GESTONORONE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H28O3
Molecular Weight	316.4345
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(=O)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@]12C

InChI

InChIKey=GTFUITFQDGVJSK-XGXHKTLJSA-N

InChI=1S/C20H28O3/c1-12(21)20(23)10-8-18-17-5-3-13-11-14(22)4-6-15(13)16(17)7-9-19(18,20)2/h11,15-18,23H,3-10H2,1-2H3/t15-,16+,17+,18-,19-,20-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C20H28O3
Molecular Weight	316.4345
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/4117437
Curator's Comment: description was created based on several sources, including, http://www.medicamentos.com.mx/DocHTM/22255.htm

Gestonorone is a progesterone analogue indicated for the treatment of benign prostatic hyperplasia and endometrial cancer. The drug is approved in many countries and used under the names Primostat and Depostat.

Originator

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Benign prostatic hyperplasia 28 Sources: http://www.medicamentos.com.mx/dochtm/18423.htm	Primary		Approved 8583	PRIMOSTAT Approved Use Conservative treatment of benign prostatic hyperplasia and palliative treatment of severe endometrial cancer.
Endometrial cancer 44 Sources: http://www.medicamentos.com.mx/dochtm/18423.htm	Palliative		Approved 8583	PRIMOSTAT Approved Use Conservative treatment of benign prostatic hyperplasia and palliative treatment of severe endometrial cancer.

F_unbound

Value	Dose	Co-administered	Analyte	Population
4.7% OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/670109_2479401A1035_1_001_1F.pdf#page=10			GESTONORONE CAPROATE plasma	Homo sapiens

Doses

Dose	Population	Adverse events
900 mg 3 times / week multiple, intramuscular Highest studied dose Dose: 900 mg, 3 times / week Route: intramuscular Route: multiple Dose: 900 mg, 3 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/4097364/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/4097364/	Other AEs: oronary insufficiency, General malaise... Other AEs: oronary insufficiency (4%) General malaise Chest tightness Sources: https://pubmed.ncbi.nlm.nih.gov/4097364/
300 mg 1 times / week multiple, intramuscular Studied dose Dose: 300 mg, 1 times / week Route: intramuscular Route: multiple Dose: 300 mg, 1 times / week Sources: https://repository.kulib.kyoto-u.ac.jp/dspace/handle/2433/121731	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://repository.kulib.kyoto-u.ac.jp/dspace/handle/2433/121731	Disc. AE: Pain, Rash... AEs leading to discontinuation/dose reduction: Pain (8%) Rash (4%) Impotence (4%) Sources: https://repository.kulib.kyoto-u.ac.jp/dspace/handle/2433/121731

AEs

AE	Significance	Dose	Population
Chest tightness		900 mg 3 times / week multiple, intramuscular Highest studied dose Dose: 900 mg, 3 times / week Route: intramuscular Route: multiple Dose: 900 mg, 3 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/4097364/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/4097364/
General malaise		900 mg 3 times / week multiple, intramuscular Highest studied dose Dose: 900 mg, 3 times / week Route: intramuscular Route: multiple Dose: 900 mg, 3 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/4097364/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/4097364/
oronary insufficiency	4%	900 mg 3 times / week multiple, intramuscular Highest studied dose Dose: 900 mg, 3 times / week Route: intramuscular Route: multiple Dose: 900 mg, 3 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/4097364/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/4097364/
Impotence	4% Disc. AE	300 mg 1 times / week multiple, intramuscular Studied dose Dose: 300 mg, 1 times / week Route: intramuscular Route: multiple Dose: 300 mg, 1 times / week Sources: https://repository.kulib.kyoto-u.ac.jp/dspace/handle/2433/121731	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://repository.kulib.kyoto-u.ac.jp/dspace/handle/2433/121731
Rash	4% Disc. AE	300 mg 1 times / week multiple, intramuscular Studied dose Dose: 300 mg, 1 times / week Route: intramuscular Route: multiple Dose: 300 mg, 1 times / week Sources: https://repository.kulib.kyoto-u.ac.jp/dspace/handle/2433/121731	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://repository.kulib.kyoto-u.ac.jp/dspace/handle/2433/121731
Pain	8% Disc. AE	300 mg 1 times / week multiple, intramuscular Studied dose Dose: 300 mg, 1 times / week Route: intramuscular Route: multiple Dose: 300 mg, 1 times / week Sources: https://repository.kulib.kyoto-u.ac.jp/dspace/handle/2433/121731	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://repository.kulib.kyoto-u.ac.jp/dspace/handle/2433/121731

PubMed

Title	Date	PubMed
Adjuvant hormonal therapy for stage I endometrial cancer.	2008-06	18596890
Gestronol hexanoate (SH582) and benign prostatic hypertrophy.	1972-02	4117436
Clinical trial of gestronol hexanoate (SH582) in benign prostatic hypertrophy.	1972-02	4117437

Patents

Sample Use Guides

In Vivo Use Guide

Slow intramuscular injection of 200 mg every week for 2 to 3 months.

Route of Administration: Intramuscular

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:57:39 GMT 2025` Edited by `admin` on `Mon Mar 31 18:57:39 GMT 2025`
Record UNII	H4G605B7VP
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

GESTONORONE

Common Name

English

19-NORPREGN-4-ENE-3,20-DIONE, 17-HYDROXY-

Preferred Name

English

Gestonorone [WHO-DD]

Common Name

English

GESTRONOL

Common Name

English

Classification Tree Code System Code

WHO-ATC

L02AB03