Details of the Drug

General Information of Drug (ID: DMJ3I1Q)

Drug Name
Niflumic Acid
Synonyms
Actol; Donalgin; Flunir; Forenol; Landruma; NFL; Niflactol; Niflam; Niflugel; Niflumate; Nifluril; Acide niflumique; Acide niflumique [French]; Acido niflumico; Acido niflumico [Italian]; Acidum niflumicum; Nifluminic acid; UPSA Conseil Brand of Niflumic Acid; Upsamedica Brand of Niflumic Acid; N 0630; SC 1332; UP 83; UPSA Brand 1 of Niflumic Acid; UPSA Brand 2 of Niflumic Acid; Acid, Niflumic; Acide niflumique [INN-French]; Acido niflumico [INN-Spanish]; Acidum niflumicum [INN-Latin]; Niflugel (TN); Niflumic acid (INN); Niflumic acid [INN:DCF]; Aza-2 dimethyl-2',3' (tetrazolyl-5)-6 diphenylamino; Aza-2 dimethyl-2',3' (tetrazolyl-5)-6 diphenylamino [French]; 2-(3-(Trifluoromethyl)-phenyl)aminonicotinic acid; 2-(3-(Trifluoromethyl)anilino)nicotinic acid; 2-(3-Trifluoromethyl-phenylamino)-nicotinic acid; 2-(3-Trifluoromethylanilino)nicotinic Acid; 2-(3-[Trifluoromethyl]anilino)nicotinic acid; 2-(A,A,A-Trifluoro-m-toluidino)nicotinic acid; 2-(alpha,alpha,alpha-Trifluoro-m-toluidino)nicotinic acid; 2-[(3-TRIFLUOROMETHYL)PHENYL]AMINO-3-PYRIDINE-CARBOXYLIC ACID; 2-[(3-Trifluoromethyl)phenyl]amino]-3-pyridinecarboxylic Acid; 2-[(3-Trifluoromethylphenyl)amino]nicotinic Acid; 2-[3-(Trifluoromethyl)anilino]nicotinic acid; 2-[3-(trifluoromethyl)anilino]pyridine-3-carboxylic acid; 2-[alpha,alpha,alpha-trifluoro-m-toluidino]-nicotinic acid; 2-{[3-(TRIFLUOROMETHYL)PHENYL]AMINO}NICOTINIC ACID; 2-{[3-(trifluoromethyl)phenyl]amino}pyridine-3-carboxylic acid; 39690A
Indication
Disease Entry ICD 11 Status REF
Rheumatoid arthritis FA20 Approved [1]
Therapeutic Class
Antiinflammatory Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 282.22
Logarithm of the Partition Coefficient (xlogp) 3.7
Rotatable Bond Count (rotbonds) 3
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 7
ADMET Property
Absorption
The drug is well absorbed after oral administration []
Half-life
The concentration or amount of drug in body reduced by one-half in 2.5 hours [2]
Metabolism
The drug is metabolized via the hepatic []
Chemical Identifiers
Formula
C13H9F3N2O2
IUPAC Name
2-[3-(trifluoromethyl)anilino]pyridine-3-carboxylic acid
Canonical SMILES
C1=CC(=CC(=C1)NC2=C(C=CC=N2)C(=O)O)C(F)(F)F
InChI
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)
InChIKey
JZFPYUNJRRFVQU-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
4488
ChEBI ID
CHEBI:34888
CAS Number
4394-00-7
DrugBank ID
DB04552
TTD ID
D00HGB
VARIDT ID
DR01158
INTEDE ID
DR1153
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Prostaglandin G/H synthase 2 (COX-2) TTVKILB PGH2_HUMAN Inhibitor [3]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
UDP-glucuronosyltransferase 1A1 (UGT1A1)
Main DME 		DEYGVN4 UD11_HUMAN Substrate [4]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Aromatase (CYP19A1) OTZ6XF74 CP19A_HUMAN Gene/Protein Processing [5]
Caspase-8 (CASP8) OTA8TVI8 CASP8_HUMAN Gene/Protein Processing [6]
Cystic fibrosis transmembrane conductance regulator (CFTR) OT6B22QH CFTR_HUMAN Gene/Protein Processing [7]
DNA damage-inducible transcript 3 protein (DDIT3) OTI8YKKE DDIT3_HUMAN Gene/Protein Processing [6]
Eukaryotic translation initiation factor 2-alpha kinase 3 (EIF2AK3) OT0DZGY4 E2AK3_HUMAN Post-Translational Modifications [6]
Eukaryotic translation initiation factor 2A (EIF2A) OTWXELQP EIF2A_HUMAN Post-Translational Modifications [6]
Peroxisome proliferator-activated receptor gamma (PPARG) OTHMARHO PPARG_HUMAN Gene/Protein Processing [6]
Poly polymerase 1 (PARP1) OT310QSG PARP1_HUMAN Protein Interaction/Cellular Processes [6]
Prostaglandin G/H synthase 2 (PTGS2) OT75U9M4 PGH2_HUMAN Gene/Protein Processing [6]
Prostaglandin reductase 1 (PTGR1) OTMAR351 PTGR1_HUMAN Gene/Protein Processing [8]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Rheumatoid arthritis
ICD Disease Classification FA20
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Prostaglandin G/H synthase 2 (COX-2) DTT PTGS2 7.93E-04 -0.29 -0.34
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME UGT1A1 1.10E-01 -5.91E-02 -3.60E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 2439).
2 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
3 Rat ovulation, implantation and decidualization are severely compromised by COX-2 inhibitors. Front Biosci. 2007 May 1;12:3333-42.
4 Identification of human UDP-glucuronosyltransferase responsible for the glucuronidation of niflumic acid in human liver. Pharm Res. 2006 Jul;23(7):1502-8.
5 Translational studies on aromatase, cyclooxygenases, and enzyme inhibitors in breast cancer. J Steroid Biochem Mol Biol. 2005 May;95(1-5):129-36.
6 Combined treatment with the Cox-2 inhibitor niflumic acid and PPARgama ligand ciglitazone induces ER stress/caspase-8-mediated apoptosis in human lung cancer cells. Cancer Lett. 2011 Jan 28;300(2):134-44.
7 Direct block of the cystic fibrosis transmembrane conductance regulator Cl(-) channel by niflumic acid. Mol Membr Biol. 2004 Jan-Feb;21(1):27-38. doi: 10.1080/09687680310001597758.
8 Human prostaglandin reductase 1 (PGR1): Substrate specificity, inhibitor analysis and site-directed mutagenesis. Chem Biol Interact. 2015 Jun 5;234:105-13.