Basic information
- CAS
644-62-2- Standard SMILES
Cc1ccc(Cl)c(Nc2ccccc2C(=O)O)c1Cl- InChIKey
SBDNJUWAMKYJOX-UHFFFAOYSA-N- Molecular formula
- C14H11Cl2NO2
- Average molar mass
- 296.1 g/mol
- Monoisotopic mass
- 295.016684
Overview
Meclofenamic acid is an aminobenzoic acid that is anthranilic acid in which one of the hydrogens attached to the nitrogen is replaced by a 2,6-dichloro-3-methylphenyl group. A non-steroidal anti-inflammatory drug, it is used as the sodium salt for the treatment of dysmenorrhoea (painful periods), osteoarthritis and rheumatoid arthritis. It has a role as a non-steroidal anti-inflammatory drug, an analgesic, an antipyretic, an EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor, an antineoplastic agent, an anticonvulsant, an antirheumatic drug and an EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor. It is an aminobenzoic acid, an organochlorine compound and a secondary amino compound. It is a conjugate acid of a meclofenamic acid(1-).
Names & identifiers
- Preferred name
- Meclofenamic Acid
- IUPAC
- 2-(2,6-dichloro-3-methylanilino)benzoic acid
- English name
- Meclofenamic acid
- Molecular formula
- C14H11Cl2NO2
- Molecular weight
- 296.15
Names & synonyms
meclofenamic acidmeclofenamate644-62-2Arquel2-[(2,6-dichloro-3-methylphenyl)amino]benzoic acidAcido meclofenamicoAcide meclofenamiqueINF 4668Acidum meclofenamicumN-(2,6-Dichloro-m-tolyl)anthranilic acidMeclomenCI-583
Show more names
MeclofenNSC 95309MeclorfenamicmeclofenamicaciMeclofemic acidMeclophenamic acidC14804500 MeclofenamiCacid
INF-4668N-(3-Methyl-2,6-dichlorophenyl)anthranilic acid2-((2,6-Dichloro-3-methylphenyl)amino)benzoic acidN-(2,6-Dichloro-3-methylphenyl)anthranilic acidNSC-95309Arquel Tablets48I5LU4ZWDCL-583
Database identifiers
- CAS
644-62-2- PubChem CID
- 4037
- DTXSID
DTXSID0048559- ChEMBL
CHEMBL509- ChEBI
CHEBI:6710- UNII
Properties
Computed structural properties
- XLogP
- 5.2
- Topological polar surface area
- 49.3 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 3
- Heavy atoms
- 19
- Formal charge
- 0
- Complexity
- 327
Experimental & physicochemical properties
Drugs
Pharmaceutical
Pharmaceuticals -> Listed in ZINC15
LogP
5
5.9
Solubility3.66e-03 g/L
Human Drugs
Breast Feeding; Lactation; Milk, Human; Analgesic Agents; Anti-inflammatory Agents, Nonsteroidal
Pharmaceuticals
Animal DrugsFDA approved animal drugs -> Active ingredient
Melting Point
248-250
257 °C
Physical DescriptionSolid
Collision Cross Section155.91 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
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)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Toxicology
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
EPA Human Health Benchmarks for Pharmaceuticals
Meclofenamate
4.7
19.7
The recommended dose is 50 mg every 4 to 6 hours.
Data used to generate the benchmarks include the following: Lowest Daily Dose (LDD): 200 mg/day, Lowest Therapeutic Dose (LTD): 2.5 mg/kg-day, and Screening Dose: 0.0008 mg/kg-day.
15-May-21
Chemistry & industry
Pharmacology
ATC Code
M - Musculo-skeletal system
M - Musculo-skeletal system
QM - Musculo-skeletal system
QM - Musculo-skeletal system
Protein BindingGreater than 99% bound to plasma proteins over a wide drug concentration range.
PharmacodynamicsMeclofenamic acid is a nonsteroidal agent which has demonstrated anti-inflammatory, analgesic, and antipyretic activity in laboratory animals.
Mechanism of Action
The mode of action, like that of other nonsteroidal anti-inflammatory agents, is not known. Therapeutic action does not result from pituitary-adrenal stimulation. In animal studies, meclofenamic acid was found to inhibit prostaglandin synthesis and to compete for binding at the prostaglandin receptor site. In vitro meclofenamic acid was found to be an inhibitor of human leukocyte 5-lipoxygenase activity. These properties may be responsible for the anti-inflammatory action of meclofenamic acid. There is no evidence that meclofenamic acid alters the course of the underlying disease.
Biological Half-LifeIn a study in 10 healthy subjects following a single oral dose the apparent elimination half-life ranged from 0.8 to 5.3 hours. Metabolite I (3-hydroxymethyl metabolite of meclofenamic acid) has a mean half-life of approximately 15 hours.
Metabolism/Metabolites
Hepatic. Meclofenamic acid is extensively metabolized to an active metabolite (Metabolite I; 3-hydroxymethyl metabolite of meclofenamic acid) and at least six other less well characterized minor metabolites. Only Metabolite I has been shown in vitro to inhibit cyclooxygenase activity with approximately one fifth the activity of meclofenamic acid.
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.
Related reactions
10 records
Compound notes
Loading…