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

| alt =

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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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| 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

{{reflist}}

{{Topical products for joint and muscular pain}}

Category:Nonsteroidal anti-inflammatory drugs

Category:Benzophenones

Category:Propionamides

Category:Pyridines

{{musculoskeletal-drug-stub}}