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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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 9 / 9
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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 TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Unknown
Diagnostic
Unknown
Primary
Tetracycline Presteron

PubMed

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.
Substance Class Chemical
Record UNII
87MLH50B7Q
Record Status Validated (UNII)
Record Version