HYDROXYPROGESTERONE ACETATE

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

Structure Search

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

Molecular Formula	C23H32O4
Molecular Weight	372.4978
Charge	0
Count

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

Description
Sources: http://www.ndrugs.com/?s=gestageno
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

Primary Target	Pharmacology	Condition	Potency
Progesterone receptor 61 Target ID: CHEMBL208 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18060946	Agonist 2752

Conditions

Condition	Modality	Highest Phase	Product
Female infertility 7 Sources: http://www.ndrugs.com/?s=gestageno	Primary	Approved 8583	Gestageno Approved Use Unknown
Hypertrichosis 2 Sources: http://www.ndrugs.com/?s=gestageno	Primary	Approved 8583	Gestageno Approved Use Unknown
Premature labour 10 Sources: http://www.ndrugs.com/?s=gestageno	Preventing	Approved 8583	Gestageno Approved Use Unknown
Recurrent miscarriage 2 Sources: http://www.ndrugs.com/?s=gestageno	Preventing	Approved 8583	Gestageno Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
5 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/021945s012lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/021945s012lbl.pdf	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

Value	Dose	Co-administered	Analyte	Population
571.4 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/021945s012lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/021945s012lbl.pdf	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
16.4 day DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/021945s012lbl.pdf	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

Dose	Population	Adverse 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: https://pubmed.ncbi.nlm.nih.gov/3140580	healthy, 31.6 Health Status: healthy Age Group: 31.6 Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/3140580	Sources: https://pubmed.ncbi.nlm.nih.gov/3140580

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B3-016212	http://www.3bsc.com/index/pro_info.php?id=38733
AA Blocks	AA005ZDQ	https://www.aablocks.com/goods/Goods/detail?id=AA005ZDQ
Aaron Chemicals	AR00605I	http://www.aaronchem.com/68-96-2
abcr GmbH	AB251432	http://www.abcr.com/shop/en/AB251432
AbMole Bioscience	M5357	http://www.abmole.com/products/17-hydroxyprogesterone.html
Acadechem	ACDS-064984	http://www.acadechemical.com/product/139683
Acadechem	ACDS-067407	http://www.acadechemical.com/product/142106
Achemtek	0104-013482	http://www.achemtek.com/68-96-2
Acorn PharmaTech	ACN-031972	http://www.acornpharmatech.com/
Active Biopharma	ABP000341	http://www.activebiopharma.com/68-96-2
AHH Chemical co.,ltd	MT-15520	http://www.ahhchemical.com/product/MT-15520.html
AK Scientific, Inc. (AKSCI)	H581	http://www.aksci.com/item_detail.php?cat=H581
AK Scientific, Inc. (AKSCI)	V1408	http://www.aksci.com/item_detail.php?cat=V1408
Alsachim	3706	http://www.alsachim.com/product-C4997-glo.bal-view.html
Aurora Fine Chemicals LLC	A13.109.440	http://online.aurorafinechemicals.com/info?ID=A13.109.440
BioCrick	BCC8996	http://www.biocrick.com/Hydroxyprogesterone-BCC8996.html
BioSynth	W-104646	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/W-104646.html
Chem Scene	CS-4354	http://www.chemscene.com/68-96-2.html
ChemMol	49425952	http://www.chemmol.com/chemmol/49425952.html
ChemMol	99130579	http://www.chemmol.com/chemmol/99130579.html
Chemspace	CSSB00000038568	https://chem-space.com/CSSB00000038568
Clearsynth	CS-O-10309	https://www.clearsynth.com/en/CSO10309.html
DC Chemicals	DC34168	http://www.dcchemicals.com//product_show-17A-Hydroxyprogesterone.html
eNovation Chemicals	D493125	https://www.enovationchem.com/ProductDetails.asp?ProductID=D493125
eNovation Chemicals	D655369	https://enovationchem.com/ProductDetails.asp?ProductID=D655369
eNovation Chemicals	D783062	https://www.enovationchem.com/ProductDetails.asp?ProductID=D783062
eNovation Chemicals	Y1046789	https://www.enovationchem.com/ProductDetails.asp?ProductID=Y1046789
Hairui	HR127789	http://www.hairuichem.com/en/product/68-96-2.html
Hairui	HR138043	http://www.hairuichem.com/en/product/604-09-1.html
iChemical	EBD34989	http://www.ichemical.com/products/68-96-2.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
Lab Network	LN00197016	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00197016
LGC Standards	DRE-C14241000	https://www.lgcstandards.com/US/en/p/DRE-C14241000
LGC Standards	MM0222.09-0025	https://www.lgcstandards.com/US/en/p/MM0222.09-0025
Matrix Scientific	96177	https://www.matrixscientific.com/096177.html
mcule	MCULE-1412596642	https://mcule.com/MCULE-1412596642/
MedChem Express	HY-B0891	https://www.medchemexpress.com/17-Hydroxyprogesterone.html
MuseChem	I004590	https://www.musechem.com/product/I004590.html
MuseChem	R034638	https://www.musechem.com/product/R034638.html
Oakwood	229937	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=110936&ExtHyperLink=1
Sigma-Aldrich	46337_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/46337?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	H-085_CERILLIAN	https://www.sigmaaldrich.com/catalog/product/cerillian/h085?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	H5752_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/h5752?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sinfoo Biotech	S049327	http://www.sinfoobiotech.com/product/1052725
Sinfoo Biotech	S051750	http://www.sinfoobiotech.com/product/1055148
Smolecule	S515733	http://www.smolecule.com/products/s515733
Smolecule	S748740	https://www.smolecule.com/products/s748740
TCI (Tokyo Chemical Industry)	H1250	http://www.tcichemicals.com/eshop/en/us/commodity/H1250/index.html
THE BioTek	bt-256584	https://www.thebiotek.com/product/inhibitors/bt-256584
TripleBond	CH0032	http://www.triplebond-canada.com/prod/1376/
VladaChem	VL267063-25G	https://www.vladachem.com/product.php?products=68-96-2

PubMed

Title	Date	PubMed
Anovulation after precocious pubarche: early markers and time course in adolescence.	1999 Aug	10443661
The presence of the 21-hydroxylase deficiency carrier status in hirsute women: phenotype-genotype correlations.	1999 Oct	10521100
The pregnane X receptor: a promiscuous xenobiotic receptor that has diverged during evolution.	2000 Jan	10628745
Extraovarian steroid cell tumor 'not otherwise specified' as a rare cause of virilization in twelve-year-old girl.	2001	11740149
Effect of low birth weight on adrenal steroids and carbohydrate metabolism in early adulthood.	2001	11598370
Endocrine and metabolic effects of insulin sensitizers in the treatment of patients with polycystic ovary syndrome and hyperinsulinaemia.	2001	11150875
Biochemical screening for subclinical cortisol-secreting adenomas amongst adrenal incidentalomas.	2001 Apr	11275951
The rate-determining step in P450 C21-catalyzing reactions in a membrane-reconstituted system.	2001 Apr 6	11154687
The natural history of incidentally discovered adrenocortical adenomas: a retrospective evaluation.	2001 Dec	11817708
High prevalence of testicular adrenal rest tumors, impaired spermatogenesis, and Leydig cell failure in adolescent and adult males with congenital adrenal hyperplasia.	2001 Dec	11739428
Gender-related plasma levels of progesterone, interleukin-8 and interleukin-10 during and after cardiopulmonary bypass in infants and children.	2001 Dec	11737923
Follistatin and activin A serum concentrations in obese and non-obese patients with polycystic ovary syndrome.	2001 Dec	11726573
Polycystic ovaries in Hirsute women with normal menses.	2001 Dec 1	11755502
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	11158012
Fertility and body composition after laparoscopic bilateral adrenalectomy in a 30-year-old female with congenital adrenal hyperplasia.	2001 Feb	11157995
Aldosterone synthase deficiency type I with no documented homozygous mutations in the CYP11B2 gene.	2001 Jan	11174838
The octadecaneuropeptide ODN stimulates neurosteroid biosynthesis through activation of central-type benzodiazepine receptors.	2001 Jan	11145985
Age, body mass index, race and other determinants of steroid hormone variability: the HERITAGE Family Study.	2001 Jul	11415846
[Smith-Lemli-Opitz syndrome].	2001 Jul	11412481
The involvement of sex steroid hormones in downstream and upstream migratory behavior of masu salmon.	2001 Jun	11399503
Specific factors predict the response to pulsatile gonadotropin-releasing hormone therapy in polycystic ovarian syndrome.	2001 Jun	11397835
The hormonal and radiological evaluation of adrenal glands, and the determination of the usefulness of low dose ACTH test in patients with renal amyloidosis.	2001 Mar	11417955
Newborn screening for congenital adrenal hyperplasia.	2001 Mar	11344933
[Effect of long-term treatment with metformin on steroid levels and parameters of insulin resistance in women with polycystic ovary syndrome].	2001 Nov 8	11789058
Salt wasting in simple virilizing congenital adrenal hyperplasia.	2001 Nov-Dec	11795656
Increased adrenal steroid secretion in response to CRF in women with hypothalamic amenorrhea.	2001 Sep	11595505
Rapid corticotropin versus corticotropin-releasing hormone test in girls with precocious pubarche.	2002 Jan	11822584
Putative activation of the peroxisome proliferator-activated receptor gamma impairs androgen and enhances progesterone biosynthesis in primary cultures of porcine theca cells.	2002 Jan	11751282

Patents

Sample Use Guides

In Vivo Use Guide

from 200 mg to 300 mg orally every 24 hours from the cycle day 15 to 28

Route of Administration: Other

In Vitro Use Guide

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:45:31 GMT 2025` Edited by `admin` on `Mon Mar 31 17:45:31 GMT 2025`
Record UNII	L124O66YSI
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-12191

Preferred Name

English

HYDROXYPROGESTERONE ACETATE

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