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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H30O3
Molecular Weight 306.4404
Optical Activity ( + )
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 7.BETA.-HYDROXY-EPI-ANDROSTERONE

SMILES

C[C@@]12CC[C@@]([H])(C[C@]2([H])C[C@@]([H])([C@@]3([H])[C@]4([H])CCC(=O)[C@@]4(C)CC[C@@]31[H])O)O

InChI

InChIKey=VFPMCLQMAUVEHD-UCPSWNCLSA-N
InChI=1S/C19H30O3/c1-18-7-5-12(20)9-11(18)10-15(21)17-13-3-4-16(22)19(13,2)8-6-14(17)18/h11-15,17,20-21H,3-10H2,1-2H3/t11-,12+,13+,14+,15+,17+,18+,19+/m1/s1

HIDE SMILES / InChI

Molecular Formula C19H30O3
Molecular Weight 306.4404
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

Substance Class Chemical
Created
by admin
on Sat Jun 26 01:45:47 UTC 2021
Edited
by admin
on Sat Jun 26 01:45:47 UTC 2021
Record UNII
OCP3E5KD08
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
7.BETA.-HYDROXY-EPI-ANDROSTERONE
Common Name English
(3S,5R,7S,8R,9S,10S,13S,14S)-3,7-DIHYDROXY-10,13-DIMETHYL-1,2,3,4,5,6,7,8,9,11,12,14,15,16-TETRADECAHYDROCYCLOPENTA(A)PHENANTHREN-17-ONE
Systematic Name English
7-BETA-HYDROXYEPIANDROSTERONE
Common Name English
7-.BETA.-HYDROXYEPIANDROSTERONE
Common Name English
ANDROSTAN-17-ONE, 3,7-DIHYDROXY-, (3.BETA.,5.ALPHA.,7.BETA.)-
Systematic Name English
(3.BETA.,5.ALPHA.,7.BETA.)-3,7-DIHYDROXYANDROSTAN-17-ONE
Systematic Name English
7BETA-OH-EPIA
Common Name English
HF-0220
Code English
Code System Code Type Description
PUBCHEM
9836181
Created by admin on Sat Jun 26 01:45:47 UTC 2021 , Edited by admin on Sat Jun 26 01:45:47 UTC 2021
PRIMARY
DRUG BANK
DB06622
Created by admin on Sat Jun 26 01:45:47 UTC 2021 , Edited by admin on Sat Jun 26 01:45:47 UTC 2021
PRIMARY
CAS
25848-69-5
Created by admin on Sat Jun 26 01:45:47 UTC 2021 , Edited by admin on Sat Jun 26 01:45:47 UTC 2021
PRIMARY
FDA UNII
OCP3E5KD08
Created by admin on Sat Jun 26 01:45:47 UTC 2021 , Edited by admin on Sat Jun 26 01:45:47 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> METABOLITE
IN VITRO
Related Record Type Details
ACTIVE MOIETY
Although all dose levels of 7beta-hydroxy-EpiA reduced PGE(2) production, only the lowest dose (0.01mg/kg) of the steroid completely prevented colitis damage and tissue inflammation. 7beta-Hydroxy-EpiA pre-treatment prevents the occurrence of DSS-induced colitis through a shift from PGE(2) to PGD(2) production, associated with an early but transient increase in COX-2 expression and a sustained increase in the production of the anti-inflammatory prostaglandin 15d-PGJ(2).
ACTIVE MOIETY
Class: 17 ketosteroid, Androstanol, Neuroprotectant, Testosterone congener; Mechanism of Action: Antioxidant and Glucocorticoid receptor antagonist; Highest Development Phase: Discontinued for Alzheimer's disease, Inflammatory bowel disease, Psoriasis and Rheumatoid arthriti; Most Recent Event: 14 Sep 2010 HF 0220 is available for licensing worldwide as of 10 Sep 2010. http:///www.newron.com
ACTIVE MOIETY
Intracerebroventricular administration of ethylcholine aziridinium (AF64A) caused cholinergic damage in the septum, and glial lesions in the lateral septal nucleus and in the lateral zones of the hippocampus. These effects were almost completely prevented when animals were treated subcutaneously (b.i.d.) for 10 days with 0.1 mg/kg 7beta-hydroxy epiandrosterone. These findings indicate that 7beta-hydroxy epiandrosterone has powerful cytoprotective effects suggesting that (a) this neurosteroid may have therapeutic potential in various neurodegenerative conditions such as Alzheimer's disease, and (b) 7beta-hydroxy steroids may constitute a novel class of endogenous neuroprotective agents.