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

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 8297
Arachidonate 5-lipoxygenase 49 Target ID: CHEMBL215 Sources: https://www.ncbi.nlm.nih.gov/pubmed/?term=3020588	Inhibitor 8297

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 8429	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 316 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=96f19af4-de8f-4fd7-90d8-55fe6ebdd81d	Palliative	Approved 8429	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 8429	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 8429	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 8429	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 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 146

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
BK channel 4	activator 214 Sources: https://pubmed.ncbi.nlm.nih.gov/11730088/	yes [EC50 24 uM]
UGT2B7 157	inhibitor 3277 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
Non-steroidal anti-inflammatory drugs inhibit the expression of cytokines and induce HSP70 in human monocytes.	1999 May	10328874
Cerebral vasoconstriction produced by vasopressin in conscious goats: role of vasopressin V(1) and V(2) receptors and nitric oxide.	2001 Apr	11309256
Pregnancy enhances G protein activation and nitric oxide release from uterine arteries.	2001 May	11299208
Screening procedure for detection of non-steroidal anti-inflammatory drugs and their metabolites in urine as part of a systematic toxicological analysis procedure for acidic drugs and poisons by gas chromatography-mass spectrometry after extractive methylation.	2001 May-Jun	11386636
[HPLC analysis of nonsteroidal antirheumatic substances in biological material. V. Fenamates].	2001 Nov	11797203
Fenamates: a novel class of reversible gap junction blockers.	2001 Sep	11504800
Diabetes abolishes the gender difference in vasopressin-mediated potentiation of sympathetic vasoconstriction.	2001 Sep 21	11567655
Vascular adaptations to pregnancy in mice: effects on myogenic tone.	2002 Dec	12388224
Native LDL induces proliferation of human vascular smooth muscle cells via redox-mediated activation of ERK 1/2 mitogen-activated protein kinases.	2002 Feb	11882624
Amide derivatives of meclofenamic acid as selective cyclooxygenase-2 inhibitors.	2002 Feb 25	11844663
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	11858641
Meclofenamic acid for inhibition of human vascular smooth muscle cell proliferation and migration: an in vitro study.	2002 Jan-Feb	11907776
Enhanced endothelin activity prevents vasodilation to insulin in insulin resistance.	2002 Jul	12105142
Differential binding mode of diverse cyclooxygenase inhibitors.	2002 Mar	11885959
Relaxation by urocortin of human saphenous veins.	2002 May	11976272
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
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	12147693
Estrogen replacement reduces PGHS-2-dependent vasoconstriction in the aged rat.	2002 Sep	12181116
Analysis of responses to valerian root extract in the feline pulmonary vascular bed.	2003 Dec	14736362
Vascular reactivity to vasopressin during diabetes: gender and regional differences.	2003 Jan 17	12524153
Identification of gap junction blockers using automated fluorescence microscopy imaging.	2003 Oct	14567776
Interactions between vasoconstrictors and vasodilators in regulating hemodynamics of distinct vascular beds.	2003 Oct	12925563
Analysis of responses to St. John's Wort in the feline pulmonary vascular bed.	2004	15829469
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
Vasopressin effects on the coronary circulation after a short ischemia in anesthetized goats: role of nitric oxide and prostanoids.	2004 Jul 14	15249167
Analysis of gamma-aminobutyric acid-mediated responses in the pulmonary vascular bed of the cat.	2004 Sep	15333407
Increased myogenic tone in 7-month-old adult male but not female offspring from rat dams exposed to hypoxia during pregnancy.	2005 Aug	15833805
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
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
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
Alpha2-adrenoreceptor mediated sympathoinhibition of heart rate during acute hypoxia is diminished in conscious prostacyclin synthase deficient mice.	2007 Apr	17120018
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.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 17:19:21 GMT 2023` Edited by `admin` on `Sat Dec 16 17:19:21 GMT 2023`
Record UNII	48I5LU4ZWD
Record Status	`Validated (UNII)`
Record Version

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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