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
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)
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
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2094253 Sources: https://www.ncbi.nlm.nih.gov/pubmed/?term=3020588 |
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Target ID: CHEMBL215 Sources: https://www.ncbi.nlm.nih.gov/pubmed/?term=3020588 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Palliative | MECLOFENAMATE SODIUM Approved UseMeclofenamate 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 Date5.26089585E11 |
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Palliative | MECLOFENAMATE SODIUM Approved UseMeclofenamate 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 Date5.26089585E11 |
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Palliative | MECLOFENAMATE SODIUM Approved UseMeclofenamate 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 Date5.26089585E11 |
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Palliative | MECLOFENAMATE SODIUM Approved UseMeclofenamate 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 Date5.26089585E11 |
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Palliative | MECLOFENAMATE SODIUM Approved UseMeclofenamate 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 Date5.26089585E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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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 |
T1/2
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: |
unhealthy Health Status: unhealthy Condition: rheumatoid arthritis Sources: |
Other AEs: Diarrhoea... |
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: |
unhealthy Health Status: unhealthy Condition: rheumatoid arthritis Sources: |
PubMed
Title | Date | PubMed |
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Vascular adaptations to pregnancy in mice: effects on myogenic tone. | 2002 Dec |
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Coronary reactivity to endothelin-1 during partial ischemia and reperfusion in anesthetized goats. Role of nitric oxide and prostanoids. | 2002 Dec 20 |
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Obesity increases prostanoid-mediated vasoconstriction and vascular thromboxane receptor gene expression. | 2002 Nov |
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Idiosyncratic NSAID drug induced oxidative stress. | 2002 Nov 10 |
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Endothelin-induced modulation of neuropeptide Y and norepinephrine release from the rat mesenteric bed. | 2002 Oct |
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Postnatal maturation in nitric oxide-induced pulmonary artery relaxation involving cyclooxygenase-1 activity. | 2002 Oct |
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NSAIDs and enantiomers of flurbiprofen target gamma-secretase and lower Abeta 42 in vivo. | 2003 Aug |
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Endothelium-dependent, vasopressin-induced contractions in rabbit renal arteries. | 2003 Dec |
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Angiotensin-(1-7) reduces renal angiotensin II receptors through a cyclooxygenase-dependent mechanism. | 2003 Feb |
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Vascular reactivity to vasopressin during diabetes: gender and regional differences. | 2003 Jan 17 |
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Pregnancy-induced alterations of vascular function in mouse mesenteric and uterine arteries. | 2003 Mar |
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Mechanism of inhibitory actions of oxidizing agents on calcium-activated potassium current in cultured pigment epithelial cells of the human retina. | 2003 Mar |
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Chronic hypoxia opposes pregnancy-induced increase in uterine artery vasodilator response to flow. | 2003 Mar |
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Regulation of intraluteal production of prostaglandins. | 2003 Nov 10 |
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In vivo coronary effects of endothelin-1 after ischemia-reperfusion. Role of nitric oxide and prostanoids. | 2003 Nov 14 |
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Effects of exogenous heme on renal function: role of heme oxygenase and cyclooxygenase. | 2003 Oct |
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Effects of lornoxicam on the physiology of severe sepsis. | 2004 Dec |
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Responses to bradykinin are mediated by NO-independent mechanisms in the rat hindlimb vascular bed. | 2004 Dec |
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Effects of chronic PGHS-2 inhibition on PGHS-dependent vasoconstriction in the aged female rat. | 2004 Feb 1 |
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Race-specific differences in endothelial function: predisposition of African Americans to vascular diseases. | 2004 Jun 1 |
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Analysis of gamma-aminobutyric acid-mediated responses in the pulmonary vascular bed of the cat. | 2004 Sep |
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Embryo transfer in the dromedary camel (Camelus dromedarius) using asynchronous, meclofenamic acid-treated recipients. | 2005 |
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Coronary effects of endothelin-1 and vasopressin during acute hypotension in anesthetized goats. | 2005 Jun 10 |
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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 |
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Enhanced response of pig coronary arteries to endothelin-1 after ischemia-reperfusion. Role of endothelin receptors, nitric oxide and prostanoids. | 2005 Nov 7 |
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Nonsynaptic GABA signaling in postnatal subventricular zone controls proliferation of GFAP-expressing progenitors. | 2005 Sep |
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Determination of fourteen non-steroidal anti-inflammatory drugs in animal serum and plasma by liquid chromatography/mass spectrometry. | 2006 |
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Starch-based microspheres produced by emulsion crosslinking with a potential media dependent responsive behavior to be used as drug delivery carriers. | 2006 Apr |
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Early aging and anatomic heterogeneity determine cyclooxygenase-mediated vasoconstriction to angiotensin II in mice. | 2006 Aug |
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Role for prostaglandins in the regulation of type 1 11beta-hydroxysteroid dehydrogenase in human granulosa-lutein cells. | 2006 Dec |
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Allosteric modulation of [3H]EBOB binding to GABAA receptors by diflunisal analogues. | 2006 Dec |
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Partial renal ischemia elicits heterogeneous control of renal sympathetic nerve activity to ischemic and nonischemic regions of the kidney. | 2006 Feb |
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QSAR analysis of meclofenamic acid analogues as selective COX-2 inhibitors. | 2006 Jan 15 |
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Vasoconstrictor prostanoids may be involved in reduced coronary reactive hyperemia after ischemia-reperfusion in anesthetized goats. | 2006 Jan 20 |
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Antiepileptic effect of gap-junction blockers in a rat model of refractory focal cortical epilepsy. | 2006 Jul |
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Use of accelerating solvent extraction for detecting non-steroidal anti-inflammatory drugs in horse feces. | 2006 Jun |
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Intermedin/adrenomedullin-2 dilates the rat pulmonary vascular bed: dependence on CGRP receptors and nitric oxide release. | 2006 Jun |
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Second-order calibration of excitation-emission matrix fluorescence spectra for the determination of N-phenylanthranilic acid derivatives. | 2006 Mar |
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Angiotensin-(1-7) potentiates responses to bradykinin but does not change responses to angiotensin I. | 2006 Nov |
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Inhibition of human phenol and estrogen sulfotransferase by certain non-steroidal anti-inflammatory agents. | 2006 Oct |
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Meclofenamic acid extends donor-recipient asynchrony in equine embryo transfer. | 2006 Sep |
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Hemopressin, a hemoglobin fragment, dilates the rat systemic vascular bed through release of nitric oxide. | 2006 Sep |
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Cyclooxygenase-2 inhibition normalizes arterial blood pressure in CYP1A1-REN2 transgenic rats with inducible ANG II-dependent malignant hypertension. | 2006 Sep |
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Analysis of responses to kava kava in the feline pulmonary vascular bed. | 2006 Spring |
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Spurious urine excretion drug profile in the horse due to bedding contamination and drug recycling: the case of meclofenamic acid. | 2007 Apr |
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Molecular expression and pharmacological identification of a role for K(v)7 channels in murine vascular reactivity. | 2007 Jul |
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Non-steroidal anti-inflammatory drugs increase insulin release from beta cells by inhibiting ATP-sensitive potassium channels. | 2007 Jun |
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Simultaneous determination of various pharmaceutical compounds in water by solid-phase extraction-liquid chromatography-tandem mass spectrometry. | 2007 Jun 22 |
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Differential effects of losartan and candesartan on vasoconstrictor responses in the rat. | 2007 Mar-Apr |
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Endothelium-dependent relaxation of isolated splanchnic arteries from cirrhotic patients: Role of reactive oxygen species. | 2007 Oct |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26622892
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.
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Classification Tree | Code System | Code | ||
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LIVERTOX |
588
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WHO-ATC |
M01AG04
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NCI_THESAURUS |
C1323
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CFR |
21 CFR 520.1330
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QM02AA18
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WHO-ATC |
M02AA18
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CFR |
21 CFR 520.1331
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4037
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Meclofenamate
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C61826
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SUB08678MIG
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6710
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CHEMBL509
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1650
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ACTIVE MOIETY
METABOLITE ACTIVE (PARENT)
METABOLITE INACTIVE (PARENT)
SALT/SOLVATE (PARENT)