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| - | '''Androstenediol''' is a term used to refer to two different [[steroid]]s with [[molecular weight]]s of 290.44. They are [[4-androstenediol]] (4-androstene-3beta,17beta-diol) and [[5-androstenediol]] (5-androstene-3beta,17beta-diol).
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| - | 4-Androstenediol is closer to [[testosterone]] structurally, and has [[androgen]]ic effects.
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| - | 5-Androstenediol is a direct [[metabolite]] of the most abundant [[steroid]] produced by the human [[adrenal cortex]], [[dehydroepiandrosterone]] (DHEA). 5-Androstenediol is less [[androgen]]ic than 4-androstenediol, and stimulates the [[immune system]]. When administered to [[rat]]s [[in vivo]], 5-androstenediol has approximately 1/70 the [[androgen]]icity of [[DHEA]], 1/185 the [[androgen]]icity of [[androstenedione]], and 1/475 the [[androgen]]icity of [[testosterone]] (Coffey, 1988). Because it induces production of [[white blood cell]]s and [[platelet]]s, 5-androstenediol is being developed as a [[radiation]] countermeasure by the [[Armed Forces Radiobiology Research Institute]]. Until 2007, it was being developed as a [[radiation]] countermeasure by Hollis-Eden Pharmaceuticals as [[Neumune]] (HE2100).
| + | <table align='right' border=1> |
| | + | <tr><td> |
| | + | <jmol><jmolApplet> |
| | + | <size>200</size> |
| | + | <script>spin on;color atoms amino;</script> |
| | + | <uploadedFileContents>NPH116.SDF</uploadedFileContents> |
| | + | <color>black</color> |
| | + | </jmolApplet> |
| | + | </jmol> |
| | + | </td></tr></table> |
| | + | ==Description== |
| | + | An intermediate in TESTOSTERONE biosynthesis, found in the TESTIS or the ADRENAL GLANDS. Androstenediol, derived from DEHYDROEPIANDROSTERONE by the reduction of the 17-keto group (17-HYDROXYSTEROID DEHYDROGENASES), is converted to TESTOSTERONE by the oxidation of the 3-beta hydroxyl group to a 3-keto group (3-HYDROXYSTEROID DEHYDROGENASES). |
| | + | ==General Properties== |
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| - | Androstenediol is on the list of substances banned by the [[Major League Baseball drug policy]].
| + | <b>*Molecular Weight</b> |
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| - | Pubchem(10634)
| + | 290.44 |
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| - | An intermediate in TESTOSTERONE biosynthesis, found in the TESTIS or the ADRENAL GLANDS. Androstenediol, derived from DEHYDROEPIANDROSTERONE by the reduction of the 17-keto group (17-HYDROXYSTEROID DEHYDROGENASES), is converted to TESTOSTERONE by the oxidation of the 3-beta hydroxyl group to a 3-keto group (3-HYDROXYSTEROID DEHYDROGENASES).
| + | <b>*Molecular Formula</b> |
| | | | |
| - | '''Drug Type''': Small Molecule; Illicit; Experimental
| + | C<sub>1</sub><sub>9</sub>H<sub>3</sub><sub>0</sub>O<sub>2</sub> |
| | | | |
| - | '''KEGG Pathway'''(C04295,D00179)
| + | <b>*IUPAC NAME</b> |
| - | *Androgen and estrogen metabolism | + | |
| - | {| border="1;width:100%; height:200px;style=text-align:center"
| + | |
| - | |+'''Physiochemical properties of Androstenediol:'''
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| - | |-
| + | |
| - | ! style="background:brown; color:white" |Physical Property
| + | |
| - | ! style="background:brown; color:white" |Value
| + | |
| - | ! style="background:brown; color:white" |Units
| + | |
| - | ! style="background:brown; color:white" |Temp (deg C)
| + | |
| - | ! style="background:brown; color:white" |Source
| + | |
| - | |-
| + | |
| - | |log P (octanol-water)
| + | |
| - | |4.580
| + | |
| - | |(none)
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| - | |
| + | |
| - | |EST
| + | |
| - | |-
| + | |
| - | |Atmospheric OH Rate Constant
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| - | |1.24E-10
| + | |
| - | |cm3/molecule-sec
| + | |
| - | |25
| + | |
| - | |EST
| + | |
| - | |-
| + | |
| - | |}
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| | + | (3S,8R,9S,10R,13S,14S,17S)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol |
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| - | ==See also==
| + | <b>*Canonical Smiles</b> |
| - | *[[Androstenedione]] | + | |
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| - | ==References==
| + | CC12CCC3C(C1CCC2O)CC=C4C3(CCC(C4)O)C |
| - | * {{MeshName|Androstenediol}}
| + | |
| - | * {{PubChem|10634}}
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| - | * Coffey, DS (1988) "Androgen action and the sex accessory tissues". In E Knobil, J Neill (eds), The Physiology of Reproduction. Raven Press, New York, pp 1081-1119.
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| - | * {{cite journal | author = Singh VK, Shafran RL, Inal CE, Jackson WE 3rd, Whitnall MH | title = Effects of whole-body gamma irradiation and 5-androstenediol administration on serum G-CSF | journal = Immunopharmacol Immunotoxicol | volume = 27 | issue = 4 | pages = 521–34 | year = 2005 | pmid = 16435574 | doi = 10.1080/08923970500416707}}
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| - | * {{cite journal | author = Brown GA, McKenzie D | title = Acute resistance exercise does not change the hormonal response to sublingual androstenediol intake | journal = Eur J Appl Physiol | volume = 97 | issue = 4 | pages = 404–12 | year = 2006 | pmid = 16636857 | doi = 10.1007/s00421-006-0194-9}}
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| - | * {{cite journal | author = Head CC, Farrow MJ, Sheridan JF, Padgett DA| title = Androstenediol reduces the anti-inflammatory effects of restraint stress during wound healing | journal = Brain Behav Immun | volume = | issue = | pages = | year = 2006| pmid = 16730942| doi = 10.1016/j.bbi.2006.03.007}}
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| - | * {{cite journal | author = Suzuki T, Shimizu T, Szalay L, Choudhry MA, Rue LW 3rd, Bland KI, Chaudry IH | title = Androstenediol ameliorates alterations in immune cells cytokine production capacity in a two-hit model of trauma-hemorrhage and sepsis | journal = Cytokine | volume = 34 | issue = 1-2 | pages = 76–84 | year = 2006 | pmid = 16737821 | doi = 10.1016/j.cyto.2006.04.007}}
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| - | * {{cite journal | author = Kiang JG, Peckham RM, Duke LE, Shimizu T, Chaudry IH, Tsokos GC | title = Androstenediol inhibits the trauma-hemorrhage-induced increase in caspase-3 by downregulating the inducible nitric oxide synthase pathway | journal = J Appl Physiol | volume = 102 | issue = 3 | pages = 933–41 | year = 2007 | pmid = 17110508 | doi = 10.1152/japplphysiol.00919.2006}}
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| - | * {{cite journal | author = Xiao M, Inal CE, Parekh VI, Chang CM, Whitnall MH | title = 5-Androstenediol promotes survival of gamma-irradiated human hematopoietic progenitors through induction of NF-kappa B activation and G-CSF expression | journal = Mol Pharmacol | volume = 72 | pages = 370-9 | year = 2007 | pmid = 17473057}}
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| - | * {{cite journal | author = Singh VK, Grace MB, Jacobsen KO, Chang CM, Parekh VI, Inal CE, Shafran RL, Whitnall AD, Kao TC, Jackson WE 3rd, Whitnall MH | title = Administration of 5-androstenediol to mice: Pharmacokinetics and cytokine gene expression | journal = Exp Molec Pathol | volume = 84 | pages = 178-188 | year = 2008 | pmid = 18262521}}
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| - | [[Category:Steroids]]
| + | <b>*Isomeric Smiles</b> |
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| | + | C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CC=C4[C@@]3(CC[C@@H](C4)O)C |
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| - | {{pharma-stub}}
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| | + | ==PhysioChemical Properties== |
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| | + | <b>*Melting Point</b> |
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| | + | <b>*LogP</b> |
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| | + | 4.58(EST) |
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| | + | <b>*Water Solubility</b> |
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| | + | ==External Links== |
| | + | *[http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=10634]Pubchem |
| | + | *[http://www.genome.jp/dbget-bin/www_bget?compound+C04295]]KEGG Compound |
| | + | *[http://www.genome.jp/dbget-bin/www_bget?drug+D00179]]KEGG Drug |
| | + | *[http://www.hmdb.ca/metabolites/HMDB03818]Human Metabolome DataBase |
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| | + | [[Categories:Hormones]] |
An intermediate in TESTOSTERONE biosynthesis, found in the TESTIS or the ADRENAL GLANDS. Androstenediol, derived from DEHYDROEPIANDROSTERONE by the reduction of the 17-keto group (17-HYDROXYSTEROID DEHYDROGENASES), is converted to TESTOSTERONE by the oxidation of the 3-beta hydroxyl group to a 3-keto group (3-HYDROXYSTEROID DEHYDROGENASES).
(3S,8R,9S,10R,13S,14S,17S)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol
