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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 of EPIDIHYDROCHOLESTERIN

SMILES

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

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

Molecular Formula C27H48O
Molecular Weight 388.6694
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 9 / 9
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
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

Curator's Comment: The blood-brain barrier was intact to the passage of cholestanol.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
Primary
Tetracycline Presteron

Approved Use

Tetracycline Presteron is an antibiotic containing an anti-flammatory agent to help treat periodontitis.

Launch Date

1960
PubMed

PubMed

TitleDatePubMed
Effects of cholestanol feeding and cholestyramine treatment on the tissue sterols in the rabbit.
1986 Dec
High cholestanol and low campesterol-to-sitosterol ratio in serum of patients with primary biliary cirrhosis before liver transplantation.
1991 Apr
High serum cholestanol and low campesterol/sitosterol ratio indicate severe liver damage and liver transplantation in primary biliary cirrhosis.
1992 Feb
Cholestanol induces apoptosis of cerebellar neuronal cells.
1999 Mar 5
Cholestanol induces apoptosis of corneal endothelial and lens epithelial cells.
2000 Apr
Cholestanol metabolism, molecular pathology, and nutritional implications.
2003 Fall
Cholestanol: a serum marker to guide LDL cholesterol-lowering therapy.
2006 Feb
Cholestanol metabolism in patients with cerebrotendinous xanthomatosis: absorption, turnover, and tissue deposition.
2007 Jan
Determination of fecal sterols by gas chromatography-mass spectrometry with solid-phase extraction and injection-port derivatization.
2009 Feb 13
Patents

Patents

Sample Use Guides

1 g of ointment contains 20 mg of Presteron
Route of Administration: Dental
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:33:46 GMT 2023
Edited
by admin
on Fri Dec 15 16:33:46 GMT 2023
Record UNII
87MLH50B7Q
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
EPIDIHYDROCHOLESTERIN
JAN  
Common Name English
EPICHOLESTANOL
MI   WHO-DD  
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
Created by admin on Fri Dec 15 16:33:46 GMT 2023 , Edited by admin on Fri Dec 15 16:33:46 GMT 2023
PRIMARY
ECHA (EC/EINECS)
208-228-4
Created by admin on Fri Dec 15 16:33:46 GMT 2023 , Edited by admin on Fri Dec 15 16:33:46 GMT 2023
PRIMARY
CAS
516-95-0
Created by admin on Fri Dec 15 16:33:46 GMT 2023 , Edited by admin on Fri Dec 15 16:33:46 GMT 2023
PRIMARY
ChEMBL
CHEMBL2107718
Created by admin on Fri Dec 15 16:33:46 GMT 2023 , Edited by admin on Fri Dec 15 16:33:46 GMT 2023
PRIMARY
MERCK INDEX
m4937
Created by admin on Fri Dec 15 16:33:46 GMT 2023 , Edited by admin on Fri Dec 15 16:33:46 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID90883420
Created by admin on Fri Dec 15 16:33:46 GMT 2023 , Edited by admin on Fri Dec 15 16:33:46 GMT 2023
PRIMARY
PUBCHEM
66066
Created by admin on Fri Dec 15 16:33:46 GMT 2023 , Edited by admin on Fri Dec 15 16:33:46 GMT 2023
PRIMARY
CHEBI
31542
Created by admin on Fri Dec 15 16:33:46 GMT 2023 , Edited by admin on Fri Dec 15 16:33:46 GMT 2023
PRIMARY
FDA UNII
87MLH50B7Q
Created by admin on Fri Dec 15 16:33:46 GMT 2023 , Edited by admin on Fri Dec 15 16:33:46 GMT 2023
PRIMARY