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Vedaprofen

From Wikipedia, the free encyclopedia
NSAID analgesic veterinary drug

Vedaprofen
Names
IUPAC name
2-(4-Cyclohexyl-1-naphthyl)propanoic acid
Other names
Quadrisol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard100.068.339Edit this at Wikidata
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 mass282.383 g·mol−1
Pharmacology
QM01AE90 (WHO)
Legal status
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Vedaprofen is anonsteroidal anti-inflammatory drug (NSAID) used inveterinary medicine for the treatment of pain and inflammation due to musculoskeletal disorders in dogs and horses and for the treatment of pain due tohorse colic.[4] It is a member of theprofen drug class.

Medical uses

[edit]

Vedaprofen isindicated for the reduction of inflammation and relief of pain associated with musculo-skeletal disorders and soft tissue lesions (traumatic injuries and surgical trauma).[1][2]

Synthesis

[edit]

Vedaprofen can be synthesized beginning with 1-cyclohexylnaphthylene (left).[5][6] Chloromethylation followed by functional group interconversion provides the ester (center right).Alkylation withmethyl iodide then gives vedaprofen (right).

Vedaprofen synthesis:

Society and culture

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Legal status

[edit]

Vedaprofen was approved for veterinary use in the European Union in April 1997.[1][2]

References

[edit]
  1. ^abc"Quadrisol EPAR".European Medicines Agency (EMA). 4 December 1997. Retrieved26 December 2024.
  2. ^abc"Vedaprofen PI".Union Register of medicinal products. 5 December 1997. Retrieved26 December 2024.
  3. ^"Quadrisol 100 mg/ml".European Medicines Agency (EMA). 3 December 1997. Retrieved26 December 2024.
  4. ^"Specific Nonsteroidal Anti-inflammatory Drugs".Merck Veterinary Manual. Merck Sharp & Dohme Corp. Archived fromthe original on 5 April 2016. Retrieved18 April 2012.
  5. ^BE 870553 
  6. ^U.S. patent 4,218,473
pyrazolones /
pyrazolidines
salicylates
acetic acid derivatives
and related substances
oxicams
propionic acid
derivatives (profens)
n-arylanthranilic
acids (fenamates)
COX-2 inhibitors
(coxibs)
other
NSAID
combinations
Key:underline indicates initially developed first-in-class compound of specific group;#WHO-Essential Medicines;withdrawn drugs;veterinary use.
Receptor
(ligands)
DP (D2)Tooltip Prostaglandin D2 receptor
DP1Tooltip Prostaglandin D2 receptor 1
DP2Tooltip Prostaglandin D2 receptor 2
EP (E2)Tooltip Prostaglandin E2 receptor
EP1Tooltip Prostaglandin EP1 receptor
EP2Tooltip Prostaglandin EP2 receptor
EP3Tooltip Prostaglandin EP3 receptor
EP4Tooltip Prostaglandin EP4 receptor
Unsorted
FP (F)Tooltip Prostaglandin F receptor
IP (I2)Tooltip Prostacyclin receptor
TP (TXA2)Tooltip Thromboxane receptor
Unsorted
Enzyme
(inhibitors)
COX
(
PTGS)
PGD2STooltip Prostaglandin D synthase
PGESTooltip Prostaglandin E synthase
PGFSTooltip Prostaglandin F synthase
PGI2STooltip Prostacyclin synthase
TXASTooltip Thromboxane A synthase
Others
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