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Details

Stereochemistry ABSOLUTE
Molecular Formula C28H44O
Molecular Weight 396.6484
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of ERGOSTEROL

SMILES

CC(C)[C@@H](C)\C=C\[C@@H](C)[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C

InChI

InChIKey=DNVPQKQSNYMLRS-APGDWVJJSA-N
InChI=1S/C28H44O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-10,18-20,22,24-26,29H,11-17H2,1-6H3/b8-7+/t19-,20+,22-,24+,25-,26-,27-,28+/m0/s1

HIDE SMILES / InChI

Description

Ergosterol was discovered over 100 years ago in the plant pathogenic ergot fungus Claviceps purpurea. Ergosterol is the major fungal membrane sterol that regulates membrane fluidity, plasma membrane biogenesis and function. Antifungal drugs such as Amphotericin B exerts its action by simply binding ergosterol. Vitamin D2 (ergocalciferol) is derived from ergosterol by UVB irradiation. Ergocalciferol is used for treating low parathyroid hormone levels, rickets (a vitamin D deficiency condition), and low phosphate levels in the body.

CNS Activity

Originator

Approval Year

Unknown
99264
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2361
Hypoparathyroidism
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Vitamin D receptor
Approved
7883
Ergocalciferol
Primary
Vitamin D receptor
Approved
7883
Ergocalciferol
Primary
Vitamin D receptor
Approved
7883
Ergocalciferol
Approved (off-label)
8
PubMed

PubMed

TitleDatePubMed
Anti-HIV-1 and anti-HIV-1-protease substances from Ganoderma lucidum.
1998 Nov
Antimycobacterial ergosterol-5,8-endoperoxide from Ajuga remota.
1999 Dec
Purification, characterization and inhibition of sterol C24-methyltransferase from Candida albicans.
2011 Jan 15
Patents

Patents

JP1022924A
1
JP2000119696A
2
JP2000157045A
2
JP2000175643A
2
JP2000239138A
1
JP2000327510A
1
JP2002080492A
1
JP2002114685A
1
JP2002308777A
1
JP2002511415A
7
JP2003267873A
1
JP2003510132A
2
JP2004300438A
1
JP2005220043A
1
JP2005532837A
5
JP2006022017A
1
JP2006230327A
1
JP2007070334A
2
JP2007076285A
1
JP2007523849A
4
JP2008063293A
1
JP2008297256A
1
JP2008510795A
64
JP2010195697A
1
JP2010504355A
1
JP2010509991A
40
JP2010540159A
31
JP2011236236A
1
JP2011509971A
149
JP2968588B2
2
JP4579415B2
2
JP4685035B2
15
JP4731319B2
4
JPH00436186A
1
JPH00624914A
1
JPH01143802A
2
JPH01246299A
1
JPH02131407A
2
JPH02178349A
1
JPH022395A
1
JPH02300131A
1
JPH03178903A
1
JPH03192141A
1
JPH03220105A
1
JPH04287661A
1
JPH04311393A
1
JPH0436186A
1
JPH04368304A
3
JPH0517311A
1
JPH05271012A
3
JPH05320005A
1

Sample Use Guides

In Vivo Use Guide
Ergoalcifediol (activated ergosterol) Usual Adult Dose for Hypoparathyroidism 50,000 to 200,000 international units orally daily, concomitantly with calcium lactate 4 g, six times per day Usual Adult Dose for Rickets 12,000 to 500,000 international units orally daily Usual Adult Dose for Familial Hypophosphatemia 12,000 to 500,000 international units orally daily
Route of Administration: Oral
In Vitro Use Guide
Ergosterol-loaded poly(lactide-co-glycolide) nanoparticles exerted much stronger cytotoxicity against human cancer cells than the free ergosterol, and showed significantly reduced IC50 values (14.69±0.48 μg/mL in glioma U251 cells; 9.43±0.52 μg/mL in breast cancer MCF-7 cells; 4.70±0.41 μg/mL in hepatoma HepG2 cells).
Name Type Language
ERGOSTEROL
HSDB   INCI   MI   USP-RS  
INCI  
Official Name English
ERGOSTEROL (CONSTITUENT OF GANODERMA LUCIDUM FRUITING BODY) [DSC]
Common Name English
ERGOSTERIN
Common Name English
ERGOSTEROL [INCI]
Common Name English
ERGOSTEROL [MI]
Common Name English
ERGOSTEROL [HSDB]
Common Name English
PROVITAMIN D2
Common Name English
(22E)-ERGOSTA-5,7,22-TRIEN-3.BETA.-OL
Systematic Name English
ERGOSTEROL [USP-RS]
Common Name English
ERGOCALCIFEROL IMPURITY B [EP]
Common Name English
(3.BETA.,22E)-ERGOSTA-5,7,22-TRIEN-3-OL
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C843
Created by admin on Tue Oct 22 05:24:28 UTC 2019 , Edited by admin on Tue Oct 22 05:24:28 UTC 2019
Code System Code Type Description
NCI_THESAURUS
C83810
Created by admin on Tue Oct 22 05:24:28 UTC 2019 , Edited by admin on Tue Oct 22 05:24:28 UTC 2019
PRIMARY
HSDB
57-87-4
Created by admin on Tue Oct 22 05:24:28 UTC 2019 , Edited by admin on Tue Oct 22 05:24:28 UTC 2019
PRIMARY
WIKIPEDIA
ERGOSTEROL
Created by admin on Tue Oct 22 05:24:28 UTC 2019 , Edited by admin on Tue Oct 22 05:24:28 UTC 2019
PRIMARY
ECHA (EC/EINECS)
200-352-7
Created by admin on Tue Oct 22 05:24:28 UTC 2019 , Edited by admin on Tue Oct 22 05:24:28 UTC 2019
PRIMARY
PUBCHEM
444679
Created by admin on Tue Oct 22 05:24:28 UTC 2019 , Edited by admin on Tue Oct 22 05:24:28 UTC 2019
PRIMARY
CAS
57-87-4
Created by admin on Tue Oct 22 05:24:28 UTC 2019 , Edited by admin on Tue Oct 22 05:24:28 UTC 2019
PRIMARY
MERCK INDEX
M4986
Created by admin on Tue Oct 22 05:24:28 UTC 2019 , Edited by admin on Tue Oct 22 05:24:28 UTC 2019
PRIMARY Merck Index
SUBSTANCE RECORD
Structure of ERGOSTEROL
NIH
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