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

Details

Stereochemistry ABSOLUTE
Molecular Formula C21H30O3
Molecular Weight 330.4611
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HYDROXYPROGESTERONE

SMILES

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

InChI

InChIKey=DBPWSSGDRRHUNT-CEGNMAFCSA-N
InChI=1S/C21H30O3/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h12,16-18,24H,4-11H2,1-3H3/t16-,17+,18+,19+,20+,21+/m1/s1

HIDE SMILES / InChI

Molecular Formula C21H30O3
Molecular Weight 330.4611
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

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
Stability of 17alpha-hydroxyprogesterone in dried blood spots after autoclaving and prolonged storage.
2002-02
Monitoring of congenital adrenal hyperplasia by microbore HPLC-electrospray ionization tandem mass spectrometry of dried blood spots.
2002-02
Salt wasting in simple virilizing congenital adrenal hyperplasia.
2002-01-25
Bone mass, gonadal function and biochemical assessment in young men with trisomy 21.
2002-01-10
Effects of some steroids and other compounds on ovarian growth of the red swamp crayfish, Procambarus clarkii, during early vitellogenesis.
2002-01-01
Rapid corticotropin versus corticotropin-releasing hormone test in girls with precocious pubarche.
2002-01
Ovarian hyperandrogenism in adult female rhesus monkeys exposed to prenatal androgen excess.
2002-01
The role of LH and FSH in ovarian androgen secretion and ovarian follicular development: clinical studies in a patient with isolated FSH deficiency and multicystic ovaries.
2002-01
Thiazolidinediones influence plasma steroids of male obese Zucker rats.
2002-01
Putative activation of the peroxisome proliferator-activated receptor gamma impairs androgen and enhances progesterone biosynthesis in primary cultures of porcine theca cells.
2002-01
Mechanisms of hypothalamic-pituitary-gonadal disruption in polycystic ovarian syndrome.
2001-12-26
Low basal androstenedione levels plus augmented 17alpha-hydroxyprogesterone and low dehydroepiandrosterone sulfate responses to adrenocorticotropic hormone stimulation in patients with adrenal incidentaloma.
2001-12-19
Hyperadrenocorticism associated with excessive sex hormone production by an adrenocortical tumor in two dogs.
2001-12-15
Polycystic ovaries in Hirsute women with normal menses.
2001-12-01
The natural history of incidentally discovered adrenocortical adenomas: a retrospective evaluation.
2001-12
High prevalence of testicular adrenal rest tumors, impaired spermatogenesis, and Leydig cell failure in adolescent and adult males with congenital adrenal hyperplasia.
2001-12
Gender-related plasma levels of progesterone, interleukin-8 and interleukin-10 during and after cardiopulmonary bypass in infants and children.
2001-12
Follistatin and activin A serum concentrations in obese and non-obese patients with polycystic ovary syndrome.
2001-12
Ovarian steroidogenic response to human chorionic gonadotrophin in obese women with polycystic ovary syndrome: effect of metformin.
2001-12
[Effect of long-term treatment with metformin on steroid levels and parameters of insulin resistance in women with polycystic ovary syndrome].
2001-11-08
Anatomical and biochemical evidence for the synthesis of unconjugated and sulfated neurosteroids in amphibians.
2001-11
Failure of cortisone acetate therapy in 21-hydroxylase deficiency in early infancy.
2001-10
Hormonal regulation of male-specific 20beta-hydroxysteroid dehydrogenase with carbonyl reductase-like activity present in kidney microsomes of rats.
2001-10
Gonadal steroidogenesis in response to estradiol-17beta administration in the sea bream (Sparus aurata L.).
2001-10
CYP21 mutations in simple virilizing congenital adrenal hyperplasia.
2001-10
Increased urinary 6-sulfatoxymelatonin excretion in women with non-classical steroid 21-hydroxylase deficiency.
2001-10
Mutational spectrum of the steroid 21-hydroxylase gene in Austria: identification of a novel missense mutation.
2001-10
Serum cortisol and 17-hydroxyprogesterone interrelation in classic 21-hydroxylase deficiency: is current replacement therapy satisfactory?
2001-10
Repeated freezing and thawing does not generally alter assay results for several commonly studied reproductive hormones.
2001-10
Neonatal screening for congenital adrenal hyperplasia: 17-hydroxyprogesterone levels and CYP21 genotypes in preterm infants.
2001-10
Clinical, endocrine and metabolic effects of acarbose, an alpha-glucosidase inhibitor, in PCOS patients with increased insulin response and normal glucose tolerance.
2001-10
Stability of salivary steroids: the influences of storage, food and dental care.
2001-10
[Causes of ambiguous external genitalia in neonates].
2001-09-06
Increased adrenal steroid secretion in response to CRF in women with hypothalamic amenorrhea.
2001-09
17alpha-hydroxylase deficiency accompanied by adrenal myelolipoma.
2001-09
Reverse dot-blot hybridization as an improved tool for the molecular diagnosis of point mutations in congenital adrenal hyperplasia caused by 21-hydroxylase deficiency.
2001-09
The longitudinal study of adrenal maturation during gonadal suppression: evidence that adrenarche is a gradual process.
2001-09
Relationship between salivary progesterone, 17-hydroxyprogesterone, and cortisol levels throughout the normal menstrual cycle of healthy postmenarcheal girls.
2001-09
Metformin directly inhibits androgen production in human thecal cells.
2001-09
Antenatal corticosteroids and newborn screening for congenital adrenal hyperplasia.
2001-09
Functional hyperandrogenism detected by corticotropin and GnRH-analogue stimulation tests in women affected by apparently idiopathic hirsutism.
2001-08-18
Heterozygous mutation in the cholesterol side chain cleavage enzyme (p450scc) gene in a patient with 46,XY sex reversal and adrenal insufficiency.
2001-08
Disruption of the synchronous secretion of leptin, LH, and ovarian androgens in nonobese adolescents with the polycystic ovarian syndrome.
2001-08
TNF-alpha and hyperandrogenism: a clinical, biochemical, and molecular genetic study.
2001-08
Impaired glucocorticoid synthesis in premature infants developing chronic lung disease.
2001-08
Hirsutism investigations-what is appropriate?
2001-05
Neonatal screening program for congenital adrenal hyperplasia: adjustments to the recall protocol.
2001
Rapid monitoring assay of congenital adrenal hyperplasia with microbore high-performance liquid chromatography/electrospray ionization tandem mass spectrometry from dried blood spots.
2001
Extraovarian steroid cell tumor 'not otherwise specified' as a rare cause of virilization in twelve-year-old girl.
2001
Effect of low birth weight on adrenal steroids and carbohydrate metabolism in early adulthood.
2001
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.
Substance Class Chemical
Created
by admin
on Wed Apr 02 08:42:37 GMT 2025
Edited
by admin
on Wed Apr 02 08:42:37 GMT 2025
Record UNII
21807M87J2
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
17.ALPHA.-HYDROXYPROGESTERONE
MI  
Preferred Name English
HYDROXYPROGESTERONE
HSDB   INN   VANDF   WHO-DD  
INN  
Official Name English
U-3096
Code English
17.ALPHA.-HYDROXYPROGESTERONE [MI]
Common Name English
17.ALPHA.-HYDROXYPREGN-4-ENE-3,20-DIONE
Systematic Name English
HYDROXYPROGESTERONE [VANDF]
Common Name English
17-ALPHA-HYDROXYPROGESTERONE
Common Name English
17-HYDROXYPROGESTERONE
Common Name English
HYDROXYPROGESTERONE [HSDB]
Common Name English
NSC-15468
Code English
PREGN-4-ENE-3,20-DIONE, 17-HYDROXY-
Systematic Name English
Hydroxyprogesterone [WHO-DD]
Common Name English
hydroxyprogesterone [INN]
Common Name English
17ALPHA-HYDROXYPROGESTERONE
Common Name English
Classification Tree Code System Code
LOINC 53337-2
Created by admin on Wed Apr 02 08:42:37 GMT 2025 , Edited by admin on Wed Apr 02 08:42:37 GMT 2025
LOINC 48616-7
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LOINC 1668-3
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LOINC 34220-4
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DSLD 4212 (Number of products:1)
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LIVERTOX 490
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LOINC 92726-9
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LOINC 14569-8
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LOINC 38473-5
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LOINC 14571-4
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LOINC 53336-4
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WHO-VATC QG03FA02
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LOINC 72490-6
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LOINC 9616-4
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LOINC 63042-6
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LOINC 32854-2
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NDF-RT N0000175602
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LOINC 34221-2
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WHO-VATC QG03DA03
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WHO-ATC G03DA03
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CFR 21 CFR 862.1395
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LOINC 26908-4
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NCI_THESAURUS C776
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LOINC 14570-6
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WHO-ATC G03FA02
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LOINC 1669-1
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LOINC 40754-4
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LOINC 53340-6
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LOINC 1670-9
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LOINC 69796-1
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Code System Code Type Description
CAS
68-96-2
Created by admin on Wed Apr 02 08:42:37 GMT 2025 , Edited by admin on Wed Apr 02 08:42:37 GMT 2025
PRIMARY
RXCUI
5542
Created by admin on Wed Apr 02 08:42:37 GMT 2025 , Edited by admin on Wed Apr 02 08:42:37 GMT 2025
PRIMARY
HSDB
3343
Created by admin on Wed Apr 02 08:42:37 GMT 2025 , Edited by admin on Wed Apr 02 08:42:37 GMT 2025
PRIMARY
ECHA (EC/EINECS)
200-699-4
Created by admin on Wed Apr 02 08:42:37 GMT 2025 , Edited by admin on Wed Apr 02 08:42:37 GMT 2025
PRIMARY
ChEMBL
CHEMBL1200848
Created by admin on Wed Apr 02 08:42:37 GMT 2025 , Edited by admin on Wed Apr 02 08:42:37 GMT 2025
PRIMARY
EPA CompTox
DTXSID6040747
Created by admin on Wed Apr 02 08:42:37 GMT 2025 , Edited by admin on Wed Apr 02 08:42:37 GMT 2025
PRIMARY
CHEBI
17252
Created by admin on Wed Apr 02 08:42:37 GMT 2025 , Edited by admin on Wed Apr 02 08:42:37 GMT 2025
PRIMARY
DRUG BANK
DB14570
Created by admin on Wed Apr 02 08:42:37 GMT 2025 , Edited by admin on Wed Apr 02 08:42:37 GMT 2025
PRIMARY
DAILYMED
21807M87J2
Created by admin on Wed Apr 02 08:42:37 GMT 2025 , Edited by admin on Wed Apr 02 08:42:37 GMT 2025
PRIMARY
WIKIPEDIA
17?-Hydroxyprogesterone
Created by admin on Wed Apr 02 08:42:37 GMT 2025 , Edited by admin on Wed Apr 02 08:42:37 GMT 2025
PRIMARY
INN
716
Created by admin on Wed Apr 02 08:42:37 GMT 2025 , Edited by admin on Wed Apr 02 08:42:37 GMT 2025
PRIMARY
FDA UNII
21807M87J2
Created by admin on Wed Apr 02 08:42:37 GMT 2025 , Edited by admin on Wed Apr 02 08:42:37 GMT 2025
PRIMARY
NSC
15468
Created by admin on Wed Apr 02 08:42:37 GMT 2025 , Edited by admin on Wed Apr 02 08:42:37 GMT 2025
PRIMARY
SMS_ID
100000083661
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PRIMARY
MERCK INDEX
m6147
Created by admin on Wed Apr 02 08:42:37 GMT 2025 , Edited by admin on Wed Apr 02 08:42:37 GMT 2025
PRIMARY Merck Index
NCI_THESAURUS
C87242
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PRIMARY
EVMPD
SUB08081MIG
Created by admin on Wed Apr 02 08:42:37 GMT 2025 , Edited by admin on Wed Apr 02 08:42:37 GMT 2025
PRIMARY
PUBCHEM
6238
Created by admin on Wed Apr 02 08:42:37 GMT 2025 , Edited by admin on Wed Apr 02 08:42:37 GMT 2025
PRIMARY
Related Record Type Details
ACTIVE MOIETY