2-[(2,6-dichloro-3-methylphenyl)amino]benzoic acid

• ChemBase ID: 815
• Molecular Formular: C14H11Cl2NO2
• Molecular Mass: 296.14864
• Monoisotopic Mass: 295.01668396
• SMILES: Clc1c(Nc2c(cccc2)C(=O)O)c(Cl)ccc1C
• Canonical SMILES: OC(=O)c1ccccc1Nc1c(Cl)ccc(c1Cl)C
• InChI: InChI=1S/C14H11Cl2NO2/c1-8-6-7-10(15)13(12(8)16)17-11-5-3-2-4-9(11)14(18)19/h2-7,17H,1H3,(H,18,19)
• InChIKey: SBDNJUWAMKYJOX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(2,6-dichloro-3-methylphenyl)amino]benzoic acid
• IUPAC Traditional name: meclofenamic acid
• Brand Name: Arquel
• Synonyms: 2-[(2,6-Dichloro-3-methylphenyl)amino]benzoic Acid; N-(2,6-Dichloro-m-tolyl)anthranilic Acid; N-(3-Methyl-2,6-dichlorophenyl)anthranilic Acid; Arquel; INF 4668; NSC 95309; Acidum meclofenamicum [INN-Latin]; Acido meclofenamico [INN-Spanish]; Acide meclofenamique [INN-French]; Meclophenamic acid; Meclomen (free acid); Meclofenamate; Meclofenamic acid

Database IDs

• CAS Number: 644-62-2
• PubChem SID: 160964278; 46507887
• PubChem CID: 4037

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.78693
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 4.377445
• LogD (pH = 7.4): 2.8239293
• Log P: 6.092265
• Molar Refractivity: 76.4512 cm^3
• Polarizability: 28.932564 Å^3
• Polar Surface Area: 49.33 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 5.11
• LOG S: -4.91
• Solubility (Water): 3.66e-03 g/l

PROPERTIES

Physical Property

• Solubility: 30 mg/L; Chloroform
• Apperance: White to Off-White Solid
• Melting Point: 257-259°C
• Hydrophobicity(logP): 5

Safety Information

• Storage Condition: Refrigerator

DETAILS

DrugBank - DB00939

• Drug Groups: approved
• Description: A non-steroidal anti-inflammatory agent with antipyretic and antigranulation activities. It also inhibits prostaglandin biosynthesis. [PubChem]
• Indication: For the relief of mild to moderate pain, for the treatment of primary dysmenorrhea and for the treatment of idiopathic heavy menstrual blood loss. Also for relief of the signs and symptoms of acute and chronic rheumatoid arthritis and osteoarthritis.
• Pharmacology: Meclofenamic acid is a nonsteroidal agent which has demonstrated anti-inflammatory, analgesic, and antipyretic activity in laboratory animals.
• Toxicity: After a massive overdose, CNS stimulation may be manifested by irrational behavior, marked agitation and generalized seizures. Following this phase, renal toxicity (falling urine output, rising creatinine, abnormal urinary cellular elements) may be noted with possible oliguria or anuria and azotemia. A 24 year-old male was anuric for approximately one week after ingesting an overdose of 6 to 7 grams of meclofenamate sodium. Spontaneous diuresis and recovery subsequently occurred.
• Affected Organisms: Humans and other mammals
• Biotransformation: 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.
• Absorption: Rapidly absorbed in man following single and multiple oral doses with peak plasma concentrations occurring in 0.5 to 2 hours. The concomitant administration of antacids (aluminum and magnesium hydroxides) does not interfere with absorption of meclofenamic acid. Unlike most NSAIDs, which when administered with food have a decrease in rate but not in extent of absorption, meclofenamic acid is decreased in both. It has been reported that following the administration of meclofenamic acid capsules one-half hour after a meal, the average extent of bioavailability decreased by 26%, the average peak concentration (C_max) decreased fourfold and the time to C_max was delayed by 3 hours.
• Half Life: In 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.
• Protein Binding: Greater than 99% bound to plasma proteins over a wide drug concentration range.
• Elimination: Other metabolites, whose excretion rates are unknown, account for the remaining 35% to 62% of the dose excreted in the urine. The remainder of the administered dose (approximately 30%) is eliminated in the feces (apparently through biliary excretion). Trace amounts of meclofenamate sodium are excreted in human breast milk.
• Distribution: * 9.1 to 43.2 L
• Clearance: * Oral cl=206 mL/min
• External Links: Wikipedia; RxList

Toronto Research Chemicals - M202750

Anti-inflammatory; antipyretic.

REFERENCES

• Juby, et al.: J. Med. Chem., 11, 111 (1968)
• Winder, et al.: J. Pharmacol. Exp. Ther., 148, 422 (1968)
• Rees, M.C.P., et al.: Lancet, 2, 541 (1968)