Fenoprofen (HCID 3342)

概要

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 non-narcotic analgesic, an antipyretic, a cyclooxygenase 2 inhibitor, a cyclooxygenase 1 inhibitor and a drug allergen. It is a conjugate acid of a fenoprofen(1-).

名称と識別子

優先名称: Fenoprofen
IUPAC: 2-(3-phenoxyphenyl)propanoic acid
現地名: 3-フェノキシ-α-メチルベンゼン酢酸
英語名: 2-(3-phenoxyphenyl)propionic acid
分子式: C15H14O3
分子量: 242.27

名称と別名

fenoprofen2-(3-Phenoxyphenyl)propanoic acid31879-05-7FenoprofeneFenoprofenoFenoprofenumNalfonalpha-Methyl-3-phenoxybenzeneacetic acid(+-)-m-Phenoxyhydratropic acid2-(m-phenoxyphenyl)propionic acid3-Phenoxyhydratropic acidLilly-53858

名称をさらに表示

α-メチル-3-フェノキシベンゼン酢酸3-フェノキシ-α-メチルベンゼン酢酸2-(3-フェノキシフェニル)プロピオン酸2-(3-フェノキシフェニル)プロパン酸Fenoprofen D3Einecs 249-770-12-(3-Phenoxyphenyl)Fenoprofen, racemic mixtureα-Methyl-3-phenoxybenzeneacetic acidBenzeneacetic acid, a-methyl-3-phenoxy-Benzeneacetic acid, α-methyl-3-phenoxy-Benzeneacetic acid, α-methyl-3-phenoxy-

(+-)-2-(3-Phenoxyphenyl)propionic acidalpha-(m-phenoxyphenyl)propionic acidRA33EAC7KYNSC-757813CHEBI:5004DL-2-(3-phenoxyphenyl)propionic acidBenzeneacetic acid, alpha-methyl-3-phenoxy-, (+-)-DTXSID9023045

データベース識別子

CAS: 29679-58-1、31879-05-7、34597-40-5
PubChem CID: 3342
DTXSID: DTXSID9023045
ChEMBL: CHEMBL1297
ChEBI: CHEBI:5004
UNII: RA33EAC7KY
EC Number: 249-770-1、250-850-3
Nikkaji: J286.928D

物性

構造計算による物性

XLogP: 3.3
極性表面積: 46.5 Å²
水素結合供与体数: 1
水素結合受容体数: 3
回転可能結合数: 4
重原子数: 18
形式電荷: 0
複雑度: 271

実験および物理化学的性質

LogP · 2 件

3.1

3.45

Color/FormVISCOUS OIL

Solubility · 2 件

Slight (calcium salt)

8.11e-02 g/L

Human Drugs · 2 件

Breast Feeding; Lactation; Milk, Human; Analgesic Agents; Anti-inflammatory Agents, Nonsteroidal

Pharmaceuticals

Boiling Point168-171 °C @ 0.11 MM HG

Melting Point168-171

物理化学的性質

沸点: 168 · 168-171 °C(Press: 0.11 Torr)
比重(密度): 1.183 · 1.183±0.06 g/cm3(Predicted)
貯蔵温度: -20 °C · Store at -20°C
溶解性: 100 mg/mL · DMSO : 100 mg/mL (412.76 mM; Need ultrasonic)
酸解離定数(Pka): 4.2 · 4.20±0.10(Predicted)
外見: Oil to Thick Oil
色: Colourless
EPAの化学物質情報: -3 · Benzeneacetic acid, ?-methyl-3-phenoxy- (29679-58-1)

安全と法規制

毒性情報

Interactions · 4 件

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.

Hepatotoxicity · 1 件

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 (above 3 times the upper limit of normal (ULN) occur in less than 1% of patients.

Human Toxicity Excerpts · 5 件

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.

Drug Induced Liver Injury · 6 件

Benchmark Dataset for the Liver Toxicity Knowledge Base (LTKB)

fenoprofen

Nalfon®

NSAIDs

8

most-DILI-concern

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

安全データ

hs_code: 2918999090

化学と産業

薬理情報

ATC Code · 2 件

M - Musculo-skeletal system

QM - Musculo-skeletal system

Protein Binding99% to albumin.

Pharmacodynamics · 1 件

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.

Mechanism of Action · 2 件

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.

Biological Half-Life · 3 件

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...

Metabolism/Metabolites · 3 件

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...