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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

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

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
Curator's Comment: Description was created based on several sources, including http://www.jbc.org/content/105/4/711.full.pdf | https://www.ncbi.nlm.nih.gov/pubmed/20526375 | https://www.ncbi.nlm.nih.gov/pubmed/24529992

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

CNS Non-penetrant
1014
Curator's Comment: After mice received Ergosterol-loaded poly(lactide-co-glycolide) nanoparticles (NPs/Erg), the ergosterol in NPs/Erg was rapidly distributed in stomach, kidneys, liver, brain, spleen, and virtually non-existent in heart and lungs. The presence of NPs/Erg in brain was particularly improved compared with the free ergosterol. No human data available.

Originator

Tanret, C.
6
Sources: Tanret C (1889) Sur un nouveau principle immediate de l'ergot deseigle ergosterine. C.R. Seances Acad Sci 108: 98–100.
Curator's Comment: 24R-methyl-cholesta-5,7,22(E)-trienol (ergosterol) was discovered over 100 years ago in the plant pathogenic ergot fungus Claviceps purpurea reference retrieved from https://www.ncbi.nlm.nih.gov/pubmed/20526375

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2678
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
Ergocalciferol

Approved Use

Ergocalciferol (activated ergosterol) is indicated for use in the treatment of hypoparathyroidism, refractory rickets, also known as vitamin D resistant rickets, and familial hypophosphatemia.

Launch Date

2009
Primary
Approved
8429
Ergocalciferol

Approved Use

Ergocalciferol (activated ergosterol) is indicated for use in the treatment of hypoparathyroidism, refractory rickets, also known as vitamin D resistant rickets, and familial hypophosphatemia.

Launch Date

2009
Primary
Approved
8429
Ergocalciferol

Approved Use

Ergocalciferol (activated ergosterol) is indicated for use in the treatment of hypoparathyroidism, refractory rickets, also known as vitamin D resistant rickets, and familial hypophosphatemia.

Launch Date

2009
PubMed

PubMed

TitleDatePubMed
Screening for new compounds with antiherpes activity.
1984 Oct
Antimycobacterial ergosterol-5,8-endoperoxide from Ajuga remota.
1999 Dec
Antimycobacterial plant terpenoids.
2001 Nov
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
6
JP2006022017A
1
JP2006230327A
1
JP2007070334A
2
JP2007076285A
1
JP2007523849A
4
JP2008063293A
1
JP2008297256A
1
JP2008510795A
76
JP2010195697A
1
JP2010504355A
1
JP2010509991A
41
JP2010540159A
31
JP2011236236A
1
JP2011509971A
151
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 IMPURITY]
Common Name English
(3.BETA.,22E)-ERGOSTA-5,7,22-TRIEN-3-OL
Systematic Name English
Classification Tree Code System Code
LOINC 15411-2
Created by admin on Fri Dec 15 15:21:19 GMT 2023 , Edited by admin on Fri Dec 15 15:21:19 GMT 2023
NCI_THESAURUS C843
Created by admin on Fri Dec 15 15:21:19 GMT 2023 , Edited by admin on Fri Dec 15 15:21:19 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C83810
Created by admin on Fri Dec 15 15:21:19 GMT 2023 , Edited by admin on Fri Dec 15 15:21:19 GMT 2023
PRIMARY
RS_ITEM_NUM
1241007
Created by admin on Fri Dec 15 15:21:19 GMT 2023 , Edited by admin on Fri Dec 15 15:21:19 GMT 2023
PRIMARY
CHEBI
16933
Created by admin on Fri Dec 15 15:21:19 GMT 2023 , Edited by admin on Fri Dec 15 15:21:19 GMT 2023
PRIMARY
HSDB
395
Created by admin on Fri Dec 15 15:21:19 GMT 2023 , Edited by admin on Fri Dec 15 15:21:19 GMT 2023
PRIMARY
WIKIPEDIA
ERGOSTEROL
Created by admin on Fri Dec 15 15:21:19 GMT 2023 , Edited by admin on Fri Dec 15 15:21:19 GMT 2023
PRIMARY
ECHA (EC/EINECS)
200-352-7
Created by admin on Fri Dec 15 15:21:19 GMT 2023 , Edited by admin on Fri Dec 15 15:21:19 GMT 2023
PRIMARY
FDA UNII
Z30RAY509F
Created by admin on Fri Dec 15 15:21:19 GMT 2023 , Edited by admin on Fri Dec 15 15:21:19 GMT 2023
PRIMARY
PUBCHEM
444679
Created by admin on Fri Dec 15 15:21:19 GMT 2023 , Edited by admin on Fri Dec 15 15:21:19 GMT 2023
PRIMARY
CAS
57-87-4
Created by admin on Fri Dec 15 15:21:19 GMT 2023 , Edited by admin on Fri Dec 15 15:21:19 GMT 2023
PRIMARY
DRUG BANK
DB04038
Created by admin on Fri Dec 15 15:21:19 GMT 2023 , Edited by admin on Fri Dec 15 15:21:19 GMT 2023
PRIMARY
MERCK INDEX
m4986
Created by admin on Fri Dec 15 15:21:19 GMT 2023 , Edited by admin on Fri Dec 15 15:21:19 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID90878679
Created by admin on Fri Dec 15 15:21:19 GMT 2023 , Edited by admin on Fri Dec 15 15:21:19 GMT 2023
PRIMARY
SUBSTANCE RECORD
Structure of ERGOSTEROL
NIH
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