U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

Description
Curator's Comment: description was created based on several sources, including http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Public_assessment_report/human/002398/WC500103075.pdf

Roflumilast is a specific phosphodiesterase type (4PDE4) inhibitor indicated for use as a treatment to reduce the risk of COPD exacerbations in patients with severe COPD associated with chronic bronchitis and a history of exacerbations.

CNS Activity

CNS Penetrant
2523
Curator's Comment: Studies in rats with radiolabeled roflumilast indicate low penetration across the blood-brain barrier.

Originator

Approval Year

2011
562
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8228
 0.8 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Secondary
Approved
8360
DALIRESP

Approved Use

Indicated as a treatment to reduce the risk of COPD exacerbations in patients with severe COPD associated with chronic bronchitis and a history of exacerbations. Limitations of Use: DALIRESP is not a bronchodilator and is not indicated for the relief of acute bronchospasm.

Launch Date

1.29885117E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
12.5 ng/mL
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/30538429
0.5 mg single, oral
dose: 0.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ROFLUMILAST plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
65.1 ng × h/mL
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/30538429
0.5 mg single, oral
dose: 0.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ROFLUMILAST plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
19.9 h
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/30538429
0.5 mg single, oral
dose: 0.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ROFLUMILAST plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
17 h
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/022522s003lbl.pdf
ROFLUMILAST plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
1%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/022522s003lbl.pdf
ROFLUMILAST plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
450 ug 1 times / day steady, oral
Recommended
Dose: 450 ug, 1 times / day
Route: oral
Route: steady
Dose: 450 ug, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022522s000lbl.pdf
unhealthy, 64 years (range: 40-91 years)
n = 4438
Health Status: unhealthy
Condition: COPD
Age Group: 64 years (range: 40-91 years)
Sex: M+F
Population Size: 4438
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022522s000lbl.pdf
Disc. AE: Diarrhea, Nausea...
AEs leading to
discontinuation/dose reduction:
Diarrhea (2.4%)
Nausea (1.6%)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022522s000lbl.pdf
5000 ug single, oral
Highest studied dose
Dose: 5000 ug
Route: oral
Route: single
Dose: 5000 ug
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022522s000lbl.pdf
healthy, adult
n = 1
Health Status: healthy
Age Group: adult
Population Size: 1
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022522s000lbl.pdf
Other AEs: Headache, Gastrointestinal disorders...
Other AEs:
Headache (1 patient)
Gastrointestinal disorders (1 patient)
Dizziness (1 patient)
Palpitations (1 patient)
Lightheadedness (1 patient)
Clamminess (1 patient)
Arterial hypotension (1 patient)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022522s000lbl.pdf
AEs

AEs

AESignificanceDosePopulation
Nausea 1.6%
Disc. AE
450 ug 1 times / day steady, oral
Recommended
Dose: 450 ug, 1 times / day
Route: oral
Route: steady
Dose: 450 ug, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022522s000lbl.pdf
unhealthy, 64 years (range: 40-91 years)
n = 4438
Health Status: unhealthy
Condition: COPD
Age Group: 64 years (range: 40-91 years)
Sex: M+F
Population Size: 4438
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022522s000lbl.pdf
Diarrhea 2.4%
Disc. AE
450 ug 1 times / day steady, oral
Recommended
Dose: 450 ug, 1 times / day
Route: oral
Route: steady
Dose: 450 ug, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022522s000lbl.pdf
unhealthy, 64 years (range: 40-91 years)
n = 4438
Health Status: unhealthy
Condition: COPD
Age Group: 64 years (range: 40-91 years)
Sex: M+F
Population Size: 4438
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022522s000lbl.pdf
Arterial hypotension 1 patient
5000 ug single, oral
Highest studied dose
Dose: 5000 ug
Route: oral
Route: single
Dose: 5000 ug
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022522s000lbl.pdf
healthy, adult
n = 1
Health Status: healthy
Age Group: adult
Population Size: 1
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022522s000lbl.pdf
Clamminess 1 patient
5000 ug single, oral
Highest studied dose
Dose: 5000 ug
Route: oral
Route: single
Dose: 5000 ug
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022522s000lbl.pdf
healthy, adult
n = 1
Health Status: healthy
Age Group: adult
Population Size: 1
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022522s000lbl.pdf
Dizziness 1 patient
5000 ug single, oral
Highest studied dose
Dose: 5000 ug
Route: oral
Route: single
Dose: 5000 ug
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022522s000lbl.pdf
healthy, adult
n = 1
Health Status: healthy
Age Group: adult
Population Size: 1
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022522s000lbl.pdf
Gastrointestinal disorders 1 patient
5000 ug single, oral
Highest studied dose
Dose: 5000 ug
Route: oral
Route: single
Dose: 5000 ug
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022522s000lbl.pdf
healthy, adult
n = 1
Health Status: healthy
Age Group: adult
Population Size: 1
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022522s000lbl.pdf
Headache 1 patient
5000 ug single, oral
Highest studied dose
Dose: 5000 ug
Route: oral
Route: single
Dose: 5000 ug
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022522s000lbl.pdf
healthy, adult
n = 1
Health Status: healthy
Age Group: adult
Population Size: 1
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022522s000lbl.pdf
Lightheadedness 1 patient
5000 ug single, oral
Highest studied dose
Dose: 5000 ug
Route: oral
Route: single
Dose: 5000 ug
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022522s000lbl.pdf
healthy, adult
n = 1
Health Status: healthy
Age Group: adult
Population Size: 1
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022522s000lbl.pdf
Palpitations 1 patient
5000 ug single, oral
Highest studied dose
Dose: 5000 ug
Route: oral
Route: single
Dose: 5000 ug
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022522s000lbl.pdf
healthy, adult
n = 1
Health Status: healthy
Age Group: adult
Population Size: 1
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022522s000lbl.pdf
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1709
inhibitor
1752

inducer
383

substrate
1010
inhibitor
1837

substrate
1193
inhibitor
1599

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A2
1509

CYP2A6
704

CYP2B6
799

CYP2C8
901

CYP2C19
1463

CYP2E1
876

CYP3A4/5
273

CYP4A9/11
37

P-gp
1437
CYP1A2
1032

P-gp
1527

CYP1A1
348

CYP2A6
523

CYP2B6
660

CYP2C8
688

CYP2C19
985

CYP2E1
648

CYP3A5
391
CYP1A2
689

CYP2A6
79

CYP2C19
290

CYP3A4/5
120

CYP2B6
538

CYP2B1/2
1

CYP3A1/2
3

CYP4A1
17

CYP4A3
5
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP1A2
1673
 no
CYP1A2
1673
 no
CYP2A6
736
 no
CYP2A6
736
 no
CYP2B1/2
4
 no
CYP2B6
985
 no
CYP2C19
1537
 no
CYP2C19
1537
 no
CYP2C8
955
 no
CYP2C9
1803
 no
CYP2C9
1803
 no
CYP2D6
1875
 no
CYP2E1
964
 no
CYP3A1/2
4
 no
CYP3A4/5
330
 no
CYP3A4/5
330
 no
CYP4A1
25
 no
CYP4A3
5
 no
CYP4A9/11
37
 no
P-gp
1626
 no
CYP2B6
985
 weak
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP1A2
1032
 major
yes (co-administration study)
Comment: fluvoxamine increased roflumilast cmax 12%, auc 156%; enoxacin increased roflumilast cmax 20%, auc 56%; cimetadine increased roflumilast cmax 46%, auc 85%
Page: 3.0
CYP3A4
1709
 major
yes (co-administration study)
Comment: erythromycin increased roflumilast cmax 40% and auc 70%; ketoconazole increased roflumilast cmax 23%, auc 99%; rifampicin decreased roflumilast cmax 68%, auc 80%
Page: 3.0
CYP1A1
348
 no
CYP2A6
523
 no
CYP2B6
660
 no
CYP2C19
985
 no
CYP2C8
688
 no
CYP2C9
1010
 no
CYP2D6
1193
 no
CYP2E1
648
 no
CYP3A5
391
 no
P-gp
1527
 no
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
1632
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:47657
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:47657
ChemicalBook
CB7412688
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB7412688
MolPort
MolPort-006-069-128
https://www.molport.com/shop/molecule-link/MolPort-006-069-128
Selleck Chemicals
Roflumilast(Daxas)
http://www.selleckchem.com/products/Roflumilast(Daxas).html
ZINC
ZINC000000592419
http://zinc15.docking.org/substances/ZINC000000592419
eMolecules
6760347
https://www.emolecules.com/cgi-bin/more?vid=6760347
PubMed

PubMed

TitleDatePubMed
Dynamic activation of cystic fibrosis transmembrane conductance regulator by type 3 and type 4D phosphodiesterase inhibitors.
2005 Aug
Roflumilast for asthma and chronic obstructive pulmonary disease.
2005 Oct
Phosphodiesterase 4 inhibitors for the treatment of asthma and COPD.
2006
Phosphodiesterase 4 inhibitors augment levels of glucocorticoid receptor in B cell chronic lymphocytic leukemia but not in normal circulating hematopoietic cells.
2007 Aug 15
Reduction in sputum neutrophil and eosinophil numbers by the PDE4 inhibitor roflumilast in patients with COPD.
2007 Dec
Roflumilast inhibits leukocyte-endothelial cell interactions, expression of adhesion molecules and microvascular permeability.
2007 Oct
Phosphodiesterase 4 inhibitors for chronic obstructive pulmonary disease.
2011 May 11
The molecular basis for the inhibition of phosphodiesterase-4D by three natural resveratrol analogs. Isolation, molecular docking, molecular dynamics simulations, binding free energy, and bioassay.
2013 Oct
Patents

Patents

07470791
1
07678363
5
08536206
1
08604064
1
08618142
1
08741319
1
JP2002538207A
2
JP2002543133A
1
JP2006508994A
3
JP2006528229A
10
JP2007016024A
1
JP2007500148A
7
JP2007512223A
2
JP2007520507A
9
JP2007520538A
2
JP2008508360A
1
JP2010513276A
4
JP2012500252A
4
JP2012500794A
10
JP2013237683A
1
JP4532115B2
9
JP4700014B2
1
JP4742026B2
1
JP5349302B2
1

Sample Use Guides

In Vivo Use Guide
The recommended dosage for patients with COPD is one 500 ug tablet per day, with or without food.
Route of Administration: Oral
In Vitro Use Guide
To study the potency of roflumilast to inhibit adhesion of PMNL (polymorphonuclear leukocytes isolated from human peripheral venous blood) to TNFa-prestimulated HUVEC (human umbilical vein endothelial cells isolated from human umbilical cords) endothelial cell monolayers were stimulated with 0.3 ng/ml1 TNFa for 3 h. Medium was removed and roflumilast (10 pM–1 mM) was added followed by PMNL (50 000 cells per well) addition for 30 min. Roflumilast reduced adherence of PMNL to HUVEC with IC50 of 3.2 nM.
Substance Class Chemical
Created
by admin
on Thu Jul 06 00:00:33 UTC 2023
Edited
by admin
on Thu Jul 06 00:00:33 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 Thu Jul 06 00:00:33 UTC 2023 , Edited by admin on Thu Jul 06 00:00:33 UTC 2023
LIVERTOX NBK548195
Created by admin on Thu Jul 06 00:00:33 UTC 2023 , Edited by admin on Thu Jul 06 00:00:33 UTC 2023
EMA ASSESSMENT REPORTS DAXAS (AUTHORIZED: PULMONARY DISEASE, CHRONIC OBSTRUCTIVE )
Created by admin on Thu Jul 06 00:00:33 UTC 2023 , Edited by admin on Thu Jul 06 00:00:33 UTC 2023
WHO-VATC QR03DX07
Created by admin on Thu Jul 06 00:00:33 UTC 2023 , Edited by admin on Thu Jul 06 00:00:33 UTC 2023
NDF-RT N0000182961
Created by admin on Thu Jul 06 00:00:33 UTC 2023 , Edited by admin on Thu Jul 06 00:00:33 UTC 2023
NCI_THESAURUS C744
Created by admin on Thu Jul 06 00:00:33 UTC 2023 , Edited by admin on Thu Jul 06 00:00:33 UTC 2023
EMA ASSESSMENT REPORTS DALIRESP (AUTHORIZED: PULMONARY DISEASE, CHRONIC OBSTRUCTIVE )
Created by admin on Thu Jul 06 00:00:33 UTC 2023 , Edited by admin on Thu Jul 06 00:00:33 UTC 2023
EMA ASSESSMENT REPORTS LIBERTEK (AUTHORIZED: PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
Created by admin on Thu Jul 06 00:00:33 UTC 2023 , Edited by admin on Thu Jul 06 00:00:33 UTC 2023
Code System Code Type Description
NCI_THESAURUS
C76890
Created by admin on Thu Jul 06 00:00:33 UTC 2023 , Edited by admin on Thu Jul 06 00:00:33 UTC 2023
PRIMARY
INN
7598
Created by admin on Thu Jul 06 00:00:33 UTC 2023 , Edited by admin on Thu Jul 06 00:00:33 UTC 2023
PRIMARY
IUPHAR
6962
Created by admin on Thu Jul 06 00:00:33 UTC 2023 , Edited by admin on Thu Jul 06 00:00:33 UTC 2023
PRIMARY
CAS
162401-32-3
Created by admin on Thu Jul 06 00:00:33 UTC 2023 , Edited by admin on Thu Jul 06 00:00:33 UTC 2023
PRIMARY
FDA UNII
0P6C6ZOP5U
Created by admin on Thu Jul 06 00:00:33 UTC 2023 , Edited by admin on Thu Jul 06 00:00:33 UTC 2023
PRIMARY
EPA CompTox
DTXSID8044123
Created by admin on Thu Jul 06 00:00:33 UTC 2023 , Edited by admin on Thu Jul 06 00:00:33 UTC 2023
PRIMARY
MESH
C424423
Created by admin on Thu Jul 06 00:00:33 UTC 2023 , Edited by admin on Thu Jul 06 00:00:33 UTC 2023
PRIMARY
USAN
OO-57
Created by admin on Thu Jul 06 00:00:33 UTC 2023 , Edited by admin on Thu Jul 06 00:00:33 UTC 2023
PRIMARY
WIKIPEDIA
ROFLUMILAST
Created by admin on Thu Jul 06 00:00:33 UTC 2023 , Edited by admin on Thu Jul 06 00:00:33 UTC 2023
PRIMARY
MERCK INDEX
M9648
Created by admin on Thu Jul 06 00:00:33 UTC 2023 , Edited by admin on Thu Jul 06 00:00:33 UTC 2023
PRIMARY Merck Index
NDF-RT
N0000182960
Created by admin on Thu Jul 06 00:00:33 UTC 2023 , Edited by admin on Thu Jul 06 00:00:33 UTC 2023
PRIMARY Phosphodiesterase 4 Inhibitors [MoA]
DRUG CENTRAL
3531
Created by admin on Thu Jul 06 00:00:33 UTC 2023 , Edited by admin on Thu Jul 06 00:00:33 UTC 2023
PRIMARY
DRUG BANK
DB01656
Created by admin on Thu Jul 06 00:00:33 UTC 2023 , Edited by admin on Thu Jul 06 00:00:33 UTC 2023
PRIMARY
SMS_ID
100000080252
Created by admin on Thu Jul 06 00:00:33 UTC 2023 , Edited by admin on Thu Jul 06 00:00:33 UTC 2023
PRIMARY
RS_ITEM_NUM
1605012
Created by admin on Thu Jul 06 00:00:33 UTC 2023 , Edited by admin on Thu Jul 06 00:00:33 UTC 2023
PRIMARY
RXCUI
1091836
Created by admin on Thu Jul 06 00:00:33 UTC 2023 , Edited by admin on Thu Jul 06 00:00:33 UTC 2023
PRIMARY RxNorm
ChEMBL
CHEMBL193240
Created by admin on Thu Jul 06 00:00:33 UTC 2023 , Edited by admin on Thu Jul 06 00:00:33 UTC 2023
PRIMARY
LACTMED
Roflumilast
Created by admin on Thu Jul 06 00:00:33 UTC 2023 , Edited by admin on Thu Jul 06 00:00:33 UTC 2023
PRIMARY
EVMPD
SUB10358MIG
Created by admin on Thu Jul 06 00:00:33 UTC 2023 , Edited by admin on Thu Jul 06 00:00:33 UTC 2023
PRIMARY
CHEBI
47657
Created by admin on Thu Jul 06 00:00:33 UTC 2023 , Edited by admin on Thu Jul 06 00:00:33 UTC 2023
PRIMARY
DAILYMED
0P6C6ZOP5U
Created by admin on Thu Jul 06 00:00:33 UTC 2023 , Edited by admin on Thu Jul 06 00:00:33 UTC 2023
PRIMARY
PUBCHEM
449193
Created by admin on Thu Jul 06 00:00:33 UTC 2023 , Edited by admin on Thu Jul 06 00:00:33 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
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966