Androstenediol

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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).  
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<script>spin on;color atoms amino;</script>
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<uploadedFileContents>NPH116.SDF</uploadedFileContents>
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==Description==
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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).
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==General Properties==
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<b>*Molecular Weight</b>
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Androstenediol is on the list of substances banned by the [[Major League Baseball drug policy]].
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290.44
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Pubchem(10634)
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<b>*Molecular Formula</b>
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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).
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C<sub>1</sub><sub>9</sub>H<sub>3</sub><sub>0</sub>O<sub>2</sub>
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'''Drug Type''':  Small Molecule; Illicit; Experimental
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<b>*IUPAC NAME</b>
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'''KEGG Pathway'''(C04295,D00179)
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*Androgen and estrogen metabolism
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{| border="1;width:100%; height:200px;style=text-align:center"
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|+'''Physiochemical properties of Androstenediol:'''
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|-
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! style="background:brown; color:white" |Physical Property
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! style="background:brown; color:white" |Value
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! style="background:brown; color:white" |Units
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! style="background:brown; color:white" |Temp (deg C)
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! style="background:brown; color:white" |Source
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|-
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|log P (octanol-water)
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|4.580
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|(none)
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|  
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|EST
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|-
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|Atmospheric OH Rate Constant
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|1.24E-10
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|cm3/molecule-sec
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|25
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|EST
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|-
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|}
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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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<b>*Canonical Smiles</b>
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==See also==
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*[[Androstenedione]]
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CC12CCC3C(C1CCC2O)CC=C4C3(CCC(C4)O)C
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==References==
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* {{MeshName|Androstenediol}}
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* {{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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<b>*Isomeric Smiles</b>
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[[Category:Steroids]]
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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==
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*[http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=10634]Pubchem
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*[http://www.genome.jp/dbget-bin/www_bget?compound+C04295]]KEGG Compound
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*[http://www.genome.jp/dbget-bin/www_bget?drug+D00179]]KEGG Drug
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*[http://www.hmdb.ca/metabolites/HMDB03818]Human Metabolome DataBase
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[[Categories:Hormones]]
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Revision as of 07:10, 13 February 2009

Androstenediol is a term used to refer to two different steroids with molecular weights of 290.44. They are 4-androstenediol (4-androstene-3beta,17beta-diol) and 5-androstenediol (5-androstene-3beta,17beta-diol).

4-Androstenediol is closer to testosterone structurally, and has androgenic effects.

5-Androstenediol is a direct metabolite of the most abundant steroid produced by the human adrenal cortex, dehydroepiandrosterone (DHEA). 5-Androstenediol is less androgenic than 4-androstenediol, and stimulates the immune system. When administered to rats in vivo, 5-androstenediol has approximately 1/70 the androgenicity of DHEA, 1/185 the androgenicity of androstenedione, and 1/475 the androgenicity of testosterone (Coffey, 1988). Because it induces production of white blood cells and platelets, 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).

Androstenediol is on the list of substances banned by the Major League Baseball drug policy.

Pubchem(10634)

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).

Drug Type: Small Molecule; Illicit; Experimental

KEGG Pathway(C04295,D00179)

  • Androgen and estrogen metabolism
Physiochemical properties of Androstenediol:
Physical Property Value Units Temp (deg C) Source
log P (octanol-water) 4.580 (none) EST
Atmospheric OH Rate Constant 1.24E-10 cm3/molecule-sec 25 EST


See also

References

  • Template:MeshName
  • Template:PubChem
  • 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.
  • Singh VK, Shafran RL, Inal CE, Jackson WE 3rd, Whitnall MH (2005). "Effects of whole-body gamma irradiation and 5-androstenediol administration on serum G-CSF". Immunopharmacol Immunotoxicol 27 (4): 521–34. doi:10.1080/08923970500416707. PMID 16435574. 
  • Brown GA, McKenzie D (2006). "Acute resistance exercise does not change the hormonal response to sublingual androstenediol intake". Eur J Appl Physiol 97 (4): 404–12. doi:10.1007/s00421-006-0194-9. PMID 16636857. 
  • Head CC, Farrow MJ, Sheridan JF, Padgett DA (2006). "Androstenediol reduces the anti-inflammatory effects of restraint stress during wound healing". Brain Behav Immun. doi:10.1016/j.bbi.2006.03.007. PMID 16730942. 
  • Suzuki T, Shimizu T, Szalay L, Choudhry MA, Rue LW 3rd, Bland KI, Chaudry IH (2006). "Androstenediol ameliorates alterations in immune cells cytokine production capacity in a two-hit model of trauma-hemorrhage and sepsis". Cytokine 34 (1-2): 76–84. doi:10.1016/j.cyto.2006.04.007. PMID 16737821. 
  • Kiang JG, Peckham RM, Duke LE, Shimizu T, Chaudry IH, Tsokos GC (2007). "Androstenediol inhibits the trauma-hemorrhage-induced increase in caspase-3 by downregulating the inducible nitric oxide synthase pathway". J Appl Physiol 102 (3): 933–41. doi:10.1152/japplphysiol.00919.2006. PMID 17110508. 
  • Xiao M, Inal CE, Parekh VI, Chang CM, Whitnall MH (2007). "5-Androstenediol promotes survival of gamma-irradiated human hematopoietic progenitors through induction of NF-kappa B activation and G-CSF expression". Mol Pharmacol 72: 370-9. PMID 17473057. 
  • Singh VK, Grace MB, Jacobsen KO, Chang CM, Parekh VI, Inal CE, Shafran RL, Whitnall AD, Kao TC, Jackson WE 3rd, Whitnall MH (2008). "Administration of 5-androstenediol to mice: Pharmacokinetics and cytokine gene expression". Exp Molec Pathol 84: 178-188. PMID 18262521. Template:Pharma-stub
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