Identification

Name
Mefenamic acid
Accession Number
DB00784  (APRD00730)
Type
Small Molecule
Groups
Approved
Description

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

Structure
Thumb
Synonyms
  • Acide méfénamique
  • Acido mefenamico
  • Acidum mefenamicum
  • CN 35355
  • INF 3355
  • Mefenaminsaeure
  • 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
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
MefenamicCapsule250 mgOralAa Pharma Inc1996-11-06Not applicableCanada
Mefenamic-250Capsule250 mgOralPro Doc Limitee1997-08-062009-07-23Canada
PonstanCapsule250 mgOralAa Pharma Inc1966-12-31Not applicableCanada
PonstelCapsule250 mg/1OralShionogi1967-03-28Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Dom-mefenamic AcidCapsule250 mgOralDominion Pharmacal1998-09-17Not applicableCanada
Mefenamic AcidCapsule250 mg/1OralBreckenridge Pharmaceutical, Inc.2014-10-132020-07-31Us
Mefenamic AcidCapsule250 mg/1OralPrasco, Laboratories1967-03-28Not applicableUs
Mefenamic AcidCapsule250 mg/1OralLupin Pharmaceuticals2011-07-22Not applicableUs68180 0185 06 nlmimage10 b33bd98e
Mefenamic acidCapsule250 mg/1OralPaddock Laboratories, Inc.2010-11-192016-03-01Us
Mefenamic AcidCapsule250 mg/1OralSolubiomix2016-03-232016-05-20Us
Mefenamic AcidCapsule250 mg/1OralBelcher Pharmaceuticals, LLC2015-06-25Not applicableUs
Mefenamic acidCapsule250 mg/1OralMicro Labs Limited2010-11-19Not applicableUs
Mefenamic AcidCapsule250 mg/1OralQualitest2014-06-022017-07-31Us
Mefenamic AcidCapsule250 mg/1OralCypress Pharmaceuticals, Inc.2013-06-032013-09-11Us
International/Other Brands
Coslan (Parke Davis) / Lysalgo (SIT) / Mefacit (SecFarm) / Parkemed (Pfizer) / Ponalar (Coronet Crown) / Ponstan Forte (Pfizer) / Ponstel / Ponstyl (Pfizer) / Ponstyl Fort (Pfizer) / Pontal (Daiichi Sankyo) / Tanston (Pfizer)
Categories
UNII
367589PJ2C
CAS number
61-68-7
Weight
Average: 241.2851
Monoisotopic: 241.110278729
Chemical Formula
C15H15NO2
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

Pharmacology

Indication

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

Associated Conditions
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
Human
UProstaglandin G/H synthase 1
inhibitor
Human
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.

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)]
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.

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Mefenamic Acid Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe risk or severity of gastrointestinal bleeding can be increased when Mefenamic acid is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of gastrointestinal bleeding can be increased when Mefenamic acid is combined with (S)-Warfarin.
4-hydroxycoumarinThe risk or severity of gastrointestinal bleeding can be increased when Mefenamic acid is combined with 4-hydroxycoumarin.
AbacavirMefenamic acid may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbciximabThe risk or severity of bleeding and hemorrhage can be increased when Mefenamic acid is combined with Abciximab.
AbirateroneThe metabolism of Mefenamic acid can be decreased when combined with Abiraterone.
AcarboseMefenamic acid may decrease the excretion rate of Acarbose which could result in a higher serum level.
AcebutololMefenamic acid may decrease the antihypertensive activities of Acebutolol.
AceclofenacThe risk or severity of adverse effects can be increased when Mefenamic acid is combined with Aceclofenac.
AcemetacinThe risk or severity of adverse effects can be increased when Mefenamic acid is combined with Acemetacin.
Food Interactions
  • Avoid alcohol.
  • Take with food.

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0014922
KEGG Drug
D00151
KEGG Compound
C02168
PubChem Compound
4044
PubChem Substance
46505405
ChemSpider
3904
BindingDB
50134036
ChEBI
6717
ChEMBL
CHEMBL686
Therapeutic Targets Database
DAP000779
PharmGKB
PA450347
IUPHAR
2593
Guide to Pharmacology
GtP Drug Page
HET
ID8
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Mefenamic_acid
ATC Codes
M01AG01 — Mefenamic acid
AHFS Codes
  • 28:08.04.92 — Other Nonsteroidal Antiimflammatory Agents
PDB Entries
2xn3 / 3r43 / 4g2z / 4jqa / 5ikr
FDA label
Download (135 KB)
MSDS
Download (59.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedBasic ScienceDiabetes Mellitus (DM)1
2CompletedTreatmentDysmenorrhea1
2CompletedTreatmentIrreversible Pulpitis / Pain NOS / Postoperative pain1
2, 3CompletedSupportive CarePrimary Dysmenorrhoea1
2, 3RecruitingTreatmentEndometriotic Cysts / Visual Analogue Pain Scale: Moderate or Severe Pain1
3RecruitingTreatmentHeavy Menstrual Bleeding / Improve Quality of Life1
4CompletedTreatmentPrimary Dysmenorrhoea1
4CompletedTreatmentUterine Hemorrhage1
Not AvailableUnknown StatusTreatmentInfertilities1

Pharmacoeconomics

Manufacturers
  • Shionogi pharma inc
Packagers
  • PD-Rx Pharmaceuticals Inc.
  • Prescript Pharmaceuticals
  • Professional Co.
  • Sciele Pharma Inc.
  • West-Ward Pharmaceuticals
Dosage forms
FormRouteStrength
CapsuleOral250 mg
CapsuleOral250 mg/1
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-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
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

Taxonomy

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
Aminobenzoic acid / Benzoic acid / Benzoyl / Aniline or substituted anilines / Xylene / O-xylene / Vinylogous amide / Amino acid / Amino acid or derivatives / Secondary amine
show 12 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
secondary amino compound, aminobenzoic acid (CHEBI:6717)

Targets

Kind
Protein
Organism
Human
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. [PubMed:7832763]
  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. [PubMed:17150210]
  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. [PubMed:15792781]
  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. [PubMed:9626023]
  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. [PubMed:10393680]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Human
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. [PubMed:11316248]
  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. [PubMed:16223958]
  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. [PubMed:9626023]
  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. [PubMed:7832763]
  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. [PubMed:9773153]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
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. [PubMed:25372302]
  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. [PubMed:19442216]
  3. Mefenamic Acid FDA label [File]
Kind
Protein
Organism
Human
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
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. 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. [PubMed:26721703]
Kind
Protein
Organism
Human
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

Carriers

Kind
Protein
Organism
Human
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. [PubMed:8946661]

Drug created on June 13, 2005 07:24 / Updated on November 14, 2018 12:46