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61-68-7 molecular structure
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2-[(2,3-dimethylphenyl)amino]benzoic acid

ChemBase ID: 664
Molecular Formular: C15H15NO2
Molecular Mass: 241.2851
Monoisotopic Mass: 241.11027873
SMILES and InChIs

SMILES:
OC(=O)c1c(Nc2c(c(ccc2)C)C)cccc1
Canonical SMILES:
OC(=O)c1ccccc1Nc1cccc(c1C)C
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)
InChIKey:
HYYBABOKPJLUIN-UHFFFAOYSA-N

Cite this record

CBID:664 http://www.chembase.cn/molecule-664.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
2-[(2,3-dimethylphenyl)amino]benzoic acid
IUPAC Traditional name
mefenamic acid
Brand Name
Bafameritin-M
Bafhameritin-M
Bonabol
Coslan
HL 1
In-M
Lysalgo
Mefacit
Namphen
Parkemed
Ponalar
Ponstan
Ponstan Forte
Ponstel
Ponstil
Ponstyl
Pontal
Tamany Bonsan
Tanston
Vialidon
Ponstel, Ponstan
Synonyms
2-[(2,3-Dimethylphenyl)amino]-benzoic Acid
Mefacit
Mefenamic acid
Acide Mefenamique
Mefanamic Acid
Mefenacid
Mefenaminsaeure
Mephenamic Acid
Mephenaminic Acid
Methenamic Acid
Mefenamic acid
2-((2,3-Dimethylphenyl)amino)benzoic acid
2-[(2,3-Dimethylphenyl)amino]benzoic acid
CAS Number
61-68-7
EC Number
200-513-1
MDL Number
MFCD00051721
PubChem SID
24896815
160964127
46505405
PubChem CID
4044
ATC CODE
M01AG01
CHEMBL
686
Chemspider ID
3904
DrugBank ID
DB00784
IUPHAR ligand ID
2593
KEGG ID
D00151
Unique Ingredient Identifier
367589PJ2C
Wikipedia Title
Mefenamic_acid
Medline Plus
a681028

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 3.885851  H Acceptors
H Donor LogD (pH = 5.5) 3.7780464 
LogD (pH = 7.4) 2.176643  Log P 5.3975973 
Molar Refractivity 71.8828 cm3 Polarizability 26.912666 Å3
Polar Surface Area 49.33 Å2 Rotatable Bonds
Lipinski's Rule of Five false 
Log P 4.58  LOG S -4.25 
Solubility (Water) 1.37e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
20 mg/L expand Show data source
Acetone expand Show data source
Chloroform expand Show data source
Dichloromethane expand Show data source
Methanol expand Show data source
Apperance
Off-White to Pale Yellow Solid expand Show data source
Melting Point
227-229°C expand Show data source
230-231 expand Show data source
Hydrophobicity(logP)
4.2 expand Show data source
Storage Condition
Refrigerator expand Show data source
Room Temperature (15-30°C) expand Show data source
Storage Warning
IRRITANT expand Show data source
RTECS
CB4550000 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
22 expand Show data source
R:22 expand Show data source
Safety Statements
S:36/37/39 expand Show data source
TSCA Listed
false expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H302 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Target
COX expand Show data source
Admin Routes
Oral expand Show data source
Bioavailability
90% expand Show data source
Excretion
Renal and fecal expand Show data source
Half Life
2 hours expand Show data source
Metabolism
Hepatic (CYP2C9) expand Show data source
Protein Bound
90% expand Show data source
Legal Status
?-only (U.S.), POM in UK expand Show data source
Pregnancy Category
C (Australia, United States) expand Show data source
Purity
95+% expand Show data source
98% expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals - 02193920 external link
(2-[(2,3-Dimethylphenyl)amino]benzoic acid)
DrugBank - DB00784 external link
Item Information
Drug Groups approved
Description A non-steroidal anti-inflammatory agent with analgesic, anti-inflammatory, and antipyretic properties. It is an inhibitor of cyclooxygenase. [PubChem]
Indication For the treatment of rheumatoid arthritis, osteoarthritis, dysmenorrhea, and mild to moderate pain, inflammation, and fever.
Pharmacology 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.
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
Biotransformation 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.
Absorption Mefenamic acid is rapidly absorbed after oral administration.
Half Life 2 hours
Protein Binding 90%
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.
Distribution * 1.06 L/kg [Normal Healthy Adults (18-45 yr)]
Clearance * Oral cl=21.23 L/hr [Healthy adults (18-45 yrs)]
External Links
Wikipedia
RxList
Drugs.com
Sigma Aldrich - M4267 external link
Application
An NSAID. Circumvents MRP-mediated multidrug resistance. Specifically and significantly potentiates the cytotoxicity of anthracyclines (doxorubicin, daunorubicin and epirubicin), as well as teniposide, VP-16 and vincristine.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. M4267.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Toronto Research Chemicals - M205050 external link
Anti-inflammatory; analgesic.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Winder, C.V., J. Pharmacol. Exp. Ther., 138, 405 (1962)
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PATENTS

PATENTS

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INTERNET

INTERNET

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