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Fenoprofen

From Wikipedia, the free encyclopedia
NSAID analgesic and anti-inflammatory drug

Pharmaceutical compound
Fenoprofen
Clinical data
Trade namesNalfon
AHFS/Drugs.comMonograph
MedlinePlusa681026
Pregnancy
category
  • C
Routes of
administration
By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
MetabolismMajor urinary metabolites are fenoprofen glucuronide and 4′-hydroxyfenoprofen glucuronide.
Eliminationhalf-life3 hours
ExcretionRenal (~90%)
Identifiers
  • 2-(3-phenoxyphenyl)propanoic acid
CAS Number
PubChemCID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.046.213 100.045.231, 100.046.213Edit this at Wikidata
Chemical and physical data
FormulaC15H14O3
Molar mass242.274 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) checkY
  • Key:RDJGLLICXDHJDY-UHFFFAOYSA-N checkY
  (verify)

Fenoprofen, sold under the brand nameNalfon among others, is anonsteroidal 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.[2] It is available as ageneric medication.[3][4]

Pharmacology

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

Chirality and biological activity

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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 calledchiral inversion.[5][6]

Contraindications

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

Adverse effects

[edit]

In October 2020, the U.S.Food and Drug Administration (FDA) required thedrug 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.[7][8] They recommend avoiding NSAIDs in pregnant women at 20 weeks or later in pregnancy.[7][8]

Drug interactions

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Laboratory test interactions

[edit]

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

Brand names

[edit]

See also

[edit]

References

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  1. ^"FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)".nctr-crs.fda.gov.FDA. Retrieved22 October 2023.
  2. ^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.
  3. ^"2022 First Generic Drug Approvals".U.S.Food and Drug Administration (FDA). 3 March 2023.Archived from the original on 30 June 2023. Retrieved30 June 2023.
  4. ^"Competitive Generic Therapy Approvals".U.S.Food and Drug Administration (FDA). 29 June 2023.Archived from the original on 29 June 2023. Retrieved29 June 2023.
  5. ^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.
  6. ^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.
  7. ^ab"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. Retrieved15 October 2020.Public Domain This article incorporates text from this source, which is in thepublic domain.
  8. ^ab"NSAIDs may cause rare kidney problems in unborn babies".U.S. Food and Drug Administration. 21 July 2017. Retrieved15 October 2020.Public Domain This article incorporates text from this source, which is in thepublic domain.

External links

[edit]
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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