Identification

Name
Flufenamic Acid
Accession Number
DB02266  (EXPT01442)
Type
Small Molecule
Groups
Experimental
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
Synonyms
Not Available
External IDs
CI 440 / CN-27,554 / INF-1837
Categories
UNII
60GCX7Y6BH
CAS number
530-78-9
Weight
Average: 281.2299
Monoisotopic: 281.066363184
Chemical Formula
C14H10F3NO2
InChI Key
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

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UProstaglandin G/H synthase 2Not AvailableHuman
UProstaglandin G/H synthase 1Not AvailableHuman
UAldo-keto reductase family 1 member C3Not AvailableHuman
UAndrogen receptorNot AvailableHuman
UPeroxisome proliferator-activated receptor alpha
activator
Human
UPeroxisome proliferator-activated receptor gamma
agonist
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AcyclovirThe excretion of Acyclovir can be decreased when combined with Flufenamic Acid.
Adefovir DipivoxilThe excretion of Adefovir Dipivoxil can be decreased when combined with Flufenamic Acid.
AlprostadilThe excretion of Alprostadil can be decreased when combined with Flufenamic Acid.
CefdinirThe excretion of Cefdinir can be decreased when combined with Flufenamic Acid.
CephalexinThe excretion of Cephalexin can be decreased when combined with Flufenamic Acid.
DidanosineThe excretion of Didanosine can be decreased when combined with Flufenamic Acid.
DinoprostoneThe excretion of Dinoprostone can be decreased when combined with Flufenamic Acid.
FluoresceinThe excretion of Fluorescein can be decreased when combined with Flufenamic Acid.
IndomethacinThe excretion of Indomethacin can be decreased when combined with Flufenamic Acid.
L-CitrullineThe excretion of L-Citrulline can be decreased when combined with Flufenamic Acid.
Food Interactions
Not 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 References
Not Available
External Links
KEGG Drug
D01581
KEGG Compound
C13038
PubChem Compound
3371
PubChem Substance
46507173
ChemSpider
3254
BindingDB
17636
ChEBI
42638
ChEMBL
CHEMBL23588
PharmGKB
PA166049190
IUPHAR
2447
Guide to Pharmacology
GtP Drug Page
HET
FLF
ATC Codes
M01AG03 — Flufenamic acid
PDB Entries
1bm7 / 1s2c / 2pix / 3ozl / 4i5x / 5dq8 / 5ikv

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)133.5 °CPhysProp
water solubility9.09 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP5.25HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.008 mg/mLALOGPS
logP4.6ALOGPS
logP5.25ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)3.88ChemAxon
pKa (Strongest Basic)-2.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.33 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity67.77 m3·mol-1ChemAxon
Polarizability24.67 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.967
Blood Brain Barrier+0.9058
Caco-2 permeable+0.7199
P-glycoprotein substrateNon-substrate0.8528
P-glycoprotein inhibitor INon-inhibitor0.8164
P-glycoprotein inhibitor IINon-inhibitor0.8312
Renal organic cation transporterNon-inhibitor0.9229
CYP450 2C9 substrateNon-substrate0.7437
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.7369
CYP450 1A2 substrateInhibitor0.9132
CYP450 2C9 inhibitorInhibitor0.8948
CYP450 2D6 inhibitorNon-inhibitor0.925
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7598
Ames testNon AMES toxic0.9372
CarcinogenicityNon-carcinogens0.5892
BiodegradationNot ready biodegradable0.9869
Rat acute toxicity3.0218 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.986
hERG inhibition (predictor II)Non-inhibitor0.7953
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 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-QFT , negativeLC-MS/MSsplash10-001r-0090000000-0f6d7c69f5f9242f5642
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-000i-0090000000-9d81e18649951a7eaa15
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-000i-0190000000-e11b32a1bfb7e88f90d6
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-002r-0490000000-ce3f3b244e22bbbe5041
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-004i-0970000000-edb73a5d62729808e5cd
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-004i-0930000000-95081e9f9d0c39c41d8a
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-0090000000-c0fd815aa73e117dbaad
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-0090000000-6e6b5ff30b2979343619
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-0090000000-9965dc3cbacd4781de3d
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-0090000000-5199ecc47f2a1651423c
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03xu-0390000000-a182566865ab68875b0d
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-014i-0970000000-575889d067845b735603
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03xr-2690000000-cd1fefcbb1a5f6e6bb0d

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
Trifluoromethylbenzenes / Benzoic acids / Benzoyl derivatives / Aniline and substituted anilines / Vinylogous amides / Amino acids / Secondary amines / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds
show 5 more
Substituents
Aminobenzoic acid / Trifluoromethylbenzene / Benzoic acid / Benzoyl / Aniline or substituted anilines / Vinylogous amide / Amino acid or derivatives / Amino acid / Carboxylic acid derivative / Secondary amine
show 15 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
organofluorine compound, aromatic amino acid (CHEBI:42638)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
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. 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:7864817]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
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. 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:7864817]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase activity
Specific Function
Catalyzes the conversion of aldehydes and ketones to alcohols. Catalyzes the reduction of prostaglandin (PG) D2, PGH2 and phenanthrenequinone (PQ) and the oxidation of 9-alpha,11-beta-PGF2 to PGD2....
Gene Name
AKR1C3
Uniprot ID
P42330
Uniprot Name
Aldo-keto reductase family 1 member C3
Molecular Weight
36852.89 Da
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:17016423]
  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:14996743]
  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:17139284]
  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:10592235]
Details
4. Androgen receptor
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription ...
Gene Name
AR
Uniprot ID
P10275
Uniprot Name
Androgen receptor
Molecular Weight
98987.9 Da
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:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Activator
General Function
Zinc ion binding
Specific Function
Ligand-activated transcription factor. Key regulator of lipid metabolism. Activated by the endogenous ligand 1-palmitoyl-2-oleoyl-sn-glycerol-3-phosphocholine (16:0/18:1-GPC). Activated by oleyleth...
Gene Name
PPARA
Uniprot ID
Q07869
Uniprot Name
Peroxisome proliferator-activated receptor alpha
Molecular Weight
52224.595 Da
References
  1. Lehmann JM, Lenhard JM, Oliver BB, Ringold GM, Kliewer SA: Peroxisome proliferator-activated receptors alpha and gamma are activated by indomethacin and other non-steroidal anti-inflammatory drugs. J Biol Chem. 1997 Feb 7;272(6):3406-10. [PubMed:9013583]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Agonist
General Function
Zinc ion binding
Specific Function
Nuclear receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the nuclear receptor binds to DNA specific PPAR response elements (PPRE...
Gene Name
PPARG
Uniprot ID
P37231
Uniprot Name
Peroxisome proliferator-activated receptor gamma
Molecular Weight
57619.58 Da
References
  1. Lehmann JM, Lenhard JM, Oliver BB, Ringold GM, Kliewer SA: Peroxisome proliferator-activated receptors alpha and gamma are activated by indomethacin and other non-steroidal anti-inflammatory drugs. J Biol Chem. 1997 Feb 7;272(6):3406-10. [PubMed:9013583]

Carriers

Details
1. Transthyretin
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Identical protein binding
Specific Function
Thyroid hormone-binding protein. Probably transports thyroxine from the bloodstream to the brain.
Gene Name
TTR
Uniprot ID
P02766
Uniprot Name
Transthyretin
Molecular Weight
15886.88 Da
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:15080795]
  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:17016423]
  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:14968122]
  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:17139284]
  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:10592235]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
Gene Name
SLC22A6
Uniprot ID
Q4U2R8
Uniprot Name
Solute carrier family 22 member 6
Molecular Weight
61815.78 Da
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:11099697]

Drug created on June 13, 2005 07:24 / Updated on October 01, 2018 13:16