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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2020-02-26 21:41:52 UTC
HMDB IDHMDB0015573
Secondary Accession Numbers
  • HMDB15573
Metabolite Identification
Common NameNiflumic Acid
DescriptionNiflumic Acid, also known as NFA or niflugel, belongs to the class of organic compounds known as trifluoromethylbenzenes. These are organofluorine compounds that contain a benzene ring substituted with one or more trifluoromethyl groups. It is categorized as an inhibitor of cyclooxygenase-2. Niflumic Acid is a drug which is used in the treatment of rheumatoid arthritis. In experimental biology, it has been employed to inhibit chloride channels. Niflumic Acid is a very strong basic compound (based on its pKa). Niflumic acid is a drug used for joint and muscular pain. It has also been reported to act on GABA-A and NMDA channels and to block T-type calcium channels.
Structure
Data?1582753312
Synonyms
ValueSource
NFAKegg
NiflugelKegg
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
UPSA brand 1 OF niflumic acidHMDB
UPSA brand 2 OF niflumic acidHMDB
UPSA conseil brand OF niflumic acidHMDB
Upsamedica brand OF niflumic acidHMDB
NiflactolHMDB
NiflurilHMDB
Acid, niflumicHMDB
DonalginHMDB
FlunirHMDB
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 KeyJZFPYUNJRRFVQU-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as trifluoromethylbenzenes. These are organofluorine compounds that contain a benzene ring substituted with one or more trifluoromethyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassTrifluoromethylbenzenes
Direct ParentTrifluoromethylbenzenes
Alternative Parents
Substituents
  • Trifluoromethylbenzene
  • Pyridine carboxylic acid
  • Pyridine carboxylic acid or derivatives
  • Aniline or substituted anilines
  • Aminopyridine
  • Pyridine
  • Imidolactam
  • Vinylogous amide
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Amino acid
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Alkyl halide
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Organic nitrogen compound
  • Alkyl fluoride
  • Amine
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point203 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.088 g/LNot Available
LogP4.43TAKACS-NOVAK,K ET AL. (1995)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available159.352http://allccs.zhulab.cn/database/detail?ID=AllCCS00000864
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.088 g/LALOGPS
logP10(4.33) g/LALOGPS
logP10(3.12) g/LChemAxon
logS10(-3.5) g/LALOGPS
pKa (Strongest Acidic)1.88ChemAxon
pKa (Strongest Basic)5.51ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area62.22 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity65.93 m³·mol⁻¹ChemAxon
Polarizability24.21 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Niflumic AcidOC(=O)C1=C(NC2=CC=CC(=C2)C(F)(F)F)N=CC=C12755.8Standard polar33892256
Niflumic AcidOC(=O)C1=C(NC2=CC=CC(=C2)C(F)(F)F)N=CC=C12034.7Standard non polar33892256
Niflumic AcidOC(=O)C1=C(NC2=CC=CC(=C2)C(F)(F)F)N=CC=C12036.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Niflumic Acid,1TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=CN=C1NC1=CC=CC(C(F)(F)F)=C11969.6Semi standard non polar33892256
Niflumic Acid,1TMS,isomer #2C[Si](C)(C)N(C1=CC=CC(C(F)(F)F)=C1)C1=NC=CC=C1C(=O)O1920.4Semi standard non polar33892256
Niflumic Acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=CN=C1N(C1=CC=CC(C(F)(F)F)=C1)[Si](C)(C)C1936.6Semi standard non polar33892256
Niflumic Acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=CN=C1N(C1=CC=CC(C(F)(F)F)=C1)[Si](C)(C)C2093.0Standard non polar33892256
Niflumic Acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=CN=C1N(C1=CC=CC(C(F)(F)F)=C1)[Si](C)(C)C2239.1Standard polar33892256
Niflumic Acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CN=C1NC1=CC=CC(C(F)(F)F)=C12184.5Semi standard non polar33892256
Niflumic Acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1=CC=CC(C(F)(F)F)=C1)C1=NC=CC=C1C(=O)O2116.8Semi standard non polar33892256
Niflumic Acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CN=C1N(C1=CC=CC(C(F)(F)F)=C1)[Si](C)(C)C(C)(C)C2334.3Semi standard non polar33892256
Niflumic Acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CN=C1N(C1=CC=CC(C(F)(F)F)=C1)[Si](C)(C)C(C)(C)C2423.2Standard non polar33892256
Niflumic Acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CN=C1N(C1=CC=CC(C(F)(F)F)=C1)[Si](C)(C)C(C)(C)C2456.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Niflumic Acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-03ei-0290000000-e3d9c9b7c6e9419c93792017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Niflumic Acid GC-MS (1 TMS) - 70eV, Positivesplash10-00dr-9175000000-795d65b7bc6672068c202017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Niflumic Acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Niflumic Acid LC-ESI-qTof , Positive-QTOFsplash10-0229-3920000000-b822873abe0cc77b65002017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Niflumic Acid LC-ESI-QFT , negative-QTOFsplash10-001r-0090000000-d212523eaa8e47f9054f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Niflumic Acid LC-ESI-QFT , negative-QTOFsplash10-000i-0090000000-7f1bc979a7f8c7077a952017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Niflumic Acid LC-ESI-QFT , negative-QTOFsplash10-000i-0090000000-dd0310ff257f2921383c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Niflumic Acid LC-ESI-QFT , negative-QTOFsplash10-000i-0490000000-b0e41ea5dbccc5a0b0f62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Niflumic Acid LC-ESI-QFT , negative-QTOFsplash10-004r-1980000000-1096f092d7eef85007822017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Niflumic Acid LC-ESI-QFT , negative-QTOFsplash10-004i-2930000000-038c8f35115d57e400ee2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Niflumic Acid LC-ESI-QFT , negative-QTOFsplash10-004l-4900000000-c2e52373f3300219b3882017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Niflumic Acid LC-ESI-QFT , negative-QTOFsplash10-0g6u-9700000000-a47c140f0903976ebc7f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Niflumic Acid LC-ESI-QFT , negative-QTOFsplash10-00dj-9200000000-4a59d785457835ab936e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Niflumic Acid LC-ESI-QTOF , positive-QTOFsplash10-014i-0090000000-1d2a69ae63d48722b5c12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Niflumic Acid LC-ESI-QTOF , positive-QTOFsplash10-014i-0190000000-30b3c58f88b7803349dd2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Niflumic Acid LC-ESI-QTOF , positive-QTOFsplash10-014j-0960000000-b837ec0e3f19a1b863162017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Niflumic Acid LC-ESI-QFT , positive-QTOFsplash10-001i-0090000000-065361d6324d9eb6997f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Niflumic Acid LC-ESI-QFT , positive-QTOFsplash10-00lr-0090000000-339e0764e241daa8de0a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Niflumic Acid LC-ESI-QFT , positive-QTOFsplash10-014i-0090000000-72bb52f92fc53b179b002017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Niflumic Acid LC-ESI-QFT , positive-QTOFsplash10-014i-0190000000-7e1966497ac2f37804a22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Niflumic Acid LC-ESI-QFT , positive-QTOFsplash10-00kb-0690000000-30e96da9f66c54d2cea72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Niflumic Acid LC-ESI-QFT , positive-QTOFsplash10-00kb-1930000000-0b215b890ef639ace9db2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Niflumic Acid 10V, Positive-QTOFsplash10-001i-0090000000-ac2f32b701b127bc2f072016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Niflumic Acid 20V, Positive-QTOFsplash10-000i-0090000000-46b3c275b275a65c82932016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Niflumic Acid 40V, Positive-QTOFsplash10-03xr-2390000000-5afdb8b679ba746755152016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Niflumic Acid 10V, Negative-QTOFsplash10-0019-0090000000-781bc798e56c97b8e8c02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Niflumic Acid 20V, Negative-QTOFsplash10-000i-0190000000-3a2c9fe221b83926f0c62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Niflumic Acid 40V, Negative-QTOFsplash10-00ku-6590000000-3aab6fc333f1b5bcd1d62016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB04552 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB04552 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04552
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4333
KEGG Compound IDC13698
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNiflumic acid
METLIN IDNot Available
PubChem Compound4488
PDB IDNFL
ChEBI ID197010
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. doi: 10.1016/j.peptides.2011.05.005. Epub 2011 May 11. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:10417314 ]