Androstenediol
From DrugPedia: A Wikipedia for Drug discovery
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| + | {{Drugbox | ||
| + | | 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 | ||
| + | | CAS_number = | ||
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| + | | ATC_suffix = BA03 | ||
| + | | ATC_supplemental = | ||
| + | | PubChem = 10634 | ||
| + | | ChemSpiderID = | ||
| + | | chemical_formula =C19H30O2 | ||
| + | | molecular_weight = 290.44 | ||
| + | | smiles = CC12CCC3C(C1CCC2O)CC=C4C3(CCC(C4)O)C | ||
| + | | synonyms = Androst-5-enediol | ||
| + | | density = | ||
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| + | | bioavailability = | ||
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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] | [http://172.141.127.22/raghava/hmrbase/test_extract.php?db=arun&table=nphormonet&id=1016&show=SHOW-3D Show 3-D Structure] | ||
| + | ==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 [[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). | '''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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Androstenediol is on the list of substances banned by the [[Major League Baseball drug policy]]. | Androstenediol is on the list of substances banned by the [[Major League Baseball drug policy]]. | ||
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{| 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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* {{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}} | * {{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}} | ||
| + | [[category:Hormones]] | ||
[[Category:Steroids]] | [[Category:Steroids]] | ||
{{pharma-stub}} | {{pharma-stub}} | ||
Revision as of 12:27, 19 February 2009
| 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 | |
| Chemical data | |
| Formula | C19H30O2 |
| Mol. mass | 290.44 |
| SMILES | & |
| Synonyms | Androst-5-enediol |
| Pharmacokinetic data | |
| Bioavailability | ? |
| Metabolism | ? |
| Half life | ? |
| Excretion | ? |
| Therapeutic considerations | |
| Pregnancy cat. |
? |
| Legal status | |
| Routes | ? |
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.
| 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
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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.
- 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:. 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:. 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:. 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:. 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:. 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
