Vedaprofen (original) (raw)

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NSAID analgesic veterinary drug

Vedaprofen
Names
IUPAC name 2-(4-Cyclohexyl-1-naphthyl)propanoic acid
Identifiers
CAS Number 71109-09-6 checkY
3D model (JSmol) Interactive image
ChEBI CHEBI:32292
ChEMBL ChEMBL2104464
ChemSpider 65131
ECHA InfoCard 100.068.339 Edit this at Wikidata
PubChem CID 72158
UNII OKX88EO7OI checkY
CompTox Dashboard (EPA) DTXSID5049077 Edit this at Wikidata
InChI InChI=1S/C19H22O2/c1-13(19(20)21)15-11-12-16(14-7-3-2-4-8-14)18-10-6-5-9-17(15)18/h5-6,9-14H,2-4,7-8H2,1H3,(H,20,21)Key: VZUGVMQFWFVFBX-UHFFFAOYSA-NInChI=1/C19H22O2/c1-13(19(20)21)15-11-12-16(14-7-3-2-4-8-14)18-10-6-5-9-17(15)18/h5-6,9-14H,2-4,7-8H2,1H3,(H,20,21)Key: VZUGVMQFWFVFBX-UHFFFAOYAU
SMILES O=C(O)C(c2ccc(c1ccccc12)C3CCCCC3)C
Properties
Chemical formula C19H22O2
Molar mass 282.383 g·mol−1
Pharmacology
ATCvet code QM01AE90 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Chemical compound

Vedaprofen is a nonsteroidal anti-inflammatory drug (NSAID) used in veterinary medicine for the treatment of pain and inflammation due to musculoskeletal disorders in dogs and horses and for the treatment of pain due to horse colic.[1] It is a member of the profen drug class.

Vedaprofen can be synthesized beginning with 1-cyclohexylnaphthylene (left).[2][3] Chloromethylation followed by functional group interconversion provides the ester (center right). Alkylation with methyl iodide then gives vedaprofen (right).

Vedaprofen synthesis:

  1. ^ "Specific Nonsteroidal Anti-inflammatory Drugs". Merck Veterinary Manual. Merck Sharp & Dohme Corp.
  2. ^ BE 870553
  3. ^ U.S. patent 4,218,473