U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

SMILES

[H][C@@]12C[C@@]3([H])[C@]4([H])CCC5=CC(=O)CC[C@]5(C)[C@@]4([H])CC[C@]3(C)[C@@]1(OC(C)(O2)C6=CC=CC=C6)C(C)=O

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
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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
TOPASEL

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
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 Jul
Efficacy, acceptability, and clinical effects of a low-dose injectable contraceptive combination of dihydroxyprogesterone acetophenide and estradiol enanthate.
2000 Apr
Comparison of two regimens of a monthly injectable contraceptive containing dihydroxyprogesterone acetophenide and estradiol enanthate.
2006 Mar
Patents

Patents

Sample Use Guides

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
Name Type Language
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-67831
Code English
NSC-68280
Code English
Code System Code Type Description
FDA UNII
T379IG5RV1
Created by admin on Sat Dec 16 08:49:29 GMT 2023 , Edited by admin on Sat Dec 16 08:49:29 GMT 2023
PRIMARY
NSC
68280
Created by admin on Sat Dec 16 08:49:29 GMT 2023 , Edited by admin on Sat Dec 16 08:49:29 GMT 2023
PRIMARY
ECHA (EC/EINECS)
214-649-4
Created by admin on Sat Dec 16 08:49:29 GMT 2023 , Edited by admin on Sat Dec 16 08:49:29 GMT 2023
PRIMARY
PUBCHEM
102011
Created by admin on Sat Dec 16 08:49:29 GMT 2023 , Edited by admin on Sat Dec 16 08:49:29 GMT 2023
PRIMARY
EPA CompTox
DTXSID40101706
Created by admin on Sat Dec 16 08:49:29 GMT 2023 , Edited by admin on Sat Dec 16 08:49:29 GMT 2023
PRIMARY
CAS
1179-87-9
Created by admin on Sat Dec 16 08:49:29 GMT 2023 , Edited by admin on Sat Dec 16 08:49:29 GMT 2023
PRIMARY
NSC
67831
Created by admin on Sat Dec 16 08:49:29 GMT 2023 , Edited by admin on Sat Dec 16 08:49:29 GMT 2023
PRIMARY