Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C21H32O2 |
| Molecular Weight | 316.4776 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 7 / 7 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C
InChI
InChIKey=XMRPGKVKISIQBV-BJMCWZGWSA-N
InChI=1S/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h14,16-19H,4-12H2,1-3H3/t14-,16-,17+,18-,19-,20-,21+/m0/s1
| Molecular Formula | C21H32O2 |
| Molecular Weight | 316.4776 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 7 / 7 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Progestin effects on expression of AKR1C1-AKR1C3, SRD5A1 and PGR in the Z-12 endometriotic epithelial cell line. | 2013-02-25 |
|
| The evolution of farnesoid X, vitamin D, and pregnane X receptors: insights from the green-spotted pufferfish (Tetraodon nigriviridis) and other non-mammalian species. | 2011-02-03 |
|
| Biotransformation of progesterone by cultured cells of Marchantia polymorpha. | 2010-12-09 |
|
| Expanding the use of fluorogenic enzyme reporter substrates to imaging metabolic flux changes: the activity measurement of 5α-steroid reductase in intact mammalian cells. | 2010-11-19 |
|
| Non-stereo-selective cytosolic human brain tissue 3-ketosteroid reductase is refractory to inhibition by AKR1C inhibitors. | 2010-11 |
|
| Fecal steroid metabolites and reproductive monitoring in a female Tsushima leopard cat (Prionailurus bengalensis euptilurus). | 2010-11 |
|
| Cellular and functional evidence for a protective action of neurosteroids against vincristine chemotherapy-induced painful neuropathy. | 2010-09 |
|
| A role for Src kinase in progestin facilitation of estrous behavior in estradiol-primed female rats. | 2010-07 |
|
| Corticosteroid and neurosteroid dysregulation in an animal model of autism, BTBR mice. | 2010-06-01 |
|
| Aldo-keto reductase 1C3 expression in MCF-7 cells reveals roles in steroid hormone and prostaglandin metabolism that may explain its over-expression in breast cancer. | 2010-02-15 |
|
| Opposing actions of the progesterone metabolites, 5alpha-dihydroprogesterone (5alphaP) and 3alpha-dihydroprogesterone (3alphaHP) on mitosis, apoptosis, and expression of Bcl-2, Bax and p21 in human breast cell lines. | 2010-01 |
|
| Immunohistochemical localization and biological activity of 3beta-hydroxysteroid dehydrogenase and 5alpha-reductase in the brain of the frog, Rana esculenta, during development. | 2010-01 |
|
| Gene expression profiles of intracellular and membrane progesterone receptor isoforms in the mediobasal hypothalamus during pro-oestrus. | 2009-12 |
|
| Estrogen increases latencies to seizures and levels of 5alpha-pregnan-3alpha-ol-20-one in hippocampus of wild-type, but not 5alpha-reductase knockout, mice. | 2009-11 |
|
| Detection and identification of plasma progesterone metabolites in the female Florida manatee (Trichechus manatus latirostris) using GC/MS/MS. | 2009-08 |
|
| The vicious cycle towards violence: focus on the negative feedback mechanisms of brain serotonin neurotransmission. | 2009 |
|
| Role of progesterone receptor isoforms in female sexual behavior induced by progestins in rats. | 2009 |
|
| GABA(A) receptor properties in catastrophic infantile epilepsy. | 2008-10 |
|
| The anti-aromatase effect of progesterone and of its natural metabolites 20alpha- and 5alpha-dihydroprogesterone in the MCF-7aro breast cancer cell line. | 2008-08-30 |
|
| The crystal structure of human Delta4-3-ketosteroid 5beta-reductase defines the functional role of the residues of the catalytic tetrad in the steroid double bond reduction mechanism. | 2008-08-12 |
|
| Progesterone metabolism in bovine endometrial cells and the effect of metabolites on the responsiveness of the cells to OT-stimulation of PGF2alpha. | 2007-11 |
|
| Steroid profiling in brain and plasma of male and pseudopregnant female rats after traumatic brain injury: analysis by gas chromatography/mass spectrometry. | 2007-05 |
|
| Studies on neurosteroids XIX. Development and validation of liquid chromatography-tandem mass spectrometric method for determination of 5alpha-reduced pregnane-type neurosteroids in rat brain and serum. | 2007-04-01 |
|
| Effects of progesterone and its reduced metabolites, dihydroprogesterone and tetrahydroprogesterone, on the expression and phosphorylation of glycogen synthase kinase-3 and the microtubule-associated protein tau in the rat cerebellum. | 2007-03 |
|
| The impact of ecological variability on the reproductive endocrinology of wild female African elephants. | 2007-03 |
|
| Regulation of estrogen receptor (ER) levels in MCF-7 cells by progesterone metabolites. | 2007-02-15 |
|
| Regulation of vascular tone during pregnancy: a novel role for the pregnane X receptor. | 2007-02 |
|
| The anticonvulsant effects of allopregnanolone against amygdala-kindled seizures in female rats. | 2007-01-10 |
|
| In silico prediction of pregnane X receptor activators by machine learning approaches. | 2007-01 |
|
| Progesterone derivatives increase expression of Krox-20 and Sox-10 in rat Schwann cells. | 2007 |
|
| Decreased cerebrospinal fluid allopregnanolone levels in women with posttraumatic stress disorder. | 2006-10-01 |
|
| Progesterone and its metabolites 5-dihydroprogesterone and 5-3-tetrahydroprogesterone decrease LPS-induced NO release in the murine microglial cell line, BV-2. | 2006-10 |
|
| Circulating levels of pregnanolone isomers during the third trimester of human pregnancy. | 2006-09-27 |
|
| Dutasteride affects progesterone metabolizing enzyme activity/expression in human breast cell lines resulting in suppression of cell proliferation and detachment. | 2006-08 |
|
| Reduced metabolites mediate neuroprotective effects of progesterone in the adult rat hippocampus. The synthetic progestin medroxyprogesterone acetate (Provera) is not neuroprotective. | 2006-08 |
|
| The anticonvulsant effects of progesterone and its metabolites on amygdala-kindled seizures in male rats. | 2006-07-26 |
|
| Influence of ginsenoside Rb1 on brain neurosteroid during acute immobilization stress. | 2006-07 |
|
| [Steroid 5alpha-reductase deficiency]. | 2006-06-28 |
|
| Comparative non-radioactive RT-PCR assay: an approach to study the neurosteroids biosynthetic pathway in humans. | 2006-06-15 |
|
| A possible role for progesterone metabolites in human parturition. | 2006-04 |
|
| Injury elicited increase in spinal cord neurosteroid content analyzed by gas chromatography mass spectrometry. | 2006-04 |
|
| [Transcriptional regulation of placental transforming growth factor-beta by calcitriol in prostate cancer cells is androgen-independent]. | 2006-03-10 |
|
| Testicular zinc finger protein recruits histone deacetylase 2 and suppresses the transactivation function and intranuclear foci formation of agonist-bound androgen receptor competitively with TIF2. | 2006-03-09 |
|
| Roles of type 10 17beta-hydroxysteroid dehydrogenase in intracrinology and metabolism of isoleucine and fatty acids. | 2006-03 |
|
| Influence of mirtazapine on plasma concentrations of neuroactive steroids in major depression and on 3alpha-hydroxysteroid dehydrogenase activity. | 2006-03 |
|
| Identification of neuroactive steroids and their precursors and metabolites in adult male rat brain. | 2006-01 |
|
| The anxiolytic etifoxine activates the peripheral benzodiazepine receptor and increases the neurosteroid levels in rat brain. | 2005-12 |
|
| 3alpha-reduced neuroactive steroids and their precursors during pregnancy and the postpartum period. | 2005-11 |
|
| Placentation in the African elephant, Loxodonta africana. IV. Growth and function of the fetal gonads. | 2005-11 |
|
| Reproductive hormonal treatments for mood disorders in women. | 2002-06 |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 19:08:41 GMT 2025
by
admin
on
Mon Mar 31 19:08:41 GMT 2025
|
| Record UNII |
98G4S1OH0Z
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Preferred Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
m1534
Created by
admin on Mon Mar 31 19:08:41 GMT 2025 , Edited by admin on Mon Mar 31 19:08:41 GMT 2025
|
PRIMARY | Merck Index | ||
|
5?-Dihydroprogesterone
Created by
admin on Mon Mar 31 19:08:41 GMT 2025 , Edited by admin on Mon Mar 31 19:08:41 GMT 2025
|
PRIMARY | |||
|
98G4S1OH0Z
Created by
admin on Mon Mar 31 19:08:41 GMT 2025 , Edited by admin on Mon Mar 31 19:08:41 GMT 2025
|
PRIMARY | |||
|
566-65-4
Created by
admin on Mon Mar 31 19:08:41 GMT 2025 , Edited by admin on Mon Mar 31 19:08:41 GMT 2025
|
PRIMARY | |||
|
92810
Created by
admin on Mon Mar 31 19:08:41 GMT 2025 , Edited by admin on Mon Mar 31 19:08:41 GMT 2025
|
PRIMARY | |||
|
18319
Created by
admin on Mon Mar 31 19:08:41 GMT 2025 , Edited by admin on Mon Mar 31 19:08:41 GMT 2025
|
PRIMARY | |||
|
209-297-3
Created by
admin on Mon Mar 31 19:08:41 GMT 2025 , Edited by admin on Mon Mar 31 19:08:41 GMT 2025
|
PRIMARY | |||
|
28952
Created by
admin on Mon Mar 31 19:08:41 GMT 2025 , Edited by admin on Mon Mar 31 19:08:41 GMT 2025
|
PRIMARY | |||
|
DTXSID301017277
Created by
admin on Mon Mar 31 19:08:41 GMT 2025 , Edited by admin on Mon Mar 31 19:08:41 GMT 2025
|
PRIMARY |