by admin on Fri Dec 15 16:35:09 UTC 2023 , Edited by admin on Fri Dec 15 16:35:09 UTC 2023
PRIMARY
RXCUI
1091836
Created by admin on Fri Dec 15 16:35:09 UTC 2023 , Edited by admin on Fri Dec 15 16:35:09 UTC 2023
PRIMARY RxNorm
ChEMBL
CHEMBL193240
Created by admin on Fri Dec 15 16:35:09 UTC 2023 , Edited by admin on Fri Dec 15 16:35:09 UTC 2023
PRIMARY
LACTMED
Roflumilast
Created by admin on Fri Dec 15 16:35:09 UTC 2023 , Edited by admin on Fri Dec 15 16:35:09 UTC 2023
PRIMARY
EVMPD
SUB10358MIG
Created by admin on Fri Dec 15 16:35:09 UTC 2023 , Edited by admin on Fri Dec 15 16:35:09 UTC 2023
PRIMARY
CHEBI
47657
Created by admin on Fri Dec 15 16:35:09 UTC 2023 , Edited by admin on Fri Dec 15 16:35:09 UTC 2023
PRIMARY
DAILYMED
0P6C6ZOP5U
Created by admin on Fri Dec 15 16:35:09 UTC 2023 , Edited by admin on Fri Dec 15 16:35:09 UTC 2023
PRIMARY
PUBCHEM
449193
Created by admin on Fri Dec 15 16:35:09 UTC 2023 , Edited by admin on Fri Dec 15 16:35:09 UTC 2023
PRIMARY
Related Record Type Details
CYTOCHROME P450 3A4
METABOLIC ENZYME -> SUBSTRATE
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
CAMP-SPECIFIC 3',5'-CYCLIC PHOSPHODIESTERASE 4A
TARGET -> INHIBITOR
Structure of Roflumilast
EXCRETED UNCHANGED
The major route of elimination for roflumilast is through hepatic metabolism. Roflumilast was not detectable in urine. Roflumilast N-oxide was only a trace metabolite in urine (less than 1%).
URINE
CYTOCHROME P450 2C19
METABOLIC ENZYME -> SUBSTRATE
CYTOCHROME P450 1A2
METABOLIC ENZYME -> SUBSTRATE
Related Record Type Details
Structure of 3,5-DICHLOROPYRIDIN-4-AMINE
METABOLITE -> PARENT
Structure of N-(3,5-DICHLORO-4-PYRIDINYL)-4-(DIFLUOROMETHOXY)-3-HYDROXYBENZAMIDE
METABOLITE -> PARENT
Structure of ROFLUMILAST N-OXIDE
METABOLITE ACTIVE -> PARENT
The N-oxide accounts for about 90% of the biological action of roflumilast and produces a long-lasting, competitive inhibition of PDE4over a 24-hr period such that roflumilast may be administered once daily.
MAJOR
Structure of (2S,3S,4S,5R)-6-(5-((3,5-DICHLORO-4-PYRIDYL)CARBAMOYL)-2-(DIFLUOROMETHOXY)PHENOXY)-3,4,5-TRIHYDROXY-TETRAHYDROPYRAN-2-CARBOXYLIC ACID
METABOLITE -> PARENT
Structure of (2S,3S,4S,5R)-6-((5-CHLORO-4-((3-(CYCLOPROPYLMETHOXY)-4-(DIFLUOROMETHOXY)BENZOYL)AMINO)-3-PYRIDYL)OXY)-3,4,5-TRIHYDROXY-TETRAHYDROPYRAN-2-CARBOXYLIC ACID
METABOLITE -> PARENT
Structure of (2S,3S,4S,5R)-6-(5-((3,5-DICHLORO-1-OXIDO-PYRIDIN-1-IUM-4-YL)CARBAMOYL)-2-(DIFLUOROMETHOXY)PHENOXY)-3,4,5-TRIHYDROXY-TETRAHYDROPYRAN-2-CARBOXYLIC ACID
METABOLITE -> PARENT
Structure of 4-AMINO-3,5-DICHLOROPYRIDINE N-OXIDE
METABOLITE INACTIVE -> PARENT
conjugated metabolite
Structure of BENZAMIDE, N-(3,5-DICHLORO-1-OXIDO-4-PYRIDINYL)-4-(DIFLUOROMETHOXY)-3-HYDROXY-
METABOLITE -> PARENT
Related Record Type Details
Structure of Roflumilast
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Tmax PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC
NIH
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