세노디올

세노디올 · CDCA · CHENODIOL · CHENODEOXYCHOLATE · 3ALPHA,7ALPHA-DIHYDROXY-5BETA-CHOLANIC ACID · Chenix · ChenodeoxychoL · URSODEOXYCHOLOC ACID

https://huagongshe.com/ko/chemical/10133

식별자 및 물리적 특성

CAS No.	474-25-9
분자식	C24H40O4
평균 분자량	392.6 g/mol
단동위원소 질량	392.29265975 g/mol
SMILES	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
InChIKey	RUDATBOHQWOJDD-BSWAIDMHSA-N
PubChem CID	10133
ChEMBL	CHEMBL240597
ChEBI	CHEBI:16755
EC No.	207-481-8
DTXSID	DTXSID2020260
현지명	세노디올

화학 및 물리적 성질

XLogP	4.9
극성 표면적	77.8
수소 결합 공여자 수	3
수소 결합 수용자 수	4
회전 가능 결합 수	4
무거운 원자 수	28
형식 전하	0
복잡도	605
LogP(분배 계수)	4.15
용해도	89.90.0899 mg/mL실질적으로 불용성
녹는점	168-171165 - 167 °C165-167 °C (lit.)
Physical Description	Solid
Collision Cross Section	203.3 Å² [M-H]- [CCS Type: DTBuffer gas: N2Ionization: ESI-Dataset: Bile Acids]202.8 Å² [M+H-H2O]+ [CCS Type: DTMethod: single field calibrated]208.5 Å² [M+K-H+HCOO]- [CCS Type: DT224.5 Å² [M+K-H+HCOO]- [CCS Type: DT205.8 Å² [M+Na-H+HCOO]- [CCS Type: DT199.2 Å² [M+Na-H+Cl]- [CCS Type: DT202.3 Å² [M-H]- [CCS Type: DT186.9 Å² [M+H-2H2O]+ [CCS Type: DT201.9 Å² [M+HCOO]- [CCS Type: DT192.83 Å² [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]198.15 Å² [M+K]+ [CCS Type: TW195.52 Å² [M+Na]+ [CCS Type: TW206.57 Å² [M-H]- [CCS Type: DTMethod: stepped-field]201.51 Å² [M-H]- [CCS Type: DTMethod: single field calibrated with Agilent tune mix (Agilent)]205.9 Å² [M-H]-
끓는 점	437.26°C (rough estimate)
밀도	0.9985 (rough estimate)
굴절률	1.4460 (estimate)
인화점	9℃
저장 조건	room temp
pKa(산도 계수)	pKa 4.34 (Uncertain)
물리적 상태	가루
색상	흰색에서 황백색까지
용해도	실질적으로 불용성
Merck	13,2062
BRN	3219887
주요 응용	의약품(소분자)
InChIKey	RUDATBOHQWOJDD-BSWAIDMHSA-N
SMILES	C[C@H](CCC(O)=O)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
LogP(분배 계수)	3.05 at 20℃
EPA	Chenodiol (474-25-9)

화학적 성질

Off-White Solid

안전 및 규제

GHS 분류	This chemical does not meet GHS hazard criteria for 8.3% (1 of 12) of reports.WarningH302 (16.7%): Harmful if swallowed [Warning Acute toxicity, oral]H312 (16.7%): Harmful in contact with skin [Warning Acute toxicity, dermal]H315 (41.7%): Causes skin irritation [Warning Skin corrosion/irritation]H319 (41.7%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H332 (16.7%): Harmful if inhaled [Warning Acute toxicity, inhalation]H335 (16.7%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]H361 (33.3%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]P203, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P318, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 12 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Reported as not meeting GHS hazard criteria per 1 of 12 reports by companies.There are 7 notifications provided by 11 of 12 reports by companies with hazard statement code(s).Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
규제 정보	Hazard Traits - Developmental ToxicityAuthoritative List - Prop 65Report - regardless of intended function of ingredient in the productStatus: Active Update: 19-04-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/5782
기타 안전 정보	IMAP assessments - Cholan-24-oic acid, 3,7-dihydroxy-, (3.alpha.,5.beta.,7.alpha.)-: Environment tier I assessmentIMAP assessments - Cholan-24-oic acid, 3,7-dihydroxy-, (3.alpha.,5.beta.,7.alpha.)-: Human health tier I assessment
Hazard Classes and Categories

용도

개요

Chenodeoxycholic acid is the first agent to be introduced into the US market for the treatment of radiolucent gallstones. Large scale clinical trials have demonstrated the safety and efficacy of this agent. Chenodeoxycholic acid reduces the biliary concentration of cholesterol relative to that of bile acids and phospholipid, reducing the saturation and thus the lithogenicity of the bile. Success rates in dissolving gallstones are in the range of 50-70% within 4-24 months of treatment. Continuation of the drug after stone dissolution may be required to prevent reoccurrence. Chenodeoxycholic acid is the 7α-isomer of ursodeoxycholic acid which was introduced into the European market in 1978. chenodeoxycholic acid structure

역사

Chenodeoxycholic acid was isolated in 1924 from goose gall by Adolf Windaus and human gall by Heinrich Wieland.Its complete structural configuation was elucidated by Hans Lettre at the University of Gottingen. In 1968, William Admirand and Donald Small at Boston University Medical School established that in patients with gallstones their bile was saturated with cholesterol, sometimes even exhibiting microcrystals, whereas this was not the case in normal people.It was then found that biliary levels of cholic acid and chenodeoxycholic acid were lower in patients with cholesterol gallstones than in normal people. Leslie Thistle and John Schoenfield at the Mayo Clinic in Rochester, Minnesota, then administered individual bile salts by mouth for four months and found that chenodeoxycholic acid reduced the amount of cholesterol in the bile.This led to a national collaborative study in the United States, which confirmed the effectiveness of chenodeoxycholic acid in bringing about dissolution of gallstones in selected patients. However, recent developments such as laparoscopic cholecystectomy and endoscopic biliary techniques have curtailed the role of chenodeoxycholic acid and ursodeoxycholic acid in the treatment of cholelithiasis.

용도

A major bile acid in many vertebrates, occurring as the N-glycine and/or N-taurine conjugate. With other bile acids, forms mixed micelles with lecithin in bile which solubilize cholesterol and thus fa cilitates its excretion. Fcilitates fat absorption in the small intestine by micellar solubilization of fatty acids and monoglycerides. Anticholelithogenic. Epimeric with Ursodiol.

일반 설명

Chenodeoxycholic acid is a bile acid synthesized in the liver from cholesterol.