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], [2]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 281.23
Topological Polar Surface Area (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 [3]
Elimination
7% of drug is excreted from urine in the unchanged form [3]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 30.4773 micromolar/kg/day [4]
Water Solubility
The ability of drug to dissolve in water is measured as 0.0265 mg/mL [3]
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 [5]
Dihydrodiol dehydrogenase type I (AKR1C3) TT5ZWB6 AK1C3_HUMAN Inhibitor [5]
Prostaglandin G/H synthase 1 (COX-1) TT8NGED PGH1_HUMAN Inhibitor [5]
Prostaglandin G/H synthase 2 (COX-2) TTVKILB PGH2_HUMAN Inhibitor [5]
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

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2 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
3 BDDCS applied to over 900 drugs
4 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
5 Ouellet M, Percival MD: Effect of inhibitor time-dependency on selectivity towards cyclooxygenase isoforms. Biochem J. 1995 Feb 15;306 ( Pt 1):247-51.
6 Dehydroepiandrosterone, glucose-6-phosphate dehydrogenase, and longevity. Ageing Res Rev. 2004 Apr;3(2):171-87.
7 Androgen receptor as a target in androgen-independent prostate cancer. Urology. 2002 Sep;60(3 Suppl 1):132-8; discussion 138-9.
8 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health Human Services. 2019
9 Molecular mechanism of androgen action. Trends Endocrinol Metab. 1998 Oct 1;9(8):317-24.
10 Androgen receptor overexpression induces tamoxifen resistance in human breast cancer cells. Breast Cancer Res Treat. 2010 May;121(1):1-11.
11 The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42.
12 2018 FDA drug approvals.Nat Rev Drug Discov. 2019 Feb;18(2):85-89.
13 CX3CR1 is expressed by prostate epithelial cells and androgens regulate the levels of CX3CL1/fractalkine in the bone marrow: potential role in prostate cancer bone tropism. Cancer Res. 2008 Mar 15;68(6):1715-22.
14 Expression of androgen receptor on fibroblast and hepatocyte of rats after deep second-degree burn caused by scalding. Sichuan Da Xue Xue Bao Yi Xue Ban. 2005 May;36(3):362-4.
15 An orally active selective androgen receptor modulator is efficacious on bone, muscle, and sex function with reduced impact on prostate. Endocrinology. 2007 Jan;148(1):363-73.
16 The C50T polymorphism of the cyclooxygenase-1 gene and the risk of thrombotic events during low-dose therapy with acetyl salicylic acid. Thromb Haemost. 2008 Jul;100(1):70-5.
17 Comparative inhibitory activity of rofecoxib, meloxicam, diclofenac, ibuprofen, and naproxen on COX-2 versus COX-1 in healthy volunteers. J Clin Pharmacol. 2000 Oct;40(10):1109-20.
18 How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
19 Cox-2 inhibitory effects of naturally occurring and modified fatty acids. J Nat Prod. 2001 Jun;64(6):745-9.
20 Comparison of cyclooxygenase inhibitory activity and ocular anti-inflammatory effects of ketorolac tromethamine and bromfenac sodium. Curr Med Res Opin. 2006 Jun;22(6):1133-40.
21 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
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23 Differential metabolism of dihomo-gamma-linolenic acid and arachidonic acid by cyclo-oxygenase-1 and cyclo-oxygenase-2: implications for cellular synthesis of prostaglandin E1 and prostaglandin E2. Biochem J. 2002 Jul 15;365(Pt 2):489-96.
24 Fenbufen based 3-[5-(substituted aryl)-1,3,4-oxadiazol-2-yl]-1-(biphenyl-4-yl)propan-1-ones as safer antiinflammatory and analgesic agents. Eur J Med Chem. 2009 Sep;44(9):3798-804.
25 Safety, tolerability and anti-tumour activity of the androgen biosynthesis inhibitor ASP9521 in patients with metastatic castration-resistant prostate cancer: multi-centre phase I/II study. Invest New Drugs. 2014 Oct;32(5):995-1004.
26 Aldo-Keto Reductase (AKR) 1C3 inhibitors: a patent review.Expert Opin Ther Pat. 2017 Dec;27(12):1329-1340.
27 Maternal toxicity of nonsteroidal anti-inflammatory drugs as an important factor affecting prenatal development. Reprod Toxicol. 2009 Sep;28(2):239-44.
28 Membranous nephropathy associated with the relatively selective cyclooxygenase-2 inhibitor, etodolac, in a patient with early rheumatoid arthritis. Intern Med. 2007;46(13):1055-8.
29 Pfizer. Product Development Pipeline. March 31 2009.
30 Renal effects of nabumetone, a COX-2 antagonist: impairment of function in isolated perfused rat kidneys contrasts with preserved renal function in vivo. Exp Nephrol. 2001;9(6):387-96.
31 Privileged structures: a useful concept for the rational design of new lead drug candidates. Mini Rev Med Chem. 2007 Nov;7(11):1108-19.
32 Flurbiprofen, a cyclooxygenase inhibitor, protects mice from hepatic ischemia/reperfusion injury by inhibiting GSK-3 signaling and mitochondrial permeability transition.Mol Med.2012 Sep 25;18:1128-35.