Piketoprofen

Piketoprofen
Clinical data
Trade names	Calmatel, Picalm
AHFS/Drugs.com	International Drug Names
Routes of; administration	Topical (cream)
ATC code	M02AA28 (WHO) ;
Identifiers
	IUPAC name 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 ;
Chemical and physical data
Formula	C22H20N2O2
Molar mass	344.414 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES 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

Thionyl chloride reacts with ketoprofen to form its acid chloride (2). Amide formation with 2-amino-4-methylpyridine (3) gives piketoprofen.^[3]^[4]

^ 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.
^ 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.
^ 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
^ "Piketoprofen". Thieme. Retrieved 2024-07-02.