566-65-4 | 5-alpha-Dihydroprogesterone

Availability
Typically In Stock

Description

• Catalog Number: AG64541
• Chemical Name: 5-alpha-Dihydroprogesterone
• CAS Number: 566-65-4
• Molecular Formula: C21H32O2
• Molecular Weight: 316.4776
• MDL Number: MFCD00067132
• SMILES: O=C1CC[C@]2([C@H](C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2C(=O)C)C)C
• NSC Number: 18319

Computed Properties

• Complexity: 538
• Covalently-Bonded Unit Count: 1
• Defined Atom Stereocenter Count: 7
• Heavy Atom Count: 23
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• XLogP3: 4.4

Literature

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  Toxicology in vitro : an international journal published in association with BIBRA 20180201

• Important roles of the AKR1C2 and SRD5A1 enzymes in progesterone metabolism in endometrial cancer model cell lines.

  Chemico-biological interactions 20150605

• Progestin effects on expression of AKR1C1-AKR1C3, SRD5A1 and PGR in the Z-12 endometriotic epithelial cell line.

  Chemico-biological interactions 20130225

• Progesterone receptors: a key for neuroprotection in experimental stroke.

  Endocrinology 20120801

• Decreased startle modulation during anticipation in the postpartum period in comparison to late pregnancy.

  Archives of women's mental health 20120401

• Type 1 5α-reductase may be required for estrous cycle changes in affective behaviors of female mice.

  Behavioural brain research 20120115

• Chronic cigarette smoking alters circulating sex hormones and neuroactive steroids in premenopausal women.

  Physiological research 20120101

• Fecal progestagens to detect and monitor pregnancy in captive female cheetahs (Acinonyx jubatus).

  The Journal of reproduction and development 20110401

• I. Levels of 5α-reduced progesterone metabolite in the midbrain account for variability in reproductive behavior of middle-aged female rats.

  Brain research 20110316

• Of sound mind and body: depression, disease, and accelerated aging.

  Dialogues in clinical neuroscience 20110301

• BTG2 is an LXXLL-dependent co-repressor for androgen receptor transcriptional activity.

  Biochemical and biophysical research communications 20110128

• The evolution of farnesoid X, vitamin D, and pregnane X receptors: insights from the green-spotted pufferfish (Tetraodon nigriviridis) and other non-mammalian species.

  BMC biochemistry 20110101

• Beyond the HPA Axis: Progesterone-Derived Neuroactive Steroids in Human Stress and Emotion.

  Frontiers in endocrinology 20110101

• Peripheral vs. Central Sex Steroid Hormones in Experimental Parkinson's Disease.

  Frontiers in endocrinology 20110101

• Neurosteroids and GABA-A Receptor Function.

  Frontiers in endocrinology 20110101

• Neurosteroids as neuromodulators in the treatment of anxiety disorders.

  Frontiers in endocrinology 20110101

• Neuroregenerative mechanisms of allopregnanolone in Alzheimer's disease.

  Frontiers in endocrinology 20110101

• Expanding the use of fluorogenic enzyme reporter substrates to imaging metabolic flux changes: the activity measurement of 5α-steroid reductase in intact mammalian cells.

  ACS chemical biology 20101119

• Fecal steroid metabolites and reproductive monitoring in a female Tsushima leopard cat (Prionailurus bengalensis euptilurus).

  Theriogenology 20101101

• Non-stereo-selective cytosolic human brain tissue 3-ketosteroid reductase is refractory to inhibition by AKR1C inhibitors.

  Biochimica et biophysica acta 20101101

• Cellular and functional evidence for a protective action of neurosteroids against vincristine chemotherapy-induced painful neuropathy.

  Cellular and molecular life sciences : CMLS 20100901

• A role for Src kinase in progestin facilitation of estrous behavior in estradiol-primed female rats.

  Hormones and behavior 20100701

• Corticosteroid and neurosteroid dysregulation in an animal model of autism, BTBR mice.

  Physiology & behavior 20100601

• 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.

  The Journal of steroid biochemistry and molecular biology 20100215

• Immunohistochemical localization and biological activity of 3beta-hydroxysteroid dehydrogenase and 5alpha-reductase in the brain of the frog, Rana esculenta, during development.

  Journal of chemical neuroanatomy 20100101

• 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.

  The Journal of steroid biochemistry and molecular biology 20100101

• Biotransformation of progesterone by cultured cells of Marchantia polymorpha.

  Zeitschrift fur Naturforschung. C, Journal of biosciences 20100101

• Gene expression profiles of intracellular and membrane progesterone receptor isoforms in the mediobasal hypothalamus during pro-oestrus.

  Journal of neuroendocrinology 20091201

• 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.

  Epilepsy & behavior : E&B 20091101

• Detection and identification of plasma progesterone metabolites in the female Florida manatee (Trichechus manatus latirostris) using GC/MS/MS.

  Theriogenology 20090801

• Role of progesterone receptor isoforms in female sexual behavior induced by progestins in rats.

  Neuroendocrinology 20090101

• The vicious cycle towards violence: focus on the negative feedback mechanisms of brain serotonin neurotransmission.

  Frontiers in behavioral neuroscience 20090101

• GABA(A) receptor properties in catastrophic infantile epilepsy.

  Epilepsy research 20081001

• 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.

  Biochemistry 20080812

• Novel potent and selective bile acid derivatives as TGR5 agonists: biological screening, structure-activity relationships, and molecular modeling studies.

  Journal of medicinal chemistry 20080327

• The anti-aromatase effect of progesterone and of its natural metabolites 20alpha- and 5alpha-dihydroprogesterone in the MCF-7aro breast cancer cell line.

  Anticancer research 20080101

• Progesterone metabolism in bovine endometrial cells and the effect of metabolites on the responsiveness of the cells to OT-stimulation of PGF2alpha.

  Steroids 20071101

• Steroid profiling in brain and plasma of male and pseudopregnant female rats after traumatic brain injury: analysis by gas chromatography/mass spectrometry.

  Endocrinology 20070501

• 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.

  Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20070401

• The impact of ecological variability on the reproductive endocrinology of wild female African elephants.

  Hormones and behavior 20070301

• 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.

  Developmental neurobiology 20070301

• Regulation of vascular tone during pregnancy: a novel role for the pregnane X receptor.

  Hypertension (Dallas, Tex. : 1979) 20070201

• The anticonvulsant effects of allopregnanolone against amygdala-kindled seizures in female rats.

  Neuroscience letters 20070110

• In silico prediction of pregnane X receptor activators by machine learning approaches.

  Molecular pharmacology 20070101

• Androgen decreases osteoprotegerin expression in prostate cancer cells.

  Prostate cancer and prostatic diseases 20070101

• Progesterone derivatives increase expression of Krox-20 and Sox-10 in rat Schwann cells.

  Journal of molecular neuroscience : MN 20070101

• Circulating levels of pregnanolone isomers during the third trimester of human pregnancy.

  The Journal of steroid biochemistry and molecular biology 20070101

• Regulation of estrogen receptor (ER) levels in MCF-7 cells by progesterone metabolites.

  The Journal of steroid biochemistry and molecular biology 20070101

• Decreased cerebrospinal fluid allopregnanolone levels in women with posttraumatic stress disorder.

  Biological psychiatry 20061001

• Progesterone and its metabolites 5-dihydroprogesterone and 5-3-tetrahydroprogesterone decrease LPS-induced NO release in the murine microglial cell line, BV-2.

  Neuro endocrinology letters 20061001

• Reduced metabolites mediate neuroprotective effects of progesterone in the adult rat hippocampus. The synthetic progestin medroxyprogesterone acetate (Provera) is not neuroprotective.

  Journal of neurobiology 20060801

• Dutasteride affects progesterone metabolizing enzyme activity/expression in human breast cell lines resulting in suppression of cell proliferation and detachment.

  The Journal of steroid biochemistry and molecular biology 20060801

• The anticonvulsant effects of progesterone and its metabolites on amygdala-kindled seizures in male rats.

  Brain research 20060726

• Influence of ginsenoside Rb1 on brain neurosteroid during acute immobilization stress.

  Archives of pharmacal research 20060701

• [Steroid 5alpha-reductase deficiency].

  Nihon rinsho. Japanese journal of clinical medicine 20060628

• Comparative non-radioactive RT-PCR assay: an approach to study the neurosteroids biosynthetic pathway in humans.

  Journal of neuroscience methods 20060615

• Injury elicited increase in spinal cord neurosteroid content analyzed by gas chromatography mass spectrometry.

  Endocrinology 20060401

• A possible role for progesterone metabolites in human parturition.

  The Australian & New Zealand journal of obstetrics & gynaecology 20060401

• 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.

  Molecular and cellular endocrinology 20060309

• Influence of mirtazapine on plasma concentrations of neuroactive steroids in major depression and on 3alpha-hydroxysteroid dehydrogenase activity.

  Molecular psychiatry 20060301

• Roles of type 10 17beta-hydroxysteroid dehydrogenase in intracrinology and metabolism of isoleucine and fatty acids.

  Endocrine, metabolic & immune disorders drug targets 20060301

• Identification of neuroactive steroids and their precursors and metabolites in adult male rat brain.

  Endocrinology 20060101

• [Transcriptional regulation of placental transforming growth factor-beta by calcitriol in prostate cancer cells is androgen-independent].

  Molekuliarnaia biologiia 20060101

• The anxiolytic etifoxine activates the peripheral benzodiazepine receptor and increases the neurosteroid levels in rat brain.

  Pharmacology, biochemistry, and behavior 20051201

• Membrane 5alpha-pregnane-3,20-dione (5alphaP) receptors in MCF-7 and MCF-10A breast cancer cells are up-regulated by estradiol and 5alphaP and down-regulated by the progesterone metabolites, 3alpha-dihydroprogesterone and 20alpha-dihydroprogesterone, with associated changes in cell proliferation and detachment.

  The Journal of steroid biochemistry and molecular biology 20051101

• Placentation in the African elephant, Loxodonta africana. IV. Growth and function of the fetal gonads.

  Reproduction (Cambridge, England) 20051101

• 3alpha-reduced neuroactive steroids and their precursors during pregnancy and the postpartum period.

  Gynecological endocrinology : the official journal of the International Society of Gynecological Endocrinology 20051101

• CAR and PXR: xenosensors of endocrine disrupters?

  Chemico-biological interactions 20050815

• Fine tuning of the specificity of an anti-progesterone antibody by first and second sphere residue engineering.

  The Journal of biological chemistry 20050701

• Inhibition of 3alpha-hydroxysteroid dehydrogenase (3alpha-HSD) activity of human lung microsomes by genistein, daidzein, coumestrol and C(18)-, C(19)- and C(21)-hydroxysteroids and ketosteroids.

  Steroids 20050701

• 5 Beta-dihydroprogesterone and steroid 5 beta-reductase decrease in association with human parturition at term.

  Molecular human reproduction 20050701

• Plasma concentrations of neuroactive steroids before and after electroconvulsive therapy in major depression.

  Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20050601

• Evidence for specific TRPM8 expression in human prostate secretory epithelial cells: functional androgen receptor requirement.

  Endocrine-related cancer 20050601

• In vitro metabolism of progesterone by canine hair follicle cells.

  Veterinary dermatology 20050601

• Intracellular oxidation of allopregnanolone by human brain type 10 17beta-hydroxysteroid dehydrogenase.

  Brain research 20050408

• Metabolites of progesterone and the pregnane X receptor: a novel pathway regulating uterine contractility in pregnancy?

  American journal of obstetrics and gynecology 20050401

• Topography and function of androgen-metabolizing enzymes in the central nervous system.

  Anatomical science international 20050301

• The role of progesterone metabolites in breast cancer: potential for new diagnostics and therapeutics.

  The Journal of steroid biochemistry and molecular biology 20050201

• Type 10 17beta-hydroxysteroid dehydrogenase catalyzing the oxidation of steroid modulators of gamma-aminobutyric acid type A receptors.

  Molecular and cellular endocrinology 20050114

• Studies on neurosteroids XVII. Analysis of stress-induced changes in neurosteroid levels in rat brains using liquid chromatography-electron capture atmospheric pressure chemical ionization-mass spectrometry.

  Steroids 20050101

• Characterization of 17alpha-hydroxysteroid dehydrogenase activity (17alpha-HSD) and its involvement in the biosynthesis of epitestosterone.

  BMC biochemistry 20050101

• Regulation of lordosis by cyclic 3',5'-guanosine monophosphate, progesterone, and its 5alpha-reduced metabolites involves mitogen-activated protein kinase.

  Endocrinology 20041201

• Progestins in the hippocampus of female rats have antiseizure effects in a pentylenetetrazole seizure model.

  Epilepsia 20041201

• Progestins and place preference conditioning after paced mating.

  Hormones and behavior 20040801

• Steroid 5alpha-reductase 1 promotes 5alpha-androstane-3alpha,17beta-diol synthesis in immature mouse testes by two pathways.

  Molecular and cellular endocrinology 20040730

• Niemann-Pick type C disease involves disrupted neurosteroidogenesis and responds to allopregnanolone.

  Nature medicine 20040701

• Insight into the mechanism of action of neuroactive steroids.

  Molecular pharmacology 20040701

• Modulation of the firing activity of female dorsal raphe nucleus serotonergic neurons by neuroactive steroids.

  The Journal of endocrinology 20040701

• Androgen inhibition of MAP kinase pathway and Elk-1 activation in proliferating osteoblasts.

  Journal of molecular endocrinology 20040201

• The nitric oxide pathway participates in estrous behavior induced by progesterone and some of its ring A-reduced metabolites.

  Hormones and behavior 20040101

• Reduced progesterone metabolites protect rat hippocampal neurones from kainic acid excitotoxicity in vivo.

  Journal of neuroendocrinology 20040101

• Expression of progesterone metabolizing enzyme genes (AKR1C1, AKR1C2, AKR1C3, SRD5A1, SRD5A2) is altered in human breast carcinoma.

  BMC cancer 20040101

• Functional effects of 17alpha-hydroxyprogesterone caproate (17P) on human myometrial contractility in vitro.

  Reproductive biology and endocrinology : RB&E 20040101

• Changes in 5alpha-pregnane steroids and neurosteroidogenic enzyme expression in fetal sheep with umbilicoplacental embolization.

  Pediatric research 20031201

• The anticonvulsant effects of progesterone and 5alpha-dihydroprogesterone on amygdala-kindled seizures in rats.

  Epilepsia 20031201

• Molecular determinants of steroid inhibition for the mouse constitutive androstane receptor.

  Journal of medicinal chemistry 20031023

• 5alpha-reduced C21 steroids are substrates for human cytochrome P450c17.

  Archives of biochemistry and biophysics 20031015

• Brain neurosteroid changes after paroxetine administration in mice.

  European neuropsychopharmacology : the journal of the European College of Neuropsychopharmacology 20031001

• Decreased plasma and cerebrospinal fluid content of neuroactive steroids in Parkinson's disease.

  Neurological sciences : official journal of the Italian Neurological Society and of the Italian Society of Clinical Neurophysiology 20031001

• Neuroactive steroid 3 alpha-hydroxy-5 alpha-pregnan-20-one modulates ethanol-induced loss of righting reflex in rats.

  Brain research 20030808

• Progesterone and its metabolites increase myelin basic protein expression in organotypic slice cultures of rat cerebellum.

  Journal of neurochemistry 20030801

• Branched fatty acids in dairy and beef products markedly enhance alpha-methylacyl-CoA racemase expression in prostate cancer cells in vitro.

  Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20030801

• Passage of progesterone into the brain changes with photoperiod in the ewe.

  The European journal of neuroscience 20030801

• Selective and potent inhibitors of human 20alpha-hydroxysteroid dehydrogenase (AKR1C1) that metabolizes neurosteroids derived from progesterone.

  Chemico-biological interactions 20030201

• Detection and characterization of 20-oxosteroids in rat brains using LC-electron capture APCI-MS after derivatization with 2-nitro-4-trifluoromethylphenylhydrazine.

  The Analyst 20030201

• Lordosis of rats is modified by neurosteroidogenic effects of membrane benzodiazepine receptors in the ventral tegmental area.

  Neuroendocrinology 20030101

• Androgen physiology: unsolved problems at the millennium.

  Molecular and cellular endocrinology 20021230

• Kinetics of allopregnanolone formation catalyzed by human 3 alpha-hydroxysteroid dehydrogenase type III (AKR1C2).

  Biochemistry 20021112

• Progesterone metabolism in human leukemic monoblast U937 cells.

  Endocrine journal 20021001

• Reproductive hormonal treatments for mood disorders in women.

  Dialogues in clinical neuroscience 20020601

• Substrate specificity of human 3(20)alpha-hydroxysteroid dehydrogenase for neurosteroids and its inhibition by benzodiazepines.

  Biological & pharmaceutical bulletin 20020401

• Placentation in the African elephant, Loxodonta africana. I. Endocrinological aspects.

  Reproduction (Cambridge, England) Supplement 20020101

• Neuroactive ring A-reduced metabolites of progesterone in human plasma during pregnancy: elevated levels of 5 alpha-dihydroprogesterone in depressed patients during the latter half of pregnancy.

  The Journal of clinical endocrinology and metabolism 20011201

• The socially-isolated mouse: a model to study the putative role of allopregnanolone and 5alpha-dihydroprogesterone in psychiatric disorders.

  Brain research. Brain research reviews 20011101

• Progesterone and 3alpha,5alpha-THP enhance sexual receptivity in mice.

  Behavioral neuroscience 20011001

• The endogenous progesterone metabolite, 5a-pregnane-3,20-dione, decreases cell-substrate attachment, adhesion plaques, vinculin expression, and polymerized F-actin in MCF-7 breast cancer cells.

  Endocrine 20011001

• Steroidogenic correlates of pregnancy in the rock hyrax (Procavia capensis).

  Life sciences 20010323

• Self-augmentation effect of male-specific products on sexually differentiated progesterone metabolism in adult male rat liver microsomes.

  The Journal of biological chemistry 20010216

• Identification of a human nuclear receptor defines a new signaling pathway for CYP3A induction.

  Proceedings of the National Academy of Sciences of the United States of America 19981013