U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of MECLOFENAMIC ACID

SMILES

Cc1ccc(c(c1Cl)Nc2ccccc2C(=O)O)Cl

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
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
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

5.26089585E11
Palliative
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

5.26089585E11
Palliative
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

5.26089585E11
Palliative
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

5.26089585E11
Palliative
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

5.26089585E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
15.1 μg/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
30.2 μg × h/mL
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.4 h
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

Doses

DosePopulationAdverse 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:
unhealthy
Health Status: unhealthy
Condition: rheumatoid arthritis
Sources:
Other AEs: Diarrhoea...
Other AEs:
Diarrhoea
Sources:
AEs

AEs

AESignificanceDosePopulation
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:
unhealthy
Health Status: unhealthy
Condition: rheumatoid arthritis
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes [EC50 24 uM]
yes [IC50 0.5 uM]
PubMed

PubMed

TitleDatePubMed
Comparison of the in vivo coronary action of endothelin-1 and vasopressin role of nitric oxide and prostanoids.
2003 Dec
Analysis of responses to valerian root extract in the feline pulmonary vascular bed.
2003 Dec
Variable effects of nonsteroidal antiinflammatory agents on thyroid test results.
2003 Dec
Endothelium-dependent, vasopressin-induced contractions in rabbit renal arteries.
2003 Dec
Endothelial-dependent vasodilation is reduced in mesenteric arteries from superoxide dismutase knockout mice.
2003 Dec 1
Regulation of intraluteal production of prostaglandins.
2003 Nov 10
In vivo coronary effects of endothelin-1 after ischemia-reperfusion. Role of nitric oxide and prostanoids.
2003 Nov 14
Interactions between vasoconstrictors and vasodilators in regulating hemodynamics of distinct vascular beds.
2003 Oct
Analysis of responses to St. John's Wort in the feline pulmonary vascular bed.
2004
Effects of lornoxicam on the physiology of severe sepsis.
2004 Dec
Responses to bradykinin are mediated by NO-independent mechanisms in the rat hindlimb vascular bed.
2004 Dec
Effects of chronic PGHS-2 inhibition on PGHS-dependent vasoconstriction in the aged female rat.
2004 Feb 1
Myogenic reactivity is enhanced in rat radial uterine arteries in a model of maternal undernutrition.
2004 Jul
Vasopressin effects on the coronary circulation after a short ischemia in anesthetized goats: role of nitric oxide and prostanoids.
2004 Jul 14
Roles for prostaglandins in the steroidogenic response of human granulosa cells to high-density lipoproteins.
2004 Jul 30
Determination of expression of cyclooxygenase-1 and -2 isozymes in canine tissues and their differential sensitivity to nonsteroidal anti-inflammatory drugs.
2004 Jun
Race-specific differences in endothelial function: predisposition of African Americans to vascular diseases.
2004 Jun 1
Role of potassium channels in the nitric oxide-independent vasodilator response to acetylcholine.
2004 Mar
Topical NSAIDs for acute pain: a meta-analysis.
2004 May 17
Coronary action of endothelin-1 and vasopressin during acute hypertension in anesthetized goats. Role of nitric oxide and prostanoids.
2004 May-Jun
Compounds exhibiting selective efficacy for different beta subunits of human recombinant gamma-aminobutyric acid A receptors.
2004 Nov
Analysis of gamma-aminobutyric acid-mediated responses in the pulmonary vascular bed of the cat.
2004 Sep
Embryo transfer in the dromedary camel (Camelus dromedarius) using asynchronous, meclofenamic acid-treated recipients.
2005
Meclofenamic acid and diclofenac, novel templates of KCNQ2/Q3 potassium channel openers, depress cortical neuron activity and exhibit anticonvulsant properties.
2005 Apr
Increased myogenic tone in 7-month-old adult male but not female offspring from rat dams exposed to hypoxia during pregnancy.
2005 Aug
Tracking acidic pharmaceuticals, caffeine, and triclosan through the wastewater treatment process.
2005 Jan
Mechanisms of the protective effects of urocortin on coronary endothelial function during ischemia-reperfusion in rat isolated hearts.
2005 Jun
Coronary effects of endothelin-1 and vasopressin during acute hypotension in anesthetized goats.
2005 Jun 10
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 Mar 15
Enhanced response of pig coronary arteries to endothelin-1 after ischemia-reperfusion. Role of endothelin receptors, nitric oxide and prostanoids.
2005 Nov 7
Nonsynaptic GABA signaling in postnatal subventricular zone controls proliferation of GFAP-expressing progenitors.
2005 Sep
Determination of fourteen non-steroidal anti-inflammatory drugs in animal serum and plasma by liquid chromatography/mass spectrometry.
2006
Starch-based microspheres produced by emulsion crosslinking with a potential media dependent responsive behavior to be used as drug delivery carriers.
2006 Apr
Partial renal ischemia elicits heterogeneous control of renal sympathetic nerve activity to ischemic and nonischemic regions of the kidney.
2006 Feb
QSAR analysis of meclofenamic acid analogues as selective COX-2 inhibitors.
2006 Jan 15
Vasoconstrictor prostanoids may be involved in reduced coronary reactive hyperemia after ischemia-reperfusion in anesthetized goats.
2006 Jan 20
Intermedin/adrenomedullin-2 dilates the rat pulmonary vascular bed: dependence on CGRP receptors and nitric oxide release.
2006 Jun
Second-order calibration of excitation-emission matrix fluorescence spectra for the determination of N-phenylanthranilic acid derivatives.
2006 Mar
Angiotensin-(1-7) potentiates responses to bradykinin but does not change responses to angiotensin I.
2006 Nov
Inhibition of human phenol and estrogen sulfotransferase by certain non-steroidal anti-inflammatory agents.
2006 Oct
Meclofenamic acid extends donor-recipient asynchrony in equine embryo transfer.
2006 Sep
Cyclooxygenase-2 inhibition normalizes arterial blood pressure in CYP1A1-REN2 transgenic rats with inducible ANG II-dependent malignant hypertension.
2006 Sep
Analysis of responses to kava kava in the feline pulmonary vascular bed.
2006 Spring
Spurious urine excretion drug profile in the horse due to bedding contamination and drug recycling: the case of meclofenamic acid.
2007 Apr
Alpha2-adrenoreceptor mediated sympathoinhibition of heart rate during acute hypoxia is diminished in conscious prostacyclin synthase deficient mice.
2007 Apr
Molecular expression and pharmacological identification of a role for K(v)7 channels in murine vascular reactivity.
2007 Jul
Non-steroidal anti-inflammatory drugs increase insulin release from beta cells by inhibiting ATP-sensitive potassium channels.
2007 Jun
Simultaneous determination of various pharmaceutical compounds in water by solid-phase extraction-liquid chromatography-tandem mass spectrometry.
2007 Jun 22
Differential effects of losartan and candesartan on vasoconstrictor responses in the rat.
2007 Mar-Apr
Endothelium-dependent relaxation of isolated splanchnic arteries from cirrhotic patients: Role of reactive oxygen species.
2007 Oct
Patents

Sample Use Guides

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
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.
Name Type Language
MECLOFENAMIC ACID
GREEN BOOK   INN   MART.   MI   USAN   VANDF   WHO-DD  
USAN   INN  
Official 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
MECLOFENAMATE
VANDF  
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 [WHO-DD]
Common Name English
MECLOFENAMIC ACID [GREEN BOOK]
Common Name English
Classification Tree Code System Code
LIVERTOX 588
Created by admin on Sat Jun 26 03:39:09 UTC 2021 , Edited by admin on Sat Jun 26 03:39:09 UTC 2021
WHO-ATC M01AG04
Created by admin on Sat Jun 26 03:39:09 UTC 2021 , Edited by admin on Sat Jun 26 03:39:09 UTC 2021
WHO-VATC QM01AG04
Created by admin on Sat Jun 26 03:39:09 UTC 2021 , Edited by admin on Sat Jun 26 03:39:09 UTC 2021
NCI_THESAURUS C1323
Created by admin on Sat Jun 26 03:39:09 UTC 2021 , Edited by admin on Sat Jun 26 03:39:09 UTC 2021
CFR 21 CFR 520.1330
Created by admin on Sat Jun 26 03:39:09 UTC 2021 , Edited by admin on Sat Jun 26 03:39:09 UTC 2021
WHO-VATC QM02AA18
Created by admin on Sat Jun 26 03:39:09 UTC 2021 , Edited by admin on Sat Jun 26 03:39:09 UTC 2021
WHO-ATC M02AA18
Created by admin on Sat Jun 26 03:39:09 UTC 2021 , Edited by admin on Sat Jun 26 03:39:09 UTC 2021
CFR 21 CFR 520.1331
Created by admin on Sat Jun 26 03:39:09 UTC 2021 , Edited by admin on Sat Jun 26 03:39:09 UTC 2021
Code System Code Type Description
FDA UNII
48I5LU4ZWD
Created by admin on Sat Jun 26 03:39:09 UTC 2021 , Edited by admin on Sat Jun 26 03:39:09 UTC 2021
PRIMARY
MESH
D008469
Created by admin on Sat Jun 26 03:39:09 UTC 2021 , Edited by admin on Sat Jun 26 03:39:09 UTC 2021
PRIMARY
MERCK INDEX
M7120
Created by admin on Sat Jun 26 03:39:09 UTC 2021 , Edited by admin on Sat Jun 26 03:39:09 UTC 2021
PRIMARY Merck Index
INN
2165
Created by admin on Sat Jun 26 03:39:09 UTC 2021 , Edited by admin on Sat Jun 26 03:39:09 UTC 2021
PRIMARY
IUPHAR
7219
Created by admin on Sat Jun 26 03:39:09 UTC 2021 , Edited by admin on Sat Jun 26 03:39:09 UTC 2021
PRIMARY
DRUG BANK
DB00939
Created by admin on Sat Jun 26 03:39:09 UTC 2021 , Edited by admin on Sat Jun 26 03:39:09 UTC 2021
PRIMARY
RXCUI
588003
Created by admin on Sat Jun 26 03:39:09 UTC 2021 , Edited by admin on Sat Jun 26 03:39:09 UTC 2021
ALTERNATIVE
CAS
644-62-2
Created by admin on Sat Jun 26 03:39:09 UTC 2021 , Edited by admin on Sat Jun 26 03:39:09 UTC 2021
PRIMARY
PUBCHEM
4037
Created by admin on Sat Jun 26 03:39:09 UTC 2021 , Edited by admin on Sat Jun 26 03:39:09 UTC 2021
PRIMARY
LACTMED
Meclofenamate
Created by admin on Sat Jun 26 03:39:09 UTC 2021 , Edited by admin on Sat Jun 26 03:39:09 UTC 2021
PRIMARY
NCI_THESAURUS
C61826
Created by admin on Sat Jun 26 03:39:09 UTC 2021 , Edited by admin on Sat Jun 26 03:39:09 UTC 2021
PRIMARY
EVMPD
SUB08678MIG
Created by admin on Sat Jun 26 03:39:09 UTC 2021 , Edited by admin on Sat Jun 26 03:39:09 UTC 2021
PRIMARY
EPA CompTox
644-62-2
Created by admin on Sat Jun 26 03:39:09 UTC 2021 , Edited by admin on Sat Jun 26 03:39:09 UTC 2021
PRIMARY
RXCUI
6678
Created by admin on Sat Jun 26 03:39:09 UTC 2021 , Edited by admin on Sat Jun 26 03:39:09 UTC 2021
PRIMARY
ECHA (EC/EINECS)
211-419-5
Created by admin on Sat Jun 26 03:39:09 UTC 2021 , Edited by admin on Sat Jun 26 03:39:09 UTC 2021
PRIMARY
ChEMBL
CHEMBL509
Created by admin on Sat Jun 26 03:39:09 UTC 2021 , Edited by admin on Sat Jun 26 03:39:09 UTC 2021
PRIMARY
DRUG CENTRAL
1650
Created by admin on Sat Jun 26 03:39:09 UTC 2021 , Edited by admin on Sat Jun 26 03:39:09 UTC 2021
PRIMARY