MECLOFENAMIC ACID

Details

Stereochemistry	ACHIRAL
Molecular Formula	C14H11Cl2NO2
Molecular Weight	296.149
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=C(Cl)C(NC2=CC=CC=C2C(O)=O)=C(Cl)C=C1

InChI

InChIKey=SBDNJUWAMKYJOX-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Molecular Formula	C14H11Cl2NO2
Molecular Weight	296.149
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=96f19af4-de8f-4fd7-90d8-55fe6ebdd81d

Meclofenamic acid, used as Meclofenamate sodium, is a non-steroidal anti-inflammatory agent with antipyretic and antigranulation activities. Meclofenamate sodium capsules are indicated for the relief of mild to moderate pain, for the treatment of primary dysmenorrhea and for the treatment of idiopathic heavy menstrual blood loss; for relief of signs and symptoms of juvenile arthritis; so as for relief of the signs and symptoms of rheumatoid arthritis; For relief of the signs and symptoms of osteoarthritis. 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, meclofenamate sodium was found to inhibit prostaglandin synthesis and to compete for binding at the prostaglandin receptor site. In vitro, meclofenamate sodium was found to be an inhibitor of human leukocyte 5-lipoxygenase activity. These properties may be responsible for the anti-inflammatory action of meclofenamate sodium. There is no evidence that meclofenamate sodium alters the course of the underlying disease.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cyclooxygenase 89 Target ID: CHEMBL2094253 Sources: https://www.ncbi.nlm.nih.gov/pubmed/?term=3020588	Inhibitor 8504
Arachidonate 5-lipoxygenase 52 Target ID: CHEMBL215 Sources: https://www.ncbi.nlm.nih.gov/pubmed/?term=3020588	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Juvenile arthritis 3 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=96f19af4-de8f-4fd7-90d8-55fe6ebdd81d	Palliative	Approved 8583	MECLOFENAMATE SODIUM Approved Use Meclofenamate sodium capsules are indicated: For reduction of fever in adults; For relief of mild to moderate pain in adults; For relief of signs and symptoms of juvenile arthritis; For relief of the signs and symptoms of rheumatoid arthritis; For relief of the signs and symptoms of osteoarthritis; For treatment of primary dysmenorrhea; For acute or long-term use in the relief of signs and symptoms of the following: Ankylosing spondylitis; Acute painful shoulder (Acute subacromial bursitis/supraspinatus tendinitis); Acute gouty arthritis. Meclofenamate sodium capsules are also indicated for the treatment of idiopathic heavy menstrual blood loss. As with all nonsteroidal anti-inflammatory drugs, selection of meclofenamate sodium capsules require a careful assessment of the benefit/risk ratio. Veclofenamate sodium capsules are not recommended in children because adequate studies to demonstrate safety and efficacy have not been carried out. Launch Date 1986
Rheumatoid arthritis 320 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=96f19af4-de8f-4fd7-90d8-55fe6ebdd81d	Palliative	Approved 8583	MECLOFENAMATE SODIUM Approved Use Meclofenamate sodium capsules are indicated: For reduction of fever in adults; For relief of mild to moderate pain in adults; For relief of signs and symptoms of juvenile arthritis; For relief of the signs and symptoms of rheumatoid arthritis; For relief of the signs and symptoms of osteoarthritis; For treatment of primary dysmenorrhea; For acute or long-term use in the relief of signs and symptoms of the following: Ankylosing spondylitis; Acute painful shoulder (Acute subacromial bursitis/supraspinatus tendinitis); Acute gouty arthritis. Meclofenamate sodium capsules are also indicated for the treatment of idiopathic heavy menstrual blood loss. As with all nonsteroidal anti-inflammatory drugs, selection of meclofenamate sodium capsules require a careful assessment of the benefit/risk ratio. Veclofenamate sodium capsules are not recommended in children because adequate studies to demonstrate safety and efficacy have not been carried out. Launch Date 1986
Osteoarthritis 157 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=96f19af4-de8f-4fd7-90d8-55fe6ebdd81d	Palliative	Approved 8583	MECLOFENAMATE SODIUM Approved Use Meclofenamate sodium capsules are indicated: For reduction of fever in adults; For relief of mild to moderate pain in adults; For relief of signs and symptoms of juvenile arthritis; For relief of the signs and symptoms of rheumatoid arthritis; For relief of the signs and symptoms of osteoarthritis; For treatment of primary dysmenorrhea; For acute or long-term use in the relief of signs and symptoms of the following: Ankylosing spondylitis; Acute painful shoulder (Acute subacromial bursitis/supraspinatus tendinitis); Acute gouty arthritis. Meclofenamate sodium capsules are also indicated for the treatment of idiopathic heavy menstrual blood loss. As with all nonsteroidal anti-inflammatory drugs, selection of meclofenamate sodium capsules require a careful assessment of the benefit/risk ratio. Veclofenamate sodium capsules are not recommended in children because adequate studies to demonstrate safety and efficacy have not been carried out. Launch Date 1986
Idiopathic heavy menstrual blood loss 3 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=96f19af4-de8f-4fd7-90d8-55fe6ebdd81d	Palliative	Approved 8583	MECLOFENAMATE SODIUM Approved Use Meclofenamate sodium capsules are indicated: For reduction of fever in adults; For relief of mild to moderate pain in adults; For relief of signs and symptoms of juvenile arthritis; For relief of the signs and symptoms of rheumatoid arthritis; For relief of the signs and symptoms of osteoarthritis; For treatment of primary dysmenorrhea; For acute or long-term use in the relief of signs and symptoms of the following: Ankylosing spondylitis; Acute painful shoulder (Acute subacromial bursitis/supraspinatus tendinitis); Acute gouty arthritis. Meclofenamate sodium capsules are also indicated for the treatment of idiopathic heavy menstrual blood loss. As with all nonsteroidal anti-inflammatory drugs, selection of meclofenamate sodium capsules require a careful assessment of the benefit/risk ratio. Veclofenamate sodium capsules are not recommended in children because adequate studies to demonstrate safety and efficacy have not been carried out. Launch Date 1986
Primary dysmenorrhea 16 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=96f19af4-de8f-4fd7-90d8-55fe6ebdd81d	Palliative	Approved 8583	MECLOFENAMATE SODIUM Approved Use Meclofenamate sodium capsules are indicated: For reduction of fever in adults; For relief of mild to moderate pain in adults; For relief of signs and symptoms of juvenile arthritis; For relief of the signs and symptoms of rheumatoid arthritis; For relief of the signs and symptoms of osteoarthritis; For treatment of primary dysmenorrhea; For acute or long-term use in the relief of signs and symptoms of the following: Ankylosing spondylitis; Acute painful shoulder (Acute subacromial bursitis/supraspinatus tendinitis); Acute gouty arthritis. Meclofenamate sodium capsules are also indicated for the treatment of idiopathic heavy menstrual blood loss. As with all nonsteroidal anti-inflammatory drugs, selection of meclofenamate sodium capsules require a careful assessment of the benefit/risk ratio. Veclofenamate sodium capsules are not recommended in children because adequate studies to demonstrate safety and efficacy have not been carried out. Launch Date 1986

C_max

Value	Dose	Co-administered	Analyte	Population
15.1 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2322633/	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:		MECLOFENAMIC ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
30.2 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2322633/	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:		MECLOFENAMIC ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2322633/	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:		MECLOFENAMIC ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Doses

Dose	Population	Adverse events
400 mg 1 times / day multiple, oral Dose: 400 mg, 1 times / day Route: oral Route: multiple Dose: 400 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7016450	unhealthy Health Status: unhealthy Sources: https://pubmed.ncbi.nlm.nih.gov/7016450	Other AEs: Diarrhoea... Other AEs: Diarrhoea Sources: https://pubmed.ncbi.nlm.nih.gov/7016450

AEs

AE	Significance	Dose	Population
Diarrhoea		400 mg 1 times / day multiple, oral Dose: 400 mg, 1 times / day Route: oral Route: multiple Dose: 400 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7016450	unhealthy Health Status: unhealthy Sources: https://pubmed.ncbi.nlm.nih.gov/7016450

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
UGT2B7 197

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
BK channel 4	activator 342 Sources: https://pubmed.ncbi.nlm.nih.gov/11730088/	yes [EC50 24 uM]
UGT2B7 210	inhibitor 4027 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2766480/	yes [IC50 0.5 uM]

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:6710	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:6710
ChemicalBook	CB7875562	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB7875562
eMolecules	5753451	https://www.emolecules.com/cgi-bin/more?vid=5753451
ZINC	ZINC000000001655	http://zinc15.docking.org/substances/ZINC000000001655

PubMed

Title	Date	PubMed
Endothelium-dependent relaxation of isolated splanchnic arteries from cirrhotic patients: Role of reactive oxygen species.	2007-10	17584193
Differential effects of losartan and candesartan on vasoconstrictor responses in the rat.	2007-07-07	17612645
Molecular expression and pharmacological identification of a role for K(v)7 channels in murine vascular reactivity.	2007-07	17519950
Simultaneous determination of various pharmaceutical compounds in water by solid-phase extraction-liquid chromatography-tandem mass spectrometry.	2007-06-22	17420027
Non-steroidal anti-inflammatory drugs increase insulin release from beta cells by inhibiting ATP-sensitive potassium channels.	2007-06	17435793
Spurious urine excretion drug profile in the horse due to bedding contamination and drug recycling: the case of meclofenamic acid.	2007-04	17348907
Alpha2-adrenoreceptor mediated sympathoinhibition of heart rate during acute hypoxia is diminished in conscious prostacyclin synthase deficient mice.	2007-04	17120018
Role for prostaglandins in the regulation of type 1 11beta-hydroxysteroid dehydrogenase in human granulosa-lutein cells.	2006-12	16959838
Allosteric modulation of [3H]EBOB binding to GABAA receptors by diflunisal analogues.	2006-12	16884828
Angiotensin-(1-7) potentiates responses to bradykinin but does not change responses to angiotensin I.	2006-11	17218981
Inhibition of human phenol and estrogen sulfotransferase by certain non-steroidal anti-inflammatory agents.	2006-10	17073578
Meclofenamic acid extends donor-recipient asynchrony in equine embryo transfer.	2006-09	16986603
Hemopressin, a hemoglobin fragment, dilates the rat systemic vascular bed through release of nitric oxide.	2006-09	16713023
Cyclooxygenase-2 inhibition normalizes arterial blood pressure in CYP1A1-REN2 transgenic rats with inducible ANG II-dependent malignant hypertension.	2006-09	16622181
Early aging and anatomic heterogeneity determine cyclooxygenase-mediated vasoconstriction to angiotensin II in mice.	2006-08	16954818
Antiepileptic effect of gap-junction blockers in a rat model of refractory focal cortical epilepsy.	2006-07	16886980
Use of accelerating solvent extraction for detecting non-steroidal anti-inflammatory drugs in horse feces.	2006-06	16839470
Intermedin/adrenomedullin-2 dilates the rat pulmonary vascular bed: dependence on CGRP receptors and nitric oxide release.	2006-06	16412533
Starch-based microspheres produced by emulsion crosslinking with a potential media dependent responsive behavior to be used as drug delivery carriers.	2006-04	16617416
Second-order calibration of excitation-emission matrix fluorescence spectra for the determination of N-phenylanthranilic acid derivatives.	2006-03	16608576
Partial renal ischemia elicits heterogeneous control of renal sympathetic nerve activity to ischemic and nonischemic regions of the kidney.	2006-02	16166203
Vasoconstrictor prostanoids may be involved in reduced coronary reactive hyperemia after ischemia-reperfusion in anesthetized goats.	2006-01-20	16386731
QSAR analysis of meclofenamic acid analogues as selective COX-2 inhibitors.	2006-01-15	16290292
Determination of fourteen non-steroidal anti-inflammatory drugs in animal serum and plasma by liquid chromatography/mass spectrometry.	2006	17066368
Analysis of responses to kava kava in the feline pulmonary vascular bed.	2006	16579730
Enhanced response of pig coronary arteries to endothelin-1 after ischemia-reperfusion. Role of endothelin receptors, nitric oxide and prostanoids.	2005-11-07	16243311
Nonsynaptic GABA signaling in postnatal subventricular zone controls proliferation of GFAP-expressing progenitors.	2005-09	16116450
Increased myogenic tone in 7-month-old adult male but not female offspring from rat dams exposed to hypoxia during pregnancy.	2005-08	15833805
Coronary effects of endothelin-1 and vasopressin during acute hypotension in anesthetized goats.	2005-06-10	15894011
Mechanisms of the protective effects of urocortin on coronary endothelial function during ischemia-reperfusion in rat isolated hearts.	2005-06	15806110
Meclofenamic acid and diclofenac, novel templates of KCNQ2/Q3 potassium channel openers, depress cortical neuron activity and exhibit anticonvulsant properties.	2005-04	15598972
Biomarkers of oxidative stress study III. Effects of the nonsteroidal anti-inflammatory agents indomethacin and meclofenamic acid on measurements of oxidative products of lipids in CCl4 poisoning.	2005-03-15	15721981
Tracking acidic pharmaceuticals, caffeine, and triclosan through the wastewater treatment process.	2005-01	15683164
Embryo transfer in the dromedary camel (Camelus dromedarius) using asynchronous, meclofenamic acid-treated recipients.	2005	15899153
Effects of lornoxicam on the physiology of severe sepsis.	2004-12	15566594
Responses to bradykinin are mediated by NO-independent mechanisms in the rat hindlimb vascular bed.	2004-12	15501695
Compounds exhibiting selective efficacy for different beta subunits of human recombinant gamma-aminobutyric acid A receptors.	2004-11	15210837
Analysis of gamma-aminobutyric acid-mediated responses in the pulmonary vascular bed of the cat.	2004-09	15333407
Roles for prostaglandins in the steroidogenic response of human granulosa cells to high-density lipoproteins.	2004-07-30	15249120
Vasopressin effects on the coronary circulation after a short ischemia in anesthetized goats: role of nitric oxide and prostanoids.	2004-07-14	15249167
Myogenic reactivity is enhanced in rat radial uterine arteries in a model of maternal undernutrition.	2004-07	15295388
Race-specific differences in endothelial function: predisposition of African Americans to vascular diseases.	2004-06-01	15159296
Determination of expression of cyclooxygenase-1 and -2 isozymes in canine tissues and their differential sensitivity to nonsteroidal anti-inflammatory drugs.	2004-06	15198222
Coronary action of endothelin-1 and vasopressin during acute hypertension in anesthetized goats. Role of nitric oxide and prostanoids.	2004-05-27	15607496
Topical NSAIDs for acute pain: a meta-analysis.	2004-05-17	15147585
Role of potassium channels in the nitric oxide-independent vasodilator response to acetylcholine.	2004-03	14726215
Effects of chronic PGHS-2 inhibition on PGHS-dependent vasoconstriction in the aged female rat.	2004-02-01	14736550
Analysis of responses to St. John's Wort in the feline pulmonary vascular bed.	2004	15829469
Comparison of the in vivo coronary action of endothelin-1 and vasopressin role of nitric oxide and prostanoids.	2003-12	15259791
Analysis of responses to valerian root extract in the feline pulmonary vascular bed.	2003-12	14736362

Patents

Sample Use Guides

In Vivo Use Guide

For Mild to Moderate Pain: The recommended dose is 50 mg every 4 to 6 hours. Doses of 100 mg may be needed in some patients for optimal pain relief For excessive menstrual blood loss and primary dysmenorrheal: The recommended dose of meclofenamate sodium is 100 mg 3 times a day, for up to 6 days, starting at the onset of menstrual flow. For rheumatoid arthritis and osteoarthritis (including acute exacerbations of chronic disease): The dosage is 200 mg to 400 mg per day, administered in three or four equal doses.

Route of Administration: Oral

In Vitro Use Guide

The meclofenamic acid was tested in murine models immunodeficient and immunocompetent) of Uterine cervical cancer (UCC), which manifested a significant reduction in tumor growth and increased mouse survival. It was demonstrated that meclofenamic acid was the most cytotoxic, with a significant antitumor effect in murine models. Cytotoxicity assay performed with two repetitions. In a first selection assay meclofenamic acid was used in concentrations of 100 µM. In a subsequent assay, the mefenamic acid was used in concentrations of 0, 7.5, 15, 30, 60, 120 and 240 µM.

Substance Class	Chemical Created by `admin` on `Wed Apr 02 08:59:10 GMT 2025` Edited by `admin` on `Wed Apr 02 08:59:10 GMT 2025`
Record UNII	48I5LU4ZWD
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MECLOFENAMIC ACID

Official Name

English

MECLOFENAMATE

Preferred Name

English

CL-583

Code

English

BENZOIC ACID, 2-((2,6-DICHLORO-3-METHYLPHENYL)AMINO)-

Common Name

English

N-(2,6-DICHLORO-M-TOLYL)ANTHRANILIC ACID

Systematic Name

English

Meclofenamic acid [WHO-DD]

Common Name

English

MECLOFENAMIC ACID [MART.]

Common Name

English

meclofenamic acid [INN]

Common Name

English

INF 4668

Code

English

MECLOFENAMATE [VANDF]

Common Name

English

NSC-95309

Code

English

INF-4668

Code

English

MECLOFENAMIC ACID [VANDF]

Common Name

English

MECLOFENAMIC ACID [MI]

Common Name

English

CI-583

Code

English

MECLOFENAMIC ACID [USAN]

Common Name

English

MECLOFENAMIC ACID [GREEN BOOK]

Common Name

English

Classification Tree Code System Code

LIVERTOX

588