Mefenamic acid

Identification

Summary

Mefenamic acid is an NSAID used to treat mild to moderate pain for no more than a week, and primary dysmenorrhea.

Brand Names
Mefenamic, Ponstel
Generic Name
Mefenamic acid
DrugBank Accession Number
DB00784
Background

A non-steroidal anti-inflammatory agent with analgesic, anti-inflammatory, and antipyretic properties. It is an inhibitor of cyclooxygenase.

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 241.2851
Monoisotopic: 241.110278729
Chemical Formula
C15H15NO2
Synonyms
  • Acide méfénamique
  • ácido mefenámico
  • Acidum mefenamicum
  • Mefenamic acid
  • Mefenaminsäure
  • N-(2,3-xylyl)-2-aminobenzoic acid
  • N-2,3-xylylanthranilic acid
External IDs
  • CI 473
  • CI-473
  • CN 35355
  • CN-35355
  • INF 3355
  • INF-3355
  • J2.344B
  • M01AG01

Pharmacology

Indication

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

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofPrimary dysmenorrhea••••••••••••
Used in combination to treatGastrointestinal crampsCombination Product in combination with: Dicyclomine (DB00804)••••••••••••••••••• ••••••• ••••••
Treatment ofMild pain••••••••••••
Treatment ofModerate pain••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

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.

Mechanism of action

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.

TargetActionsOrganism
AProstaglandin G/H synthase 2
inhibitor
Humans
UProstaglandin G/H synthase 1
inhibitor
Humans
Absorption

Mefenamic acid is rapidly absorbed after oral administration.

Volume of distribution
  • 1.06 L/kg [Normal Healthy Adults (18-45 yr)]
Protein binding

90%

Metabolism

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.

Hover over products below to view reaction partners

Route of elimination

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.

Half-life

2 hours

Clearance
  • Oral cl=21.23 L/hr [Healthy adults (18-45 yrs)]
Adverse Effects
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Toxicity

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.

Pathways
PathwayCategory
Mefenamic Acid Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirMefenamic acid may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbametapirThe serum concentration of Mefenamic acid can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Mefenamic acid can be increased when combined with Abatacept.
AbciximabThe risk or severity of bleeding and hemorrhage can be increased when Mefenamic acid is combined with Abciximab.
AbirateroneThe serum concentration of Mefenamic acid can be increased when it is combined with Abiraterone.
Food Interactions
  • Avoid alcohol.
  • Take with food.

Products

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Product Images
International/Other Brands
Coslan (Parke Davis) / Lysalgo (SIT) / Mefacit (SecFarm) / Parkemed (Pfizer) / Ponalar (Coronet Crown) / Ponstan Forte (Pfizer) / Ponstyl (Pfizer) / Ponstyl Fort (Pfizer) / Pontal (Daiichi Sankyo) / Tanston (Pfizer)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
MefenamicCapsule250 mgOralAa Pharma Inc1996-11-06Not applicableCanada flag
Mefenamic-250Capsule250 mgOralPro Doc Limitee1997-08-062009-07-23Canada flag
PonstanCapsule250 mgOralAa Pharma Inc1966-12-31Not applicableCanada flag
PonstelCapsule250 mg/1OralSHIONOGI INC.1967-03-282019-12-31US flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Dom-mefenamic AcidCapsule250 mgOralDominion Pharmacal1998-09-172023-05-08Canada flag
Mefenamic AcidCapsule250 mg/1OralLupin Pharmaceuticals, Inc.2011-09-06Not applicableUS flag
Mefenamic AcidCapsule250 mg/1OralSolubiomix2016-03-232016-05-20US flag
Mefenamic acidCapsule250 mg/1OralMicro Labs Limited2010-11-19Not applicableUS flag
Mefenamic acidCapsule250 mg/1OralPaddock Laboratories, Inc.2010-11-192016-03-01US flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
ซีนามิค 500Tablet, coated500 mgOralบริษัท ซีฟาม จำกัด จำกัด2001-03-21Not applicableThailand flag
เมดนิล - 500 ชนิดเม็ดTablet, coated500 mgOralบริษัท สหแพทย์เภสัช จำกัด2007-04-10Not applicableThailand flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
ORCIGESIC CAPSULEMefenamic acid (250 mg) + Orphenadrine citrate (35 mg)CapsuleOralSUNWARD PHARMACEUTICAL PRIVATE LIMITED1992-10-07Not applicableSingapore flag
ORCIGESIC TABLETSMefenamic acid (250 mg) + Orphenadrine citrate (35 mg)Tablet, film coatedOralSUNWARD PHARMACEUTICAL PRIVATE LIMITED1991-05-24Not applicableSingapore flag
ยูเทอร์แกนMefenamic acid (250 MG) + Dicyclomine (10 MG)Tabletห้างหุ้นส่วนจำกัด โรงงานเลิศสิงห์เภสัชกรรม1997-01-09Not applicableThailand flag
เมนนอกซ์Mefenamic acid (250 MG) + Dicyclomine (15 MG)Tablet, film coatedบริษัท เจริญเภสัชแล็บ จำกัด1983-12-15Not applicableThailand flag
แอนพัส 520Mefenamic acid (500 MG) + Dicyclomine (20 MG)Tablet, film coatedบริษัท ไทยนครพัฒนา จำกัด2009-08-11Not applicableThailand flag

Categories

ATC Codes
M01AG01 — Mefenamic acid
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as aminobenzoic acids. These are benzoic acids containing an amine group attached to the benzene moiety.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzoic acids and derivatives
Direct Parent
Aminobenzoic acids
Alternative Parents
Benzoic acids / o-Xylenes / Benzoyl derivatives / Aniline and substituted anilines / Vinylogous amides / Amino acids / Secondary amines / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds
show 3 more
Substituents
Amine / Amino acid / Amino acid or derivatives / Aminobenzoic acid / Aniline or substituted anilines / Aromatic homomonocyclic compound / Benzoic acid / Benzoyl / Carboxylic acid / Carboxylic acid derivative
show 12 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
secondary amino compound, aminobenzoic acid (CHEBI:6717)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
367589PJ2C
CAS number
61-68-7
InChI Key
HYYBABOKPJLUIN-UHFFFAOYSA-N
InChI
InChI=1S/C15H15NO2/c1-10-6-5-9-13(11(10)2)16-14-8-4-3-7-12(14)15(17)18/h3-9,16H,1-2H3,(H,17,18)
IUPAC Name
2-[(2,3-dimethylphenyl)amino]benzoic acid
SMILES
CC1=C(C)C(NC2=CC=CC=C2C(O)=O)=CC=C1

References

General References
Not Available
Human Metabolome Database
HMDB0014922
KEGG Drug
D00151
KEGG Compound
C02168
PubChem Compound
4044
PubChem Substance
46505405
ChemSpider
3904
BindingDB
50134036
RxNav
6693
ChEBI
6717
ChEMBL
CHEMBL686
ZINC
ZINC000000020241
Therapeutic Targets Database
DAP000779
PharmGKB
PA450347
Guide to Pharmacology
GtP Drug Page
PDBe Ligand
ID8
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Mefenamic_acid
PDB Entries
2xn3 / 3r43 / 4g2z / 4jqa / 5ikr
FDA label
Download (135 KB)
MSDS
Download (59.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentChronic Lower Back Pain (CLBP)2
4CompletedTreatmentPrimary Dysmenorrhoea1
4CompletedTreatmentSub-acute Back Pain1
4CompletedTreatmentUterine Hemorrhage1
3CompletedTreatmentHeavy Menstrual Bleeding / Improve Quality of Life1

Pharmacoeconomics

Manufacturers
  • Shionogi pharma inc
Packagers
  • PD-Rx Pharmaceuticals Inc.
  • Prescript Pharmaceuticals
  • Professional Co.
  • Sciele Pharma Inc.
  • West-Ward Pharmaceuticals
Dosage Forms
FormRouteStrength
Injection, powder, for suspensionParenteral500 mg
Tablet; tablet, film coatedOral500 MG
SuspensionOral50 MG/5ML
Tablet, delayed releaseOral
SyrupOral
Tablet, sugar coatedOral
SuspensionOral
Tablet, film coatedOral
Tablet; tablet, film coatedOral
CapsuleOral250 mg/1
TabletOral
SuspensionOral
CapsuleOral
Tablet, film coatedOral250 mg
Suppository125 mg
Suppository500 mg
SyrupOral50 mg/5ml
TabletOral500.000 mg
CapsuleOral50 mg
CapsuleOral500 mg
SuspensionOral125 mg/5ml
Capsule, coatedOral500 mg
CapsuleOral
Tablet, delayed releaseOral500 mg
Tablet, coatedOral500 mg
Tablet
CapsuleOral250 mg
Tablet, film coatedOral250 mg
Tablet, film coatedOral500 mg
Tablet, coatedOral250 mg
TabletOral250 mg
TabletOral500 mg
Tablet, film coated
Prices
Unit descriptionCostUnit
Ponstel 250 mg capsule11.85USD capsule
Mefenamic acid powder2.85USD g
Ponstel 250 mg kapseals1.59USD each
Apo-Mefenamic 250 mg Capsule0.52USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)230-231 °CPhysProp
water solubility20 mg/L (at 30 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP5.12HANSCH,C ET AL. (1995)
logS-3.78ADME Research, USCD
pKa4.2SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.0137 mg/mLALOGPS
logP4.58ALOGPS
logP5.4Chemaxon
logS-4.2ALOGPS
pKa (Strongest Acidic)3.89Chemaxon
pKa (Strongest Basic)-1.6Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area49.33 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity71.88 m3·mol-1Chemaxon
Polarizability26.22 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9156
Blood Brain Barrier+0.762
Caco-2 permeable+0.8866
P-glycoprotein substrateNon-substrate0.7948
P-glycoprotein inhibitor INon-inhibitor0.8632
P-glycoprotein inhibitor IINon-inhibitor0.9147
Renal organic cation transporterNon-inhibitor0.9191
CYP450 2C9 substrateNon-substrate0.6814
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.7019
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorInhibitor0.8949
CYP450 2D6 inhibitorNon-inhibitor0.9483
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.9175
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6613
Ames testNon AMES toxic0.812
CarcinogenicityNon-carcinogens0.5833
BiodegradationNot ready biodegradable0.822
Rat acute toxicity2.5445 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9727
hERG inhibition (predictor II)Non-inhibitor0.8706
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-00fv-0970000000-ac788fb2c3de77e0c447
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-02t9-0900000000-97aeacf66e8410c23139
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0002-0900000000-e81bfb47482e34427f9d
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0006-0090000000-c35efe26003cb812152a
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0005-0960000000-902cd19e4e1d6d83389b
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0002-0900000000-36a2c798555c3d7096f2
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0002-0900000000-0aaa97d98cb6e792e5da
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0005-0900000000-8550ea073cfe0222a6cc
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0006-2900000000-fc439b80f6648ed94d76
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0006-0090000000-be477416d623ed244bdb
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0005-0960000000-414fb8a03460842ef79a
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0002-0900000000-0acd19e33bc790381da7
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0002-0900000000-c2637ad61718ba056356
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0005-0900000000-cf0ec9e01efae551956c
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0006-1900000000-e53da7b0c2cd925ff45f
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0002-0900000000-6d3e988a836ba090f290
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-0090000000-9e70a08d5d730c15aa69
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0005-0950000000-a6ebc54abcd1d821d31e
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0002-0900000000-58bf82bda5da2fed93cc
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0005-0900000000-f699cc613c8f7da1d256
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-3900000000-86af1c13a0381dd04e17
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0006-0190000000-ecb78baad04fc2f4355c
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0002-0930000000-0a152876555200d131b8
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0002-0900000000-aba2be8411ff7386275c
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0002-0900000000-ac95f80f5af8cd4cf117
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0005-0940000000-4113d0740f35e76f2ef6
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-006x-0090000000-db87114292c560ed2e52
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0090000000-32d4f9a01377ca15fd68
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-05fr-0090000000-7faf1c288c838bc4a5da
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-0290000000-d0d29acc835fac894358
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-053r-0950000000-1dfdc98a6ce819e1b45c
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0090000000-485704bd58d04b652429
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-006x-0090000000-b36ba086dbc7808ce7b4
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0090000000-64e74fe61d57cf454499
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0090000000-d99f36b9b37ad8b5f347
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0090000000-6059a0c5fd606fd95762
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0190000000-e3e4066b0c9dee521863
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a59-0590000000-21ef2913dd162c4c0e76
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-006x-0090000000-5a1c44509aa114a5d978
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0090000000-33608cca6c41790ea955
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0090000000-ad559fa5a64b1e302e21
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0090000000-25fb2fbc92a9991d211d
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0190000000-b0038b9b3106f617c0ad
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a59-0590000000-275c39ed3a3112547312
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0090000000-24acd06c5a077a346741
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-00di-0090000000-c7603994df1966ee96dd
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0090000000-353273fcd3979749e8f6
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0290000000-a11afbd475c970348c66
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0090000000-f2ca32c0928bd17bd214
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0090000000-55e1b157a860f450cedd
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-006x-0090000000-c2b5392823249597db3c
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0090000000-57351977917ca6084bc3
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-0190000000-e584894bf2d4649f7af3
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-053r-0960000000-4989f46132493ca56669
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-001i-0910000000-6c544c83832b76f09f1c
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00di-0190000000-39925554c1603783e315
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00di-0190000000-e40c01ca726c562c76ca
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0ac0-2790000000-91f5d0bd861b4773414c
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00di-0090000000-6dbfa8810502239d9e5d
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00dl-0090000000-a31df4058ab2ede8e1c1
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0930000000-0923cce966f10f296760
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0090000000-4cdbfd23b37b86a37d7e
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0005-1930000000-730debe76c06ced3a254
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ac4-3920000000-200308fd5c56c75ed9fe
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9400000000-347768293206f1be8c3f
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-166.5072124
predicted
DarkChem Lite v0.1.0
[M-H]-154.916232
predicted
DarkChem Lite v0.1.0
[M-H]-166.5825124
predicted
DarkChem Lite v0.1.0
[M-H]-151.12675
predicted
DeepCCS 1.0 (2019)
[M+H]+166.7130124
predicted
DarkChem Lite v0.1.0
[M+H]+168.2685124
predicted
DarkChem Lite v0.1.0
[M+H]+168.1066124
predicted
DarkChem Lite v0.1.0
[M+H]+153.48476
predicted
DeepCCS 1.0 (2019)
[M+Na]+167.0256124
predicted
DarkChem Lite v0.1.0
[M+Na]+171.5570481
predicted
DarkChem Lite v0.1.0
[M+Na]+167.0705124
predicted
DarkChem Lite v0.1.0
[M+Na]+159.5779
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and...
Gene Name
PTGS2
Uniprot ID
P35354
Uniprot Name
Prostaglandin G/H synthase 2
Molecular Weight
68995.625 Da
References
  1. Gierse JK, Hauser SD, Creely DP, Koboldt C, Rangwala SH, Isakson PC, Seibert K: Expression and selective inhibition of the constitutive and inducible forms of human cyclo-oxygenase. Biochem J. 1995 Jan 15;305 ( Pt 2):479-84. [Article]
  2. Bhat AS, Tandan SK, Kumar D, Krishna V, Prakash VR: Interaction between inhibitors of inducible nitric oxide synthase and cyclooxygenase in adjuvant-induced arthritis in female albino rats: an isobolographic study. Eur J Pharmacol. 2007 Feb 5;556(1-3):190-9. Epub 2006 Oct 27. [Article]
  3. Bhat AS, Tandan SK, Kumar D, Krishna V, Prakash VR: Interaction between inhibitors of inducible nitric oxide synthase and cyclooxygenase in Brewer's yeast induced pyrexia in mice: an isobolographic study. Eur J Pharmacol. 2005 Mar 28;511(2-3):137-42. [Article]
  4. Cryer B, Feldman M: Cyclooxygenase-1 and cyclooxygenase-2 selectivity of widely used nonsteroidal anti-inflammatory drugs. Am J Med. 1998 May;104(5):413-21. [Article]
  5. Walton LJ, Franklin IJ, Bayston T, Brown LC, Greenhalgh RM, Taylor GW, Powell JT: Inhibition of prostaglandin E2 synthesis in abdominal aortic aneurysms: implications for smooth muscle cell viability, inflammatory processes, and the expansion of abdominal aortic aneurysms. Circulation. 1999 Jul 6;100(1):48-54. [Article]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gas...
Gene Name
PTGS1
Uniprot ID
P23219
Uniprot Name
Prostaglandin G/H synthase 1
Molecular Weight
68685.82 Da
References
  1. Sinniah R, Lye WC: Acute renal failure from hemoglobinuric and interstitial nephritis secondary to iodine and mefenamic acid. Clin Nephrol. 2001 Mar;55(3):254-8. [Article]
  2. Joo Y, Kim HS, Woo RS, Park CH, Shin KY, Lee JP, Chang KA, Kim S, Suh YH: Mefenamic acid shows neuroprotective effects and improves cognitive impairment in in vitro and in vivo Alzheimer's disease models. Mol Pharmacol. 2006 Jan;69(1):76-84. Epub 2005 Oct 13. [Article]
  3. Cryer B, Feldman M: Cyclooxygenase-1 and cyclooxygenase-2 selectivity of widely used nonsteroidal anti-inflammatory drugs. Am J Med. 1998 May;104(5):413-21. [Article]
  4. Gierse JK, Hauser SD, Creely DP, Koboldt C, Rangwala SH, Isakson PC, Seibert K: Expression and selective inhibition of the constitutive and inducible forms of human cyclo-oxygenase. Biochem J. 1995 Jan 15;305 ( Pt 2):479-84. [Article]
  5. Laudanno OM, Cesolari JA, Esnarriaga J, Flaherty P, Vada J, Guastalli G, San Miguel P, Bedini OA: [In vivo selectivity of nonsteroidal anti-inflammatory drugs on COX-1-COX-2 and gastrointestinal ulcers, in rats]. Acta Gastroenterol Latinoam. 1998;28(3):249-55. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Venkataraman H, den Braver MW, Vermeulen NP, Commandeur JN: Cytochrome P450-mediated bioactivation of mefenamic acid to quinoneimine intermediates and inactivation by human glutathione S-transferases. Chem Res Toxicol. 2014 Dec 15;27(12):2071-81. doi: 10.1021/tx500288b. Epub 2014 Nov 18. [Article]
  2. Wang JF, Yan JY, Wei DQ, Chou KC: Binding of CYP2C9 with diverse drugs and its implications for metabolic mechanism. Med Chem. 2009 May;5(3):263-70. [Article]
  3. Lee B, Ji HK, Lee T, Liu KH: Simultaneous Screening of Activities of Five Cytochrome P450 and Four Uridine 5'-Diphospho-glucuronosyltransferase Enzymes in Human Liver Microsomes Using Cocktail Incubation and Liquid Chromatography-Tandem Mass Spectrometry. Drug Metab Dispos. 2015 Jul;43(7):1137-46. doi: 10.1124/dmd.114.063016. Epub 2015 Apr 22. [Article]
  4. Mefenamic Acid FDA label [File]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Venkataraman H, den Braver MW, Vermeulen NP, Commandeur JN: Cytochrome P450-mediated bioactivation of mefenamic acid to quinoneimine intermediates and inactivation by human glutathione S-transferases. Chem Res Toxicol. 2014 Dec 15;27(12):2071-81. doi: 10.1021/tx500288b. Epub 2014 Nov 18. [Article]
  2. Lee B, Ji HK, Lee T, Liu KH: Simultaneous Screening of Activities of Five Cytochrome P450 and Four Uridine 5'-Diphospho-glucuronosyltransferase Enzymes in Human Liver Microsomes Using Cocktail Incubation and Liquid Chromatography-Tandem Mass Spectrometry. Drug Metab Dispos. 2015 Jul;43(7):1137-46. doi: 10.1124/dmd.114.063016. Epub 2015 Apr 22. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Retinoic acid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols. Isoform 2 lacks trans...
Gene Name
UGT1A9
Uniprot ID
O60656
Uniprot Name
UDP-glucuronosyltransferase 1-9
Molecular Weight
59940.495 Da
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Glucuronosyltransferase activity
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.Its unique specificity for 3,4-catechol estrogens and estriol su...
Gene Name
UGT2B7
Uniprot ID
P16662
Uniprot Name
UDP-glucuronosyltransferase 2B7
Molecular Weight
60694.12 Da
References
  1. Lee B, Ji HK, Lee T, Liu KH: Simultaneous Screening of Activities of Five Cytochrome P450 and Four Uridine 5'-Diphospho-glucuronosyltransferase Enzymes in Human Liver Microsomes Using Cocktail Incubation and Liquid Chromatography-Tandem Mass Spectrometry. Drug Metab Dispos. 2015 Jul;43(7):1137-46. doi: 10.1124/dmd.114.063016. Epub 2015 Apr 22. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Backman JT, Filppula AM, Niemi M, Neuvonen PJ: Role of Cytochrome P450 2C8 in Drug Metabolism and Interactions. Pharmacol Rev. 2016 Jan;68(1):168-241. doi: 10.1124/pr.115.011411. [Article]
  2. Jenkins SM, Zvyaga T, Johnson SR, Hurley J, Wagner A, Burrell R, Turley W, Leet JE, Philip T, Rodrigues AD: Studies to further investigate the inhibition of human liver microsomal CYP2C8 by the acyl-beta-glucuronide of gemfibrozil. Drug Metab Dispos. 2011 Dec;39(12):2421-30. doi: 10.1124/dmd.111.041947. Epub 2011 Sep 12. [Article]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Dasgupta A, Emerson L: Interaction of valproic acid with nonsteroidal antiinflammatory drugs mefenamic acid and fenoprofen in normal and uremic sera: lack of interaction in uremic sera due to the presence of endogenous factors. Ther Drug Monit. 1996 Dec;18(6):654-9. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 18, 2024 16:48