Androstenediol

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'''Androstenediol'''
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{{Drugbox
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| IUPAC_name        = (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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| CAS_number        =
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| CAS_supplemental  =
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| ATC_suffix = BA03
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| ATC_supplemental  =
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| PubChem          = 10634
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| ChemSpiderID      =
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| chemical_formula  =C19H30O2
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| molecular_weight  = 290.44
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| smiles            = CC12CCC3C(C1CCC2O)CC=C4C3(CCC(C4)O)C
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| synonyms          = Androst-5-enediol
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| density          =
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| melting_point    =
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| boiling_point    =
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| solubility        =
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| specific_rotation =
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| sec_combustion    =
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| bioavailability  =
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| protein_bound    =
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| metabolism        =
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| elimination_half-life =
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| excretion        =
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| pregnancy_category=
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| dependency_liability =
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| routes_of_administration =
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}}
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[http://172.141.127.22/raghava/hmrbase/test_extract.php?db=arun&table=nphormonet&id=1016&show=SHOW-3D Show 3-D Structure]
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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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Pubchem(10634)
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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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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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4-Androstenediol is closer to [[testosterone]] structurally, and has [[androgen]]ic effects.  
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'''Drug Type''':  Small Molecule; Illicit; Experimental
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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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'''KEGG Pathway'''(C04295,D00179)
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Androstenediol is on the list of substances banned by the [[Major League Baseball drug policy]].
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*Androgen and estrogen metabolism
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==physiochemical Properties==
{| border="1;width:100%; height:200px;style=text-align:center"
{| border="1;width:100%; height:200px;style=text-align:center"
|+'''Physiochemical properties of Androstenediol:'''
|+'''Physiochemical properties of Androstenediol:'''
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|EST
|EST
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|Atmospheric OH Rate Constant
|Atmospheric OH Rate Constant
|1.24E-10
|1.24E-10
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==See also==
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*[[Androstenedione]]
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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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[[category:Hormones]]
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[[Category:Steroids]]
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{{pharma-stub}}

Current revision

Androstenediol
Systematic (IUPAC) name
(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
Identifiers
CAS number  ?
ATC code  ?
PubChem 10634
Chemical data
Formula C19H30O2
Mol. mass 290.44
SMILES eMolecules & PubChem
Synonyms Androst-5-enediol
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.

?

Legal status
Routes  ?

Show 3-D Structure

Contents

[edit] 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).

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.

[edit] physiochemical Properties

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


[edit] See also

[edit] 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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