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Record Information
Version3.6
Creation Date2012-09-06 15:16:52 UTC
Update Date2016-02-11 01:33:27 UTC
HMDB IDHMDB15573
Secondary Accession NumbersNone
Metabolite Identification
Common NameNiflumic Acid
DescriptionNiflumic Acid is only found in individuals that have used or taken this drug. It is an analgesic and anti-inflammatory agent used in the treatment of rheumatoid arthritis. [PubChem]Niflumic acid is able to inhibit both phospholipase A2 as well as COX-2, thereby acting as an antiinflamatory and pain reduction agent.
Structure
Thumb
Synonyms
ValueSource
NiflugelKegg
NFAKegg
NiflumateGenerator
2-(3-(Trifluoromethyl)-phenyl)aminonicotinic acidHMDB
2-(3-(Trifluoromethyl)anilino)nicotinic acidHMDB
2-(3-Trifluoromethyl-phenylamino)-nicotinic acidHMDB
2-(alpha,alpha,alpha-trifluoro-m-toluidino)Nicotinic acidHMDB
2-[(3-Trifluoromethyl)phenyl]amino-3-pyridine-carboxylic acidHMDB
2-[3-(Trifluoromethyl)anilino]nicotinic acidHMDB
Lopac-N-0630HMDB
NFLHMDB
Nifluminic acidHMDB
Chemical FormulaC13H9F3N2O2
Average Molecular Weight282.218
Monoisotopic Molecular Weight282.061612157
IUPAC Name2-{[3-(trifluoromethyl)phenyl]amino}pyridine-3-carboxylic acid
Traditional Nameniflumic acid
CAS Registry Number4394-00-7
SMILES
OC(=O)C1=C(NC2=CC=CC(=C2)C(F)(F)F)N=CC=C1
InChI Identifier
InChI=1S/C13H9F3N2O2/c14-13(15,16)8-3-1-4-9(7-8)18-11-10(12(19)20)5-2-6-17-11/h1-7H,(H,17,18)(H,19,20)
InChI KeyInChIKey=JZFPYUNJRRFVQU-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as pyridinecarboxylic acids. These are compounds containing a pyridine ring bearing a carboxylic acid group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassPyridinecarboxylic acids and derivatives
Direct ParentPyridinecarboxylic acids
Alternative Parents
Substituents
  • Pyridine carboxylic acid
  • Aminopyridine
  • Imidolactam
  • Benzenoid
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Vinylogous amide
  • Azacycle
  • Secondary amine
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Carbonyl group
  • Amine
  • Alkyl halide
  • Alkyl fluoride
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Cyclooxygenase Inhibitors
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point203 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility8.83e-02 g/LNot Available
LogP4.43TAKACS-NOVAK,K ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.088 mg/mLALOGPS
logP4.33ALOGPS
logP3.12ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)1.88ChemAxon
pKa (Strongest Basic)5.51ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area62.22 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity65.93 m3·mol-1ChemAxon
Polarizability24.21 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB04552
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB04552
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04552
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4333
KEGG Compound IDC13698
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB15573
Metagene LinkHMDB15573
METLIN IDNot Available
PubChem Compound4488
PDB IDNFL
ChEBI ID197010
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Criddle DN, de Moura RS, Greenwood IA, Large WA: Inhibitory action of niflumic acid on noradrenaline- and 5-hydroxytryptamine-induced pressor responses in the isolated mesenteric vascular bed of the rat. Br J Pharmacol. 1997 Mar;120(5):813-8. [9138686 ]

Enzymes

General function:
Involved in metabolic process
Specific function:
Selectively hydrolyzes arachidonyl phospholipids in the sn-2 position releasing arachidonic acid. Together with its lysophospholipid activity, it is implicated in the initiation of the inflammatory response.
Gene Name:
PLA2G4A
Uniprot ID:
P47712
Molecular weight:
85210.19
References
  1. Jabeen T, Singh N, Singh RK, Sharma S, Somvanshi RK, Dey S, Singh TP: Non-steroidal anti-inflammatory drugs as potent inhibitors of phospholipase A2: structure of the complex of phospholipase A2 with niflumic acid at 2.5 Angstroms resolution. Acta Crystallogr D Biol Crystallogr. 2005 Dec;61(Pt 12):1579-86. Epub 2005 Nov 19. [16301791 ]
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides.
Gene Name:
PLA2G1B
Uniprot ID:
P04054
Molecular weight:
16359.535
References
  1. Jabeen T, Singh N, Singh RK, Sharma S, Somvanshi RK, Dey S, Singh TP: Non-steroidal anti-inflammatory drugs as potent inhibitors of phospholipase A2: structure of the complex of phospholipase A2 with niflumic acid at 2.5 Angstroms resolution. Acta Crystallogr D Biol Crystallogr. 2005 Dec;61(Pt 12):1579-86. Epub 2005 Nov 19. [16301791 ]
  2. 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. [10592235 ]
General function:
Involved in transferase activity, transferring hexosyl groups
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.
Gene Name:
UGT1A9
Uniprot ID:
O60656
Molecular weight:
59940.495
References
  1. Mano Y, Usui T, Kamimura H: In vitro inhibitory effects of non-steroidal anti-inflammatory drugs on 4-methylumbelliferone glucuronidation in recombinant human UDP-glucuronosyltransferase 1A9--potent inhibition by niflumic acid. Biopharm Drug Dispos. 2006 Jan;27(1):1-6. [16278927 ]
General function:
Involved in peroxidase activity
Specific function:
Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
Gene Name:
PTGS2
Uniprot ID:
P35354
Molecular weight:
68995.625
References
  1. Jabeen T, Singh N, Singh RK, Sharma S, Somvanshi RK, Dey S, Singh TP: Non-steroidal anti-inflammatory drugs as potent inhibitors of phospholipase A2: structure of the complex of phospholipase A2 with niflumic acid at 2.5 Angstroms resolution. Acta Crystallogr D Biol Crystallogr. 2005 Dec;61(Pt 12):1579-86. Epub 2005 Nov 19. [16301791 ]
  2. Diao HL, Zhu H, Ma H, Tan HN, Cong J, Su RW, Yang ZM: Rat ovulation, implantation and decidualization are severely compromised by COX-2 inhibitors. Front Biosci. 2007 May 1;12:3333-42. [17485303 ]
  3. Alpert E, Gruzman A, Tennenbaum T, Sasson S: Selective cyclooxygenase-2 inhibitors stimulate glucose transport in L6 myotubes in a protein kinase Cdelta-dependent manner. Biochem Pharmacol. 2007 Feb 1;73(3):368-77. Epub 2006 Oct 13. [17098211 ]
General function:
Involved in peroxidase activity
Specific function:
May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:
PTGS1
Uniprot ID:
P23219
Molecular weight:
68685.82
References
  1. Talbot S, Lin JC, Lahjouji K, Roy JP, Senecal J, Morin A, Couture R: Cigarette smoke-induced kinin B1 receptor promotes NADPH oxidase activity in cultured human alveolar epithelial cells. Peptides. 2011 Jul;32(7):1447-56. Epub 2011 May 11. [21600945 ]
General function:
Involved in ion channel activity
Specific function:
Voltage-gated chloride channel. Chloride channels have several functions including the regulation of cell volume; membrane potential stabilization, signal transduction and transepithelial transport. May be important in urinary concentrating mechanisms
Gene Name:
CLCNKA
Uniprot ID:
P51800
Molecular weight:
75284.1
References
  1. Picollo A, Liantonio A, Babini E, Camerino DC, Pusch M: Mechanism of interaction of niflumic acid with heterologously expressed kidney CLC-K chloride channels. J Membr Biol. 2007 Apr;216(2-3):73-82. Epub 2007 Jul 21. [17659402 ]

Transporters

General function:
Involved in transmembrane transport
Specific function:
Proton-linked monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucine, valine and isoleucine, and the ketone bodies acetoacetate, beta-hydroxybutyrate and acetate
Gene Name:
SLC16A1
Uniprot ID:
P53985
Molecular weight:
53957.7
References
  1. Broer S, Broer A, Schneider HP, Stegen C, Halestrap AP, Deitmer JW: Characterization of the high-affinity monocarboxylate transporter MCT2 in Xenopus laevis oocytes. Biochem J. 1999 Aug 1;341 ( Pt 3):529-35. [10417314 ]
General function:
Involved in transmembrane transport
Specific function:
Proton-linked monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucine, valine and isoleucine, and the ketone bodies acetoacetate, beta-hydroxybutyrate and acetate. MCT2 is a high affinity pyruvate transporter
Gene Name:
SLC16A7
Uniprot ID:
O60669
Molecular weight:
52185.7
References
  1. Broer S, Broer A, Schneider HP, Stegen C, Halestrap AP, Deitmer JW: Characterization of the high-affinity monocarboxylate transporter MCT2 in Xenopus laevis oocytes. Biochem J. 1999 Aug 1;341 ( Pt 3):529-35. [10417314 ]