Details of the Drug

General Information of Drug (ID: DMZDCS0)

Drug Name
Bezafibrate
Synonyms
Azufibrat; Befibrat; Befizal; BezaLande; BezaPuren; Bezabeta; Bezacur; Bezafibrat; Bezafibrato; Bezafibratum; Bezafisal;Bezalip; Bezamerck; Bezatol; Cedur; Difaterol; Durabezur; Eulitop; Lipox; Reducterol; Sklerofibrat; Solibay; Azupharma Brand of Bezafibrate; Bayer Brand of Bezafibrate; Berlin Chemie Brand of Bezafibrate; Betapharm Brand of Bezafibrate; Beza Lande; Beza Puren; Bezafibrat PB; Bezafibrate Azupharma Brand; Bezafibrate Bayer Brand; Bezafibrate Betapharm Brand; Bezafibrate Cryopharma Brand; Bezafibrate Elfar Brand; Bezafibrate Hennig Brand; Bezafibrate Hexal Brand; Bezafibrate Isis Brand; Bezafibrate Lakeside Brand; Bezafibrate Merckle Brand; Bezafibrate Roche Brand; Bezafibrate Synthelabo Brand; Bezafibrate TAD Brand; Bezafibrate Teva Brand; Bezafibrato [Spanish]; Bezalip Retard; Bezatol SR; Boehringer Mannheim Brand of Bezafibrate; Cryopharma Brand of Bezafibrate; Elfar Brand of Bezafibrate;Hennig Brand of Bezafibrate; Hexal Brand of Bezafibrate; Isis Brand of Bezafibrate; Lakeside Brand of Bezafibrate; Merckle Brand of Bezafibrate; Regadrin B; Roche Brand of Bezafibrate; Synthelabo Brand of Bezafibrate; TAD Brand of Bezafibrate; Teva Brand of Bezafibrate; BM 15075; LO 44; BF-759; BM 15.075; BM-15075; BM15.075; Berlin-Chemie Brand of Bezafibrate; Beza-Lande; Beza-Puren; Bezafibrate Berlin-Chemie Brand; Bezafibrato [INN-Spanish]; Bezafibratum [INN-Latin]; Bezalip (TN); Bezatol SR (TN); PB, Bezafibrat; BM-15.075; Bezafibrate (JP15/USAN/INN); Bezafibrate [USAN:BAN:INN:JAN]; A-[4-(4-chlorobenzoylaminoethyl)phenoxy]isobutyric acid; 2-(4-{2-[(4-chlorobenzoyl)amino]ethyl}phenoxy)-2-methylpropanoic acid; 2-(p-(2-(p-Chlorobenzamido)ethyl)phenoxy)-2-methylpropionic acid; 2-[4-(2-[4-Chlorobenzamido]ethyl)-phenoxy]-2-methylpropanoic acid; 2-[4-[2-(4-Chlorobenzamido)ethyl]phenoxy]-2-methylpropanoic acid; 2-[4-[2-(4-Chlorobenzamido)ethyl]phenoxy]isobutyric Acid; 2-[4-[2-[(4-chlorobenzoyl)amino]ethyl]phenoxy]-2-methylpropanoic acid
Indication
Disease Entry ICD 11 Status REF
Hypercholesterolaemia 5C80.0 Approved [1]
Hyperlipidaemia 5C80 Approved [2]
Hyperlipidemia 5C80.Z Approved [3]
Therapeutic Class
Antilipemic Agents
Affected Organisms
Humans and other mammals
ATC Code
C10AB02: Bezafibrate
C10AB: Fibrates
C10A: LIPID MODIFYING AGENTS, PLAIN
C10: LIPID MODIFYING AGENTS
C: CARDIOVASCULAR SYSTEM
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 361.8
Logarithm of the Partition Coefficient (xlogp) 3.8
Rotatable Bond Count (rotbonds) 7
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 4
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [4]
Bioavailability
99% of drug becomes completely available to its intended biological destination(s) [5]
Elimination
40% of drug is excreted from urine in the unchanged form [4]
Half-life
The concentration or amount of drug in body reduced by one-half in 1 - 2 hours [6]
Metabolism
The drug is metabolized via the hepatic []
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 23.6891 micromolar/kg/day [7]
Chemical Identifiers
Formula
C19H20ClNO4
IUPAC Name
2-[4-[2-[(4-chlorobenzoyl)amino]ethyl]phenoxy]-2-methylpropanoic acid
Canonical SMILES
CC(C)(C(=O)O)OC1=CC=C(C=C1)CCNC(=O)C2=CC=C(C=C2)Cl
InChI
InChI=1S/C19H20ClNO4/c1-19(2,18(23)24)25-16-9-3-13(4-10-16)11-12-21-17(22)14-5-7-15(20)8-6-14/h3-10H,11-12H2,1-2H3,(H,21,22)(H,23,24)
InChIKey
IIBYAHWJQTYFKB-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
39042
ChEBI ID
CHEMBL47612
CAS Number
41859-67-0
UNII
Y9449Q51XH
DrugBank ID
DB01393
TTD ID
D00WCX
VARIDT ID
DR00491
INTEDE ID
DR0209
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Peroxisome proliferator-activated receptor alpha (PPARA) TTJ584C PPARA_HUMAN Agonist [8]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4)
Main DME 		DE4LYSA CP3A4_HUMAN Substrate [9]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Achaete-scute homolog 2 (ASCL2) OT3D62WB ASCL2_HUMAN Gene/Protein Processing [10]
Aldehyde dehydrogenase family 3 member A2 (ALDH3A2) OT714BUO AL3A2_HUMAN Gene/Protein Processing [11]
ATP-binding cassette sub-family C member 4 (ABCC4) OTO27PAL MRP4_HUMAN Regulation of Drug Effects [12]
ATP-binding cassette sub-family G member 5 (ABCG5) OT1OMY93 ABCG5_HUMAN Gene/Protein Processing [13]
Bile salt export pump (ABCB11) OTRU7THO ABCBB_HUMAN Gene/Protein Processing [14]
C-reactive protein (CRP) OT0RFT8F CRP_HUMAN Gene/Protein Processing [15]
Carnitine O-palmitoyltransferase 1, liver isoform (CPT1A) OTI862QH CPT1A_HUMAN Gene/Protein Processing [16]
Carnitine O-palmitoyltransferase 2, mitochondrial (CPT2) OTIN6G20 CPT2_HUMAN Gene/Protein Processing [17]
CD40 ligand (CD40LG) OT75Z6A6 CD40L_HUMAN Gene/Protein Processing [18]
Choriogonadotropin subunit beta 3 (CGB3) OTVM2SU3 CGB3_HUMAN Protein Interaction/Cellular Processes [10]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Hypercholesterolaemia
ICD Disease Classification 5C80.0
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Peroxisome proliferator-activated receptor alpha (PPARA) DTT PPARA 1.74E-01 -0.17 -0.3
Cytochrome P450 3A4 (CYP3A4) DME CYP3A4 2.76E-01 -4.64E-01 -9.16E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Simvastatin and bezafibrate: effects on serum lipoproteins and lecithin: cholesterol acyltransferase activity in familial hypercholesterolaemia. Eur J Clin Pharmacol. 1988;35(6):579-83.
2 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: 2668).
3 Postprandial Hyperlipidemia: Its Pathophysiology, Diagnosis, Atherogenesis, and Treatments. Int J Mol Sci. 2023 Sep 11;24(18):13942.
4 BDDCS applied to over 900 drugs
5 Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
6 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
7 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
8 Bezafibrate at clinically relevant doses decreases serum/liver triglycerides via down-regulation of sterol regulatory element-binding protein-1c in... Mol Pharmacol. 2009 Apr;75(4):782-92.
9 Clinical pharmacokinetics of fibric acid derivatives (fibrates). Clin Pharmacokinet. 1998 Feb;34(2):155-62.
10 Expression of cFABP and PPAR in trophoblast cells: effect of PPAR ligands on linoleic acid uptake and differentiation. Biochim Biophys Acta. 2005 Feb 21;1687(1-3):181-94. doi: 10.1016/j.bbalip.2004.11.017.
11 Bezafibrate induces FALDH in human fibroblasts; implications for Sj?gren-Larsson syndrome. Mol Genet Metab. 2006 Sep-Oct;89(1-2):111-5. doi: 10.1016/j.ymgme.2006.05.009. Epub 2006 Jul 11.
12 Multichannel liquid chromatography-tandem mass spectrometry cocktail method for comprehensive substrate characterization of multidrug resistance-associated protein 4 transporter. Pharm Res. 2007 Dec;24(12):2281-96.
13 Fibrates modify the expression of key factors involved in bile-acid synthesis and biliary-lipid secretion in gallstone patients. Eur J Clin Pharmacol. 2004 Feb;59(12):855-61. doi: 10.1007/s00228-003-0704-1. Epub 2003 Dec 18.
14 Bezafibrate stimulates canalicular localization of NBD-labeled PC in HepG2 cells by PPARalpha-mediated redistribution of ABCB4. J Lipid Res. 2004 Oct;45(10):1813-25. doi: 10.1194/jlr.M400132-JLR200. Epub 2004 Jul 16.
15 Severe hypertriglyceridemia with insulin resistance is associated with systemic inflammation: reversal with bezafibrate therapy in a randomized controlled trial. Am J Med. 2002 Mar;112(4):275-80. doi: 10.1016/s0002-9343(01)01123-8.
16 Osthole, a potential antidiabetic agent, alleviates hyperglycemia in db/db mice. Chem Biol Interact. 2009 Oct 30;181(3):309-15. doi: 10.1016/j.cbi.2009.08.003. Epub 2009 Aug 12.
17 Bezafibrate upregulates carnitine palmitoyltransferase II expression and promotes mitochondrial energy crisis dissipation in fibroblasts of patients with influenza-associated encephalopathy. Mol Genet Metab. 2011 Nov;104(3):265-72. doi: 10.1016/j.ymgme.2011.07.009. Epub 2011 Jul 20.
18 Treatment of primary CLL cells with bezafibrate and medroxyprogesterone acetate induces apoptosis and represses the pro-proliferative signal of CD40-ligand, in part through increased 15dDelta12,14,PGJ2. Leukemia. 2009 Feb;23(2):292-304. doi: 10.1038/leu.2008.283. Epub 2008 Oct 16.