5-Androstenediol

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

5-Androstenediol (androst-5-ene-3beta,17beta-diol or 5-AED) is one of two androstenediols. 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.[1]

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.[2]

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".[3][4] No further explanation was given. As a result, Hollis-Eden has now withdrawn from the radiation countermeasure field.

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.[5] 5-AED's value as a radiation countermeasure is based mainly on its stimulation of production of white blood cells and platelets.[1]

See also

References

  1. ^ a b Whitnall MH, Elliott TB, Harding RA et al. (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. 
  2. ^ 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.
  3. ^ Government Nukes Hollis-Eden's Radiation Drug, by Val Brickates Kennedy and Angela Moore, March 8, 2007
  4. ^ US cancels radiation contract with Hollis-Eden, March 9, 2007
  5. ^ 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.

External links

Mevalonate pathway
Geranyl-
Non-mevalonate pathway
DOXP · MEP · CDP-ME · CDP-MEP · MEcPP · HMB-PP · IPP · DMAPP
To Cholesterol
Steroid
Androgens
(C19 androstane)
Estrogens
(C18 estrane)
Nonhuman

M: MET

mt, k, c/g/r/p/y/i, f/h/s/l/o/e, a/u, n, m

k, cgrp/y/i, f/h/s/l/o/e, au, n, m, epon

m(A16/C10),i(k, c/g/r/p/y/i, f/h/s/o/e, a/u, n, m)

M: END

anat/phys/devp/horm

noco(d)/cong/tumr, sysi/epon

proc, drug (A10/H1/H2/H3/H5)
biochemical families: prot · nucl · carb (glpr, alco, glys) · lipd (fata/i, phld, strd, gllp, eico) · amac/i · ncbs/i · ttpy/i