ROFLUMILAST N-OXIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H14Cl2F2N2O4
Molecular Weight	419.207
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[O-][N+]1=CC(Cl)=C(NC(=O)C2=CC(OCC3CC3)=C(OC(F)F)C=C2)C(Cl)=C1

InChI

InChIKey=PCGSQNPMMSALEJ-UHFFFAOYSA-N

InChI=1S/C17H14Cl2F2N2O4/c18-11-6-23(25)7-12(19)15(11)22-16(24)10-3-4-13(27-17(20)21)14(5-10)26-8-9-1-2-9/h3-7,9,17H,1-2,8H2,(H,22,24)

HIDE SMILES / InChI

Molecular Formula	C17H14Cl2F2N2O4
Molecular Weight	419.207
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Phosphodiesterase 4 52 Target ID: CHEMBL2093863 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20226872	Inhibitor 8228

PubMed

Title	Date	PubMed
Roflumilast inhibits the release of chemokines and TNF-α from human lung macrophages stimulated with lipopolysaccharide.	2012 Mar	21913898

Patents

Substance Class	Chemical Created by `admin` on `Thu Jul 06 15:25:10 UTC 2023` Edited by `admin` on `Thu Jul 06 15:25:10 UTC 2023`
Record UNII	F08MQ6CZCS
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

ROFLUMILAST N-OXIDE

Common Name

English

BYK22890

Code

English

N-(3,5-DICHLORO-1-OXOPYRIDIN-4-YL)-4-DIFLUOROMETHOXY-3-CYCLOPROPYLMETHOXYBENZAMIDE

Systematic Name

English

ROFLUMILAST METABOLITE M07

Common Name

English

Code System Code Type Description

CAS

292135-78-5

Created by admin on Thu Jul 06 15:25:10 UTC 2023 , Edited by admin on Thu Jul 06 15:25:10 UTC 2023

PRIMARY

FDA UNII

F08MQ6CZCS

Created by admin on Thu Jul 06 15:25:10 UTC 2023 , Edited by admin on Thu Jul 06 15:25:10 UTC 2023

PRIMARY

EPA CompTox

DTXSID80433059

Created by admin on Thu Jul 06 15:25:10 UTC 2023 , Edited by admin on Thu Jul 06 15:25:10 UTC 2023

PRIMARY

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TUMOR NECROSIS FACTOR-.ALPHA. HUMAN (PLASMA DERIVED, SOLUBLE FORM)

TARGET->INHIBITOR OF RELEASE

Comments:

In human PBMCs

Qualification:

IC50

Amount:


					0OZR2PJ20Q

CAMP-SPECIFIC 3',5'-CYCLIC PHOSPHODIESTERASE PDE4D2

TARGET -> INHIBITOR

Qualification:

IC50

Amount:


					IO8PGY0Q5C

CAMP-SPECIFIC 3',5'-CYCLIC PHOSPHODIESTERASE PDE4C2

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Qualification:

IC50

Amount:


					651CFC5G66

CAMP-SPECIFIC 3',5'-CYCLIC PHOSPHODIESTERASE 4A

TARGET -> INHIBITOR

Qualification:

IC50

Amount:


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HUMAN INTERLEUKIN-2

TARGET->INHIBITOR OF RELEASE

Comments:

In human PBMCs

Amount:


					6D53G0FD0Z

PLASMA PROTEIN FRACTION (HUMAN)

BINDER->LIGAND

Amount:


					ZV2ALJ5YXA

CAMP-SPECIFIC 3',5'-CYCLIC PHOSPHODIESTERASE PDE4B2

TARGET -> INHIBITOR

Qualification:

IC50

Amount:


					0FY8X1RL72

CAMP-SPECIFIC 3',5'-CYCLIC PHOSPHODIESTERASE PDE4A1

TARGET -> INHIBITOR

Comments:

2-3 fold less active than ROFLUMILAST but much higher concentration in plasma.

Amount:


					6B9RDG48CY

CAMP-SPECIFIC 3',5'-CYCLIC PHOSPHODIESTERASE PDE4C1

TARGET -> INHIBITOR

Comments:

10 fold less active that PDE4A

Amount:

Related Record Type Details


					0P6C6ZOP5U

Roflumilast

PARENT -> METABOLITE ACTIVE

Comments:

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.

Interaction Type:

MAJOR

Amount:

Name	Property Type	Amount	Referenced Substance	Defining	Parameters	References
Tmax	PHARMACOKINETIC

Biological Half-life	PHARMACOKINETIC