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Details

Stereochemistry ABSOLUTE
Molecular Formula C23H32O4
Molecular Weight 372.4978
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HYDROXYPROGESTERONE ACETATE

SMILES

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

InChI

InChIKey=VTHUYJIXSMGYOQ-KOORYGTMSA-N
InChI=1S/C23H32O4/c1-14(24)23(27-15(2)25)12-9-20-18-6-5-16-13-17(26)7-10-21(16,3)19(18)8-11-22(20,23)4/h13,18-20H,5-12H2,1-4H3/t18-,19+,20+,21+,22+,23+/m1/s1

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/18060946

17α-Hydroxyprogesterone (17α-OHP), or hydroxyprogesterone (OHP), also known as 17α-hydroxypregn-4-ene-3, 20-dione is used under the brand name Gestageno, and has been marketed for clinical use in Argentina. It was indicated for female infertility, hypertrichosis, menstrual disorders, premature labour, threatened or recurrent miscarriage. It is used to properly regulate the menstrual cycle and treat unusual stopping of the menstrual periods (amenorrhea). To help a pregnancy occur during egg donor or infertility procedures in women who do not produce enough progesterone. To prevent estrogen from thickening the lining of the uterus (endometrial hyperplasia) in women around menopause who are being treated with estrogen for ovarian hormone therapy (OHT). To treat a condition called endometriosis, to help prevent endometrial hyperplasia, or to treat unusual and heavy bleeding of the uterus (dysfunctional uterine bleeding) by starting or stopping the menstrual cycle. 17α-OHP is an agonist of the progesterone receptor (PR) similarly to progesterone. In addition, it is an antagonist of the mineralocorticoid receptor (MR) as well as a partial agonist of the glucocorticoid receptor (GR), albeit with very low potency (EC50 >100-fold less relative to cortisol) at the latter site, also similarly to progesterone.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Gestageno

Approved Use

Unknown
Primary
Gestageno

Approved Use

Unknown
Preventing
Gestageno

Approved Use

Unknown
Preventing
Gestageno

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
5 ng/mL
250 mg 1 times / week multiple, intramuscular
dose: 250 mg
route of administration: Intramuscular
experiment type: MULTIPLE
co-administered:
HYDROXYPROGESTERONE CAPROATE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
12.5 ng/mL
250 mg 1 times / week steady-state, intramuscular
dose: 250 mg
route of administration: Intramuscular
experiment type: STEADY-STATE
co-administered:
HYDROXYPROGESTERONE CAPROATE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
571.4 ng × h/mL
250 mg 1 times / week multiple, intramuscular
dose: 250 mg
route of administration: Intramuscular
experiment type: MULTIPLE
co-administered:
HYDROXYPROGESTERONE CAPROATE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
1269.6 ng × h/mL
250 mg 1 times / week steady-state, intramuscular
dose: 250 mg
route of administration: Intramuscular
experiment type: STEADY-STATE
co-administered:
HYDROXYPROGESTERONE CAPROATE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
16.4 day
250 mg 1 times / week multiple, intramuscular
dose: 250 mg
route of administration: Intramuscular
experiment type: MULTIPLE
co-administered:
HYDROXYPROGESTERONE CAPROATE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
500 mg 1 times / week multiple, intramuscular
Higher than recommended
Dose: 500 mg, 1 times / week
Route: intramuscular
Route: multiple
Dose: 500 mg, 1 times / week
Sources:
healthy, 31.6
Health Status: healthy
Age Group: 31.6
Sex: F
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Diagnosis of adrenal cortical dysfunction by liquid chromatography-tandem mass spectrometry.
2001 Apr
Expression and localization of cytochrome P450 17 alpha-hydroxylase/c17,20-lyase in the avian brain.
2001 Apr 27
Ovarian steroidogenic response to human chorionic gonadotrophin in obese women with polycystic ovary syndrome: effect of metformin.
2001 Dec
Hyperadrenocorticism associated with excessive sex hormone production by an adrenocortical tumor in two dogs.
2001 Dec 15
Food-dependent androgen and cortisol secretion by a gastric inhibitory polypeptide-receptor expressive adrenocortical adenoma leading to hirsutism and subclinical Cushing's syndrome: in vivo and in vitro studies.
2001 Feb
Changes in steroid hormone profiles and ovarian histology during salmon pituitary-induced vitellogenesis and ovulation in female New Zealand longfinned eels, Anguilla dieffenbachii gray.
2001 Feb 1
The octadecaneuropeptide ODN stimulates neurosteroid biosynthesis through activation of central-type benzodiazepine receptors.
2001 Jan
Steroidogenic response of adrenal tissues after administration of ACTH to dogs with hypercortisolemia.
2001 Jan 15
Genomic organization of a human 5beta-reductase and its pseudogene and substrate selectivity of the expressed enzyme.
2001 Jan 26
Functional hyperandrogenism detected by corticotropin and GnRH-analogue stimulation tests in women affected by apparently idiopathic hirsutism.
2001 Jul-Aug
The involvement of sex steroid hormones in downstream and upstream migratory behavior of masu salmon.
2001 Jun
Specific factors predict the response to pulsatile gonadotropin-releasing hormone therapy in polycystic ovarian syndrome.
2001 Jun
Reconstitution of the enzymatic activities of cytochrome P450s using recombinant flavocytochromes containing rat cytochrome b(5) fused to NADPH--cytochrome P450 reductase with various membrane-binding segments.
2001 Jun 15
Sex hormone-binding globulin as a marker of the effect of hormonal treatment in Turner's syndrome.
2001 Mar
[Causes of ambiguous external genitalia in neonates].
2001 Mar-Apr
Mechanisms of hypothalamic-pituitary-gonadal disruption in polycystic ovarian syndrome.
2001 Nov-Dec
Failure of cortisone acetate therapy in 21-hydroxylase deficiency in early infancy.
2001 Oct
Clinical, endocrine and metabolic effects of acarbose, an alpha-glucosidase inhibitor, in PCOS patients with increased insulin response and normal glucose tolerance.
2001 Oct
Stability of salivary steroids: the influences of storage, food and dental care.
2001 Oct
The longitudinal study of adrenal maturation during gonadal suppression: evidence that adrenarche is a gradual process.
2001 Sep
Relationship between salivary progesterone, 17-hydroxyprogesterone, and cortisol levels throughout the normal menstrual cycle of healthy postmenarcheal girls.
2001 Sep
Metformin directly inhibits androgen production in human thecal cells.
2001 Sep
Antenatal corticosteroids and newborn screening for congenital adrenal hyperplasia.
2001 Sep
Ovarian hyperandrogenism in adult female rhesus monkeys exposed to prenatal androgen excess.
2002 Jan
Patents

Sample Use Guides

from 200 mg to 300 mg orally every 24 hours from the cycle day 15 to 28
Route of Administration: Other
Linear regression analysis showed statistically significant linear inhibition of transactivation of the human mineralocorticoid receptor (hMR) by 10(-10) M aldosterone in the presence of increasing 17-hydroxyprogesterone (17OHP) [F(1,5) = 11.34, p = 0.019] and progesterone [F(1,5) = 11.08, p = 0.021] concentrations.
Name Type Language
NSC-12191
Preferred Name English
HYDROXYPROGESTERONE ACETATE
WHO-DD   WHO-IP  
Common Name English
MEDROXYPROGESTERONE ACETATE IMPURITY H [EP IMPURITY]
Common Name English
17.ALPHA.-ACETOXYPROGESTERONE
Common Name English
U 5533
Code English
U5533
Code English
3,20-DIOXOPREGN-4-EN-17-YL ACETATE [WHO-IP]
Common Name English
U-5533
Code English
Hydroxyprogesterone acetate [WHO-DD]
Common Name English
MEDROXYPROGESTERONE ACETATE IMPURITY H [WHO-IP]
Common Name English
17.ALPHA.-HYDROXY-4-PREGNENE-3,20-DIONE ACETATE
Common Name English
HYDROXYPROGESTERONE ACETATE [WHO-IP]
Common Name English
MEGESTROL ACETATE IMPURITY K [EP IMPURITY]
Common Name English
Code System Code Type Description
CAS
302-23-8
Created by admin on Mon Mar 31 17:45:31 GMT 2025 , Edited by admin on Mon Mar 31 17:45:31 GMT 2025
PRIMARY
PUBCHEM
10156152
Created by admin on Mon Mar 31 17:45:31 GMT 2025 , Edited by admin on Mon Mar 31 17:45:31 GMT 2025
PRIMARY
WIKIPEDIA
Hydroxyprogesterone acetate
Created by admin on Mon Mar 31 17:45:31 GMT 2025 , Edited by admin on Mon Mar 31 17:45:31 GMT 2025
PRIMARY
SMS_ID
100000078583
Created by admin on Mon Mar 31 17:45:31 GMT 2025 , Edited by admin on Mon Mar 31 17:45:31 GMT 2025
PRIMARY
ECHA (EC/EINECS)
206-119-6
Created by admin on Mon Mar 31 17:45:31 GMT 2025 , Edited by admin on Mon Mar 31 17:45:31 GMT 2025
PRIMARY
NSC
12191
Created by admin on Mon Mar 31 17:45:31 GMT 2025 , Edited by admin on Mon Mar 31 17:45:31 GMT 2025
PRIMARY
RXCUI
1101886
Created by admin on Mon Mar 31 17:45:31 GMT 2025 , Edited by admin on Mon Mar 31 17:45:31 GMT 2025
PRIMARY RxNorm
FDA UNII
L124O66YSI
Created by admin on Mon Mar 31 17:45:31 GMT 2025 , Edited by admin on Mon Mar 31 17:45:31 GMT 2025
PRIMARY
EVMPD
SUB16436MIG
Created by admin on Mon Mar 31 17:45:31 GMT 2025 , Edited by admin on Mon Mar 31 17:45:31 GMT 2025
PRIMARY
EPA CompTox
DTXSID90894096
Created by admin on Mon Mar 31 17:45:31 GMT 2025 , Edited by admin on Mon Mar 31 17:45:31 GMT 2025
PRIMARY