Fevipiprant
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MedKoo CAT#: 319671

CAS#: 872365-14-5

Description: 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.


Price and Availability

Size
Price

10mg
USD 90
100mg
USD 450
1g
USD 2250
Size
Price

25mg
USD 150
200mg
USD 750
2g
USD 3850
Size
Price

50mg
USD 250
500mg
USD 1550
5g
Ask price

Fevipiprant, purity > 98%, is in stock. The same day shipping out after order is received. Note: the estimated shipping out time for order > 5g may be 2 weeks.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 319671
Name: Fevipiprant
CAS#: 872365-14-5
Chemical Formula: C19H17F3N2O4S
Exact Mass: 426.0861
Molecular Weight: 426.4102
Elemental Analysis: C, 53.52; H, 4.02; F, 13.37; N, 6.57; O, 15.01; S, 7.52


Synonym: NVP-QAW039; NVP-QAW 039; NVP-QAW-039 QAW-039; QAW039; QAW 039; Fevipiprant

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

InChi Key: GFPPXZDRVCSVNR-UHFFFAOYSA-N

InChi Code: 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)

SMILES Code: O=C(O)CC1=C(C)N(CC2=CC=C(S(=O)(C)=O)C=C2C(F)(F)F)C3=NC=CC=C31


Technical Data

Appearance:
White to off-white solid powder

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

Certificate of Analysis:

Safety Data Sheet (MSDS):

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO, not in water

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


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: Erpenbeck VJ, Vets E, Gheyle L, Osuntokun W, Larbig M, Neelakantham S, Sandham D, Dubois G, Elbast W, Goldsmith P, Weiss M. Pharmacokinetics, Safety, and Tolerability of Fevipiprant (QAW039), a Novel CRTh2 Receptor Antagonist: Results From 2 Randomized, Phase 1, Placebo-Controlled Studies in Healthy Volunteers. Clin Pharmacol Drug Dev. 2016 Jul;5(4):306-13. doi: 10.1002/cpdd.244. Epub 2016 Mar 28. PubMed PMID: 27310331.

4: Sykes DA, Bradley ME, Riddy DM, Willard E, Reilly J, Miah A, Bauer C, Watson SJ, Sandham DA, Dubois G, Charlton SJ. Fevipiprant (QAW039), a Slowly Dissociating CRTh2 Antagonist with the Potential for Improved Clinical Efficacy. Mol Pharmacol. 2016 May;89(5):593-605. doi: 10.1124/mol.115.101832. Epub 2016 Feb 25. PubMed PMID: 26916831.

5: 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.