EPIESTRIOL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H24O3
Molecular Weight	288.3814
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12C[C@H](O)[C@H](O)[C@@]1(C)CC[C@]3([H])C4=C(CC[C@@]23[H])C=C(O)C=C4

InChI

InChIKey=PROQIPRRNZUXQM-ZMSHIADSSA-N

InChI=1S/C18H24O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-17,19-21H,2,4,6-7,9H2,1H3/t13-,14-,15+,16+,17+,18+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C18H24O3
Molecular Weight	288.3814
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	6 / 6
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.ncbi.nlm.nih.gov/pubmed/9120824
Curator's Comment: description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/?term=9858313

Epiestriol (INN) (brand names Actriol, Arcagynil, Klimadoral), or epioestriol (BAN), also known as 16β-epiestriol or simply 16-epiestriol as well as 16β-hydroxy-17β-estradiol, is an endogenous, steroidal, weak estrogen, and the 16-epimer of estriol (which is 16α-hydroxy-17β-estradiol). Epiestriol is (or has previously been) used clinically in the treatment of acne. In addition to its estrogenic actions, epiestriol has been found to possess significant anti-inflammatory properties without glycogenic activity or immunosuppressive effects, an interesting finding that is in contrast to conventional anti-inflammatory steroids like hydrocortisone (aglucocorticoid).

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Acne vulgaris 34 Sources: http://www.ncbi.nlm.nih.gov/pubmed/14495355	Curative		Preclinical	Actriol Approved Use Unknown Launch Date 1961

PubMed

Title	Date	PubMed
Studies on steroid conjugates. XII. Occurrence of 16-epiestriol 16-glucuronide in human pregnancy urine.	1974 Oct	4377544
Intestinal metabolism of estrogens.	1976 Sep	956337
Differentiation of stereoisomeric steroids by reactions with phosphenium ions.	2002 Apr	11951974
Measuring fifteen endogenous estrogens simultaneously in human urine by high-performance liquid chromatography-mass spectrometry.	2005 Oct 15	16223252
Microbial structure of nitrifying granules and their estrogens degradation properties.	2009	19448323

Patents

Sample Use Guides

In Vivo Use Guide

2.5 mg per gram in a cream base for a 3 months

Route of Administration: Topical

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:12:31 GMT 2023` Edited by `admin` on `Fri Dec 15 16:12:31 GMT 2023`
Record UNII	8XZ32LI44K
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

EPIESTRIOL

Official Name

English

ESTRA-1,3,5(10)-TRIENE-3,16.BETA.,17.BETA.-TRIOL

Systematic Name

English

NSC-26646

Code

English

epiestriol [INN]

Common Name

English

NSC-758892

Code

English

16-EPIESTRIOL [MI]

Common Name

English

EPIOESTRIOL

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C2181