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Identification
NameFlufenamic Acid
Accession NumberDB02266  (EXPT01442)
Typesmall molecule
Groupsexperimental
Description

An anthranilic acid derivative with analgesic, anti-inflammatory, and antipyretic properties. It is used in musculoskeletal and joint disorders and administered by mouth and topically. (From Martindale, The Extra Pharmacopoeia, 30th ed, p16)

Structure
Thumb
SynonymsNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number530-78-9
WeightAverage: 281.2299
Monoisotopic: 281.066363184
Chemical FormulaC14H10F3NO2
InChI KeyInChIKey=LPEPZBJOKDYZAD-UHFFFAOYSA-N
InChI
InChI=1S/C14H10F3NO2/c15-14(16,17)9-4-3-5-10(8-9)18-12-7-2-1-6-11(12)13(19)20/h1-8,18H,(H,19,20)
IUPAC Name
2-{[3-(trifluoromethyl)phenyl]amino}benzoic acid
SMILES
OC(=O)C1=CC=CC=C1NC1=CC(=CC=C1)C(F)(F)F
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassBenzoic Acid and Derivatives
Direct parentAminobenzoic Acid Derivatives
Alternative parentsBenzoic Acids; Benzoyl Derivatives; Secondary Amines; Polyamines; Carboxylic Acids; Enolates; Organofluorides; Alkyl Fluorides
Substituentsbenzoyl; secondary amine; enolate; carboxylic acid derivative; polyamine; carboxylic acid; organofluoride; organohalogen; amine; organonitrogen compound; alkyl halide; alkyl fluoride
Classification descriptionThis compound belongs to the aminobenzoic acid derivatives. These are benzoic acids (or derivative thereof) containing an amine group attached to the benzene moiety.
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.967
Blood Brain Barrier + 0.9058
Caco-2 permeable + 0.7199
P-glycoprotein substrate Non-substrate 0.8528
P-glycoprotein inhibitor I Non-inhibitor 0.8164
P-glycoprotein inhibitor II Non-inhibitor 0.8312
Renal organic cation transporter Non-inhibitor 0.9229
CYP450 2C9 substrate Non-substrate 0.7437
CYP450 2D6 substrate Non-substrate 0.9116
CYP450 3A4 substrate Non-substrate 0.7369
CYP450 1A2 substrate Inhibitor 0.9132
CYP450 2C9 substrate Inhibitor 0.8948
CYP450 2D6 substrate Non-inhibitor 0.925
CYP450 2C19 substrate Non-inhibitor 0.9025
CYP450 3A4 substrate Non-inhibitor 0.8309
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7598
Ames test Non AMES toxic 0.9372
Carcinogenicity Non-carcinogens 0.5892
Biodegradation Not ready biodegradable 0.9869
Rat acute toxicity 3.0218 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.986
hERG inhibition (predictor II) Non-inhibitor 0.7953
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point133.5 °CPhysProp
water solubility9.09 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP5.25HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
water solubility8.00e-03 g/lALOGPS
logP4.6ALOGPS
logP5.25ChemAxon
logS-4.5ALOGPS
pKa (strongest acidic)3.88ChemAxon
pKa (strongest basic)-2.1ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count3ChemAxon
hydrogen donor count2ChemAxon
polar surface area49.33ChemAxon
rotatable bond count4ChemAxon
refractivity67.77ChemAxon
polarizability24.67ChemAxon
number of rings2ChemAxon
bioavailability1ChemAxon
rule of fiveNoChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Gunter Metz, “Method of producing 2-(2-hydroxyethoxy)-ethanol ester of flufenamic acid.” U.S. Patent US4980498, issued October, 1984.

US4980498
General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD01581
KEGG CompoundC13038
PubChem Compound3371
PubChem Substance46507173
ChemSpider3254
BindingDB17636
ChEBI31619
ChEMBL
IUPHAR2447
Guide to Pharmacology2447
HETFLF
ATC CodesM01AG03
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

1. Prostaglandin G/H synthase 2

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Prostaglandin G/H synthase 2 P35354 Details

References:

  1. Ouellet M, Percival MD: Effect of inhibitor time-dependency on selectivity towards cyclooxygenase isoforms. Biochem J. 1995 Feb 15;306 ( Pt 1):247-51. Pubmed

2. Prostaglandin G/H synthase 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Prostaglandin G/H synthase 1 P23219 Details

References:

  1. Ouellet M, Percival MD: Effect of inhibitor time-dependency on selectivity towards cyclooxygenase isoforms. Biochem J. 1995 Feb 15;306 ( Pt 1):247-51. Pubmed

3. Aldo-keto reductase family 1 member C3

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Aldo-keto reductase family 1 member C3 P42330 Details

References:

  1. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  2. Lovering AL, Ride JP, Bunce CM, Desmond JC, Cummings SM, White SA: Crystal structures of prostaglandin D(2) 11-ketoreductase (AKR1C3) in complex with the nonsteroidal anti-inflammatory drugs flufenamic acid and indomethacin. Cancer Res. 2004 Mar 1;64(5):1802-10. Pubmed
  3. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  4. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

4. Androgen receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Androgen receptor P10275 Details

References:

  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

1. Transthyretin

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Transthyretin P02766 Details

References:

  1. Almeida MR, Macedo B, Cardoso I, Alves I, Valencia G, Arsequell G, Planas A, Saraiva MJ: Selective binding to transthyretin and tetramer stabilization in serum from patients with familial amyloidotic polyneuropathy by an iodinated diflunisal derivative. Biochem J. 2004 Jul 15;381(Pt 2):351-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Miller SR, Sekijima Y, Kelly JW: Native state stabilization by NSAIDs inhibits transthyretin amyloidogenesis from the most common familial disease variants. Lab Invest. 2004 May;84(5):545-52. Pubmed
  4. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  5. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

1. Solute carrier family 22 member 6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 6 Q4U2R8 Details

References:

  1. Uwai Y, Saito H, Inui K: Interaction between methotrexate and nonsteroidal anti-inflammatory drugs in organic anion transporter. Eur J Pharmacol. 2000 Dec 1;409(1):31-6. Pubmed

Comments
Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:17