Vedaprofen

Last updated
Vedaprofen
Vedaprofen.svg
Names
IUPAC name
2-(4-Cyclohexyl-1-naphthyl)propanoic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.068.339 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • 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-N
  • InChI=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
  • O=C(O)C(c2ccc(c1ccccc12)C3CCCCC3)C
Properties
C19H22O2
Molar mass 282.383 g·mol−1
Pharmacology
QM01AE90 ( WHO )
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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.

Synthesis

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: Vedaprofen synthesis.png
Vedaprofen synthesis:

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References

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