Piketoprofen

Chemical compound
  • M02AA28 (WHO)
Identifiers
  • 2-(3-Benzoylphenyl)-N-(4-methyl-2-pyridyl)propionamide
CAS Number
  • 60576-13-8
PubChem CID
  • 68801
ChemSpider
  • 62038
UNII
  • 362QBC4NL0
KEGG
  • D08374
ChEMBL
  • ChEMBL2106966
CompTox Dashboard (EPA)
  • DTXSID801021570 Edit this at Wikidata
Chemical and physical dataFormulaC22H20N2O2Molar mass344.414 g·mol−13D model (JSmol)
  • Interactive image
  • Cc1ccnc(c1)NC(=O)C(C)c2cccc(c2)C(=O)c3ccccc3
InChI
  • InChI=1S/C22H20N2O2/c1-15-11-12-23-20(13-15)24-22(26)16(2)18-9-6-10-19(14-18)21(25)17-7-4-3-5-8-17/h3-14,16H,1-2H3,(H,23,24,26)
  • Key:ASFKKFRSMGBFRO-UHFFFAOYSA-N

Piketoprofen (INN; trade names Calmatel, Picalm) is a nonsteroidal anti-inflammatory drug (NSAID) for topical use in form of a cream.[1][2]

Chemically, it is the 4-picolineamide of the NSAID ketoprofen.

Synthesis

Thieme ChemDrug Synthesis:[3] Patent:[4]

The halogenation of ketoprofen [22071-15-4] (1) with thionyl chloride gives 2-(3-benzoylphenyl)propanoyl Chloride, PC10912667 (2). Amide formation with 2-amino-4-methylpyridine [695-34-1] (3) completes the synthesis of piketoprofen (4).

References

  1. ^ Fabregas JL, Cucala J, Segura J, Tarrus E (May 1986). "Percutaneous absorption of piketoprofen in rabbits: effect of nonionic surface-active agents". Il Farmaco; Edizione Pratica. 41 (5): 177–83. PMID 3487466.
  2. ^ Burgos A, Busquier MP, Reino JG, Ferreiro JL, Navarro F, Valverde J, Moreno E (2001). "Double-Blind, Double-Dummy Comparative Study of Local Action Transcutaneous Flurbiprofen (Flurbiprofen LAT) versus Piketoprofen Cream in the Treatment of Extra-Articular Rheumatism". Clin Drug Investig. 21 (2): 95–102. doi:10.2165/00044011-200121020-00002. S2CID 56907918.
  3. ^ Spickett, R.G.W. et al, Eur. J. Med. Chem.-Chim. Ther. 1976, 11, 7.
  4. ^ R. G. W. Spickett, et al., GB1436502 (1976 to Antonio Gallardo S A).
Stub icon

This drug article relating to the musculoskeletal system is a stub. You can help Wikipedia by expanding it.

  • v
  • t
  • e