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{{Short description|NSAID analgesic and anti-inflammatory drug}} |
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{{drugbox |
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{{Use dmy dates|date=November 2022}} |
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| Verifiedfields = changed |
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{{Drugbox |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| Watchedfields = changed |
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| UNII = RA33EAC7KY |
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| verifiedrevid = 413970229 |
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| verifiedrevid = 443756471 |
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| IUPAC_name = 2-(3-phenoxyphenyl)propanoic acid |
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| IUPAC_name = 2-(3-phenoxyphenyl)propanoic acid |
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| image = fenoprofen.png |
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| image = fenoprofen2DACS.svg |
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| image2 = Fenoprofen-3D-balls.png |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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<!--Clinical data--> |
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| tradename = Nalfon |
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| Drugs.com = {{drugs.com|monograph|fenoprofen-calcium}} |
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| MedlinePlus = a681026 |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_US = D |
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| pregnancy_category = C |
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> |
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| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_UK = POM |
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| legal_US = Rx-only |
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| legal_status = |
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| routes_of_administration = ] |
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<!--Pharmacokinetic data--> |
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| bioavailability = |
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| protein_bound = |
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| metabolism = Major urinary metabolites are fenoprofen glucuronide and 4′-hydroxyfenoprofen glucuronide. |
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| elimination_half-life = 3 hours |
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| excretion = ] (~90%) |
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<!--Identifiers--> |
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| IUPHAR_ligand = 4820 |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 29679-58-1 |
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| ATC_prefix = M01 |
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| ATC_suffix = AE04 |
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| PubChem = 3342 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = DB00573 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 3225 |
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| ChemSpiderID = 3225 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| InChI = 1/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) |
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| UNII = RA33EAC7KY |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D02350 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 5004 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 1297 |
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<!--Chemical data--> |
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| C=15 | H=14 | O=3 |
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| smiles = O=C(O)C(c2cc(Oc1ccccc1)ccc2)C |
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| smiles = O=C(O)C(c2cc(Oc1ccccc1)ccc2)C |
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| InChIKey = RDJGLLICXDHJDY-UHFFFAOYAH |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 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) |
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| StdInChI = 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) |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = RDJGLLICXDHJDY-UHFFFAOYSA-N |
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| StdInChIKey = RDJGLLICXDHJDY-UHFFFAOYSA-N |
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| CAS_number = 29679-58-1 |
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| ATC_prefix = M01 |
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| ATC_suffix = AE04 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 1297 |
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| ChEBI = 5004 |
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| PubChem = 3342 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = DB00573 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D02350 |
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| C=15|H=14|O=3 |
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| molecular_weight = 242.26986 g/mol |
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| bioavailability = |
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| protein_bound = |
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| metabolism = Major urinary metabolites are fenoprofen glucuronide and 4′-hydroxyfenoprofen glucuronide. |
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| elimination_half-life = 3 hours |
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<!-- | V<sub>d</sub>(l/kg)= 0.10 --> |
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| excretion = ] (~90%) |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| pregnancy_category= C |
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> |
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| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_UK = POM |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| legal_status = |
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| routes_of_administration = Oral |
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}} |
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}} |
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'''Fenoprofen''', sold under the brand name '''Nalfon''' among others, is a ] (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.<ref name="Traa_2011">{{cite journal | vauthors = Traa MX, Derry S, Moore RA | title = Single dose oral fenoprofen for acute postoperative pain in adults | journal = The Cochrane Database of Systematic Reviews | volume = 2011 | issue = 2 | pages = CD007556 | date = February 2011 | pmid = 21328296 | pmc = 4171001 | doi = 10.1002/14651858.CD007556.pub2 }}</ref> It is available as a ].<ref>{{cite web | title=2022 First Generic Drug Approvals | website=U.S. ] (FDA) | date=3 March 2023 | url=https://www.fda.gov/drugs/drug-and-biologic-approval-and-ind-activity-reports/2022-first-generic-drug-approvals | archive-url=https://web.archive.org/web/20230630003602/https://www.fda.gov/drugs/drug-and-biologic-approval-and-ind-activity-reports/2022-first-generic-drug-approvals | archive-date=30 June 2023 | url-status=live | access-date=30 June 2023}}</ref><ref>{{cite web | title=Competitive Generic Therapy Approvals | website=U.S. ] (FDA) | date=29 June 2023 | url=https://www.fda.gov/drugs/generic-drugs/competitive-generic-therapy-approvals | access-date=29 June 2023 | archive-date=29 June 2023 | archive-url=https://web.archive.org/web/20230629233651/https://www.fda.gov/drugs/generic-drugs/competitive-generic-therapy-approvals | url-status=live }}</ref> |
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'''Fenoprofen''' is a ]. Fenoprofen calcium is used for symptomatic relief for rheumatoid arthritis, osteoarthritis, and mild to moderate pain. Fenoprofen is marketed in the USA as Nalfon. |
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==Pharmacology== |
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==Pharmacology== |
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Decreases inflammation, pain, and fever, probably through inhibition of cyclooxygenase activity and prostaglandin synthesis. |
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Decreases inflammation, pain, and fever, probably through inhibition of cyclooxygenase (]) activity and prostaglandin synthesis. |
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=== 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 called ].<ref>{{cite journal | vauthors = Rubin A, Knadler MP, Ho PP, Bechtol LD, Wolen RL | title = Stereoselective inversion of (R)-fenoprofen to (S)-fenoprofen in humans | journal = Journal of Pharmaceutical Sciences | volume = 74 | issue = 1 | pages = 82–84 | date = January 1985 | pmid = 3920382 | doi = 10.1002/jps.2600740122 }}</ref><ref>{{cite journal | vauthors = Caldwell J, Hutt AJ, Fournel-Gigleux S | title = The metabolic chiral inversion and dispositional enantioselectivity of the 2-arylpropionic acids and their biological consequences | journal = Biochemical Pharmacology | volume = 37 | issue = 1 | pages = 105–114 | date = January 1988 | pmid = 3276314 | doi = 10.1016/0006-2952(88)90762-9 }}</ref> |
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==Contraindications== |
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==Contraindications== |
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History of significantly impaired renal function; patients with known hypersensitivity to any component of the product; patients who have experienced ], ], or allergic-type reactions after taking aspirin or other ]; treatment of perioperative pain in the setting of ] (CABG) surgery. |
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History of significantly impaired renal function; patients with known hypersensitivity to any component of the product; patients who have experienced ], ], or allergic-type reactions after taking aspirin or other NSAIDs; treatment of perioperative pain in the setting of ] (CABG) surgery. |
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== Adverse effects == |
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==Drug Interactions== |
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In October 2020, the U.S. ] (FDA) required the ] 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.<ref name="FDA PR 20201015" /><ref name="FDA safety 20201015" /> They recommend avoiding NSAIDs in pregnant women at 20 weeks or later in pregnancy.<ref name="FDA PR 20201015">{{cite press release | title=FDA Warns that Using a Type of Pain and Fever Medication in Second Half of Pregnancy Could Lead to Complications | website=U.S. ] (FDA) | date=15 October 2020 | url=https://www.fda.gov/news-events/press-announcements/fda-warns-using-type-pain-and-fever-medication-second-half-pregnancy-could-lead-complications | access-date=15 October 2020}} {{PD-notice}}</ref><ref name="FDA safety 20201015">{{cite web | title=NSAIDs may cause rare kidney problems in unborn babies | website=U.S. Food and Drug Administration | date=21 July 2017 | url=https://www.fda.gov/drugs/drug-safety-and-availability/fda-recommends-avoiding-use-nsaids-pregnancy-20-weeks-or-later-because-they-can-result-low-amniotic | access-date=15 October 2020}} {{PD-notice}}</ref> |
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''']s''' (eg, ]): Plasma aminoglycoside levels may be elevated.<br /> |
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'''] (ACE) inhibitors''': Antihypertensive effect of ACE inhibitors may be diminished.<br /> |
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''']s''': Coadministration may prolong ].<br /> |
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'''Aspirin''': Fenoprofen Cl may be increased; coadministration is not recommended.<br /> |
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'''Diuretics''': Patients treated with fenoprofen may be resistant to the effects of ]s and ]s.<br /> |
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'''], ], ]s''': Fenoprofen may displace these drugs from their binding site.<br /> |
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'''Lithium''': Renal Cl of ] may be reduced and plasma levels may be elevated, which may increase the risk of lithium toxicity.<br /> |
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'''Methotrexate''': May increase ] levels.<br /> |
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'''Phenobarbital''': May decrease fenoprofen t ½ . Dosage adjustments of fenoprofen may be required if ] is added or withdrawn.<br /> |
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'''SSRIs''' (eg, ], ]): The risk of GI effects may be increased. |
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==Drug interactions== |
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==Laboratory Test Interactions== |
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* ]s (e.g. ]): Plasma aminoglycoside levels may be elevated. |
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False elevation in free and total serum T 3 as measured by Amerlex-M kit. |
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* ] (ACE) inhibitors: Antihypertensive effect of ACE inhibitors may be diminished. |
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* ]s: Coadministration may prolong ]. |
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* Aspirin: Fenoprofen Cl may be increased; coadministration is not recommended. |
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* Diuretics: Patients treated with fenoprofen may be resistant to the effects of ]s and ]s. |
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* ], ], ]s: Fenoprofen may displace these drugs from their binding site. |
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* Lithium: Renal Cl of ] may be reduced and plasma levels may be elevated, which may increase the risk of lithium toxicity. |
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* Methotrexate: May increase ] levels. |
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* Phenobarbital: May decrease fenoprofen t<sub>{{frac|1|2}}</sub>. Dosage adjustments of fenoprofen may be required if ] is added or withdrawn. |
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* SSRIs (e.g. ], ]): The risk of GI effects may be increased. |
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==Laboratory test interactions== |
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False elevation in free and total serum T 3<!-- presumably ], but without a source, can't be sure --> as measured by Amerlex-M kit.{{medcn|date=October 2023}} |
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==Brand names== |
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==Brand names== |
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*UK - ''Fenopron'' (]) |
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* UK{{snd}} ''Fenopron'' (]) |
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==References== |
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== See also == |
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* ] |
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{{reflist}} |
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* ] |
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* ] |
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* ] |
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* ] |
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* ] |
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== References == |
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{{Anti-inflammatory and antirheumatic products}} |
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{{NSAIDs}} |
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{{Reflist}} |
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== External links == |
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{{Anti-inflammatory and antirheumatic products}} |
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{{musculoskeletal-drug-stub}} |
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{{Prostanoidergics}} |
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