Piketoprofen

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

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

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]