Basic information
- CAS
66934-18-7- Standard SMILES
C[C@H](C(=O)O)c1ccc2oc(-c3ccc(F)cc3)nc2c1- InChIKey
ARPYQKTVRGFPIS-VIFPVBQESA-N- Molecular formula
- C16H12FNO3
- Average molar mass
- 285.27 g/mol
- Monoisotopic mass
- 285.08012141
Overview
Flunoxaprofen is a monocarboxylic acid that is propionic acid substituted at position 2 by a 2-(4-chlorophenyl)-1,3-benzoxazol-5-yl group (the S-enantiomer). Although it was shown to be effective in treatment of rheumatoid arthritis and osteoarthritis, the clinical use of flunoxaprofen was discontinued due to possible hepatotoxic side-effects. It has a role as a non-steroidal anti-inflammatory drug, an antirheumatic drug, a hepatotoxic agent and a protein kinase C agonist. It is a monocarboxylic acid, an organofluorine compound and a member of 1,3-benzoxazoles. It is functionally related to a propionic acid.
Names & identifiers
- Preferred name
- Flunoxaprofen
- IUPAC
- (2S)-2-[2-(4-fluorophenyl)-1,3-benzoxazol-5-yl]propanoic acid
- English name
- Flunoxaprofen
- Molecular formula
- C16H12FNO3
- Molecular weight
- 285.273
Names & synonyms
Flunoxaprofen66934-18-7Flunoxaprofeno(2s)-2-[2-(4-fluorophenyl)-1,3-benzoxazol-5-yl]propanoic acidFlunoxaprofenum(S)-(+)-FlunoxaprofenflunoxaprofeneUKU5U19W9M(S)-2-(4-Fluorophenyl)-alpha-methyl-5-benzoxazoleacetic acid(+)-2-(p-Fluorophenyl)-alpha-methyl-5-benzoxazoleacetic acidCHEBI:76154DTXSID00912311
Show more names
S-(+)-FlunoxaprofenFlunoxaprofen USP/EP/BP(S)-2-(4-Fluorophenyl)-α-methyl-5-benzoxazoleacetic acid5-Benzoxazoleacetic acid, 2-(4-fluorophenyl)-α-methyl-, (αS)-
(2S)-2-(2-(4-fluorophenyl)-1,3-benzoxazol-5-yl)propanoic acid(+)-FlunoxaprofenRefChem:599355G02CC04M01AE15DTXCID701341333PriaximFlunoxaprofen [INN]
Database identifiers
- CAS
66934-18-7- PubChem CID
- 68869
- DTXSID
DTXSID00912311
Properties
Computed structural properties
- XLogP
- 3.6
- Topological polar surface area
- 63.3 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 3
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 384
Experimental & physicochemical properties
DrugsPharmaceuticals -> Musculo-skeletal system -> Anti-inflammatory and antirheumatic products
Physicochemical properties
- Melting point
- 162 · 162-164°
- alpha
- 20 · D20 +50° (c = 2% in DMF)
- Boiling point
- 419.4 · 419.4±30.0 °C(Predicted)
- Density
- 1.334 · 1.334±0.06 g/cm3(Predicted)
- pka
- 4.36 · 4.36±0.30(Predicted)
- FDA UNII
- 5 U19W9M · UKU5U19W9M
- ATC code
- 2 CC04,M01AE15 · G02CC04,M01AE15
- Toxicity
- 50 orally · LD50 orally in mice: ~1200 mg/kg (Dunwell)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Toxicity
- LD50 orally in mice: ~1200 mg/kg (Dunwell)
Chemistry & industry
Pharmacology
ATC Code
M - Musculo-skeletal system
G - Genito urinary system and sex hormones
QG - Genito urinary system and sex hormones
QM - Musculo-skeletal system
MeSH Pharmacological Classification
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.
Applications
DescriptionFlunoxaprofen is an antiinflammatory related to now withdrawn benoxaprofen, reportedly useful in the treatment of rheumatoid arthritis, myositis, synovitis and osteoarthritis. Its major mechanism of action is reported to be lipoxygenase inhibition, thus enabling the control of inflammation with less severe gastric disturbances.
Suppliers1 total
Dideu Industries Group Limited+86-29-81148696 +86-15129568250 · [email protected]
Additional notes
DefinitionChEBI: A monocarboxylic acid that is propionic acid substituted at position 2 by a 2-(4-chlorophenyl)-1,3-benzoxazol-5-yl group (the S-enantiomer). Although it was shown to be effective in treatment of rheumatoid arthritis and osteoarthritis, the clinical use of flunoxaprofen was discontinued due to possible hepatotoxic side-effects.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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