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
[H][C@@]12CC[C@](OC(C)=O)(C(C)=O)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])CCC4=CC(=O)CC[C@]34C
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
| 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 |
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 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Gestageno Approved UseUnknown |
|||
| Primary | Gestageno Approved UseUnknown |
|||
| Preventing | Gestageno Approved UseUnknown |
|||
| Preventing | Gestageno Approved UseUnknown |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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
| 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 |
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: 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 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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 |
|
| Analysis of cortisol secretion in hormonally inactive adrenocortical incidentalomas: study of in vitro steroid secretion and immunohistochemical localization of steroidogenic enzymes. | 2001 Apr |
|
| Diagnosis of adrenal cortical dysfunction by liquid chromatography-tandem mass spectrometry. | 2001 Apr |
|
| Biochemical screening for subclinical cortisol-secreting adenomas amongst adrenal incidentalomas. | 2001 Apr |
|
| Leuprolide acetate treatment of adrenocortical disease in ferrets. | 2001 Apr 15 |
|
| Expression and localization of cytochrome P450 17 alpha-hydroxylase/c17,20-lyase in the avian brain. | 2001 Apr 27 |
|
| 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 |
|
| A new ultrasound criterion for the diagnosis of polycystic ovary syndrome: the ovarian stroma/total area ratio. | 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 |
|
| 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 |
|
| [Use of a dynamic test with HCG for evaluation of endocrine function in gonads of men with chronic alcohol abuse]. | 2001 Feb |
|
| The quantification of endogenous steroids in bovine aqueous humour and vitreous humour using isotope dilution GC-NCI-MS. | 2001 Feb |
|
| Genomic organization of a human 5beta-reductase and its pseudogene and substrate selectivity of the expressed enzyme. | 2001 Jan 26 |
|
| [Precocious puberty caused by a testicular Leydig cell tumor]. | 2001 Jan 28 |
|
| Ovulation rate and litter size in gilts immunized against androstenedione and 17alpha-hydroxyprogesterone. | 2001 Jul |
|
| Missense mutations cluster within the carboxyl-terminal region of DAX-1 and impair transcriptional repression. | 2001 Jul |
|
| Functional hyperandrogenism detected by corticotropin and GnRH-analogue stimulation tests in women affected by apparently idiopathic hirsutism. | 2001 Jul-Aug |
|
| Specific factors predict the response to pulsatile gonadotropin-releasing hormone therapy in polycystic ovarian syndrome. | 2001 Jun |
|
| A role for src tyrosine kinase in regulating adrenal aldosterone production. | 2001 Jun |
|
| Congenital adrenal hyperplasia owing to 21-hydroxylase deficiency. Growth, development, and therapeutic considerations. | 2001 Mar |
|
| Newborn screening for congenital adrenal hyperplasia. | 2001 Mar |
|
| Assessment of endocrine status in patients undergoing in-vitro fertilization treatment. Is it necessary? | 2001 Mar |
|
| Sex hormone-binding globulin as a marker of the effect of hormonal treatment in Turner's syndrome. | 2001 Mar |
|
| Steroidogenic correlates of pregnancy in the rock hyrax (Procavia capensis). | 2001 Mar 23 |
|
| An overview of molecular diagnosis of steroid 21-hydroxylase deficiency. | 2001 May |
|
| CYP21 mutations and congenital adrenal hyperplasia. | 2001 May |
|
| Role of the follistatin gene in women with polycystic ovary syndrome. | 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| Relationship between salivary progesterone, 17-hydroxyprogesterone, and cortisol levels throughout the normal menstrual cycle of healthy postmenarcheal girls. | 2001 Sep |
|
| 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 |
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
Edited
Fri Dec 15 15:04:27 GMT 2023
by
admin
on
Fri Dec 15 15:04:27 GMT 2023
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| Record UNII |
L124O66YSI
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| Record Status |
Validated (UNII)
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| Record Version |
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302-23-8
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10156152
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Hydroxyprogesterone acetate
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L124O66YSI
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SUB16436MIG
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DTXSID90894096
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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PARENT -> IMPURITY |
The following peaks are eluted at the following relative retention with reference to the peak of medroxyprogesterone acetate (retention time about 27 minutes): impurity H about 0.65. The test is not valid unless in the chromatogram obtained with solution (4) the resolution factor between the peaks due to impurity G and due to medroxyprogesterone acetate is at least 3.3.
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ACTIVE MOIETY |
