Mefenamic acid

241.29

241.29

200-513-1

367589PJ2C

757834|94437

DTXSID5023243

C47599

CRYSTALS|WHITE TO OFF-WHITE, CRYSTALLINE POWDER

M - Musculo-skeletal system

28142000

49.3

5.1

Solid

1.0944 (rough estimate)

230-231 °C

384.06°C (rough estimate)

195ºC

1.639

It is soluble in acetone, chloroform, dichloromethane, methanol. Insoluble in water.

Refrigerator

LD50 orally in mice, rats: 630, 790 mg/kg (Jahn, Adrian)

4.2None

4.2|PKA 4.2

153.3 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]|150.5 Ų [M+H]+ [CCS Type: TW]|161.3 Ų [M-H]-

EFFERVESCENCE

3

22-40-20/21/22

22-36

CB4550000

Xn

DARKENS ON PROLONGED EXPOSURE TO LIGHT, IS STABLE @ 25 DEG, 37 DEG, & 45 DEG C.

P201, P202, P260, P263, P264, P270, P281, P301+P312, P307+P311, P308+P313, P309+P311, P314, P321, P330, P405, P501

H302

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P264, P270, P281, P301+P312, P308+P313, P330, P405, and P501|Aggregated GHS information provided by 125 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Danger|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P260, P263, P264, P270, P281, P301+P312, P307+P311, P308+P313, P309+P311, P314, P321, P330, P405, and P501

Oral, rat LD50: 740 mg/kg. Symptoms of overdose may include severe stomach pain, coffee ground-like vomit, dark stool, ringing in the ears, change in amount of urine, unusually fast or slow heartbeat, muscle weakness, slow or shallow breathing, confusion, severe headache or loss of consciousness.

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

...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.

90%

For the treatment of rheumatoid arthritis, osteoarthritis, dysmenorrhea, and mild to moderate pain, inflammation, and fever.|FDA Label

Mefenamic acid is a nonsteroidal antiinflammatory drug (NSAID) used largely for acute treatment of pain. Mefanamic acid has been linked to rare instances of clinically apparent, acute liver injury.

Nonsteroidal Antiinflammatory Drugs

Anti-Inflammatory Agents, Non-Steroidal; Cyclooxygenase Inhibitors|MEFENAMIC ACID (PONSTEL) ... PROVIDES ANALGESIA IN MAN SIMILAR TO THAT PRODUCED BY ASPIRIN.|...INDICATED FOR RELIEF OF PAIN RESULTING FROM DENTAL EXTRACTIONS.|DRUG PREFERABLY SHOULD BE TAKEN WITH FOOD.|MEFENAMIC ACID SHOWED FAVORABLE RESULTS RELATIVE TO SOME ANALGESICS.

SINCE IT IS NOT SUPERIOR TO ESTABLISHED ANALGESICS & CAN CAUSE SERIOUS TOXICITY, USE OF MEFENAMIC ACID IS NOT RECOMMENDED. IF IT IS USED, ADMIN SHOULD NOT BE EXTENDED BEYOND 7 DAYS. IF DIARRHEA OCCURS, DRUG MUST BE DISCONTINUED & NOT USED AGAIN. IT SHOULD NOT BE USED IN CHILDREN OR IN WOMEN OF CHILDBEARING AGE.|IT IS CONTRAINDICATED IN PT WITH ULCERATION OF UPPER OR LOWER INTESTINAL TRACT...& PT KNOWN TO BE HYPERSENSITIVE TO DRUG. ...CONSIDER ITS USE ONLY IN CASES WHICH EITHER CAN NOT TOLERATE OR DO NOT RESPOND TO LESS TOXIC AGENTS.|MEFENAMIC ACID IS CONTRAINDICATED IN PT...WITH IMPAIRED RENAL FUNCTION, & SHOULD BE USED WITH CAUTION IN ASTHMATICS BECAUSE IT MAY EXACERBATE CONDITION.|Maternal Medication usually Compatible with Breast-Feeding: Mefenamic acid: Reported Sign or Symptom in Infant or Effect on Lactation: None. /from Table 6/

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.

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. (See all compounds classified as Anti-Inflammatory Agents, Non-Steroidal.)|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. (See all compounds classified as Cyclooxygenase Inhibitors.)

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/

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.

2 hours|...ABOUT 50%...IS EXCRETED IN URINE WITHIN 24 HR /HUMAN, ORAL/

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.

...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.

Acid, Mefenamic

CAPSULES: 250 MG.

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.

HPLC DETERMINATION IN PLASMA.|HPLC DETERMINATION IN SERUM.|GLC DETERMINATION IN HUMAN SERUM.

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Pharmaceuticals