Fevipiprant | QAW 039 | CAS#872365-14-5 | CRTh2 receptor antagonist

MedKoo Cat#: 319671 | Name: Fevipiprant

Description:

WARNING: This product is for research use only, not for human or veterinary use.

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.

Chemical Structure

Fevipiprant

CAS#872365-14-5

Theoretical Analysis

MedKoo Cat#: 319671

Name: Fevipiprant

CAS#: 872365-14-5

Chemical Formula: C19H17F3N2O4S

Exact Mass: 426.0861

Molecular Weight: 426.41

Elemental Analysis: C, 53.52; H, 4.02; F, 13.37; N, 6.57; O, 15.01; S, 7.52

Price and Availability

Size	Price	Availability
10mg	USD 90.00	Ready to ship
25mg	USD 150.00	Ready to ship
50mg	USD 250.00	Ready to ship
100mg	USD 450.00	Ready to ship
200mg	USD 750.00	Ready to ship
500mg	USD 1,550.00	Ready to ship
1g	USD 2,250.00	Ready to ship
2g	USD 3,850.00	Ready to ship

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Related CAS #

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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

Appearance

White to off-white solid powder

Purity

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

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).

HS Tariff Code

2934.99.9001

More Info

Certificate of Analysis

View CoA: current batch, Lot#SSC61026

View CoA: current batch, Lot#S21S02B08

QC Data

View QC data: current batch, Lot#SSC61026

View QC data: current batch, Lot#S21S02B08

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

	Solvent	mg/mL	mM
Solubility
	Soluble in DMSO, not in water	0.0	100.00

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 426.41 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: White C, Wright A, Brightling C. Fevipiprant in the treatment of asthma. Expert Opin Investig Drugs. 2018 Feb;27(2):199-207. doi: 10.1080/13543784.2018.1432592. Epub 2018 Jan 30. PMID: 29363343. 2: Jahangir A, Sattar SBA, Rafay Khan Niazi M, Muhammad M, Jahangir A, Sahra S, Sharif MA, Anwar MY, Chalhoub M. Efficacy and Safety of Fevipiprant in Asthma: A Review and Meta-Analysis. Cureus. 2022 May 1;14(5):e24641. doi: 10.7759/cureus.24641. PMID: 35663651; PMCID: PMC9153206. 3: Kao CC, Parulekar AD. Spotlight on fevipiprant and its potential in the treatment of asthma: evidence to date. J Asthma Allergy. 2019 Jan 3;12:1-5. doi: 10.2147/JAA.S167973. PMID: 30662272; PMCID: PMC6324611. 4: Brightling C, Kulkarni S, Lambrecht BN, Sandham D, Weiss M, Altman P. The pharmacology of the prostaglandin D2 receptor 2 (DP2) receptor antagonist, fevipiprant. Pulm Pharmacol Ther. 2021 Jun;68:102030. doi: 10.1016/j.pupt.2021.102030. Epub 2021 Apr 4. PMID: 33826946. 5: Cahill KN. Fevipiprant in CRSwNP and comorbid asthma: Wrong target population or wrong PGD2 receptor? J Allergy Clin Immunol. 2022 May;149(5):1587-1589. doi: 10.1016/j.jaci.2022.03.001. Epub 2022 Mar 15. PMID: 35304159. 6: Brightling CE, Gaga M, Inoue H, Li J, Maspero J, Wenzel S, Maitra S, Lawrence D, Brockhaus F, Lehmann T, Brindicci C, Knorr B, Bleecker ER. Effectiveness of fevipiprant in reducing exacerbations in patients with severe asthma (LUSTER-1 and LUSTER-2): two phase 3 randomised controlled trials. Lancet Respir Med. 2021 Jan;9(1):43-56. doi: 10.1016/S2213-2600(20)30412-4. Epub 2020 Sep 24. PMID: 32979986. 7: Pelaia C, Crimi C, Vatrella A, Busceti MT, Gaudio A, Garofalo E, Bruni A, Terracciano R, Pelaia G. New treatments for asthma: From the pathogenic role of prostaglandin D2 to the therapeutic effects of fevipiprant. Pharmacol Res. 2020 May;155:104490. doi: 10.1016/j.phrs.2019.104490. Epub 2019 Nov 1. PMID: 31682916. 8: Yang D, Guo X, Liu T, Li Y, Du Z, Liu C. Efficacy and Safety of Prostaglandin D2 Receptor 2 Antagonism with Fevipiprant for Patients with Asthma: a Systematic Review and Meta-analysis of Randomized Controlled Trials. Curr Allergy Asthma Rep. 2021 Aug 13;21(7):39. doi: 10.1007/s11882-021-01017-8. PMID: 34387775. 9: Poller B, Woessner R, Barve A, Tillmann HC, Vemula J, Nica A, Elbast W, Schiller H, End P, Camenisch G, Weiss M. Fevipiprant has a low risk of influencing co-medication pharmacokinetics: Impact on simvastatin and rosuvastatin in different SLCO1B1 genotypes. Pulm Pharmacol Ther. 2019 Aug;57:101809. doi: 10.1016/j.pupt.2019.101809. Epub 2019 Jun 10. PMID: 31195091. 10: Kulkarni S, Poller B, Drollmann A, Shah B, Gray C, Greco E, Rahmanzadeh G, Hanna I, Weiss HM. Fevipiprant (QAW039) does not affect the pharmacokinetics of zidovudine, its glucuronide, and penicillin G via inhibition of UGT2B7 and/or OAT3. Pulm Pharmacol Ther. 2022 Feb;72:102097. doi: 10.1016/j.pupt.2021.102097. Epub 2021 Nov 17. PMID: 34800680. 11: Gevaert P, Bachert C, Maspero JF, Cuevas M, Steele D, Acharya S, Altman P. Phase 3b randomized controlled trial of fevipiprant in patients with nasal polyposis with asthma (THUNDER). J Allergy Clin Immunol. 2022 May;149(5):1675-1682.e3. doi: 10.1016/j.jaci.2021.12.759. Epub 2022 Jan 29. PMID: 35094848. 12: Shamri R, Dubois G, Erpenbeck VJ, Mankuta D, Sandham DA, Levi-Schaffer F. Fevipiprant, a DP2 receptor antagonist, inhibits eosinophil migration towards mast cells. Clin Exp Allergy. 2019 Feb;49(2):255-257. doi: 10.1111/cea.13304. Epub 2018 Nov 25. PMID: 30379368. 13: Weiss HM, Umehara KI, Erpenbeck VJ, Cain M, Vemula J, Elbast W, Zollinger M. A Study of the Effect of Cyclosporine on Fevipiprant Pharmacokinetics and its Absolute Bioavailability Using an Intravenous Microdose Approach. Drug Metab Dispos. 2020 Oct;48(10):917-924. doi: 10.1124/dmd.120.090852. Epub 2020 Aug 1. PMID: 32739890. 14: Bateman ED, Guerreros AG, Brockhaus F, Holzhauer B, Pethe A, Kay RA, Townley RG. Fevipiprant, an oral prostaglandin DP2 receptor (CRTh2) antagonist, in allergic asthma uncontrolled on low-dose inhaled corticosteroids. Eur Respir J. 2017 Aug 24;50(2):1700670. doi: 10.1183/13993003.00670-2017. PMID: 28838980. 15: Gonem S, Berair R, Singapuri A, Hartley R, Laurencin MFM, Bacher G, Holzhauer B, Bourne M, Mistry V, Pavord ID, Mansur AH, Wardlaw AJ, Siddiqui SH, Kay RA, Brightling CE. Fevipiprant, a prostaglandin D2 receptor 2 antagonist, in patients with persistent eosinophilic asthma: a single-centre, randomised, double-blind, parallel-group, placebo-controlled trial. Lancet Respir Med. 2016 Sep;4(9):699-707. doi: 10.1016/S2213-2600(16)30179-5. Epub 2016 Aug 5. PMID: 27503237. 16: Maspero J, Agache IO, Kamei T, Yoshida M, Boone B, Felser JM, Kawakami F, Knorr B, Lawrence D, Lehmann T, Wang W, Pedinoff AJ. Long-term safety and exploratory efficacy of fevipiprant in patients with inadequately controlled asthma: the SPIRIT randomised clinical trial. Respir Res. 2021 Dec 11;22(1):311. doi: 10.1186/s12931-021-01904-8. PMID: 34895218; PMCID: PMC8666007. 17: Hardman C, Chen W, Luo J, Batty P, Chen YL, Nahler J, Wu Y, Pavord ID, Erpenbeck VJ, Sandham DA, Xue L, Ogg G. Fevipiprant, a selective prostaglandin D2 receptor 2 antagonist, inhibits human group 2 innate lymphoid cell aggregation and function. J Allergy Clin Immunol. 2019 Jun;143(6):2329-2333. doi: 10.1016/j.jaci.2019.02.015. Epub 2019 Feb 28. PMID: 30825466. 18: Castro M, Kerwin E, Miller D, Pedinoff A, Sher L, Cardenas P, Knorr B, Lawrence D, Ossa D, Wang W, Maspero JF. Efficacy and safety of fevipiprant in patients with uncontrolled asthma: Two replicate, phase 3, randomised, double- blind, placebo-controlled trials (ZEAL-1 and ZEAL-2). EClinicalMedicine. 2021 Apr 25;35:100847. doi: 10.1016/j.eclinm.2021.100847. PMID: 33997741; PMCID: PMC8099656. 19: Murillo JC, Dimov V, Gonzalez-Estrada A. An evaluation of fevipiprant for the treatment of asthma: a promising new therapy? Expert Opin Pharmacother. 2018 Dec;19(18):2087-2093. doi: 10.1080/14656566.2018.1540589. Epub 2018 Nov 3. PMID: 30394155. 20: Weiss HM, Langenickel T, Cain M, Kulkarni S, Shah B, Vemula J, Rahmanzadeh G, Poller B. Clinical Investigation of Metabolic and Renal Clearance Pathways Contributing to the Elimination of Fevipiprant Using Probenecid as Perpetrator. Drug Metab Dispos. 2021 May;49(5):389-394. doi: 10.1124/dmd.120.000273. Epub 2021 Feb 25. PMID: 33632715.

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