Details of the Drug

General Information of Drug (ID: DMC8VNH)

Drug Name
Flufenamic Acid
Synonyms
flufenamic acid; 530-78-9; Fluphenamic acid; Nichisedan; Achless; Arlef; Tecramine; Paraflu; Lanceat; Flufacid; Plostene; Fullsafe; Parlef; Surika; Parlif; Flufenaminsaeure; Reumajust A; Acido flufenamico; N-(3-Trifluoromethylphenyl)anthranilic acid; Ristogen; Sastridex; Meralen; Ansatin; 2-((3-(Trifluoromethyl)phenyl)amino)benzoic acid; Fluore-200; 2-{[3-(trifluoromethyl)phenyl]amino}benzoic acid; ANT-1; Acide flufenamique; Acidum flufenamicum; TVX 916; INF 1837; 3'-Trifluoromethyldiphenylamine-2-carboxylic acid; NSC-82699; CI 440
Indication
Disease Entry ICD 11 Status REF
Dysmenorrhea GA34.3 Approved [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 281.23
Logarithm of the Partition Coefficient (xlogp) 5.2
Rotatable Bond Count (rotbonds) 3
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 6
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [2]
Elimination
7% of drug is excreted from urine in the unchanged form [2]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 30.4773 micromolar/kg/day [3]
Water Solubility
The ability of drug to dissolve in water is measured as 0.0265 mg/mL [2]
Chemical Identifiers
Formula
C14H10F3NO2
IUPAC Name
2-[3-(trifluoromethyl)anilino]benzoic acid
Canonical SMILES
C1=CC=C(C(=C1)C(=O)O)NC2=CC=CC(=C2)C(F)(F)F
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)
InChIKey
LPEPZBJOKDYZAD-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
3371
ChEBI ID
CHEBI:42638
CAS Number
530-78-9
DrugBank ID
DB02266
TTD ID
D0B2WJ

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Androgen receptor (AR) TTS64P2 ANDR_HUMAN Inhibitor [4]
Dihydrodiol dehydrogenase type I (AKR1C3) TT5ZWB6 AK1C3_HUMAN Inhibitor [4]
Prostaglandin G/H synthase 1 (COX-1) TT8NGED PGH1_HUMAN Inhibitor [4]
Prostaglandin G/H synthase 2 (COX-2) TTVKILB PGH2_HUMAN Inhibitor [4]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Aldo-keto reductase family 1 member C1 (AKR1C1) OTQKR4CM AK1C1_HUMAN Gene/Protein Processing [5]
Aldo-keto reductase family 1 member C2 (AKR1C2) OTQ2XMO3 AK1C2_HUMAN Gene/Protein Processing [5]
Aldo-keto reductase family 1 member C3 (AKR1C3) OTU2SXBA AK1C3_HUMAN Gene/Protein Processing [5]
Aldo-keto reductase family 1 member C4 (AKR1C4) OTW2MMOF AK1C4_HUMAN Gene/Protein Processing [5]
Cystic fibrosis transmembrane conductance regulator (CFTR) OT6B22QH CFTR_HUMAN Gene/Protein Processing [6]
Dehydrogenase/reductase SDR family member 11 (DHRS11) OTU3J0ZL DHR11_HUMAN Gene/Protein Processing [7]
L-selectin (SELL) OT6RAJZR LYAM1_HUMAN Gene/Protein Processing [8]
Low-density lipoprotein receptor (LDLR) OTH559LU LDLR_HUMAN Gene/Protein Processing [9]
Peroxisome proliferator-activated receptor gamma (PPARG) OTHMARHO PPARG_HUMAN Gene/Protein Processing [10]
Prostaglandin G/H synthase 2 (PTGS2) OT75U9M4 PGH2_HUMAN Gene/Protein Processing [10]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Dysmenorrhea
ICD Disease Classification GA34.3
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Androgen receptor (AR) DTT AR 2.13E-01 -0.07 -0.11
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: 2447).
2 BDDCS applied to over 900 drugs
3 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
4 Ouellet M, Percival MD: Effect of inhibitor time-dependency on selectivity towards cyclooxygenase isoforms. Biochem J. 1995 Feb 15;306 ( Pt 1):247-51.
5 Selective and potent inhibitors of human 20alpha-hydroxysteroid dehydrogenase (AKR1C1) that metabolizes neurosteroids derived from progesterone. Chem Biol Interact. 2003 Feb 1;143-144:503-13.
6 Discovery of glycine hydrazide pore-occluding CFTR inhibitors: mechanism, structure-activity analysis, and in vivo efficacy. J Gen Physiol. 2004 Aug;124(2):125-37. doi: 10.1085/jgp.200409059.
7 Rabbit dehydrogenase/reductase SDR family member 11 (DHRS11): Its identity with acetohexamide reductase with broad substrate specificity and inhibitor sensitivity, different from human DHRS11. Chem Biol Interact. 2019 May 25;305:12-20. doi: 10.1016/j.cbi.2019.03.026. Epub 2019 Mar 26.
8 Structure-function relationship and role of tumor necrosis factor-alpha-converting enzyme in the down-regulation of L-selectin by non-steroidal anti-inflammatory drugs. J Biol Chem. 2002 Oct 11;277(41):38212-21. doi: 10.1074/jbc.M205142200. Epub 2002 Jul 29.
9 Enhancement of low density lipoprotein catabolism by non-steroidal anti-inflammatory drugs in cultured HepG2 cells. Eur J Pharmacol. 1999 May 21;372(3):311-8. doi: 10.1016/s0014-2999(99)00246-0.
10 Two opposing effects of non-steroidal anti-inflammatory drugs on the expression of the inducible cyclooxygenaseMediation through different signaling pathways. J Biol Chem. 2000 Sep 8;275(36):28173-9.