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]
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Therapeutic Class

Antilipemic Agents

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)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

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: CHEBI:47612
CAS Number: 41859-67-0
DrugBank ID: DB01393
TTD ID: D00WCX
VARIDT ID: DR00491
INTEDE ID: DR0209

Combinatorial Drugs (CBD)

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Repurposed Drugs (RPD)

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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]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 3A4 (CYP3A4)_{Main DME}	DE4LYSA	CP3A4_HUMAN	Substrate	[9]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
3-hydroxy-3-methylglutaryl-coenzyme A reductase (HMGCR)	OTRT3F3U	HMDH_HUMAN	Gene/Protein Processing	[10]
Achaete-scute homolog 2 (ASCL2)	OT3D62WB	ASCL2_HUMAN	Gene/Protein Processing	[11]
Adiponectin (ADIPOQ)	OTNX23LE	ADIPO_HUMAN	Gene/Protein Processing	[12]
Aldehyde dehydrogenase family 3 member A2 (ALDH3A2)	OT714BUO	AL3A2_HUMAN	Gene/Protein Processing	[13]
Alkaline phosphatase, tissue-nonspecific isozyme (ALPL)	OTG7J4BP	PPBT_HUMAN	Gene/Protein Processing	[14]
Apolipoprotein A-I (APOA1)	OT5THARI	APOA1_HUMAN	Gene/Protein Processing	[15]
Apolipoprotein A-II (APOA2)	OTQ3HGTC	APOA2_HUMAN	Gene/Protein Processing	[16]
Apolipoprotein B-100 (APOB)	OTH0UOCZ	APOB_HUMAN	Gene/Protein Processing	[17]
Apolipoprotein C-III (APOC3)	OTW3520C	APOC3_HUMAN	Gene/Protein Processing	[18]
Apolipoprotein E (APOE)	OTFOWL2H	APOE_HUMAN	Gene/Protein Processing	[19]

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Molecular Interaction Atlas (MIA)

MIA Detail

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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)

MEA Detail

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	Effects of Bezafibrate on Hepatic Cholesterol Metabolism Eur J Clin Pharmacol. 1991;40 Suppl 1:S33-6.
11	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.
12	Comparison of effects of bezafibrate and fenofibrate on circulating proprotein convertase subtilisin/kexin type 9 and adipocytokine levels in dyslipidemic subjects with impaired glucose tolerance or type 2 diabetes mellitus: results from a crossover study. Atherosclerosis. 2011 Jul;217(1):165-70. doi: 10.1016/j.atherosclerosis.2011.02.012. Epub 2011 Feb 22.
13	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.
14	The effect of bezafibrate treatment on serum alkaline phosphatase isoenzyme activities. Metabolism. 1993 Jul;42(7):839-42.
15	Negative regulation of the human apolipoprotein A-I promoter by fibrates can be attenuated by the interaction of the peroxisome proliferator-activated receptor with its response element. J Biol Chem. 1994 Dec 9;269(49):31012-8.
16	Effect of bezafibrate on lipids, lipoproteins, apolipoproteins and platelet aggregation in hypertriglyceridemic patients. Arzneimittelforschung. 1994 Nov;44(11):1217-22.
17	Effect of bezafibrate on lipoprotein (a) and triglyceride-rich lipoproteins, including intermediate-density lipoproteins, in patients with chronic renal failure receiving haemodialysis. Nephrol Dial Transplant. 1992;7(7):623-6. doi: 10.1093/ndt/7.7.623.
18	The hypolipidemic action of bezafibrate therapy in hypertriglyceridemia is mediated by upregulation of lipoprotein lipase: no effects on VLDL substrate affinity to lipolysis or LDL receptor binding. Atherosclerosis. 2000 Dec;153(2):363-71. doi: 10.1016/s0021-9150(00)00409-3.
19	Treatment of primary hypercholesterolemia: fluvastatin versus bezafibrate. Am J Med. 1994 Jun 6;96(6A):55S-63S. doi: 10.1016/0002-9343(94)90233-x.