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
| 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 |
|---|---|---|---|---|
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 |
|---|---|---|
| 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
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| Record UNII |
L124O66YSI
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| Record Status |
Validated (UNII)
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302-23-8
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10156152
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Hydroxyprogesterone acetate
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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 |
