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

Details

Stereochemistry ABSOLUTE
Molecular Formula C21H30O3
Molecular Weight 330.4619
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HYDROXYPROGESTERONE

SMILES

CC(=O)[C@]1(CC[C@@]2([H])[C@]3([H])CCC4=CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@@]21C)O

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

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
Target ID: P06401
Gene ID: 5241.0
Gene Symbol: PGR
Target Organism: Homo sapiens (Human)
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
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
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
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
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
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
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: Page: p.179
healthy, 31.6
n = 16
Health Status: healthy
Condition: Preterm birth
Age Group: 31.6
Sex: F
Population Size: 16
Sources: Page: p.179
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
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
Heterozygous mutation in the cholesterol side chain cleavage enzyme (p450scc) gene in a patient with 46,XY sex reversal and adrenal insufficiency.
2001 Aug
Disruption of the synchronous secretion of leptin, LH, and ovarian androgens in nonobese adolescents with the polycystic ovarian syndrome.
2001 Aug
TNF-alpha and hyperandrogenism: a clinical, biochemical, and molecular genetic study.
2001 Aug
Impaired glucocorticoid synthesis in premature infants developing chronic lung disease.
2001 Aug
The natural history of incidentally discovered adrenocortical adenomas: a retrospective evaluation.
2001 Dec
High prevalence of testicular adrenal rest tumors, impaired spermatogenesis, and Leydig cell failure in adolescent and adult males with congenital adrenal hyperplasia.
2001 Dec
Gender-related plasma levels of progesterone, interleukin-8 and interleukin-10 during and after cardiopulmonary bypass in infants and children.
2001 Dec
Follistatin and activin A serum concentrations in obese and non-obese patients with polycystic ovary syndrome.
2001 Dec
Ovarian steroidogenic response to human chorionic gonadotrophin in obese women with polycystic ovary syndrome: effect of metformin.
2001 Dec
Polycystic ovaries in Hirsute women with normal menses.
2001 Dec 1
Hyperadrenocorticism associated with excessive sex hormone production by an adrenocortical tumor in two dogs.
2001 Dec 15
Functional hyperandrogenism detected by corticotropin and GnRH-analogue stimulation tests in women affected by apparently idiopathic hirsutism.
2001 Jul-Aug
[Causes of ambiguous external genitalia in neonates].
2001 Mar-Apr
Hirsutism investigations-what is appropriate?
2001 May
Anatomical and biochemical evidence for the synthesis of unconjugated and sulfated neurosteroids in amphibians.
2001 Nov
[Effect of long-term treatment with metformin on steroid levels and parameters of insulin resistance in women with polycystic ovary syndrome].
2001 Nov 8
Salt wasting in simple virilizing congenital adrenal hyperplasia.
2001 Nov-Dec
Mechanisms of hypothalamic-pituitary-gonadal disruption in polycystic ovarian syndrome.
2001 Nov-Dec
Low basal androstenedione levels plus augmented 17alpha-hydroxyprogesterone and low dehydroepiandrosterone sulfate responses to adrenocorticotropic hormone stimulation in patients with adrenal incidentaloma.
2001 Nov-Dec
Failure of cortisone acetate therapy in 21-hydroxylase deficiency in early infancy.
2001 Oct
Hormonal regulation of male-specific 20beta-hydroxysteroid dehydrogenase with carbonyl reductase-like activity present in kidney microsomes of rats.
2001 Oct
Gonadal steroidogenesis in response to estradiol-17beta administration in the sea bream (Sparus aurata L.).
2001 Oct
CYP21 mutations in simple virilizing congenital adrenal hyperplasia.
2001 Oct
Increased urinary 6-sulfatoxymelatonin excretion in women with non-classical steroid 21-hydroxylase deficiency.
2001 Oct
Mutational spectrum of the steroid 21-hydroxylase gene in Austria: identification of a novel missense mutation.
2001 Oct
Serum cortisol and 17-hydroxyprogesterone interrelation in classic 21-hydroxylase deficiency: is current replacement therapy satisfactory?
2001 Oct
Repeated freezing and thawing does not generally alter assay results for several commonly studied reproductive hormones.
2001 Oct
Neonatal screening for congenital adrenal hyperplasia: 17-hydroxyprogesterone levels and CYP21 genotypes in preterm infants.
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
Increased adrenal steroid secretion in response to CRF in women with hypothalamic amenorrhea.
2001 Sep
17alpha-hydroxylase deficiency accompanied by adrenal myelolipoma.
2001 Sep
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 Sep
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
Stability of 17alpha-hydroxyprogesterone in dried blood spots after autoclaving and prolonged storage.
2002 Feb
Monitoring of congenital adrenal hyperplasia by microbore HPLC-electrospray ionization tandem mass spectrometry of dried blood spots.
2002 Feb
Rapid corticotropin versus corticotropin-releasing hormone test in girls with precocious pubarche.
2002 Jan
Ovarian hyperandrogenism in adult female rhesus monkeys exposed to prenatal androgen excess.
2002 Jan
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 Jan
Thiazolidinediones influence plasma steroids of male obese Zucker rats.
2002 Jan
Putative activation of the peroxisome proliferator-activated receptor gamma impairs androgen and enhances progesterone biosynthesis in primary cultures of porcine theca cells.
2002 Jan
Effects of some steroids and other compounds on ovarian growth of the red swamp crayfish, Procambarus clarkii, during early vitellogenesis.
2002 Jan 1
Bone mass, gonadal function and biochemical assessment in young men with trisomy 21.
2002 Jan 10
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
HYDROXYPROGESTERONE
HSDB   INN   VANDF   WHO-DD  
INN  
Official Name English
17.ALPHA.-HYDROXYPROGESTERONE
MI  
Common 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-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 Sat Jun 26 14:28:11 UTC 2021 , Edited by admin on Sat Jun 26 14:28:11 UTC 2021
LOINC 48616-7
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LOINC 1668-3
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LOINC 34220-4
Created by admin on Sat Jun 26 14:28:11 UTC 2021 , Edited by admin on Sat Jun 26 14:28:11 UTC 2021
DSLD 4212 (Number of products:1)
Created by admin on Sat Jun 26 14:28:11 UTC 2021 , Edited by admin on Sat Jun 26 14:28:11 UTC 2021
LIVERTOX 490
Created by admin on Sat Jun 26 14:28:11 UTC 2021 , Edited by admin on Sat Jun 26 14:28:11 UTC 2021
LOINC 92726-9
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LOINC 14569-8
Created by admin on Sat Jun 26 14:28:11 UTC 2021 , Edited by admin on Sat Jun 26 14:28:11 UTC 2021
LOINC 38473-5
Created by admin on Sat Jun 26 14:28:11 UTC 2021 , Edited by admin on Sat Jun 26 14:28:11 UTC 2021
LOINC 14571-4
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LOINC 53336-4
Created by admin on Sat Jun 26 14:28:11 UTC 2021 , Edited by admin on Sat Jun 26 14:28:11 UTC 2021
WHO-VATC QG03FA02
Created by admin on Sat Jun 26 14:28:11 UTC 2021 , Edited by admin on Sat Jun 26 14:28:11 UTC 2021
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
Created by admin on Sat Jun 26 14:28:11 UTC 2021 , Edited by admin on Sat Jun 26 14:28:11 UTC 2021
LOINC 34221-2
Created by admin on Sat Jun 26 14:28:11 UTC 2021 , Edited by admin on Sat Jun 26 14:28:11 UTC 2021
WHO-VATC QG03DA03
Created by admin on Sat Jun 26 14:28:11 UTC 2021 , Edited by admin on Sat Jun 26 14:28:11 UTC 2021
WHO-ATC G03DA03
Created by admin on Sat Jun 26 14:28:11 UTC 2021 , Edited by admin on Sat Jun 26 14:28:11 UTC 2021
CFR 21 CFR 862.1395
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LOINC 26908-4
Created by admin on Sat Jun 26 14:28:11 UTC 2021 , Edited by admin on Sat Jun 26 14:28:11 UTC 2021
NCI_THESAURUS C776
Created by admin on Sat Jun 26 14:28:11 UTC 2021 , Edited by admin on Sat Jun 26 14:28:11 UTC 2021
LOINC 14570-6
Created by admin on Sat Jun 26 14:28:11 UTC 2021 , Edited by admin on Sat Jun 26 14:28:11 UTC 2021
WHO-ATC G03FA02
Created by admin on Sat Jun 26 14:28:11 UTC 2021 , Edited by admin on Sat Jun 26 14:28:11 UTC 2021
LOINC 1669-1
Created by admin on Sat Jun 26 14:28:11 UTC 2021 , Edited by admin on Sat Jun 26 14:28:11 UTC 2021
LOINC 40754-4
Created by admin on Sat Jun 26 14:28:11 UTC 2021 , Edited by admin on Sat Jun 26 14:28:11 UTC 2021
LOINC 53340-6
Created by admin on Sat Jun 26 14:28:11 UTC 2021 , Edited by admin on Sat Jun 26 14:28:11 UTC 2021
LOINC 1670-9
Created by admin on Sat Jun 26 14:28:11 UTC 2021 , Edited by admin on Sat Jun 26 14:28:11 UTC 2021
LOINC 69796-1
Created by admin on Sat Jun 26 14:28:11 UTC 2021 , Edited by admin on Sat Jun 26 14:28:11 UTC 2021
Code System Code Type Description
CAS
68-96-2
Created by admin on Sat Jun 26 14:28:11 UTC 2021 , Edited by admin on Sat Jun 26 14:28:11 UTC 2021
PRIMARY
RXCUI
5542
Created by admin on Sat Jun 26 14:28:11 UTC 2021 , Edited by admin on Sat Jun 26 14:28:11 UTC 2021
PRIMARY
HSDB
3343
Created by admin on Sat Jun 26 14:28:11 UTC 2021 , Edited by admin on Sat Jun 26 14:28:11 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-699-4
Created by admin on Sat Jun 26 14:28:11 UTC 2021 , Edited by admin on Sat Jun 26 14:28:11 UTC 2021
PRIMARY
ChEMBL
CHEMBL1200848
Created by admin on Sat Jun 26 14:28:11 UTC 2021 , Edited by admin on Sat Jun 26 14:28:11 UTC 2021
PRIMARY
EPA CompTox
68-96-2
Created by admin on Sat Jun 26 14:28:11 UTC 2021 , Edited by admin on Sat Jun 26 14:28:11 UTC 2021
PRIMARY
DRUG BANK
DB14570
Created by admin on Sat Jun 26 14:28:11 UTC 2021 , Edited by admin on Sat Jun 26 14:28:11 UTC 2021
PRIMARY
INN
716
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PRIMARY
FDA UNII
21807M87J2
Created by admin on Sat Jun 26 14:28:11 UTC 2021 , Edited by admin on Sat Jun 26 14:28:11 UTC 2021
PRIMARY
MERCK INDEX
M6147
Created by admin on Sat Jun 26 14:28:11 UTC 2021 , Edited by admin on Sat Jun 26 14:28:11 UTC 2021
PRIMARY Merck Index
NCI_THESAURUS
C87242
Created by admin on Sat Jun 26 14:28:11 UTC 2021 , Edited by admin on Sat Jun 26 14:28:11 UTC 2021
PRIMARY
EVMPD
SUB08081MIG
Created by admin on Sat Jun 26 14:28:11 UTC 2021 , Edited by admin on Sat Jun 26 14:28:11 UTC 2021
PRIMARY
PUBCHEM
6238
Created by admin on Sat Jun 26 14:28:11 UTC 2021 , Edited by admin on Sat Jun 26 14:28:11 UTC 2021
PRIMARY