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

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
Relationship between the production of prostaglandins and progesterone by luteinizing human granulosa cells.
2001 Dec
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
NO and prostaglandin interactions during hemodynamic stress in the fetal ovine pulmonary circulation.
2001 Nov
Role of COX-2-derived metabolites in regulation of the renal hemodynamic response to norepinephrine.
2001 Nov
Differential responses to ATPgammaS in the mesenteric and hindlimb vascular bed of the cat.
2001 Oct 12
Cyclic adenosine monophosphate-dependent vascular responses to purinergic agonists adenosine triphosphate and uridine triphosphate in the anesthetized mouse.
2002 Jan
Relaxation by urocortin of human saphenous veins.
2002 May
Analysis of responses to valerian root extract in the feline pulmonary vascular bed.
2003 Dec
Endothelial-dependent vasodilation is reduced in mesenteric arteries from superoxide dismutase knockout mice.
2003 Dec 1
Angiotensin-(1-7) reduces renal angiotensin II receptors through a cyclooxygenase-dependent mechanism.
2003 Feb
Analysis of responses to St. John's Wort in the feline pulmonary vascular bed.
2004
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
Embryo transfer in the dromedary camel (Camelus dromedarius) using asynchronous, meclofenamic acid-treated recipients.
2005
Increased myogenic tone in 7-month-old adult male but not female offspring from rat dams exposed to hypoxia during pregnancy.
2005 Aug
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
Nonsynaptic GABA signaling in postnatal subventricular zone controls proliferation of GFAP-expressing progenitors.
2005 Sep
Angiotensin-(1-7) potentiates responses to bradykinin but does not change responses to angiotensin I.
2006 Nov
Hemopressin, a hemoglobin fragment, dilates the rat systemic vascular bed through release of nitric oxide.
2006 Sep
Cyclooxygenase-2 inhibition normalizes arterial blood pressure in CYP1A1-REN2 transgenic rats with inducible ANG II-dependent malignant hypertension.
2006 Sep
Alpha2-adrenoreceptor mediated sympathoinhibition of heart rate during acute hypoxia is diminished in conscious prostacyclin synthase deficient mice.
2007 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 Sat Jun 26 03:39:09 UTC 2021
Edited
by admin
on Sat Jun 26 03:39:09 UTC 2021
Record UNII
48I5LU4ZWD
Record Status Validated (UNII)
Record Version
  • Download
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
Related Record Type Details
METABOLIC ENZYME -> INHIBITOR
POTENT
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY