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
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
DescriptionSources: http://www.ndrugs.com/?s=gestagenoCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/18060946
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 |
---|---|---|---|
Target ID: CHEMBL208 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18060946 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Gestageno Approved UseUnknown |
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Sources: http://www.ndrugs.com/?s=gestageno |
Primary | Gestageno Approved UseUnknown |
||
Sources: http://www.ndrugs.com/?s=gestageno |
Preventing | Gestageno Approved UseUnknown |
||
Preventing | Gestageno Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
PubMed
Title | Date | PubMed |
---|---|---|
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 |
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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 |
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Genomic organization of a human 5beta-reductase and its pseudogene and substrate selectivity of the expressed enzyme. | 2001 Jan 26 |
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Functional hyperandrogenism detected by corticotropin and GnRH-analogue stimulation tests in women affected by apparently idiopathic hirsutism. | 2001 Jul-Aug |
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The involvement of sex steroid hormones in downstream and upstream migratory behavior of masu salmon. | 2001 Jun |
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Specific factors predict the response to pulsatile gonadotropin-releasing hormone therapy in polycystic ovarian syndrome. | 2001 Jun |
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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 |
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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 |
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The longitudinal study of adrenal maturation during gonadal suppression: evidence that adrenarche is a gradual process. | 2001 Sep |
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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
In Vivo Use Guide
Sources: http://mx.prvademecum.com/producto/?producto=10729
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25896481
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.
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302-23-8
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10156152
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Hydroxyprogesterone acetate
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100000078583
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206-119-6
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12191
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1101886
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L124O66YSI
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SUB16436MIG
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DTXSID90894096
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ACTIVE MOIETY
SUBSTANCE RECORD