FENOPROFEN SODIUM

Details

Stereochemistry	RACEMIC
Molecular Formula	C15H13O3.Na
Molecular Weight	264.2517
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Na+].CC(C([O-])=O)C1=CC(OC2=CC=CC=C2)=CC=C1

InChI

InChIKey=WVKIYGXHDKTNFO-UHFFFAOYSA-M

InChI=1S/C15H14O3.Na/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);/q;+1/p-1

HIDE SMILES / InChI

Molecular Formula	Na
Molecular Weight	22.9898
Charge	1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C15H13O3
Molecular Weight	241.2619
Charge	-1
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: http://www.drugbank.ca/drugs/DB00573
Curator's Comment: Description was created based on several sources, including https://www.drugs.com/pro/fenoprofen.html

Fenoprofen is a propionic acid derivative with analgesic, antiinflammatory and antipyretic properties. Fenoprofen inhibits prostaglandin synthesis by decreasing the enzyme needed for biosynthesis. In patients with rheumatoid arthritis, the anti-inflammatory action of fenoprofen has been evidenced by relief of pain, increase in grip strength, and reductions in joint swelling, duration of morning stiffness, and disease activity (as assessed by both the investigator and the patient). In patients with osteoarthritis, the anti-inflammatory and analgesic effects of fenoprofen have been demonstrated by reduction in tenderness as a response to pressure and reductions in night pain, stiffness, swelling, and overall disease activity (as assessed by both the patient and the investigator). These effects have also been demonstrated by relief of pain with motion and at rest and increased range of motion in involved joints. In patients with rheumatoid arthritis and osteoarthritis, clinical studies have shown fenoprofen to be comparable to aspirin in controlling the aforementioned measures of disease activity, but mild gastrointestinal reactions (nausea, dyspepsia) and tinnitus occurred less frequently in patients treated with fenoprofen than in aspirin-treated patients. It is not known whether fenoprofen causes less peptic ulceration than does aspirin. In patients with pain, the analgesic action of fenoprofen has produced a reduction in pain intensity, an increase in pain relief, improvement in total analgesia scores, and a sustained analgesic effect. Indicated for relief of the signs and symptoms of rheumatoid arthritis and osteoarthritis. Also for the relief of mild to moderate pain.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cyclooxygenase-2 196 Target ID: CHEMBL230 Sources: http://www.drugbank.ca/drugs/DB00573	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Pain 614 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/017604s046lbl.pdf	Palliative	Approved 8429	NALFON Approved Use NALFON is a nonsteroidal anti-inflammatory drug indicated for: • Relief of mild to moderate pain in adults. • Relief of the signs and symptoms of rheumatoid arthritis. • Relief of the signs and symptoms of osteoarthritis. Launch Date 1.95696001E11
Rheumatoid arthritis 316 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/017604s046lbl.pdf	Primary	Approved 8429	NALFON Approved Use NALFON is a nonsteroidal anti-inflammatory drug indicated for: • Relief of mild to moderate pain in adults. • Relief of the signs and symptoms of rheumatoid arthritis. • Relief of the signs and symptoms of osteoarthritis. Launch Date 1.95696001E11
Osteoarthritis 157 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/017604s046lbl.pdf	Primary	Approved 8429	NALFON Approved Use NALFON is a nonsteroidal anti-inflammatory drug indicated for: • Relief of mild to moderate pain in adults. • Relief of the signs and symptoms of rheumatoid arthritis. • Relief of the signs and symptoms of osteoarthritis. Launch Date 1.95696001E11

C_max

Value	Dose	Co-administered	Analyte	Population
28.3 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/501526/	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:		FENOPROFEN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
105.2 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/501526/	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:		FENOPROFEN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/501526/	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:		FENOPROFEN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
1% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/501526/	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:		FENOPROFEN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Doses

Dose	Population	Adverse events
400 mg 3 times / day steady, oral Recommended Dose: 400 mg, 3 times / day Route: oral Route: steady Dose: 400 mg, 3 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/017604s046lbl.pdf	unhealthy n = 6786 Health Status: unhealthy Condition: rheumatoid arthritis\| osteoarthritis Population Size: 6786 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/017604s046lbl.pdf	Disc. AE: Reaction gastrointestinal, Reaction skin... Other AEs: Dyspepsia, Nausea... AEs leading to discontinuation/dose reduction: Reaction gastrointestinal (2%) Reaction skin (1%) Cardiovascular disorder (NOS) (0.5%) Other AEs: Dyspepsia (10%) Nausea (7.7%) Constipation (7%) Vomiting (2.6%) Abdominal pain (2%) Diarrhea (1.8%) Headache (8.7%) Somnolence (8.5%) Dizziness (6.5%) Tremor (2.2%) Confusion (1.4%) Sweating increased (4.6%) Pruritus (4.2%) Rash (3.7%) Tinnitus (4.5%) Blurred vision (2.2%) Hearing decreased (1.6%) Palpitations (2.5%) Nervousness (5.7%) Asthenia (5.4%) Peripheral edema (5%) Dyspnea (2.8%) Fatigue (1.7%) Upper respiratory infection (1.5%) Nasopharyngitis (1.2%) Gastritis (<1%) Ulcer peptic with perforation (<1%) Ulcer peptic with perforation (<1%) Gastrointestinal hemorrhage (<1%) Anorexia (<1%) Flatulence (<1%) Dry mouth (<1%) Blood in stool (<1%) Alkaline phosphatase increased (<1%) LDH increased (<1%) SGOT increased (<1%) Jaundice (<1%) Cholestatic hepatitis (<1%) Buccal mucosa aphthous ulceration (<1%) Taste metallic (<1%) Pancreatitis (<1%) Atrial fibrillation (<1%) Pulmonary edema (<1%) Electrocardiogram change (<1%) Supraventricular tachycardia (<1%) Renal failure (<1%) Dysuria (<1%) Cystitis (<1%) Hematuria (<1%) Oliguria (<1%) Azotemia (<1%) Anuria (<1%) Nephritis interstitial (<1%) Nephrosis (<1%) Acute papillary necrosis (<1%) Angioedema (<1%) Purpura (<1%) Bruising (<1%) Hemorrhage (<1%) Thrombocytopenia (<1%) Hemolytic anemia (<1%) Aplastic anemia (<1%) Agranulocytosis (<1%) Pancytopenia (<1%) Depression (<1%) Disorientation (<1%) Seizures (<1%) Trigeminal neuralgia (<1%) Burning tongue (<1%) Diplopia (<1%) Optic neuritis (<1%) Exfoliative dermatitis (<1%) Toxic epidermal necrolysis (<1%) Stevens-Johnson syndrome (<1%) Alopecia (<1%) Anaphylaxis (<1%) Urticaria (<1%) Malaise (<1%) Insomnia (<1%) Tachycardia (<1%) Personality change (<1%) Lymphadenopathy (<1%) Mastodynia (<1%) Fever (<1%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/017604s046lbl.pdf

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737	substrate 1037

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
UGT1A1 204 UGT1A3 84 UGT1A4 77 UGT1A6 108 UGT1A9 116 UGT2B7 146	CYP1A2 1054 CYP2C8 693 CYP2E1 667 UGT2B7 389

Drug as perpetrator

Target	Modality	Activity
UGT1A1 254	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/25522350/	no
UGT1A3 93	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/25522350/	no
UGT1A4 80	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/25522350/	no
UGT1A6 141	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/25522350/	no
UGT1A9 121	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/25522350/	no
UGT2B7 157	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/25522350/	no

Drug as victim

Target	Modality	Activity
CYP1A2 1054	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/9004453/	no
CYP2C8 693	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/9004453/	no
CYP2E1 667	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/9004453/	no
CYP3A4 1737	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/9004453/	no
CYP2C9 1037	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/9004453/	yes
UGT2B7 389	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/23362865/	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:5004	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:5004
ChemicalBook	CB3290884	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB3290884
MolPort	MolPort-003-666-345	https://www.molport.com/shop/molecule-link/MolPort-003-666-345
eMolecules	901876	https://www.emolecules.com/cgi-bin/more?vid=901876

PubMed

Title	Date	PubMed
Letter: Aspirin sensitivity: other drugs.	1975 Feb	1115460
Thioesterification of 2-arylpropionic acids by recombinant acyl-coenzyme A synthetases (ACS1 and ACS2).	2000 Apr	10725307
Risk of upper gastrointestinal bleeding and perforation associated with low-dose aspirin as plain and enteric-coated formulations.	2001	11228592
Screening procedure for detection of non-steroidal anti-inflammatory drugs and their metabolites in urine as part of a systematic toxicological analysis procedure for acidic drugs and poisons by gas chromatography-mass spectrometry after extractive methylation.	2001 May-Jun	11386636
[Chiral separation by capillary electrochromatography on stationary phase adsorbed with protein].	2001 Sep	12545430
Detection of pharmaceutical contaminations of river, pond, and tap water from Cologne (Germany) and surroundings.	2002 Jul	12173539
Macromolecular prodrugs: X. Kinetics of fenoprofen release from PHEA-fenoprofen conjugate.	2002 Jul 25	12100850
Chiral inversion of (R)-(-)-fenoprofen in guinea-pigs pretreated with clofibrate.	2002 Jun	12184503
Identification of 8-iso-prostaglandin F(2alpha) in rat brain neuronal endings: a possible marker of membrane phospholipid peroxidation.	2002 Oct 4	12231405
Quadrupole time-of-flight versus triple-quadrupole mass spectrometry for the determination of non-steroidal antiinflammatory drugs in surface water by liquid chromatography/tandem mass spectrometry.	2003	12717759
Influence of rheumatoid arthritis in the enantioselective disposition of fenoprofen.	2004 Nov	15390088
Enantioselective kinetic disposition of fenoprofen in rats with experimental diabetes or adjuvant-induced arthritis.	2004 Oct	15331913
Cationic vesicles as chiral selector for enantioseparations of nonsteroidal antiinflammatory drugs by micellar electrokinetic chromatography.	2004 Sep 3	15453427
Using terahertz pulsed spectroscopy to quantify pharmaceutical polymorphism and crystallinity.	2005 Apr	15736195
Effects of non-ionic surfactants on isotachophoretic separations of 2-arylpropionic acids.	2005 Aug 19	16114248
Pharmaceutical liquid crystals: the relevance of partially ordered systems.	2005 Sep	16052511
The inflammatory process of gout and its treatment.	2006	16820042
Interaction of ibuprofen and other structurally related NSAIDs with the sodium-coupled monocarboxylate transporter SMCT1 (SLC5A8).	2006 Jun	16729224
Determination of acidic drugs and caffeine in municipal wastewaters and receiving waters by gas chromatography-ion trap tandem mass spectrometry.	2006 May 26	16545821
Pharmaceutical chemicals and endocrine disrupters in municipal wastewater in Tokyo and their removal during activated sludge treatment.	2006 Oct	16938339
Prophylaxis of migraine.	2006 Sep	19412475
Immunomodulatory effect of nonsteroidal anti-inflammatory drugs (NSAIDs) at the clinically available doses.	2007 Jan	17328244
Enantioseparation by CE with vancomycin as chiral selector: Improving the separation performance by dynamic coating of the capillary with poly(dimethylacrylamide).	2007 Mar	17309047
Removal of selected pharmaceuticals and personal care products (PPCPs) and endocrine-disrupting chemicals (EDCs) during sand filtration and ozonation at a municipal sewage treatment plant.	2007 Nov	17632207
Interactions between APP secretases and inflammatory mediators.	2008 Jun 18	18564425
The Nuclear Receptor PPARgamma as a Therapeutic Target for Cerebrovascular and Brain Dysfunction in Alzheimer's Disease.	2010	20725514
Sumatriptan-naproxen fixed combination for acute treatment of migraine: a critical appraisal.	2010 Feb 18	20368903
Cyclooxygenase Inhibitors, Aspirin and Ibuprofen, Inhibit MHC-restricted Antigen Presentation in Dendritic Cells.	2010 Jun	20631879
Electrokinetic supercharging focusing in capillary zone electrophoresis of weakly ionizable analytes in environmental and biological samples.	2010 Sep	20715126

Patents

Sample Use Guides

In Vivo Use Guide

400 mg to 600 mg orally 3 or 4 times a day -Maximum dose: 3200 mg/day

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:33:00 UTC 2023` Edited by `admin` on `Fri Dec 15 15:33:00 UTC 2023`
Record UNII	869607J16Q
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FENOPROFEN SODIUM

Common Name

English

SODIUM 2-(3-PHENOXYPHENYL)PROPIONATE

Systematic Name

English

BENZENEACETIC ACID, .ALPHA.-METHYL-3-PHENOXY-, SODIUM SALT, (±)-

Common Name

English

FENOPROFEN SODIUM [USP-RS]

Common Name

English

BENZENEACETIC ACID, .ALPHA.-METHYL-3-PHENOXY-, SODIUM SALT

Common Name

English

SODIUM FENOPROFEN

Common Name

English

BENZENEACETIC ACID, .ALPHA.-METHYL-3-PHENOXY-, SODIUM SALT (1:1)

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1323