Fevipiprant

Fevipiprant
Clinical data
Routes of; administration	Oral
ATC code	none;
Legal status
Legal status	Investigational;
Pharmacokinetic data
Bioavailability	Unaffected by food
Metabolism	Hepatic glucuronidation
Elimination half-life	~20 hours
Excretion	Renal (≤30%)
Identifiers
	IUPAC name {2-methyl-1-[4-(methylsulfonyl)-2-(trifluoromethyl)benzyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}acetic acid;
CAS Number	872365-14-5;
PubChem CID	23582412;
ChemSpider	23582412;
UNII	2PEX5N7DQ4;
KEGG	D10631;
CompTox Dashboard (EPA)	DTXSID501336031 ;
ECHA InfoCard	100.243.911
Chemical and physical data
Formula	C19H17F3N2O4S
Molar mass	426.41 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC1=C(C2=C(N1CC3=C(C=C(C=C3)S(=O)(=O)C)C(F)(F)F)N=CC=C2)CC(=O)O;
	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); Key:GFPPXZDRVCSVNR-UHFFFAOYSA-N;

Fevipiprant (INN; code name QAW039) is a drug being developed by Novartis which acts as a selective, orally available antagonist of the prostaglandin D₂ receptor 2 (DP₂ or CRTh2).^[1]^[2]^[3]

As of 2016^[update], it is in phase III^[4] clinical trials for the treatment of asthma.^[5]

On Monday, December 16, 2019, Switzerland-based Novartis officially announced that it was jettisoning fevipiprant from its development program, given that the medicine has failed in two additional clinical trials in patients with moderate-to-severe asthma. The firm said that it had hoped fevipiprant would be a billion-dollar-selling asthma drug.^[6]

References

^ ^a ^b Erpenbeck VJ, Vets E, Gheyle L, Osuntokun W, Larbig M, Neelakantham S, et al. (2016). "Pharmacokinetics, Safety, and Tolerability of Fevipiprant (QAW039), a Novel CRTh2 Receptor Antagonist: Results From 2 Randomized, Phase 1, Placebo-Controlled Studies in Healthy Volunteers". Clinical Pharmacology in Drug Development. 5 (4): 306–13. doi:10.1002/cpdd.244. PMC 5071756. PMID 27310331.
^ Sykes DA, Bradley ME, Riddy DM, Willard E, Reilly J, Miah A, Bauer C, Watson SJ, Sandham DA, Dubois G, Charlton SJ (May 2016). "Fevipiprant (QAW039), a Slowly Dissociating CRTh2 Antagonist with the Potential for Improved Clinical Efficacy". Mol Pharmacol. 89 (5): 593–605. doi:10.1124/mol.115.101832. PMID 26916831.
^ Erpenbeck VJ, Popov TA, Miller D, Weinstein SF, Spector S, Magnusson B, et al. (2016). "The oral CRTh2 antagonist QAW039 (fevipiprant): A phase II study in uncontrolled allergic asthma". Pulm Pharmacol Ther. 39: 54–63. doi:10.1016/j.pupt.2016.06.005. PMID 27354118.
^ https://clinicaltrials.gov/ct2/show/NCT02555683
^ Gonem S, Berair R, Singapuri A, Hartley R, Laurencin M, Bacher G, et al. (2016). "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. 4 (9): 699–707. doi:10.1016/S2213-2600(16)30179-5. hdl:2381/38430. PMID 27503237.
^ Novartis drops asthma drug fevipiprant after trial failures. Reuters News. https://www.reuters.com/article/us-novartis-asthma/novartis-drops-asthma-drug-fevipiprant-after-trial-failures-idUSKBN1YK0DR - Accessed Sunday, December 15, 2019, from North America.

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[pmid27310331-1] Erpenbeck VJ, Vets E, Gheyle L, Osuntokun W, Larbig M, Neelakantham S, et al. (2016). "Pharmacokinetics, Safety, and Tolerability of Fevipiprant (QAW039), a Novel CRTh2 Receptor Antagonist: Results From 2 Randomized, Phase 1, Placebo-Controlled Studies in Healthy Volunteers". Clinical Pharmacology in Drug Development. 5 (4): 306–13. doi:10.1002/cpdd.244. PMC 5071756. PMID 27310331.

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

[pmid27354118-3] Erpenbeck VJ, Popov TA, Miller D, Weinstein SF, Spector S, Magnusson B, et al. (2016). "The oral CRTh2 antagonist QAW039 (fevipiprant): A phase II study in uncontrolled allergic asthma". Pulm Pharmacol Ther. 39: 54–63. doi:10.1016/j.pupt.2016.06.005. PMID 27354118.

[4] ttps://clinicaltrials.gov/ct2/show/NCT02555683

[5] Gonem S, Berair R, Singapuri A, Hartley R, Laurencin M, Bacher G, et al. (2016). "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. 4 (9): 699–707. doi:10.1016/S2213-2600(16)30179-5. hdl:2381/38430. PMID 27503237.

[6] Novartis drops asthma drug fevipiprant after trial failures. Reuters News. https://www.reuters.com/article/us-novartis-asthma/novartis-drops-asthma-drug-fevipiprant-after-trial-failures-idUSKBN1YK0DR - Accessed Sunday, December 15, 2019, from North America.

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See also

References