Gefapixant citrateProduct ingredient for Gefapixant
- Name
- Gefapixant citrate
- Drug Entry
- Gefapixant
It has been estimated that 5-10% of adults globally suffer from chronic cough, which is defined as a cough lasting longer than eight weeks.4 A subset of these patients remain symptomatic despite thorough investigation and treatment, termed refractory chronic cough (RCC) if they have a cough that does not respond to conventional treatment or unexplained chronic cough (UCC) when no diagnosable cause for the cough can be determined.3 Existing treatments for chronic cough have been associated with considerable side effects, in particular opioids such as codeine or dextromethorphan.3
Gefapixant is a novel antagonist of the P2X3 receptor that works to reduce the cough reflex in patients with chronic cough. It received approval in both Japan and Switzerland in 2022 for the treatment of adult patients with RCC and UCC, and received subsequent approval in the EU in September 2023 for the same indications.3,2 It is the first therapy to be approved for the treatment of RCC or UCC in the EU.4
- Accession Number
- DBSALT003486
- Structure
Structure for Gefapixant citrate (DBSALT003486)
- Synonyms
- Not Available
- External IDs
- AF-219 citrate / MK-7264 / MK7264
- UNII
- DFK0FC2VVV
- CAS Number
- 2310299-91-1
- Weight
- Average: 545.52
Monoisotopic: 545.142777883 - Chemical Formula
- C20H27N5O11S
- InChI Key
- AIJVJYUOMCRFOE-UHFFFAOYSA-N
- InChI
- InChI=1S/C14H19N5O4S.C6H8O7/c1-7(2)8-4-10(22-3)12(24(17,20)21)5-9(8)23-11-6-18-14(16)19-13(11)15;7-3(8)1-6(13,5(11)12)2-4(9)10/h4-7H,1-3H3,(H2,17,20,21)(H4,15,16,18,19);13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)
- IUPAC Name
- 2-hydroxypropane-1,2,3-tricarboxylic acid; 5-[(2,4-diimino-1,2,3,4-tetrahydropyrimidin-5-yl)oxy]-2-methoxy-4-(propan-2-yl)benzene-1-sulfonamide
- SMILES
- OC(=O)CC(O)(CC(O)=O)C(O)=O.COC1=C(C=C(OC2=CNC(=N)NC2=N)C(=C1)C(C)C)S(N)(=O)=O
- External Links
- ChemSpider
- 81367260
- ChEMBL
- CHEMBL4594278
- Predicted Properties
Property Value Source logP 0.17 Chemaxon pKa (Strongest Acidic) 1.66 Chemaxon pKa (Strongest Basic) 22.64 Chemaxon Physiological Charge 2 Chemaxon Hydrogen Acceptor Count 8 Chemaxon Hydrogen Donor Count 5 Chemaxon Polar Surface Area 150.38 Å2 Chemaxon Rotatable Bond Count 10 Chemaxon Refractivity 109.95 m3·mol-1 Chemaxon Polarizability 34.65 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon