Basic information
- CAS
1189656-64-1- Standard SMILES
O=C(O)Cc1ccccc1Nc1c(Cl)cc(O)cc1Cl- InChIKey
KGVXVPRLBMWZLG-UHFFFAOYSA-N- Molecular formula
- C14H11Cl2NO3
- Average molar mass
- 312.1 g/mol
- Monoisotopic mass
- 311.01159857
Overview
4'-hydroxydiclofenac is a monocarboxylic acid that is the 4'-hydroxylated metabolite of diclofenac. It has a role as a drug metabolite and an allergen. It is a dichlorobenzene, a monocarboxylic acid, a member of phenols and a secondary amino compound. It is functionally related to a diclofenac.
Names & identifiers
- Preferred name
- 4'-Hydroxydiclofenac
- IUPAC
- 2-[2-(2,6-dichloro-4-hydroxyanilino)phenyl]acetic acid
- English name
- 2-[((2',6'-Dichloro-4'-hydroxy)phenyl)amino]benzeneacetic acid
- Molecular formula
- C14H11Cl2NO3
- Molecular weight
- 312.15
Names & synonyms
4'-Hydroxydiclofenac64118-84-94'-Hydroxy Diclofenac4-hydroxy diclofenac(o-(2,6-Dichloro-4-hydroxyanilino)phenyl)acetic acidCHEBI:596132-(2-((2,6-Dichloro-4-hydroxyphenyl)amino)phenyl)acetic acidNJF5O599EF4'-OH DCF4'-HYDROXY-DICLOFENAC{2-[(2,6-dichloro-4-hydroxyphenyl)amino]phenyl}acetic acidBRN 4198042
Show more names
4-OHD4'-OHDHydroxydiclofenac4-HYDROXY DICLOFECDiclofenac Impurity 15DICLOFENAC, 4'-HYDROXY-4'-HYDROXYDICLOFENAC STANDARD4′-Hydroxydiclofenac solution
Benzeneacetic acid, 2-((2,6-dichloro-4-hydroxyphenyl)amino)-2-[(2,6-Dichloro-4-hydroxyphenyl)amino]benzeneacetic AcidCHEMBL1030HYDROXYDICLOFENAC, 4'-DTXSID402143262-{2-[(2,6-dichloro-4-hydroxyphenyl)amino]phenyl}acetic acid2-((2,6-Dichloro-4-hydroxyphenyl)amino)benzeneacetic acid(2-((2,6-dichloro-4-hydroxyphenyl)amino)phenyl)acetic acid
Database identifiers
Properties
Computed structural properties
- XLogP
- 3.7
- Topological polar surface area
- 69.6 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 4
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 330
Experimental & physicochemical properties
DrugsPharmaceuticals -> Metabolite of Diclofenac
LogP3.7
Physicochemical properties
- Melting point
- 178 · 178-185°C dec.
- Boiling point
- 432.7 · 432.7±45.0 °C(Predicted)
- Density
- 1.52 · 1.520±0.06 g/cm3(Predicted)
- Flash point
- 2 ℃ · 2℃
- storage temp.
- -20 °C · -20°C
- solubility
- Soluble in DMSO, ethanol or methanol
- pka
- 4.17 · 4.17±0.10(Predicted)
- form
- Solid
- color
- White to off-white
- BRN
- 4198042 · 4198042
- Stability
- Light Sensitive
- Major Application
- clinical testing
- InChI
Safety & regulation
GHS classification
GHS Classification
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P305+P354+P338, P317, P319, P321, P330, P332+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 46 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
Hazard information
Hazard Classes and Categories
Acute Tox. 3 (100%)
Acute Tox. 3 (100%)
Safety data
- wgk
- 3
- rtecs
- AG6542800
- ridadr
- UN 2811 6.1/PG 3
- risk_code
- 25-37/38-41-50/53-36-20/21/22-11
- Signal word
- Danger
- Symbol(GHS)
- GHS05,GHS06,GHS09
- hazard_code
- T,N,Xn,F
- safety_code
- 26-39-45-60-61-36/37-16
- hazard_class
- 6.1
- Storage Class
- 3 - Flammable liquids
- Hazard statements
- H301-H315-H318-H335-H410
- Hazard Classifications
- Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Flam. Liq. 2
- Precautionary statements
- P261-P273-P280-P301+P310-P302+P352-P305+P351+P338
Chemistry & industry
Pharmacology
Metabolism/Metabolites4'-hydroxydiclofenac has known human metabolites that include (2S,3S,4S,5R)-6-[4-[2-(carboxymethyl)anilino]-3,5-dichlorophenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid and 2-[2-(2,6-dichloro-4-sulfooxyanilino)phenyl]acetic acid.
Tissue LocationsKidney
Cellular LocationsExtracellular
Metabolite PathwaysDiclofenac Action Pathway
Uses & manufacturing
Use ClassificationPharmaceuticals -> Transformation products
Applications
Description4-hydroxy Diclofenac is a CYP2C9 metabolite of the NSAID diclofenac . By inhibiting COX and subsequently suppressing PGE2 synthesis, it demonstrates anti-inflammatory and analgesic properties.
UsesA metabolite of Diclofenac, a nonsteroidal anti-inflammatory compound and cyclooxygenase (COX) inhibitor
UsesA Cytochrome P450 2C9 (CYP2C9) metabolite of diclofenac
UsesA metabolite of Diclofenac, a nonsteroidal inflammatory compound and cyclooxygenase (COX) inhibitor.
General Description4′-Hydroxydiclofenac is one of the metabolites of diclofenac, a nonsteroidal anti-inflammatory drug (NSAID) used in human and veterinary medicine.
Suppliers73 total
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Related reactions
4 records
Compound notes
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