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Details

Stereochemistry ACHIRAL
Molecular Formula C14H10Cl2NO2.Na.H2O
Molecular Weight 336.1462
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MECLOFENAMATE SODIUM

SMILES

Cc1ccc(c(c1Cl)Nc2ccccc2C(=O)[O-])Cl.[Na+].O

InChI

InChIKey=QHJLLDJTVQAFAN-UHFFFAOYSA-M
InChI=1S/C14H11Cl2NO2.Na.H2O/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);;1H2/q;+1;/p-1

HIDE SMILES / InChI

Molecular Formula HO
Molecular Weight 17.0073
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

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
Contribution of nitric oxide and prostanoids to the cardiac electrophysiological and coronary vasomotor effects of diadenosine polyphosphates.
2001 Aug
Relationship between the production of prostaglandins and progesterone by luteinizing human granulosa cells.
2001 Dec
Vasodilator responses to ATP and UTP are cAMP dependent in the mesenteric vascular bed of the cat.
2001 Jul
Pregnancy enhances G protein activation and nitric oxide release from uterine arteries.
2001 May
[HPLC analysis of nonsteroidal antirheumatic substances in biological material. V. Fenamates].
2001 Nov
Nitric oxide buffers renal medullary vasoconstriction induced by prostaglandins synthesis blockade.
2001 Nov
Fenamates stimulate BKCa channel osteoblast-like MG-63 cells activity in the human.
2001 Nov
Diabetes abolishes the gender difference in vasopressin-mediated potentiation of sympathetic vasoconstriction.
2001 Sep 21
Vascular adaptations to pregnancy in mice: effects on myogenic tone.
2002 Dec
Native LDL induces proliferation of human vascular smooth muscle cells via redox-mediated activation of ERK 1/2 mitogen-activated protein kinases.
2002 Feb
Amide derivatives of meclofenamic acid as selective cyclooxygenase-2 inhibitors.
2002 Feb 25
Molecular modelling of the differential interaction between several non-steroidal anti-inflammatory drugs and human prostaglandin endoperoxide H synthase-2 (h-PGHS-2).
2002 Jan
Cyclic adenosine monophosphate-dependent vascular responses to purinergic agonists adenosine triphosphate and uridine triphosphate in the anesthetized mouse.
2002 Jan
Differential binding mode of diverse cyclooxygenase inhibitors.
2002 Mar
Relaxation by urocortin of human saphenous veins.
2002 May
Endothelin-induced modulation of neuropeptide Y and norepinephrine release from the rat mesenteric bed.
2002 Oct
Structure-function relationship and role of tumor necrosis factor-alpha-converting enzyme in the down-regulation of L-selectin by non-steroidal anti-inflammatory drugs.
2002 Oct 11
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
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
Vascular reactivity to vasopressin during diabetes: gender and regional differences.
2003 Jan 17
Chronic hypoxia opposes pregnancy-induced increase in uterine artery vasodilator response to flow.
2003 Mar
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
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
Topical NSAIDs for acute pain: a meta-analysis.
2004 May 17
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
Meclofenamic acid and diclofenac, novel templates of KCNQ2/Q3 potassium channel openers, depress cortical neuron activity and exhibit anticonvulsant properties.
2005 Apr
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
Determination of fourteen non-steroidal anti-inflammatory drugs in animal serum and plasma by liquid chromatography/mass spectrometry.
2006
Early aging and anatomic heterogeneity determine cyclooxygenase-mediated vasoconstriction to angiotensin II in mice.
2006 Aug
Role for prostaglandins in the regulation of type 1 11beta-hydroxysteroid dehydrogenase in human granulosa-lutein cells.
2006 Dec
Allosteric modulation of [3H]EBOB binding to GABAA receptors by diflunisal analogues.
2006 Dec
Use of accelerating solvent extraction for detecting non-steroidal anti-inflammatory drugs in horse feces.
2006 Jun
Intermedin/adrenomedullin-2 dilates the rat pulmonary vascular bed: dependence on CGRP receptors and nitric oxide release.
2006 Jun
Meclofenamic acid extends donor-recipient asynchrony in equine embryo transfer.
2006 Sep
Hemopressin, a hemoglobin fragment, dilates the rat systemic vascular bed through release of nitric oxide.
2006 Sep
Analysis of responses to kava kava in the feline pulmonary vascular bed.
2006 Spring
Differential effects of losartan and candesartan on vasoconstrictor responses in the rat.
2007 Mar-Apr
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.
Substance Class Chemical
Created
by admin
on Fri Jun 25 20:57:13 UTC 2021
Edited
by admin
on Fri Jun 25 20:57:13 UTC 2021
Record UNII
94NJ818U2W
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MECLOFENAMATE SODIUM
MART.   ORANGE BOOK   USAN   USP   VANDF  
USAN  
Official Name English
BENZOIC ACID, 2-((2,6-DICHLORO-3-METHYLPHENYL)AMINO)-, SODIUM SALT, HYDRATE (1:1:1)
Common Name English
BENZOIC ACID, 2-((2,6-DICHLORO-3-METHYLPHENYL)AMINO)-, MONOSODIUM SALT, MONOHYDRATE
Common Name English
MECLOFENAMATE SODIUM [VANDF]
Common Name English
MECLOMEN
Brand Name English
MECLOFENAMATE SODIUM [ORANGE BOOK]
Common Name English
MECLOFENAMATE SODIUM [USAN]
Common Name English
SODIUM MECLOFENAMATE
Common Name English
MECLODIUM
Brand Name English
MONOSODIUM N-(2,6-DICHLORO-M-TOLYL)ANTHRANILATE MONOHYDRATE
Systematic Name English
MECLOFENAMATE SODIUM [USP MONOGRAPH]
Common Name English
MECLOFENAMATE SODIUM [USP-RS]
Common Name English
MECLOFENAMIC ACID SODIUM
Common Name English
MECLOFENAMATE SODIUM HYDRATE
Common Name English
MECLOFENAMATE SODIUM [MART.]
Common Name English
CL-583.NA SALT
Code English
SODIUM MECLOFENAMATE MONOHYDRATE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C257
Created by admin on Fri Jun 25 20:57:14 UTC 2021 , Edited by admin on Fri Jun 25 20:57:14 UTC 2021
Code System Code Type Description
PUBCHEM
23663959
Created by admin on Fri Jun 25 20:57:14 UTC 2021 , Edited by admin on Fri Jun 25 20:57:14 UTC 2021
PRIMARY
ChEMBL
CHEMBL509
Created by admin on Fri Jun 25 20:57:14 UTC 2021 , Edited by admin on Fri Jun 25 20:57:14 UTC 2021
PRIMARY
USP_CATALOG
1377803
Created by admin on Fri Jun 25 20:57:14 UTC 2021 , Edited by admin on Fri Jun 25 20:57:14 UTC 2021
PRIMARY USP-RS
CAS
67254-91-5
Created by admin on Fri Jun 25 20:57:14 UTC 2021 , Edited by admin on Fri Jun 25 20:57:14 UTC 2021
PRIMARY
EVMPD
SUB03106MIG
Created by admin on Fri Jun 25 20:57:14 UTC 2021 , Edited by admin on Fri Jun 25 20:57:14 UTC 2021
PRIMARY
FDA UNII
94NJ818U2W
Created by admin on Fri Jun 25 20:57:14 UTC 2021 , Edited by admin on Fri Jun 25 20:57:14 UTC 2021
PRIMARY
DRUG BANK
DBSALT001241
Created by admin on Fri Jun 25 20:57:14 UTC 2021 , Edited by admin on Fri Jun 25 20:57:14 UTC 2021
PRIMARY
NCI_THESAURUS
C47597
Created by admin on Fri Jun 25 20:57:14 UTC 2021 , Edited by admin on Fri Jun 25 20:57:14 UTC 2021
PRIMARY
RXCUI
6677
Created by admin on Fri Jun 25 20:57:14 UTC 2021 , Edited by admin on Fri Jun 25 20:57:14 UTC 2021
PRIMARY RxNorm
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY