Piketoprofen

Piketoprofen
Clinical data
Trade namesCalmatel, Picalm
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Topical (cream)
ATC code
Identifiers
  • 2-(3-Benzoylphenyl)-N-(4-methyl-2-pyridyl)propionamide
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC22H20N2O2
Molar mass344.414 g·mol−1
3D model (JSmol)
  • Cc1ccnc(c1)NC(=O)C(C)c2cccc(c2)C(=O)c3ccccc3
  • 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

Thionyl chloride reacts with ketoprofen to form its acid chloride (2). Amide formation with 2-amino-4-methylpyridine (3) gives piketoprofen.[3][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. ^ GB patent 1436502, Spickett, R.G.W; Noverola, A.V; Soto, J.P, "Amide derivatives of 3-benzoyl-phemylalkanoic acids", issued 1976-05-19, assigned to Antonio Gallardo S A 
  4. ^ "Piketoprofen". Thieme. Retrieved 2024-07-02.
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