piketoprofen
{{Short description|Chemical compound}}
{{Infobox drug
| IUPAC_name = 2-(3-Benzoylphenyl)-N-(4-methyl-2-pyridyl)propionamide
| image = Piketoprofen skeletal.svg
| image_class = skin-invert-image
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| pronounce =
| tradename = Calmatel, Picalm
| Drugs.com = {{drugs.com|international|piketoprofen}}
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| routes_of_administration = Topical (cream)
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| protein_bound =
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| CAS_number = 60576-13-8
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| ATCvet =
| ATC_prefix = M02
| ATC_suffix = AA28
| PubChem = 68801
| DrugBank =
| ChemSpiderID = 62038
| UNII = 362QBC4NL0
| KEGG = D08374
| ChEMBL = 2106966
| chemical_formula =
| C=22 | H=20 | N=2 | O=2
| smiles = Cc1ccnc(c1)NC(=O)C(C)c2cccc(c2)C(=O)c3ccccc3
| StdInChI=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)
| StdInChIKey = ASFKKFRSMGBFRO-UHFFFAOYSA-N
}}
Piketoprofen (INN; trade names Calmatel, Picalm) is a nonsteroidal anti-inflammatory drug (NSAID) for topical use in form of a cream.{{cite journal | vauthors = Fabregas JL, Cucala J, Segura J, Tarrus E | title = Percutaneous absorption of piketoprofen in rabbits: effect of nonionic surface-active agents | journal = Il Farmaco; Edizione Pratica | volume = 41 | issue = 5 | pages = 177–83 | date = May 1986 | pmid = 3487466 }}{{cite journal | vauthors = Burgos A, Busquier MP, Reino JG, Ferreiro JL, Navarro F, Valverde J, Moreno E |s2cid=56907918 |title=Double-Blind, Double-Dummy Comparative Study of Local Action Transcutaneous Flurbiprofen (Flurbiprofen LAT) versus Piketoprofen Cream in the Treatment of Extra-Articular Rheumatism |journal=Clin Drug Investig |year=2001 |volume=21 |issue=2 |pages=95–102 |doi=10.2165/00044011-200121020-00002 }}
Chemically, it is the 4-picolineamide of the NSAID ketoprofen.
Synthesis
:File:Piketoprofen synthesis.svg
Thionyl chloride reacts with ketoprofen to form its acid chloride (2). Amide formation with 2-amino-4-methylpyridine (3) gives piketoprofen.{{cite patent |country=GB |number=1436502 |status=patent |gdate=1976-05-19 |fdate=1974-10-04 |pridate=1973-10-04 |inventor=Spickett, R.G.W; Noverola, A.V; Soto, J.P |title=Amide derivatives of 3-benzoyl-phemylalkanoic acids |assign1=Antonio Gallardo S A }}{{cite web |url=https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-16-0098 |title=Piketoprofen |publisher=Thieme |access-date=2024-07-02}}
References
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{{Topical products for joint and muscular pain}}
Category:Nonsteroidal anti-inflammatory drugs
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