61-68-7Cc1cccc(Nc2ccccc2C(=O)O)c1CHYYBABOKPJLUIN-UHFFFAOYSA-NMefenamic acid is an aminobenzoic acid that is anthranilic acid in which one of the hydrogens attached to the nitrogen is replaced by a 2,3-dimethylphenyl group. Although classed as a non-steroidal anti-inflammatory drug, its anti-inflammatory properties are considered to be minor. It is used to relieve mild to moderate pain, including headaches, dental pain, osteoarthritis and rheumatoid arthritis. It has a role as a non-steroidal anti-inflammatory drug, an analgesic, an antipyretic, an EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor, a xenobiotic, an antirheumatic drug and an environmental contaminant. It is an aminobenzoic acid and a secondary amino compound.
61-68-7DTXSID5023243CHEMBL686CHEBI:6717DEA NFLIS-Drug Category -> Analgesics
Pharmaceuticals -> Used in Switzerland
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals
Pharmaceuticals -> NSAIDs
4.2
4.38
CRYSTALS
WHITE TO OFF-WHITE, CRYSTALLINE POWDER
WHITE POWDER; SOLUBILITY IN WATER: GREATER THAN 5 G/100 ML /SODIUM SALT/
IN WATER @ PH 7.1: 0.0041 G/100 ML @ 25 °C, 0.008 G/100 ML @ 37 °C; SOL IN SOLN OF ALKALI HYDROXIDES; SPARINGLY SOL IN ETHER, CHLOROFORM; SLIGHTLY SOL IN ETHANOL
1 G SOL IN 26 ML DIMETHYLFORMAMIDE & 220 ML ALCOHOL
1.37e-02 g/L
>36.2 [ug/mL] (The mean of the results at pH 7.4)
Breast Feeding; Lactation; Milk, Human; Analgesic Agents; Antii-nflammatory Agents, Nonsteroidal
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Pharmaceuticals
230-231 °C
230-231 °C
DECARBOXYLATES @ TEMP ABOVE ITS MELTING POINT (@ 300 °C, 100% IS DECARBOXYLATED IN 3 MIN)
230 - 231 °C
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
This chemical does not meet GHS hazard criteria for 0.8% (1 of 126) of reports.
Warning
H302 (99.2%): Harmful if swallowed [Warning Acute toxicity, oral]
P203, P264, P270, P280, P301+P317, P318, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 126 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Danger
Acute Tox. 4 (99.2%)
Acute toxicity (Oral) - Category 4
...WARFARIN CAN BE DISPLACED FROM PLASMA PROTEIN BY MEFENAMIC ACID...INCR IN FREE WARFARIN CAN RANGE FROM 66-400% WITH CORRESPONDING INCR IN ANTICOAGULANT ACTION. BECAUSE OF DOSAGES INVOLVED, INTERACTIONS ARE MORE LIKELY TO BE IMPORTANT IN PT TREATED WITH WARFARIN THAN IN WORKERS WHO USE IT AS PESTICIDE...
EFFECTS OF ORAL ANTICOAGULANT AGENTS ARE ENHANCED.
In prospective studies less than 5% of patients taking mefenamic acid experienced transient serum aminotransferase elevations. The abnormalities usually resolved even while continuing the drug and without dose modification. Marked aminotransferase elevations (>3 fold elevated) occurred in
M - Musculo-skeletal system
QM - Musculo-skeletal system
Mefenamic acid, an anthranilic acid derivative, is a member of the fenamate group of nonsteroidal anti-inflammatory drugs (NSAIDs). It exhibits anti-inflammatory, analgesic, and antipyretic activities. Similar to other NSAIDs, mefenamic acid inhibits prostaglandin synthetase.
Mefenamic acid binds the prostaglandin synthetase receptors COX-1 and COX-2, inhibiting the action of prostaglandin synthetase. As these receptors have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity, the symptoms of pain are temporarily reduced.
2 hours
...ABOUT 50%...IS EXCRETED IN URINE WITHIN 24 HR /HUMAN, ORAL/
Mefenamic acid undergoes metabolism by CYP2C9 to 3-hydroxymethyl mefenamic acid, and further oxidation to a 3-carboxymefenamic acid may occur. The activity of these metabolites has not been studied. Mefenamic acid is also glucuronidated directly.
MEFENAMIC ACID...IS TRANSFORMED TO HYDROXYMETHYL DERIVATIVE & TO ACID BY MAJOR, IF NOT ONLY, METABOLIC PATHWAY IN DOG, MONKEY, & HUMAN.
Mefenamic acid has known human metabolites that include 3-hydroxymethyl mefenamic aci.
367589PJ2C
MEFENAMIC ACID
Mechanisms of Action [MoA] - Cyclooxygenase Inhibitors
Chemical Structure [CS] - Anti-Inflammatory Agents, Non-Steroidal
Established Pharmacologic Class [EPC] - Nonsteroidal Anti-inflammatory Drug
Mefenamic acid is a Nonsteroidal Anti-inflammatory Drug. The mechanism of action of mefenamic acid is as a Cyclooxygenase Inhibitor.
불러오는 중…
4.2
4.5
4.2
PKA 4.2
152.3 Ų [M]+ [CCS Type: DT; Buffer gas: N2; Ionization: APCI+; Dataset: TOXCAST; Source Identifier: DTXSID5023243]
150.5 Ų [M+H]+ [CCS Type: TW]
153.3 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
153.25 Ų [M+H]+
white or light yellow crystalline powder, odorless, insoluble in water, slightly soluble in ethanol, chloroform, slightly soluble in ether. Melting point 230-231°C, mefenamic acid is an anti-inflammatory analgesic with antipyretic, analgesic and anti-inflammatory effects.
...DIARRHEA IS COMMON & OFTEN SEVERE, & GI ULCERATION & BLEEDING HAVE BEEN REPORTED. EXACERBATION OF ASTHMA, AUTOIMMUNE HEMOLYTIC ANEMIA, ALBUMINURIA, & SLIGHT ELEVATION OF BLOOD UREA NITROGEN MAY OCCUR. AGRANULOCYTOSIS, THROMBOCYTOPENIC PURPURA, MEGALOBLASTIC ANEMIA, & PANCYTOPENIA HAVE BEEN REPORTED.
...UNDESIRED EFFECTS INCL DROWSINESS, NAUSEA, DIZZINESS, NERVOUSNESS, & HEADACHE.
MINOR REACTIONS INCL...VOMITING, URTICARIA, RASH, EOSINOPHILIA, BLURRED VISION, INSOMNIA, & PERSPIRATION. RARELY, PALPITATIONS, FACIAL EDEMA, DYSPNEA, EYE PAIN, EAR PAIN, DYSURIA, HEMATURIA, REVERSIBLE LOSS OF COLOR VISION, & INCR INSULIN NEED IN DIABETIC PT. MILD RENAL & HEPATIC TOXICITY HAVE ALSO BEEN REPORTED.
MEFENAMIC ACID IS A PROSTAGLANDIN SYNTHETASE INHIBITOR.
For more Human Toxicity Excerpts (Complete) data for MEFENAMIC ACID (7 total), please visit the HSDB record page.
Drug Induced Liver Injury Rank (DILIrank 2.0)
Mefenamic acid
vMost-DILI-concern
8
Warnings & precautions
DOI:10.1016/j.drudis.2016.02.015
1.25-10 MUG/KG CATS & 5-40 MG RATS GAVE PROGRESSIVE DOSE-RELATED INCR OF VOLTAGE OF BASELINE EEG PATTERNS. HIGH DOSES: SLOW WAVES & FUSIFORM COMPLEXES; IRRITATIVE ACTIVITY WITH SPIKES & COMPLEXES OF POLYSPIKES.
EEG MEFENAMIC ACID IN CATS & RATS GIVES CENTRAL SHORT-LASTING DEPRESSANT EFFECTS @ LOW DOSES & FACILILTATING OR STIMULANT EFFECTS @ HIGH DOSES.
Mefenamic acid
23.3
98.6
For the relief of acute pain in adults and adolescents ≥ 14 years of age, the recommended dose is 500 mg as an initial dose followed by 250 mg every 6 hours as needed, usually not to exceed one week.
Data used to generate the benchmarks include the following: Lowest Daily Dose (LDD): 1000 mg/day, Lowest Therapeutic Dose (LTD): 12.5 mg/kg-day, and Screening Dose: 0.004 mg/kg-day.
29-Nov-21
Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects.
Compounds or agents that combine with cyclooxygenase (PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES) and thereby prevent its substrate-enzyme combination with arachidonic acid and the formation of eicosanoids, prostaglandins, and thromboxanes.
Mefenamic acid is rapidly absorbed after oral administration.
The fecal route of elimination accounts for up to 20% of the dose, mainly in the form of unconjugated 3-carboxymefenamic acid.3 The elimination half-life of mefenamic acid is approximately two hours. Mefenamic acid, its metabolites and conjugates are primarily excreted by the kidneys. Both renal and hepatic excretion are significant pathways of elimination.
1.06 L/kg [Normal Healthy Adults (18-45 yr)]
Oral cl=21.23 L/hr [Healthy adults (18-45 yrs)]
CROSSES PLACENTAL BARRIER IN MONKEYS...EXCRETED IN URINE, BILE &/OR FECES...
ABSORBED SLOWLY FROM GI TRACT...HIGH PERCENTAGE...BOUND TO PLASMA PROTEINS. PEAK PLASMA LEVELS APPEAR IN 2 TO 4 HR...ANALGESIA MAY PERSIST FOR UP TO 6 HR...ABOUT 50%...IS EXCRETED IN URINE WITHIN 24 HR /HUMAN, ORAL/
MEDICATION
Use (kg) in Switzerland (2009): >10000
PREPD BY COPPER-CATALYZED CONDENSATION OF O-CHLOROBENZOIC ACID & 2,3-DIMETHYLANILINE: WINDER...J PHARMACOL EXP THER 138, 405 (1962); BELG PATENT 605,302 (1961 TO PARKE, DAVIS).
O-CHLOROBENOZIC ACID IS CONDENSED WITH 2,3-XYLIDENE WITH AID OF POTASSIUM CARBONATE & RESULTING POTASSIUM SALT IS TREATED WITH MINERAL ACID TO LIBERATE DESIRED ACID. US PATENT 3,138,636.
MEFENAMIC ACID IS DERIVATIVE OF ANTHRANILIC ACID, AMINE ANALOG OF SALICYLIC ACID. IT IS ONLY FENAMATE AVAIL FOR CLINICAL USE IN US, BUT IT WAS RELEASED IN 1967 ONLY FOR RESTRICTED USE AS ANALGESIC. ...TOXICITY OF MEFENAMIC ACID TENDS TO DISCOURAGE INTEREST IN GROUP.
용도Mefenamic acid is used for the same indications as flufenamic acid. Synonyms for this drug are parkemed, ponstan, ponstel, and others.
일반 설명Mefenamic acid (Ponstel, Ponstan) is one of the oldestNSAIDs, introduced into the market in 1967 for mild tomoderate pain and for primary dysmenorrhea. It is rapidly absorbed with peak plasma levels occurring 2 to 4 hoursafter oral administration. It undergoes hepatic benzylic hydroxylationof its 3'methyl group regioselectively into twoinactive metabolites, 3'-hydroxymethylmefenamic acid andthe 3'carboxylate metabolite (via further oxidation of thebenzylic alcohol group). The parent drugs and these metabolitesare conjugated with glucuronic acid and excreted primarilyin the urine. Thus, although patients with knownliver deficiency may be given lower doses, it is contraindicatedin patients with preexisting renal dysfunction.Common side effects associated with its use include diarrhea,drowsiness, and headache. The possibility of blood disordershas also prompted limitation of its administration to 7days. It is not recommended for children or during pregnancy.
정의ChEBI: An aminobenzoic acid that is anthranilic acid in which one of the hydrogens attached to the nitrogen is replaced by a 2,3-dimethylphenyl group. Although classed as a non-steroidal anti-inflammatory drug, its anti-inflammatory properties are considered to b minor. It is used to relieve mild to moderate pain, including headaches, dental pain, osteoarthritis and rheumatoid arthritis.