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=CC=C(Cl)C(NC2=C(C=CC=C2)C(O)=O)=C1Cl

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

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 8146
Arachidonate 5-lipoxygenase 49 Target ID: CHEMBL215 Sources: https://www.ncbi.nlm.nih.gov/pubmed/?term=3020588	Inhibitor 8146

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 8307	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
Rheumatoid arthritis 310 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=96f19af4-de8f-4fd7-90d8-55fe6ebdd81d	Palliative	Approved 8307	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
Osteoarthritis 155 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=96f19af4-de8f-4fd7-90d8-55fe6ebdd81d	Palliative	Approved 8307	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
Idiopathic heavy menstrual blood loss 3 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=96f19af4-de8f-4fd7-90d8-55fe6ebdd81d	Palliative	Approved 8307	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
Primary dysmenorrhea 14 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=96f19af4-de8f-4fd7-90d8-55fe6ebdd81d	Palliative	Approved 8307	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

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 Condition: rheumatoid arthritis 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 Condition: rheumatoid arthritis Sources: https://pubmed.ncbi.nlm.nih.gov/7016450

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
UGT2B7 145

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
BK channel 4	activator 208 Sources: https://pubmed.ncbi.nlm.nih.gov/11730088/	yes [EC50 24 uM]
UGT2B7 156	inhibitor 3185 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
ZINC	ZINC000000001655	http://zinc15.docking.org/substances/ZINC000000001655
eMolecules	5753451	https://www.emolecules.com/cgi-bin/more?vid=5753451

PubMed

Title	Date	PubMed
Vascular adaptations to pregnancy in mice: effects on myogenic tone.	2002 Dec	12388224
Coronary reactivity to endothelin-1 during partial ischemia and reperfusion in anesthetized goats. Role of nitric oxide and prostanoids.	2002 Dec 20	12464362
Obesity increases prostanoid-mediated vasoconstriction and vascular thromboxane receptor gene expression.	2002 Nov	12409963
Idiosyncratic NSAID drug induced oxidative stress.	2002 Nov 10	12399153
Endothelin-induced modulation of neuropeptide Y and norepinephrine release from the rat mesenteric bed.	2002 Oct	12234805
Postnatal maturation in nitric oxide-induced pulmonary artery relaxation involving cyclooxygenase-1 activity.	2002 Oct	12225961
NSAIDs and enantiomers of flurbiprofen target gamma-secretase and lower Abeta 42 in vivo.	2003 Aug	12897211
Endothelium-dependent, vasopressin-induced contractions in rabbit renal arteries.	2003 Dec	14639090
Angiotensin-(1-7) reduces renal angiotensin II receptors through a cyclooxygenase-dependent mechanism.	2003 Feb	12548089
Vascular reactivity to vasopressin during diabetes: gender and regional differences.	2003 Jan 17	12524153
Pregnancy-induced alterations of vascular function in mouse mesenteric and uterine arteries.	2003 Mar	12604662
Mechanism of inhibitory actions of oxidizing agents on calcium-activated potassium current in cultured pigment epithelial cells of the human retina.	2003 Mar	12601054
Chronic hypoxia opposes pregnancy-induced increase in uterine artery vasodilator response to flow.	2003 Mar	12433660
Regulation of intraluteal production of prostaglandins.	2003 Nov 10	14613533
In vivo coronary effects of endothelin-1 after ischemia-reperfusion. Role of nitric oxide and prostanoids.	2003 Nov 14	14637182
Effects of exogenous heme on renal function: role of heme oxygenase and cyclooxygenase.	2003 Oct	12900432
Effects of lornoxicam on the physiology of severe sepsis.	2004 Dec	15566594
Responses to bradykinin are mediated by NO-independent mechanisms in the rat hindlimb vascular bed.	2004 Dec	15501695
Effects of chronic PGHS-2 inhibition on PGHS-dependent vasoconstriction in the aged female rat.	2004 Feb 1	14736550
Race-specific differences in endothelial function: predisposition of African Americans to vascular diseases.	2004 Jun 1	15159296
Analysis of gamma-aminobutyric acid-mediated responses in the pulmonary vascular bed of the cat.	2004 Sep	15333407
Embryo transfer in the dromedary camel (Camelus dromedarius) using asynchronous, meclofenamic acid-treated recipients.	2005	15899153
Coronary effects of endothelin-1 and vasopressin during acute hypotension in anesthetized goats.	2005 Jun 10	15894011
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	15721981
Enhanced response of pig coronary arteries to endothelin-1 after ischemia-reperfusion. Role of endothelin receptors, nitric oxide and prostanoids.	2005 Nov 7	16243311
Nonsynaptic GABA signaling in postnatal subventricular zone controls proliferation of GFAP-expressing progenitors.	2005 Sep	16116450
Determination of fourteen non-steroidal anti-inflammatory drugs in animal serum and plasma by liquid chromatography/mass spectrometry.	2006	17066368
Starch-based microspheres produced by emulsion crosslinking with a potential media dependent responsive behavior to be used as drug delivery carriers.	2006 Apr	16617416
Early aging and anatomic heterogeneity determine cyclooxygenase-mediated vasoconstriction to angiotensin II in mice.	2006 Aug	16954818
Role for prostaglandins in the regulation of type 1 11beta-hydroxysteroid dehydrogenase in human granulosa-lutein cells.	2006 Dec	16959838
Allosteric modulation of [3H]EBOB binding to GABAA receptors by diflunisal analogues.	2006 Dec	16884828
Partial renal ischemia elicits heterogeneous control of renal sympathetic nerve activity to ischemic and nonischemic regions of the kidney.	2006 Feb	16166203
QSAR analysis of meclofenamic acid analogues as selective COX-2 inhibitors.	2006 Jan 15	16290292
Vasoconstrictor prostanoids may be involved in reduced coronary reactive hyperemia after ischemia-reperfusion in anesthetized goats.	2006 Jan 20	16386731
Antiepileptic effect of gap-junction blockers in a rat model of refractory focal cortical epilepsy.	2006 Jul	16886980
Use of accelerating solvent extraction for detecting non-steroidal anti-inflammatory drugs in horse feces.	2006 Jun	16839470
Intermedin/adrenomedullin-2 dilates the rat pulmonary vascular bed: dependence on CGRP receptors and nitric oxide release.	2006 Jun	16412533
Second-order calibration of excitation-emission matrix fluorescence spectra for the determination of N-phenylanthranilic acid derivatives.	2006 Mar	16608576
Angiotensin-(1-7) potentiates responses to bradykinin but does not change responses to angiotensin I.	2006 Nov	17218981
Inhibition of human phenol and estrogen sulfotransferase by certain non-steroidal anti-inflammatory agents.	2006 Oct	17073578
Meclofenamic acid extends donor-recipient asynchrony in equine embryo transfer.	2006 Sep	16986603
Hemopressin, a hemoglobin fragment, dilates the rat systemic vascular bed through release of nitric oxide.	2006 Sep	16713023
Cyclooxygenase-2 inhibition normalizes arterial blood pressure in CYP1A1-REN2 transgenic rats with inducible ANG II-dependent malignant hypertension.	2006 Sep	16622181
Analysis of responses to kava kava in the feline pulmonary vascular bed.	2006 Spring	16579730
Spurious urine excretion drug profile in the horse due to bedding contamination and drug recycling: the case of meclofenamic acid.	2007 Apr	17348907
Molecular expression and pharmacological identification of a role for K(v)7 channels in murine vascular reactivity.	2007 Jul	17519950
Non-steroidal anti-inflammatory drugs increase insulin release from beta cells by inhibiting ATP-sensitive potassium channels.	2007 Jun	17435793
Simultaneous determination of various pharmaceutical compounds in water by solid-phase extraction-liquid chromatography-tandem mass spectrometry.	2007 Jun 22	17420027
Differential effects of losartan and candesartan on vasoconstrictor responses in the rat.	2007 Mar-Apr	17612645
Endothelium-dependent relaxation of isolated splanchnic arteries from cirrhotic patients: Role of reactive oxygen species.	2007 Oct	17584193

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.

Name

Type

Language

MECLOFENAMIC ACID

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

Common 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