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34597-40-5 molecular structure
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2-(3-phenoxyphenyl)propanoic acid

ChemBase ID: 455
Molecular Formular: C15H14O3
Molecular Mass: 242.26986
Monoisotopic Mass: 242.09429431
SMILES and InChIs

SMILES:
O(c1cc(C(C)C(=O)O)ccc1)c1ccccc1
Canonical SMILES:
OC(=O)C(c1cccc(c1)Oc1ccccc1)C
InChI:
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)
InChIKey:
RDJGLLICXDHJDY-UHFFFAOYSA-N

Cite this record

CBID:455 http://www.chembase.cn/molecule-455.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
2-(3-phenoxyphenyl)propanoic acid
IUPAC Traditional name
fenoprofen
Brand Name
Nalfon
Synonyms
Feneprofen calcium salt dihydrate
Fenoprofen calcium
Fenoprofen calcium hydrate
Fenoprofen
2-(3-Phenoxyphenyl)propanoic acid
CAS Number
34597-40-5
29679-58-1
31879-05-7
MDL Number
MFCD00072027
PubChem SID
160963918
46504597
PubChem CID
3342
CHEBI ID
5004
ATC CODE
M01AE04
CHEMBL
1297
Chemspider ID
3225
DrugBank ID
DB00573
KEGG ID
D02350
Unique Ingredient Identifier
RA33EAC7KY
Wikipedia Title
Fenoprofen
Medline Plus
a681026

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
Bide Pharmatech
BD130237 Please log in.

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 3.9589744  H Acceptors
H Donor LogD (pH = 5.5) 2.10536 
LogD (pH = 7.4) 0.47214115  Log P 3.6542675 
Molar Refractivity 68.1809 cm3 Polarizability 26.6848 Å3
Polar Surface Area 46.53 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 3.87  LOG S -3.48 
Solubility (Water) 8.11e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
Slight (calcium salt) expand Show data source
Hydrophobicity(logP)
3.1 expand Show data source
Admin Routes
Oral expand Show data source
Excretion
Renal (~90%) expand Show data source
Half Life
3 hours expand Show data source
Metabolism
Major urinary metabolites are fenoprofen glucuronide and 4′-hydroxyfenoprofen glucuronide. expand Show data source
Legal Status
POM (UK) expand Show data source
Rx-only (US) expand Show data source
Pregnancy Category
C expand Show data source
D (US) expand Show data source
Purity
95+% expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia
DrugBank - DB00573 external link
Item Information
Drug Groups approved
Description An anti-inflammatory analgesic and antipyretic highly bound to plasma proteins. It is pharmacologically similar to aspirin, but causes less gastrointestinal bleeding. [PubChem]
Indication For relief of the signs and symptoms of rheumatoid arthritis and osteoarthritis. Also for the relief of mild to moderate pain.
Pharmacology 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.
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.
Affected Organisms
Humans and other mammals
Biotransformation 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.
Absorption 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.
Half Life Plasma half-life is approximately 3 hours.
Protein Binding 99% to albumin.
External Links
Wikipedia
RxList
Drugs.com

REFERENCES

REFERENCES

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