FEVIPIPRANT

Details

Stereochemistry	ACHIRAL
Molecular Formula	C19H17F3N2O4S
Molecular Weight	426.409
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=C(CC(O)=O)C2=CC=CN=C2N1CC3=CC=C(C=C3C(F)(F)F)S(C)(=O)=O

InChI

InChIKey=GFPPXZDRVCSVNR-UHFFFAOYSA-N

InChI=1S/C19H17F3N2O4S/c1-11-15(9-17(25)26)14-4-3-7-23-18(14)24(11)10-12-5-6-13(29(2,27)28)8-16(12)19(20,21)22/h3-8H,9-10H2,1-2H3,(H,25,26)

HIDE SMILES / InChI

Molecular Formula	C19H17F3N2O4S
Molecular Weight	426.409
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/mesh/2011556 | https://www.ncbi.nlm.nih.gov/pubmed/26916831 | https://www.ncbi.nlm.nih.gov/pubmed/27354118

Fevipiprant is a selective reversible antagonist of the prostaglandin D2 receptor (also known as CRTH2). It is currently in development for the treatment of allergic diseases.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Prostaglandin D2 receptor 2 3 Target ID: Q9Y5Y4 Gene ID: 11251.0 Gene Symbol: PTGDR2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/27310331	Antagonist 2778		1.1 nM [Kd]

PubMed

Title	Date	PubMed
The oral CRTh2 antagonist QAW039 (fevipiprant): A phase II study in uncontrolled allergic asthma.	2016 Aug	27354118
Pharmacokinetics, Safety, and Tolerability of Fevipiprant (QAW039), a Novel CRTh2 Receptor Antagonist: Results From 2 Randomized, Phase 1, Placebo-Controlled Studies in Healthy Volunteers.	2016 Jul	27310331
Fevipiprant (QAW039), a Slowly Dissociating CRTh2 Antagonist with the Potential for Improved Clinical Efficacy.	2016 May	26916831
An evaluation of fevipiprant for the treatment of asthma: a promising new therapy?	2018 Dec	30394155

Patents

Sample Use Guides

In Vivo Use Guide

500 mg once daily.

Route of Administration: Oral

In Vitro Use Guide

Fevipiprant (QAW039) is currently in development for the treatment of allergic diseases. [3H]-QAW039 displayed high affinity for the human CRTh2 receptor (1.14 +/- 0.44 nM) expressed in Chinese hamster ovary cells, the binding being reversible and competitive with the native agonist prostaglandin D2.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 08:19:31 GMT 2023` Edited by `admin` on `Sat Dec 16 08:19:31 GMT 2023`
Record UNII	2PEX5N7DQ4
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FEVIPIPRANT

Official Name

English

FEVIPIPRANT [USAN]

Common Name

English

2-(1-((4-METHANESULFONYL-2-(TRIFLUOROMETHYL)PHENYL)METHYL(-2-METHYL-1H-PYRROLO(2,3-B)PYRIDIN-3-YL)ACETIC ACID

Common Name

English

QAW039

Code

English

FEVIPIPRANT [JAN]

Common Name

English

NVP-QAW039

Code

English

QAW-039

Code

English

(1-(4-((METHANE)SULFONYL)-2-TRIFLUOROMETHYLBENZYL)-2-METHYL-1H-PYRROLO(2,3-B)PYRIDIN-3-YL)ACETIC ACID

Common Name

English

Fevipiprant [WHO-DD]

Common Name

English

fevipiprant [INN]

Common Name

English

Code System Code Type Description

DRUG BANK

DB12011