Loxoprofen trans-alcohol, (2S,1'R,2'S)-
Basic information
- CAS
83648-76-4- Standard SMILES
C[C@H](C(=O)O)c1ccc(C[C@H]2CCC[C@@H]2O)cc1- InChIKey
SHAHPWSYJFYMRX-GDLCADMTSA-N- Molecular formula
- C15H20O3
- Average molar mass
- 248.32 g/mol
- Monoisotopic mass
- 248.1412445
Overview
(2S)-2-(4-{[(1R,2S)-2-hydroxycyclopentyl]methyl}phenyl)propanoic acid is a monocarboxylic acid that is propionic acid in which one of the hydrogens at position 2 is substituted by a 4-[(2-hydroxycyclopentyl)methyl]phenyl group (the 2S,1'R,2'S-stereoisomer. The active metabolite of loxoprofen. It has a role as a non-steroidal anti-inflammatory drug, a non-narcotic analgesic, an antipyretic, an EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor, a drug metabolite, a xenobiotic metabolite and a human metabolite. It is a member of cyclopentanols and a monocarboxylic acid. It is functionally related to a propionic acid and a loxoprofen.
Names & identifiers
- Preferred name
- Loxoprofen trans-alcohol, (2S,1'R,2'S)-
- IUPAC
- (2S)-2-[4-[[(1R,2S)-2-hydroxycyclopentyl]methyl]phenyl]propanoic acid
- English name
- Benzeneacetic acid, 4-[[(1R,2S)-2-hydroxycyclopentyl]methyl]-α-methyl-, (αS)-
- Molecular formula
- C15H20O3
- Molecular weight
- 248.32
Names & synonyms
loxoprofen active metabolite83648-76-4Loxoprofen srsLoxoprofen trans-alcohol, (2S,1'R,2'S)-926CB5J9Z0Loxoprofen-(2S,1'R,2'S)-trans-alcoholBenzeneacetic acid, 4-(((1R,2S)-2-hydroxycyclopentyl)methyl)-alpha-methyl-, (alphaS)-Benzeneacetic acid, 4-(((1R,2S)-2-hydroxycyclopentyl)methyl)-alpha-methyl-, rel-RefChem:1088564Loxoprofenol-SRSUNII-926CB5J9Z0Loxoprofen trans alcohol
Show more names
Loxoprofen Impurity 52(2S)-2-(4-[[(1R,2S)-2-Hydroxycyclopentyl]methyl]phenyl)propanoic acidBenzeneacetic acid, 4-[[(1R,2S)-2-hydroxycyclopentyl]methyl]-α-methyl-, (αS)-
CHEMBL441414HR1405-01(2S)-2-(4-{[(1R,2S)-2-hydroxycyclopentyl]methyl}phenyl)propanoic acid(2S)-2-[4-[[(1R,2S)-2-hydroxycyclopentyl]methyl]phenyl]propanoic acid(S)-2-(4-(((1R,2S)-2-Hydroxycyclopentyl)methyl)phenyl)propanoic acidloxoprofen-SRSLoxoprofen metaboliteloxoprofen trans-alcohol
Properties
Computed structural properties
- XLogP
- 2.7
- Topological polar surface area
- 57.5 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 4
- Heavy atoms
- 18
- Formal charge
- 0
- Complexity
- 281
Physicochemical properties
- Boiling point
- 418.6 · 418.6±20.0 °C(Predicted)
- Density
- 1.189 · 1.189±0.06 g/cm3(Predicted)
- solubility
- Acetonitrile: SolubleMethanol: Soluble
- pka
- 4.42 · 4.42±0.10(Predicted)
- FDA UNII
- 926 CB5J9Z0 · 926CB5J9Z0
Chemistry & industry
Applications
UsesLoxoprofenol-SRS, an active metabolite of Loxoprofen, is a new intravenous NSAID. Loxoprofenol-SRS exhibits significantly stronger anti-inflammatory and analgesic activities[1].
Upstream & downstream products
Upstream raw materials
Additional notes
DefinitionChEBI: (2S)-2-(4-{[(1R,2S)-2-hydroxycyclopentyl]methyl}phenyl)propanoic acid is a monocarboxylic acid that is propionic acid in which one of the hydrogens at position 2 is substituted by a 4-[(2-hydroxycyclopentyl)methyl]phenyl group (the 2S,1'R,2'S-stereoisomer. The active metabolite of loxoprofen. It has a role as a non-steroidal anti-inflammatory drug, a non-narcotic analgesic, an EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor, an antipyretic, a xenobiotic metabolite, a human metabolite and a drug metabolite. It is a monocarboxylic acid and a member of cyclopentanols. It is functionally related to a propionic acid and a loxoprofen.
Related reactions
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Compound notes
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