Fevipiprant

Fevipiprant, also known as NVP-QAW039 or QAW039, is an oral active and potent CRTh2 receptor antagonist and potentially useful for asthma treatment. [(3)H]-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(PGD2). QAW039 was also a potent inhibitor of PGD2-induced cytokine release in human Th2 cells. Fevipiprant reduces eosinophilic airway inflammation and is well tolerated in patients with persistent moderate-to-severe asthma and raised sputum eosinophil counts despite inhaled corticosteroid treatment. Fevipiprant demonstrates a favorable safety profile.

Product information

CAS Number: 872365-14-5

Molecular Weight: 426.41

Formula: C19H17F3N2O4S

Synonym:

NVP-QAW039

NVP-QAW-039

QAW-039

NVP-QAW 039

QAW039

QAW 039

Chemical Name: 2-(2-methyl-1-(4-(methylsulfonyl)-2-(trifluoromethyl)benzyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)acetic acid

Smiles: CC1=C(CC(O)=O)C2=CC=CN=C2N1CC1=CC=C(C=C1C(F)(F)F)S(C)(=O)=O

InChiKey: GFPPXZDRVCSVNR-UHFFFAOYSA-N

InChi: 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)

Technical Data

Appearance: Solid Power.

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: Soluble in DMSO, not in water

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined.

HS Tariff Code: 382200

References:

1. Gonem S, Berair R, Singapuri A, Hartley R, Laurencin MF, Bacher G, Holzhauer B, Bourne M, Mistry V, Pavord ID, Mansur AH, Wardlaw AJ, Siddiqui SH, Kay RA, Brightling CE. Fevipiprant, a prostaglandin D(2) receptor 2 antagonist, in patients with persistent eosinophilic asthma: a single-centre, randomised, double-blind, parallel-group, placebo-controlled trial. Lancet Respir Med. 2016 Aug 5. pii: S2213-2600(16)30179-5. doi: 10.1016/S2213-2600(16)30179-5. [Epub ahead of print] PubMed PMID: 27503237.
2. Erpenbeck VJ, Popov TA, Miller D, Weinstein SF, Spector S, Magnusson B, Osuntokun W, Goldsmith P, Weiss M, Beier J. The oral CRTh2 antagonist QAW039 (fevipiprant): A phase II study in uncontrolled allergic asthma. Pulm Pharmacol Ther. 2016 Aug;39:54-63. doi: 10.1016/j.pupt.2016.06.005. Epub 2016 Jun 21. PubMed PMID: 27354118.
3. Luu VT, Goujon JY, Meisterhans C, Frommherz M, Bauer C. Synthesis of a high specific activity methyl sulfone tritium isotopologue of fevipiprant (NVP-QAW039). J Labelled Comp Radiopharm. 2015 May 15;58(5):188-95. doi: 10.1002/jlcr.3281. Epub 2015 Apr 16. PubMed PMID: 25881897.

Products are for research use only. Not for human use.