Fenoprofen

Last updated

Fenoprofen
Fenoprofen2DACS.svg
Fenoprofen-3D-balls.png
Clinical data
Trade names Nalfon
AHFS/Drugs.com Monograph
MedlinePlus a681026
Pregnancy
category
  • C
Routes of
administration 		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Metabolism Major urinary metabolites are fenoprofen glucuronide and 4′-hydroxyfenoprofen glucuronide.
Elimination half-life 3 hours
Excretion Renal (~90%)
Identifiers
  • 2-(3-phenoxyphenyl)propanoic acid
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.045.231 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C15H14O3
Molar mass 242.274 g·mol−1
3D model (JSmol)
  • O=C(O)C(c2cc(Oc1ccccc1)ccc2)C
  • InChI=1S/C15H14O3/c1-11(15(16)17)12-6-5-9-14(10-12)18-13-7-3-2-4-8-13/h2-11H,1H3,(H,16,17) Yes check.svgY
  • Key:RDJGLLICXDHJDY-UHFFFAOYSA-N Yes check.svgY
   (verify)

Fenoprofen, sold under the brand name Nalfon among others, is a nonsteroidal anti-inflammatory drug (NSAID). Fenoprofen calcium is used for symptomatic relief for rheumatoid arthritis, osteoarthritis, and mild to moderate pain. It has also been used to treat postoperative pain. [1] It is available as a generic medication. [2] [3]

Contents

Pharmacology

Decreases inflammation, pain, and fever, probably through inhibition of cyclooxygenase (COX-2 inhibitor) activity and prostaglandin synthesis.

Chirality and biological activity

Fenoprofen is chiral drug with one stereogenic center and exists as chiral twins. (S)-enantiomer has the desired pharmacological action where as the (R)-isomer is less active. It is observed that there is stereoselective bioconversion of the (R)- to (S)-fenoprofen. This stereoselective conversion is called chiral inversion. [4] [5]

Contraindications

History of significantly impaired renal function; patients with known hypersensitivity to any component of the product; patients who have experienced asthma, urticaria, or allergic-type reactions after taking aspirin or other NSAIDs; treatment of perioperative pain in the setting of coronary artery bypass graft (CABG) surgery.

Adverse effects

In October 2020, the U.S. Food and Drug Administration (FDA) required the drug label to be updated for all nonsteroidal anti-inflammatory medications to describe the risk of kidney problems in unborn babies that result in low amniotic fluid. [6] [7] They recommend avoiding NSAIDs in pregnant women at 20 weeks or later in pregnancy. [6] [7]

Drug interactions

Laboratory test interactions

False elevation in free and total serum T 3 as measured by Amerlex-M kit.[ medical citation needed ]

Brand names

See also

Related Research Articles

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References

  1. ↑ Traa MX, Derry S, Moore RA (February 2011). "Single dose oral fenoprofen for acute postoperative pain in adults". The Cochrane Database of Systematic Reviews. 2011 (2): CD007556. doi:10.1002/14651858.CD007556.pub2. PMC   4171001 . PMID   21328296.
  2. ↑ "2022 First Generic Drug Approvals". U.S. Food and Drug Administration (FDA). 3 March 2023. Archived from the original on 30 June 2023. Retrieved 30 June 2023.
  3. ↑ "Competitive Generic Therapy Approvals". U.S. Food and Drug Administration (FDA). 29 June 2023. Archived from the original on 29 June 2023. Retrieved 29 June 2023.
  4. ↑ Rubin A, Knadler MP, Ho PP, Bechtol LD, Wolen RL (January 1985). "Stereoselective inversion of (R)-fenoprofen to (S)-fenoprofen in humans". Journal of Pharmaceutical Sciences. 74 (1): 82–84. doi:10.1002/jps.2600740122. PMID   3920382.
  5. ↑ Caldwell J, Hutt AJ, Fournel-Gigleux S (January 1988). "The metabolic chiral inversion and dispositional enantioselectivity of the 2-arylpropionic acids and their biological consequences". Biochemical Pharmacology. 37 (1): 105–114. doi:10.1016/0006-2952(88)90762-9. PMID   3276314.
  6. 1 2 "FDA Warns that Using a Type of Pain and Fever Medication in Second Half of Pregnancy Could Lead to Complications". U.S. Food and Drug Administration (FDA) (Press release). 15 October 2020. Retrieved 15 October 2020.PD-icon.svg This article incorporates text from this source, which is in the public domain .
  7. 1 2 "NSAIDs may cause rare kidney problems in unborn babies". U.S. Food and Drug Administration. 21 July 2017. Retrieved 15 October 2020.PD-icon.svg This article incorporates text from this source, which is in the public domain .
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