Basic information
- CAS
22131-79-9- Standard SMILES
C=CCOc1ccc(CC(=O)O)cc1Cl- InChIKey
ARHWPKZXBHOEEE-UHFFFAOYSA-N- Molecular formula
- C11H11ClO3
- Average molar mass
- 226.65 g/mol
- Monoisotopic mass
- 226.0396719
Overview
Alclofenac is an aromatic ether in which the ether oxygen links an allyl group to the 4-position of (3-chlorophenyl)acetic acid.A non-steroidal anti-inflammatory drug, it was withdrawn from the UK market in 1979 due to concerns with its association with vasculitis and rash. It has a role as a non-steroidal anti-inflammatory drug, a non-narcotic analgesic and a drug allergen. It is a monocarboxylic acid, an aromatic ether and a member of monochlorobenzenes.
Names & identifiers
- Preferred name
- Alclofenac
- IUPAC
- 2-(3-chloro-4-prop-2-enoxyphenyl)acetic acid
- English name
- ALCLOFENAC
- Molecular formula
- C11H11ClO3
- Molecular weight
- 226.66
Names & synonyms
alclofenac22131-79-9MedifenacPrinalginMervanAlclophenacAllopydinReufenacNeostenNeostonZumarilAlclofenaco
Show more names
Argunw7320MY 101
EpinalAlclofenacum[4-(Allyloxy)-3-chlorophenyl]acetic acidW 73203-Chloro-4-(2-propenyloxy)benzeneacetic acidBenzeneacetic acid, 3-chloro-4-(2-propenyloxy)-(4-Allyloxy-3-chlorphenyl)essigsaeureDTXSID4020038
Database identifiers
- CAS
22131-79-9- PubChem CID
- 30951
- DTXSID
DTXSID4020038- ChEMBL
CHEMBL94081- ChEBI
CHEBI:31183- UNII
- M9CP5H21N8
- EC Number
- 244-795-4
- Nikkaji
- J3.154B
Properties
Computed structural properties
- XLogP
- 2.5
- Topological polar surface area
- 46.5 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 5
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 230
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
LogP2.97
Human DrugsPharmaceuticals
Physicochemical properties
- Melting point
- 90 · 90-91°C
- Boiling point
- 324.6 °C · 324.6°C (rough estimate)
- Density
- 1.2401 · 1.2401 (rough estimate)
- refractive index
- 1.453 · 1.4530 (estimate)
- storage temp.
- Refrigerator
- solubility
- Chloroform (Slightly), Methanol (Slightly)
- pka
- 10.3 · pKa 10.3 (Uncertain)
- form
- Solid
- color
- Off-White to Pale Yellow
- Water Solubility
- 13.1 mg/L · 13.1mg/L(25 ºC)
- FDA UNII
- 9 CP5H21N8 · M9CP5H21N8
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 1 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Toxicology
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Alclofenac
vMost-DILI-concern
8
Withdrawn
DOI:10.1016/j.drudis.2016.02.015
Safety data
- Toxicity
- LD50 in mice, rats (mg/kg): 1100, 1050 orally; 600, 630 s.c.; 555, 530 i.p. (Lambelin)
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302
- Precautionary statements
- P264-P270-P301+P312-P330-P501
Chemistry & industry
Pharmacology
ATC Code
M - Musculo-skeletal system
QM - Musculo-skeletal system
Protein BindingThe binding to plasma proteins is 90-99%.
Mechanism of Action
Alclofenac is an inhibitor of prostaglandin H2 synthase. The inhibition of the enzyme occurs through the reversible block of cyclooxygenase enzyme. Therefore, it prevents the production of inflammatory mediators (and pain) as prostacyclins and prostaglandins. Aclofenac has the ability to inhibit the biosynthesis of prostaglandins which may be an important factor in the action of these drugs, but in addition, the effect of these agents in displacing endogenous anti-inflammatory substances from plasma protein binding sites is thought to be an equally important effect in their mechanism of action
Biological Half-LifeThe plasma half-life varies between 1.5 and 5.5 hours.
Metabolism/Metabolitesthe main metabolic product is alclofenac itself and alclofenac glucuronide
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.
Drugs that mimic the effects of stimulating postganglionic adrenergic sympathetic nerves. Included here are drugs that directly stimulate adrenergic receptors and drugs that act indirectly by provoking the release of adrenergic transmitters.
Absorption, Distribution and Excretion
The absorption of alclofenac from the gastrointestinal tract is irregular. After oral or rectal administration maximum plasma concentrations are reached within 1-4 hours.
Related reactions
9 records
Compound notes
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