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Bezafibrate

HCID 39042
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
41859-67-0
표준 SMILES
CC(C)(Oc1ccc(CCNC(=O)c2ccc(Cl)cc2)cc1)C(=O)O
InChIKey
IIBYAHWJQTYFKB-UHFFFAOYSA-N
분자식
C19H20ClNO4
평균 분자량
361.8 g/mol
단동위원소 질량
361.1080858

개요

Bezafibrate is a monocarboxylic acid amide obtained by the formal condensation of the carboxy group of 4-chlorobenzoic acid with the amino group of 2-[4-(2-aminoethyl)phenoxy]-2-methylpropanoic acid. Benafibrate is used for the treatment of hyperlipidaemia. It has a role as a geroprotector, an antilipemic drug, a xenobiotic and an environmental contaminant. It is a monocarboxylic acid, a monocarboxylic acid amide, an aromatic ether and a member of monochlorobenzenes. It is functionally related to a propionic acid.

이름 및 식별자

우선 이름
Bezafibrate
IUPAC
2-[4-[2-[(4-chlorobenzoyl)amino]ethyl]phenoxy]-2-methylpropanoic acid
영어명
Bezafibrate
분자식
C19H20ClNO4
분자량
361.82

이름 및 동의어

bezafibrate41859-67-0BezalipBezafibratoBezatol SRBezafibratumBM-15075BM-15.075DTXSID3029869BM 15.075NSC-758174Y9449Q51XH
이름 더 보기
CEDURbf-759bm15075BefizalBezatolBenzabetDifaterolBezabrateBenzabate
Propanoic acid, 2-(4-(2-((4-chlorobenzoyl)amino)ethyl)phenoxy)-2-methyl-DTXCID909869CHEBI:47612Propanoic acid, 2-[4-[2-[(4-chlorobenzoyl)amino]ethyl]phenoxy]-2-methyl-Beza LandeBeza PurenBM15.075Bezalip-mono

데이터베이스 식별자

CAS
41859-67-0
PubChem CID
39042
DTXSID
DTXSID3029869
ChEMBL
CHEMBL264374
ChEBI
CHEBI:47612
UNII
Y9449Q51XH
EC Number
255-567-9、941-659-2
Nikkaji
J16.626J

물성

구조 계산 물성

XLogP
3.8
극성 표면적
75.6 Ų
수소 결합 공여자 수
2
수소 결합 수용자 수
4
회전 가능 결합 수
7
무거운 원자 수
25
형식 전하
0
복잡도
452

실험 및 물리화학적 성질

Drugs · 4건

Pharmaceuticals

Pharmaceuticals -> Antilipidemics

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Used in Switzerland

Solubility · 2건

1.55e-03 g/L

>54.3 [ug/mL] (The mean of the results at pH 7.4)

Melting Point186 °C
Physical DescriptionSolid
Collision Cross Section · 4건

189.0 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID3029869]

177.3 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

180.44 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

183.8 Ų [M-H]-

물리화학적 성질

녹는점
184 °C · 184 °C
끓는 점
572.1 · 572.1±45.0 °C(Predicted)
밀도
1.26 · 1.260±0.06 g/cm3(Predicted)
저장 조건
2 · 2-8°C
용해도
에 용해됨DMF
물리적 상태
고체

안전 및 규제

GHS 분류

GHS Classification · 6건

Warning

H302 (50.9%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P264, P270, P280, P301+P317, P318, P330, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 106 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

유해성 정보

Other Safety InformationIMAP assessments - Propanoic acid, 2-[4-[2-[(4-chlorobenzoyl)amino]ethyl]phenoxy]-2-methyl-: Environment tier I assessment
Hazard Classes and Categories · 2건

Acute Tox. 4 (50.9%)

Acute Tox. 4 (100%)

독성 정보

Drug Induced Liver Injury · 5건

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

bezafibrate

DILI Negative

oral

DOI:10.1016/j.drudis.2019.09.022

안전 데이터

wgk
1
rtecs
UE8755000
독성
LD50 oral in rat: 1082mg/kg
HS 번호
29242990
risk_code
22
hazard_code
Xn
safety_code
36
Hazard Classifications
Acute Tox. 4 Oral
스토리지 클래스
11 - Combustible Solids

화학 및 산업

약리 정보

ATC Code · 4건

C10AB02

C10AB02

C - Cardiovascular system

QC - Cardiovascular system

Protein Binding94-96% of bezafibrate is bound to protein in human serum.
Pharmacodynamics · 1건

Bezafibrate is an antilipemic agent that lowers cholesterol and triglycerides. It decreases low density lipoproteins and increases high density lipoproteins. Bezafibrate lowers elevated blood lipids (triglycerides and cholesterol). Elevated VLDL and LDL are reduced by treatment with bezafibrate, whilst HDL-levels are increased. The activity of triglyceride lipases (lipoprotein lipase and hepatic lipoproteinlipase) involved in the catabolism of triglyceride-rich lipoproteins is increased by bezafibrate. In the course of the intensified degradation of triglyceride-rich lipoproteins (chylomicrons, VLDL) precursors for the formation of HDL are formed which explains an increase in HDL. Furthermore, cholesterol biosynthesis is reduced by bezafibrate, which is accompanied by a stimulation of the LDL-receptor-mediated lipoprotein catabolism. Elevated fibrinogen appears to be an important risk-factor, alongside the lipids, smoking and hypertension, in the development of atheroma. Fibrinogen plays an important role in viscosity, and therefore blood flow, and also appears to play an important role in thrombus development and lysability. Bezafibrate exerts an effect on thrombogenic factors. A significant decrease in elevated plasma fibrinogen levels can be achieved. This may lead, amongst other things, to a reduction in both blood and plasma viscosity. Inhibition of platelet aggregation has also been observed. A reduction in blood glucose concentration due to an increase in glucose tolerance has been reported in diabetic patients. In the same patients, the concentration of fasting and postprandial free fatty acids was reduced by bezafibrate.

Mechanism of ActionIt is generally accepted that bezafibrate is likely an agonist of PPAR-alpha. However, certain other investigations have also suggested that the substance might also elicit some effects on PPAR-gamma and PPAR-delta too.
Biological Half-Life1-2 hours

관련 반응

2건
반응 기록 만들기
HRID 1033230 반응식
HRID 1033230반응물로uspto-grants-1994_05
HRID 2129330 반응식
HRID 2129330반응물로Training data from https://doi.org/10.1039/C8SC04228D (4/10)

화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
산도 계수 (pKa)
3.29 · 3.29±0.10(Predicted)
색상
흰색에서 황백색까지
Merck
14 · 14,1195
안정성
흡습성
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
SMILES
C(O)(=O)C(OC1=CC=C(CCNC(=O)C2=CC=C(Cl)C=C2)C=C1)(C)C
LogP
2.504 · 2.504 (est)
EPA
2 · Propanoic acid, 2-[4-[2-[(4-chlorobenzoyl)amino]ethyl]phenoxy]-2-methyl- (41859-67-0)

화학적 성질

Off-White Solid

Metabolism/Metabolites
Hepatic.
MeSH Pharmacological ClassificationSubstances that lower the levels of certain LIPIDS in the BLOOD. They are used to treat HYPERLIPIDEMIAS.
Absorption, Distribution and ExcretionBezafibrate is almost completely absorbed after oral administration. The relative bioavailability of bezafibrate retard compared to the standard form is about 70%.
Cellular LocationsCytoplasm

용도 및 제조

UsesUse (kg) in Switzerland (2009): >500
Use ClassificationPharmaceuticals -> Cardiovascular system -> Lipid modifying agents -> Lipid modifying agents, plain -> Fibrates -> Antilipemics
응용 분야 · 2건

개요Bezafibrate is a non-selective agonist of peroxisome proliferator-activated receptors (PPARs; EC50s = 50, 60, and 20 μM for human PPARα, PPARγ, and PPARδ, respectively). It reduces triglyceride levels and the size of lipid droplets in an oleic acid-induced HepaRG hepatocyte model of steatosis when used at a concentration of 25 μM. Bezafibrate (10 mg/kg per day) reduces plasma VLDL and LDL mass and triglyceride and free fatty acid levels in a high-fructose plus lard diet-induced rat model of insulin resistance.

용도Bezafibrate has been used:a supplement in the standard diet (SD)for mice to study its effect on diabetesto evaluate its effect on hepatitis C virus (HCV) assembly and secretionto evaluate its effect on gonadal steroidogenesis andspermatogenesisof zebrafish and also used as standard for HPLC

상·하류 제품 정보

상류 원료

p-클로로벤조일 클로라이드티라민에틸 2-브로모아이소뷰티레이트나트륨

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