Product
Supplier
Encyclopedia
Inquiry
Home > Encyclopedia > Fenoprofen

Fenoprofen

Fenoprofen structure

Fenoprofen 

structure
  • CAS No:

    29679-58-1

  • Formula:

    C15H14O3

  • Chemical Name:

    Fenoprofen

  • Synonyms:

    Benzeneacetic acid,α-methyl-3-phenoxy-;Hydratropic acid,m-phenoxy-;α-Methyl-3-phenoxybenzeneacetic acid;2-(3-Phenoxyphenyl)propionic acid;3-Phenoxyhydratropic acid;2-(m-Phenoxyphenyl)propionic acid;Fenoprofen;(±)-m-Phenoxyhydratropic acid;dl-2-(3-Phenoxyphenyl)propionic acid;(±)-2-(3-Phenoxyphenyl)propionic acid;(±)-Fenoprofen;Lilly 53858;2-(3-Phenoxyphenyl)-1-propanoic acid;2-(3-Phenoxyphenyl)propanoic acid;m-Phenoxyhydratropic acid;31879-05-7

  • Categories:

    Pharmaceutical Intermediates  >  Bulk Drug Intermediates

Description

Solid


Fenoprofen is a monocarboxylic acid that is propanoic acid in which one of the hydrogens at position 2 is substituted by a 3-phenoxyphenyl group. A non-steroidal anti-inflammatory drug, the dihydrate form of the calcium salt is used for the management of mild to moderate pain and for the relief of pain and inflammation associated with disorders such as arthritis. It is pharmacologically similar to aspirin, but causes less gastrointestinal bleeding. It has a role as a non-steroidal anti-inflammatory drug, a cyclooxygenase 2 inhibitor, a cyclooxygenase 1 inhibitor, an antipyretic, a non-narcotic analgesic and a drug allergen. It is a conjugate acid of a fenoprofen(1-).|An anti-inflammatory analgesic and antipyretic highly bound to plasma proteins. It is pharmacologically similar to aspirin, but causes less gastrointestinal bleeding.|Fenoprofen is a nonsteroidal antiinflammatory drug (NSAID) used in the treatment of acute pain and chronic arthritis. Fenoprofen has been linked to a low rate of serum enzyme elevations during therapy and to rare instances of clinically apparent acute liver injury.|A propionic acid derivative that is used as a non-steroidal anti-inflammatory agent.

Fenoprofen Basic Attributes

242.27

242.27

249-770-1

757813

DTXSID9023045

VISCOUS OIL

M - Musculo-skeletal system

Characteristics

46.5 Ų

3.1

1.183±0.06 g/cm3

168-171

168-171 °C @ Press: 0.11 Torr

INDEX OF REFRACTION: 1.5742 @ 25 °C/D

Slight (calcium salt)|8.11e-02 g/L

4.20±0.10

4.5|PKA= 7.3

Safety Information

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Toxicity

Symptoms of overdose appear within several hours and generally involve the gastrointestinal and central nervous systems. They include dyspepsia, nausea, vomiting, abdominal pain, dizziness, headache, ataxia, tinnitus, tremor, drowsiness, and confusion. Hyperpyrexia, tachycardia, hypotension, and acute renal failure may occur rarely following overdose. Respiratory depression and metabolic acidosis have also been reported following overdose with certain NSAIDs.

Prospective studies show that up to 15% of patients taking fenoprofen experience at least transient serum aminotransferase elevations. These elevations are generally transient, mild and asymptomatic, and may resolve even with drug continuation. Marked aminotransferase elevations (>3 fold elevated) occur in

WHEN FENOPROFEN WAS ADDED TO REGIMEN OF...PT WITH RHEUMATOID ARTHRITIS WHO WERE RECEIVING CORTICOSTEROID OR GOLD THERAPY, THERE WAS SOME EVIDENCE THAT DOSE OF STEROID COULD BE REDUCED & COMBINATION WITH GOLD WAS MORE EFFECTIVE.|FOOD DELAYS ABSORPTION...& REDUCES PEAK PLASMA CONCN (ABOUT 30%) & TOTAL ABSORPTION (ABOUT 20%), AS DOES COADMIN OF...ANTACIDS.|/PLASMA PROTEIN/ BINDING OF FENOPROFEN IS INHIBITED BY CONCOMITANT ADMIN OF INDOMETHACIN & PHENYLBUTAZONE... PLASMA T/2 OF FENOPROFEN IS DECR BY ASPIRIN...|FENPROFEN & PROPOXYPHENE ARE ADDITIVE WHEN GIVEN TOGETHER.

99% to albumin.

Drug Information

For relief of the signs and symptoms of rheumatoid arthritis and osteoarthritis. Also for the relief of mild to moderate pain.|FDA Label

Fenoprofen is a nonsteroidal antiinflammatory drug (NSAID) used in the treatment of acute pain and chronic arthritis. Fenoprofen has been linked to a low rate of serum enzyme elevations during therapy and to rare instances of clinically apparent acute liver injury.

Nonsteroidal Antiinflammatory Drugs

Cyclooxygenase Inhibitors; Anti-Inflammatory Agents, Non-Steroidal|...FENOPROFEN...MAY BE TRIED IN PT WHO CANNOT TOLERATE ASPIRIN BECAUSE OF GI DISTURBANCES. .../HAS/ ANTIINFLAMMATORY, ANALGESIC, & ANTIPYRETIC ACTIONS. ... EFFECTIVENESS IN RHEUMATOID ARTHRITIS APPEARS...COMPARABLE TO...ASPIRIN &...GI REACTIONS & AMT OF GI BLEEDING IS LESS...|...FENOPROFEN...FOUND TO BE EFFECTIVE IN TREATMENT OF RHEUMATOID ARTHRITIS AS JUDGED BY DECR IN PAIN, JOINT STIFFNESS, SWELLING, & TENDERNESS. ...IN PT WITH RHEUMATOID ARTHRITIS...EFFICACY OF DAILY DOSES OF 2.4 G FENOPROFEN WAS APPROX EQUIVALENT TO...3.9 G ASPIRIN.|WHEN FENOPROFEN WAS ADDED TO REGIMEN OF...PT WITH RHEUMATOID ARTHRITIS WHO WERE RECEIVING CORTICOSTEROID OR GOLD THERAPY, THERE WAS SOME EVIDENCE THAT DOSE OF STEROID COULD BE REDUCED & COMBINATION WITH GOLD WAS MORE EFFECTIVE.|For more Therapeutic Uses (Complete) data for FENOPROFEN (7 total), please visit the HSDB record page.

...CLINICAL EXPERIENCE WITH...NEWER AGENTS /INCL FENOPROFEN/ IS NOT YET SUFFICIENT TO DETERMINE THEIR COMPARATIVE EFFICACIES & ULTIMATE ROLE IN THERAPY OF RHEUMATIC DISEASES.|.../FENOPROFEN/ SHOULD NOT BE USED IN PT WITH BLEEDING DISORDERS & SHOULD BE USED WITH CAUTION IN PT RECEIVING ANTICOAGULANTS.|.../FENOPROFEN/ IS HIGHLY BOUND TO PLASMA PROTEIN, & IT MAY DISPLACE OTHER PROTEIN-BOUND DRUGS FROM THEIR BINDING SITES, LEADING TO DRUG INTERACTIONS.

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.

Compounds or agents that combine with cyclooxygenase (PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES) and thereby prevent its substrate-enzyme combination with arachidonic acid and the formation of eicosanoids, prostaglandins, and thromboxanes. (See all compounds classified as Cyclooxygenase Inhibitors.)|Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions.They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects. (See all compounds classified as Anti-Inflammatory Agents, Non-Steroidal.)

Rapidly absorbed under fasting conditions, and peak plasma levels of 50 µg/mL are achieved within 2 hours after oral administration of 600 mg doses.|...RAPIDLY ABSORBED AFTER ORAL ADMIN; PEAK PLASMA LEVEL OCCURS WITHIN 90 MIN. ...ABSORPTION & AVAILABILITY ARE REDUCED WHEN...AGENT IS GIVEN WITH FOOD, BUT ARE NOT AFFECTED BY CONCOMITANT ADMIN OF AN ANTACID...|...FENOPROFEN...IS WELL ABSORBED FROM GI TRACT AS NA OR CA SALT, & IS RAPIDLY CLEARED BY KIDNEYS...|IN USUAL DOSES, FENOPROFEN...WELL ABSORBED (OVER 80%), RAPIDLY /ACHIEVES/... STEADY-STATE BLOOD LEVELS...HIGHLY PROTEIN BOUND (95-99%). ...BIOTRANSFORMED IN LIVER, & METABOLITES ARE EXCRETED IN URINE. ...T/2...2.5-3 HR...|FOLLOWING ABSORPTION, FENOPROFEN IS METAB & EXCRETED ALMOST EXCLUSIVELY IN URINE IN CONJUGATED FORM. ...IS HIGHLY BOUND TO PLASMA PROTEIN, & IT MAY DISPLACE OTHER PROTEIN-BOUND DRUGS FROM THEIR BINDING SITES, LEADING TO DRUG INTERACTIONS.|HUMAN PLASMA & URINE PHARMACOKINETICS AFTER ORAL & IV ADMIN OF FENOPROFEN.

About 90% of a single oral dose is eliminated within 24 hours as fenoprofen glucuronide and 4'-hydroxyfenoprofen glucuronide, the major urinary metabolites of fenoprofen.|...FENOPROFEN...FOUND TO YIELD 2 URINARY GLUCURONIDES IN MAN. ONE...ACCOUNTING FOR ALMOST 1/2 THE DOSE, IS THE ACYL GLUCURONIDE... THE SECOND...ACCOUNTING FOR THE OTHER 1/2 OF THE DOSE, IS A GLUCURONIDE OF THE PHENOLIC DERIVATIVE /OF FENOPROFEN/...AN ACYL GLUCURONIDE WITH A FREE PHENOLIC GROUP.|...FENOPROFEN...FOUND TO YIELD SMALL AMT OF ACID-LABILE CONJUGATE BEING NEITHER A GLYCINE NOR A GLUTAMINE CONJUGATE...

Plasma half-life is approximately 3 hours.|...RAPIDLY ABSORBED AFTER ORAL ADMIN; PEAK PLASMA LEVEL OCCURS WITHIN 90 MIN. IT HAS PLASMA T/2 OF ABOUT 160 MIN, WHICH DOES NOT APPEAR...DOSE DEPENDENT. ABSORPTION & AVAILABILITY ARE REDUCED WHEN...AGENT IS GIVEN WITH FOOD, BUT ARE NOT AFFECTED BY CONCOMITANT ADMIN OF AN ANTACID...|...T/2...2.5-3 HR...

Fenoprofen's exact mode of action is unknown, but it is thought that prostaglandin synthetase inhibition is involved. Fenoprofen has been shown to inhibit prostaglandin synthetase isolated from bovine seminal vesicles.|LIKE ASPIRIN, FENOPROFEN INHIBITS PROSTAGLANDIN SYNTHETASE, BUT SIGNIFICANCE OF THIS ACTION IN RELATION TO CLINICAL EFFECTS PRODUCED IS NOT KNOWN.

MOST COMMON ADVERSE REACTIONS /ORAL ADMIN/...GI EFFECTS (EG, DYSPEPSIA, CONSTIPATION, NAUSEA, VOMITING)...FEW CASES OF ULCERATION... CNS REACTIONS INCL DROWSINESS, DIZZINESS, HEADACHE, NERVOUSNESS, & CONFUSION. PRURITUS, RASH, SWEATING, PALPITATIONS, TREMOR, TINNITUS, BLURRED VISION, & DECR HEARING...SENSITIVITY TO DRUG...|ELEVATIONS OF SERUM TRANSAMINASE, LACTIC DEHYDROGENASE, & ALKALINE PHOSPHATASE LEVELS...IN SOME PT. DECR IN HEMOGLOBIN & HEMATOCRIT...OCCASIONALLY. FENOPROFEN REDUCES PLATELET AGGREGATION & ADHESIVENESS & INCR BLEEDING TIME /ORAL ADMIN/.|.../FENOPROFEN, ORALLY/ EFFECTIVENESS IN RHEUMATOID ARTHRITIS APPEARS... COMPARABLE TO...ASPIRIN &...INCIDENCE OF GI REACTIONS & AMT OF GI BLEEDING IS LESS THAN WITH ASPIRIN.|...DRUGS /INCL FENOPROFEN/ HAVE BEEN ASSOC WITH FATAL GI HEMORRHAGE IN RARE CASES.|For more Human Toxicity Excerpts (Complete) data for FENOPROFEN (10 total), please visit the HSDB record page.

Fenoprofen

Fenoprofen Use and Manufacturing

Methods of Manufacturing

MARSHALL, FRENCH PATENT 2,015,718 CORRESPONDING TO US PATENT 3,600,437 (1970, 1971 TO LILLY).

LILLY 69323; FENOPRON; FEPRONA /CALCIUM SALT DIHYDRATE/|NALFON (DISTA). ORAL: CAPSULES 300 MG

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Pharmaceuticals

Computed Properties

Molecular Weight:242.27
XLogP3:3.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:4
Exact Mass:242.094294304
Monoisotopic Mass:242.094294304
Topological Polar Surface Area:46.5
Heavy Atom Count:18
Complexity:271
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Recommended Suppliers of Fenoprofen

Scan the QR Code to Share

Feedback & Suggestions
Send Message

Thank you for your feedback. If you require further assistance, please contact us by email at info@echemi.com or call us at +86-532-55729510.