5-Androstenediol

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5-Androstenediol
5-Androstenediol.png
5-Androstenediol3D.png
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
Clinical data
Legal status ?
Identifiers
CAS number 521-17-5
ATC code ?
PubChem CID 10634
ChemSpider 10188 YesY
UNII 95PS51EMXY YesY
ChEBI CHEBI:2710 YesY
ChEMBL CHEMBL440283 YesY
Chemical data
Formula C19H30O2 
Mol. mass 290.44
 YesY (what is this?)  (verify)

5-Androstenediol (androst-5-ene-3β,17β-diol or 5-AED) is one of two androstenediols, the other being 4-androstenediol.

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.[1]

Steroidogenesis, with 5-Androstenediol at bottom left.

Use as radiation countermeasure[edit]

5-AED's value as a radiation countermeasure is based mainly on its stimulation of production of white blood cells and platelets.[2] Its potential use as a radiation countermeasure was introduced by the Armed Forces Radiobiology Research Institute (AFRRI) and subsequently studied by AFRRI and Hollis-Eden Pharmaceuticals under the tradename Neumune for the treatment of acute radiation syndrome.[2][3]

The clinical trials on rhesus monkeys were successful. According to the Hollis-Eden report, only 12.5% of the 40 Neumune-treated animals died versus 32.5% in the placebo group.[4]

Hollis-Eden had applied for a contract from the US Government under the BioShield Request for Proposals (RFP) for radiation countermeasures. After being encouraged for 2.5 years that Neumune was in the competitive range, on March 9, 2007, the RFP was canceled by HHS. According to HHS, "the product was no longer in the competitive range".[5][6] No further explanation was given. As a result, Hollis-Eden has now withdrawn from the radiation countermeasure field.

See also[edit]

References[edit]

  1. ^ 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.
  2. ^ a b Whitnall MH, Elliott TB, Harding RA, Inal CE, Landauer MR, Wilhelmsen CL, McKinney L, Miner VL, Jackson WE 3rd, Loria RM, Ledney GD, Seed TM (2000). "Androstenediol stimulates myelopoiesis and enhances resistance to infection in gamma-irradiated mice". Int. J. Immunopharmacol. 22 (1): 1–14. doi:10.1016/s0192-0561(99)00059-4. PMID 10684984.  edit
  3. ^ Grace MB, Singh VK, Rhee JG, Jackson WE 3rd, Kao TC, Whitnall MH (2012). "5-AED enhances survival of irradiated mice in a G-CSF-dependent manner, stimulates innate immune cell function, reduces radiation-induced DNA damage and induces genes that modulate cell cycle progression and apoptosis". J. Radiat. Res. 53 (6): 840–853. doi:10.1093/jrr/rrs060. PMID 22843381.  edit
  4. ^ Hollis-Eden Pharmaceuticals Reports Publication of Results Demonstrating the Ability of NEUMUNE(R) to Increase Survival in a Primate Model of Lethal Radiation Injury, February 26, 2007.
  5. ^ Government Nukes Hollis-Eden's Radiation Drug, by Val Brickates Kennedy and Angela Moore, March 8, 2007
  6. ^ US cancels radiation contract with Hollis-Eden, March 9, 2007

External links[edit]