16.ALPHA.,17.ALPHA.-DIHYDROXYPROGESTERONEACETOPHENIDE

Details

Stereochemistry	EPIMERIC
Molecular Formula	C29H36O4
Molecular Weight	448.5937
Optical Activity	UNSPECIFIED
Defined Stereocenters	7 / 8
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of 16.ALPHA.,17.ALPHA.-DIHYDROXYPROGESTERONEACETOPHENIDE

Structure Search

SMILES

CC(=O)[C@@]12OC(C)(O[C@@H]1C[C@H]3[C@@H]4CCC5=CC(=O)CC[C@]5(C)[C@H]4CC[C@]23C)C6=CC=CC=C6

InChI

InChIKey=AHBKIEXBQNRDNL-BXXPAUNWSA-N

InChI=1S/C29H36O4/c1-18(30)29-25(32-28(4,33-29)19-8-6-5-7-9-19)17-24-22-11-10-20-16-21(31)12-14-26(20,2)23(22)13-15-27(24,29)3/h5-9,16,22-25H,10-15,17H2,1-4H3/t22-,23+,24+,25-,26+,27+,28?,29-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C29H36O4
Molecular Weight	448.5937
Charge	0
Count

Stereochemistry	EPIMERIC
Additional Stereochemistry	No
Defined Stereocenters	7 / 8
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9743892 | https://www.ncbi.nlm.nih.gov/pubmed/4537624

Dihydroxyprogesterone acetophenide (DHPA; brand name Topasel), also known as algestone acetophenide, is a steroidal progestin that is used as a contraceptive in combination with estradiol enanthate. Unlike many other 17α-hydroxyprogesterone derivatives, dihydroxyprogesterone acetophenide was reported to possess no glucocorticoid activity.

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pregnancy 65 Sources: http://www.medicamentos.com.mx/dochtm/27615.htm	Preventing		Not Provided 511	TOPASEL Approved Use Unknown

PubMed

Title	Date	PubMed
Comparison of two regimens of a monthly injectable contraceptive containing dihydroxyprogesterone acetophenide and estradiol enanthate.	2006-03	16472564
Efficacy, acceptability, and clinical effects of a low-dose injectable contraceptive combination of dihydroxyprogesterone acetophenide and estradiol enanthate.	2000-04	10899484
Vaginal bleeding patterns in users of Perlutal, a once-a-month injectable contraceptive consisting of 10 mg estradiol enanthate combined with 150 mg dihydroxyprogesterone acetophenide. A trial of 5462 woman-months.	1998-07	9743892
Studies on hormonal actions of dihydroxyprogesterone acetophenide, estradiol enanthate and their mixtures.	1972-02	4537624

Patents

Sample Use Guides

In Vivo Use Guide

Intramuscular ampule, preferably in the gluteal region, eight days after the onset of menstruation. If it is impossible to apply the medication in the 8th. day of the cycle, the same results are obtained administering it between the 7th. and 10th. days. In the following cycles a light bulb will be applied eight days after the start of menstruation.

Route of Administration: Intramuscular

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 22:19:39 GMT 2025` Edited by `admin` on `Mon Mar 31 22:19:39 GMT 2025`
Record UNII	T379IG5RV1
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-67831

Preferred Name

English

16.ALPHA.,17.ALPHA.-DIHYDROXYPROGESTERONEACETOPHENIDE

Common Name

English

16.ALPHA.,17-DIHYDROXYPROGESTERONE ACETOPHENIDE

Common Name

English

PREGN-4-ENE-3,20-DIONE, 16,17-((1-PHENYLETHYLIDENE)BIS(OXY))-, (16.ALPHA.)-

Systematic Name

English

NSC-68280

Code

English

Code System Code Type Description

FDA UNII

T379IG5RV1