EPIDIHYDROCHOLESTERIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C27H48O
Molecular Weight	388.6694
Optical Activity	UNSPECIFIED
Defined Stereocenters	9 / 9
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C

InChI

InChIKey=QYIXCDOBOSTCEI-FBVYSKEZSA-N

InChI=1S/C27H48O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h18-25,28H,6-17H2,1-5H3/t19-,20+,21-,22+,23-,24+,25+,26+,27-/m1/s1

HIDE SMILES / InChI

Description
Sources: https://www.jstage.jst.go.jp/article/jsotp1982/25/2/25_2_39/_pdf
Curator's Comment: description was created based on several sources, including https://www.jstage.jst.go.jp/article/jsotp/31/1/31_1_13/_pdf http://www.nishika.co.jp/upfiles/2_pdf_2/TCPS-IF.pdf https://www.ncbi.nlm.nih.gov/pubmed/14585188

Epidihydrocholesterin (Cholestanol) is a sterol that differs from cholesterol by the absence of a double bond in the B ring and, in humans, is present in far lower concentrations than cholesterol. Epidihydrocholesterin is reported as an ingredient of Presteron. Presteron is an anti-inflammatory drug. It was reported that Presteron had no side effects like steroids on oral administration and intramuscular injection in human. Presteron partly inhibited ovine COX-1 by 10.4%, but it did not inhibit human recombinant COX-2 at all. Presteron inhibits the action of bradykinin, a potent inflammatory mediator, by suppressing Ca2+ dependent cellular PLA2 (cPLA2) and/or secretory PLA2 (sPLA2), and COX-1, resulting in alleviation of inflammation.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
arachidonic acid secretion 1 Target ID: GO:0050482 Sources: https://www.jstage.jst.go.jp/article/jsotp1982/25/2/25_2_39/_pdf	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Cerebrotendinous xanthomatosis 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17012751	Diagnostic	Phase II 1147	Unknown Approved Use Unknown
Primary biliary cirrhosis 4 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1539326	Diagnostic	Phase II 1147	Unknown Approved Use Unknown
Periodontitis 23 Sources: https://www.jstage.jst.go.jp/article/jsotp1982/25/2/25_2_39/_pdf	Primary	Approved 8583	Tetracycline Presteron Approved Use Tetracycline Presteron is an antibiotic containing an anti-flammatory agent to help treat periodontitis. Launch Date 1960

PubMed

Title	Date	PubMed
Determination of fecal sterols by gas chromatography-mass spectrometry with solid-phase extraction and injection-port derivatization.	2009-02-13	19147150
Cholestanol metabolism in patients with cerebrotendinous xanthomatosis: absorption, turnover, and tissue deposition.	2007-01	17012751
Cholestanol: a serum marker to guide LDL cholesterol-lowering therapy.	2006-02	16216250
Cholestanol metabolism, molecular pathology, and nutritional implications.	2003	14585188
Cholestanol induces apoptosis of corneal endothelial and lens epithelial cells.	2000-04	10752932
Cholestanol induces apoptosis of cerebellar neuronal cells.	1999-03-05	10066446
High serum cholestanol and low campesterol/sitosterol ratio indicate severe liver damage and liver transplantation in primary biliary cirrhosis.	1992-02	1539326
High cholestanol and low campesterol-to-sitosterol ratio in serum of patients with primary biliary cirrhosis before liver transplantation.	1991-04	2010161
Effects of cholestanol feeding and cholestyramine treatment on the tissue sterols in the rabbit.	1986-12	3821387

Patents

Sample Use Guides

In Vivo Use Guide

1 g of ointment contains 20 mg of Presteron

Route of Administration: Dental

In Vitro Use Guide

Clonal rat dental pulp cells RDP4-1 were labeled with [3H]-arachidonic acid for 24 h. The cells, pre-incubated with presteron (Epidihydrocholesterin) or a counterpart for three minutes, were stimulated with bradykinin or a calcium ionophore: A23187. A23187, as well as bradykinin, induced release of arachidonic acid and its metabolites not from subconfluent cells but only from confluent cells at concentrations around 0.5 uM. Presteron at 0.1-0.3 uM suppressed the releases in a dose-dependent manner without affecting cell viability, while indomethacin did not. In addition, 0.1 uM presteron partly inhibited ovine COX-1 by 10.4%, but it did not inhibit human recombinant COX-2 at all.

Name

Type

Language

EPICHOLESTANOL

Preferred Name

English

EPIDIHYDROCHOLESTERIN

Common Name

English

EPIDIHYDROCHOLESTERIN [JAN]

Common Name

English

(3.ALPHA.,5.ALPHA.)-CHOLESTAN-3-OL

Systematic Name

English

Epicholestanol [WHO-DD]

Common Name

English

EPICHOLESTANOL [MI]

Common Name

English

Code System Code Type Description

SMS_ID

300000038930