Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C19H30O2 |
Molecular Weight | 290.441 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 7 / 7 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@@]12CC[C@@]([H])(CC2=CC[C@@]3([H])[C@]4([H])CC[C@@]([H])([C@@]4(C)CC[C@@]31[H])O)O
InChI
InChIKey=QADHLRWLCPCEKT-LOVVWNRFSA-N
InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h3,13-17,20-21H,4-11H2,1-2H3/t13-,14-,15-,16-,17-,18-,19-/m0/s1
DescriptionSources: http://www.rxlist.com/androstenediol/supplements.htmCurator's Comment:: description was created based on several sources, including:
http://www.drugbank.ca/drugs/DB01524
http://www.webmd.com/vitamins-supplements/ingredientmono-595-androstenediol.aspx?activeingredientid=595&activeingredientname=androstenediol
Sources: http://www.rxlist.com/androstenediol/supplements.htm
Curator's Comment:: description was created based on several sources, including:
http://www.drugbank.ca/drugs/DB01524
http://www.webmd.com/vitamins-supplements/ingredientmono-595-androstenediol.aspx?activeingredientid=595&activeingredientname=androstenediol
This compound belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans. The value of Δ5-diol as a radiation countermeasure is based mainly on its stimulation of production of white blood cells and platelets. Androstenediol used by the body to make testosterone and estrogen. There is some concern that androstenediol might increase the risk of coronary heart disease. There is also developing evidence that androstenediol might help prostate cancer cells grow. Taking androstenediol along with estrogen and testosterone pills might cause too much estrogen or testosterone in the body.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: 1.05586152E8 Gene Symbol: AR Sources: http://www.ncbi.nlm.nih.gov/pubmed/9736693 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Neumune Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Sport nutritional supplements: quality and doping controls. | 2001 |
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Synthesis and steroid sulphatase inhibitory activity of C19- and C21-steroidal derivatives bearing a benzyl-inhibiting group. | 2001 Jul-Aug |
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Hormonal steroidogenesis in liver and small intestine of the green frog, Rana esculenta L. | 2001 Nov 2 |
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Endocrine and lipid responses to chronic androstenediol-herbal supplementation in 30 to 58 year old men. | 2001 Oct |
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[Urinary nandrolone metabolites in antidoping control]. | 2001 Sep |
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Cytopathological changes in early stages of benign prostatic hyperplasia upon exposure to sustained delivery of androgens. | 2002 |
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The role of cytokines in regulating estrogen synthesis: implications for the etiology of breast cancer. | 2002 |
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Human nutritional supplements in the horse: comparative effects of 19-norandrostenedione and 19-norandrostenediol on the 19-norsteroid profile and consequences for doping control. | 2002 Jan 25 |
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Dehydroepiandrosterone (DHEA) metabolism in Saccharomyces cerevisiae expressing mammalian steroid hydroxylase CYP7B: Ayr1p and Fox2p display 17beta-hydroxysteroid dehydrogenase activity. | 2002 Jul |
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Aromatase overexpression enhances the stimulatory effects of adrenal androgens on MCF7 breast cancer cells. | 2002 Jul 31 |
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Identification of dehydroepiandrosterone metabolites formed from human prostate homogenate using liquid chromatography-mass spectrometry and gas chromatography-mass spectrometry. | 2002 Jun 28 |
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Induction of CYP3A expression by dehydroepiandrosterone: involvement of the pregnane X receptor. | 2002 May |
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Radioprotective efficacy and acute toxicity of 5-androstenediol after subcutaneous or oral administration in mice. | 2002 Nov |
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Steroid and sterol 7-hydroxylation: ancient pathways. | 2002 Nov |
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Sex steroid hormones differentially regulate nitric oxide synthase and arginase activities in the proximal and distal rabbit vagina. | 2003 Dec |
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Sterol structure and sphingomyelin acyl chain length modulate lateral packing elasticity and detergent solubility in model membranes. | 2003 Dec |
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Oral andro-related prohormone supplementation: do the potential risks outweigh the benefits? | 2003 Feb |
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Characterisation of estrogenic 17beta-hydroxysteroid dehydrogenase (17beta-HSD) activity in the human brain. | 2003 Jul |
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The effects of androstenediol and dehydroepiandrosterone on the immune response to BCG at puberty. | 2003 Jun |
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The human kidney is a progesterone-metabolizing and androgen-producing organ. | 2003 Jun |
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Asynchronous bilateral achilles tendon ruptures and androstenediol use. | 2003 Nov-Dec |
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Simultaneous determination of androstenediol 3-sulfate and dehydroepiandrosterone sulfate in human serum using isotope diluted liquid chromatography-electrospray ionization-mass spectrometry. | 2003 Oct 25 |
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Steroid sulphatase inhibitors for breast cancer therapy. | 2003 Sep |
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Adrenal steroid hormones and metaphyseal bone in children. | 2004 |
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Plasma lipoprotein profile in the male cynomolgus monkey under normal, hypogonadal, and combined androgen blockade conditions. | 2004 Apr |
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Anabolic-androgenic steroids and testosterone precursors: ergogenic aids and sport. | 2004 Aug |
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Salutary effects of androstenediol on cardiac function and splanchnic perfusion after trauma-hemorrhage. | 2004 Aug |
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Effect of estrogen receptor agonists treatment in MPTP mice: evidence of neuroprotection by an ER alpha agonist. | 2004 Dec |
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In vivo effects of an intrafollicular injection of insulin-like growth factor 1 on the mechanism of follicle deviation in heifers and mares. | 2004 Jan |
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Virilization of young children after topical androgen use by their parents. | 2004 Jul |
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Expression of cytochrome P450c17 and other steroid-converting enzymes in the rat kidney throughout the life-span. | 2004 Jun |
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Lack of defects in androgen production in children with hypospadias. | 2004 Jun |
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Amelioration of murine antigen-induced arthritis by dehydroepiandrosterone (DHEA). | 2004 May |
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Androgen conversion in osteoarthritis and rheumatoid arthritis synoviocytes--androstenedione and testosterone inhibit estrogen formation and favor production of more potent 5alpha-reduced androgens. | 2005 |
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Molecular specificity of 5-androstenediol as a systemic radioprotectant in mice. | 2005 |
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Dehydroepiandrosterone (DHEA) modulates GHRH, somatostatin and angiotensin II action at the pituitary level. | 2005 Apr |
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Steroid sulfatase: molecular biology, regulation, and inhibition. | 2005 Apr |
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Salutary effects of androstenediol on hepatic function after trauma-hemorrhage are mediated via peroxisome proliferators-activated receptor gamma. | 2005 Aug |
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Androgens induce relaxation of contractile activity in pregnant human myometrium at term: a nongenomic action on L-type calcium channels. | 2005 Aug |
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Anti-inflammatory and immune regulatory properties of 5-androsten-3beta, 17beta-diol (HE2100), and synthetic analogue HE3204: implications for treatment of autoimmune diseases. | 2005 Jun |
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Binding of estrogenic compounds to recombinant estrogen receptor-alpha: application to environmental analysis. | 2005 Mar |
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Specific modulation of nongenomic androgen signaling in the ovary. | 2005 May-Jun |
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Application of stable carbon isotope analysis to the detection of 17beta-estradiol administration to cattle. | 2005 Nov 4 |
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Enzymic conversion of 3beta-hydroxy-5-ene-steroids and their sulfates to 3-oxo-4-ene-steroids for increasing sensitivity in LC-APCI-MS. | 2005 Sep 15 |
|
Circulating neuroactive C21- and C19-steroids in young men before and after ejaculation. | 2006 |
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Androstenediol administration after trauma-hemorrhage attenuates inflammatory response, reduces organ damage, and improves survival following sepsis. | 2006 Aug |
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Androstenediol analogs as ER-beta-selective SERMs. | 2006 Feb 15 |
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Modulation of neurosteroid production in human neuroblastoma cells by Alzheimer's disease key proteins. | 2006 Jul |
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Acute resistance exercise does not change the hormonal response to sublingual androstenediol intake. | 2006 Jul |
|
Metabolism of steroid hormones by Taenia solium and Taenia crassiceps cysticerci. | 2006 Jun |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/21149931
Curator's Comment:: In Phase I human safety studies conducted in the U.S. and The Netherlands, as of December 2005, a total of 111 volunteers had been enrolled, with 39 volunteers having completed the 5-day treatment course.
The 200 mg dose given over 5 days may be effective as a radiation countermeasure for humans
Route of Administration:
Intramuscular
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NCI_THESAURUS |
C2360
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LOINC |
55851-0
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25314-6
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34238-6
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DEA NO. |
4000
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34237-8
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56033-4
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LOINC |
34236-0
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Code System | Code | Type | Description | ||
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C95979
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208-306-8
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95PS51EMXY
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521-17-5
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PRIMARY | |||
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214
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PRIMARY | |||
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521-17-5
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D015114
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CHEMBL440283
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M1900
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PRIMARY | Merck Index | ||
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SUB12899MIG
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10634
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DB01524
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ACTIVE MOIETY
PARENT (METABOLITE)