Androstenediol

Last updated • 2 min readFrom Wikipedia, The Free Encyclopedia
Androstenediol
Androstendiol.svg
Androstenediol molecule ball.png
Clinical data
Other namesA5; Δ5-Diol; Androstenediol; Androst-5-ene-3β,17β-diol; Hermaphrodiol; HE2100
Routes of
administration 		By mouth
Drug class Androgen; Anabolic steroid
Identifiers
  • (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
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.007.553 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C19H30O2
Molar mass 290.447 g·mol−1
3D model (JSmol)
  • O[C@@H]4C/C3=C/C[C@@H]1[C@H](CC[C@@]2([C@@H](O)CC[C@@H]12)C)[C@@]3(C)CC4
  • InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h3,13-17,20-21H,4-11H2,1-2H3/t13-,14-,15-,16-,17-,18-,19-/m0/s1 Yes check.svgY
  • Key:QADHLRWLCPCEKT-LOVVWNRFSA-N Yes check.svgY
   (verify)

Androstenediol, or 5-androstenediol (abbreviated as A5 or Δ5-diol), also known as androst-5-ene-3β,17β-diol, is an endogenous weak androgen and estrogen steroid hormone and intermediate in the biosynthesis of testosterone from dehydroepiandrosterone (DHEA). It is closely related to androstenedione (androst-4-ene-3,17-dione).

Contents

Biological activity

Androstenediol is a direct metabolite of the most abundant steroid produced by the human adrenal cortex, DHEA. It is less androgenic than the related compound, Δ4-androstenediol, and has been found to stimulate the immune system. When administered to rats, androstenediol, in vivo , has approximately 1.4% of the androgenicity of DHEA, 0.54% of the androgenicity of androstenedione, and 0.21% of the androgenicity of testosterone. [1]

Androstenediol possesses potent estrogenic activity, similarly to DHEA and 3β-androstanediol. [2] It has approximately 6% and 17% of the affinity of estradiol at the ERα and ERβ, respectively. [3] Although androstenediol has far lower affinity for the ERs compared to the major estrogen estradiol, it circulates at approximately 100-fold higher concentrations, and so is thought may play a significant role as an estrogen in the body. [4]

Affinities of estrogen receptor ligands for the ERα and ERβ
Ligand Other names Relative binding affinities (RBA, %)a Absolute binding affinities (Ki, nM)aAction
ERα ERβ ERα ERβ
Estradiol E2; 17β-Estradiol1001000.115 (0.04–0.24)0.15 (0.10–2.08)Estrogen
Estrone E1; 17-Ketoestradiol16.39 (0.7–60)6.5 (1.36–52)0.445 (0.3–1.01)1.75 (0.35–9.24)Estrogen
Estriol E3; 16α-OH-17β-E212.65 (4.03–56)26 (14.0–44.6)0.45 (0.35–1.4)0.7 (0.63–0.7)Estrogen
Estetrol E4; 15α,16α-Di-OH-17β-E24.03.04.919Estrogen
Alfatradiol 17α-Estradiol20.5 (7–80.1)8.195 (2–42)0.2–0.520.43–1.2Metabolite
16-Epiestriol 16β-Hydroxy-17β-estradiol7.795 (4.94–63)50 ? ?Metabolite
17-Epiestriol 16α-Hydroxy-17α-estradiol55.45 (29–103)79–80 ? ?Metabolite
16,17-Epiestriol 16β-Hydroxy-17α-estradiol1.013 ? ?Metabolite
2-Hydroxyestradiol 2-OH-E222 (7–81)11–352.51.3Metabolite
2-Methoxyestradiol 2-MeO-E20.0027–2.01.0 ? ?Metabolite
4-Hydroxyestradiol 4-OH-E213 (8–70)7–561.01.9Metabolite
4-Methoxyestradiol 4-MeO-E22.01.0 ? ?Metabolite
2-Hydroxyestrone 2-OH-E12.0–4.00.2–0.4 ? ?Metabolite
2-Methoxyestrone 2-MeO-E1<0.001–<1<1 ? ?Metabolite
4-Hydroxyestrone 4-OH-E11.0–2.01.0 ? ?Metabolite
4-Methoxyestrone 4-MeO-E1<1<1 ? ?Metabolite
16α-Hydroxyestrone 16α-OH-E1; 17-Ketoestriol2.0–6.535 ? ?Metabolite
2-Hydroxyestriol 2-OH-E32.01.0 ? ?Metabolite
4-Methoxyestriol 4-MeO-E31.01.0 ? ?Metabolite
Estradiol sulfate E2S; Estradiol 3-sulfate<1<1 ? ?Metabolite
Estradiol disulfate Estradiol 3,17β-disulfate0.0004 ? ? ?Metabolite
Estradiol 3-glucuronide E2-3G0.0079 ? ? ?Metabolite
Estradiol 17β-glucuronide E2-17G0.0015 ? ? ?Metabolite
Estradiol 3-gluc. 17β-sulfate E2-3G-17S0.0001 ? ? ?Metabolite
Estrone sulfate E1S; Estrone 3-sulfate<1<1>10>10Metabolite
Estradiol benzoate EB; Estradiol 3-benzoate10 ? ? ?Estrogen
Estradiol 17β-benzoate E2-17B11.332.6 ? ?Estrogen
Estrone methyl ether Estrone 3-methyl ether0.145 ? ? ?Estrogen
ent-Estradiol 1-Estradiol1.31–12.349.44–80.07 ? ?Estrogen
Equilin 7-Dehydroestrone13 (4.0–28.9)13.0–490.790.36Estrogen
Equilenin 6,8-Didehydroestrone2.0–157.0–200.640.62Estrogen
17β-Dihydroequilin 7-Dehydro-17β-estradiol7.9–1137.9–1080.090.17Estrogen
17α-Dihydroequilin 7-Dehydro-17α-estradiol18.6 (18–41)14–320.240.57Estrogen
17β-Dihydroequilenin 6,8-Didehydro-17β-estradiol35–6890–1000.150.20Estrogen
17α-Dihydroequilenin 6,8-Didehydro-17α-estradiol20490.500.37Estrogen
Δ8-Estradiol 8,9-Dehydro-17β-estradiol68720.150.25Estrogen
Δ8-Estrone 8,9-Dehydroestrone19320.520.57Estrogen
Ethinylestradiol EE; 17α-Ethynyl-17β-E2120.9 (68.8–480)44.4 (2.0–144)0.02–0.050.29–0.81Estrogen
Mestranol EE 3-methyl ether ?2.5 ? ?Estrogen
Moxestrol RU-2858; 11β-Methoxy-EE35–435–200.52.6Estrogen
Methylestradiol 17α-Methyl-17β-estradiol7044 ? ?Estrogen
Diethylstilbestrol DES; Stilbestrol129.5 (89.1–468)219.63 (61.2–295)0.040.05Estrogen
Hexestrol Dihydrodiethylstilbestrol153.6 (31–302)60–2340.060.06Estrogen
Dienestrol Dehydrostilbestrol37 (20.4–223)56–4040.050.03Estrogen
Benzestrol (B2) –114 ? ? ?Estrogen
Chlorotrianisene TACE1.74 ?15.30 ?Estrogen
Triphenylethylene TPE0.074 ? ? ?Estrogen
Triphenylbromoethylene TPBE2.69 ? ? ?Estrogen
Tamoxifen ICI-46,4743 (0.1–47)3.33 (0.28–6)3.4–9.692.5SERM
Afimoxifene 4-Hydroxytamoxifen; 4-OHT100.1 (1.7–257)10 (0.98–339)2.3 (0.1–3.61)0.04–4.8SERM
Toremifene 4-Chlorotamoxifen; 4-CT ? ?7.14–20.315.4SERM
Clomifene MRL-4125 (19.2–37.2)120.91.2SERM
Cyclofenil F-6066; Sexovid151–152243 ? ?SERM
Nafoxidine U-11,000A30.9–44160.30.8SERM
Raloxifene –41.2 (7.8–69)5.34 (0.54–16)0.188–0.5220.2SERM
Arzoxifene LY-353,381 ? ?0.179 ?SERM
Lasofoxifene CP-336,15610.2–16619.00.229 ?SERM
Ormeloxifene Centchroman ? ?0.313 ?SERM
Levormeloxifene 6720-CDRI; NNC-460,0201.551.88 ? ?SERM
Ospemifene Deaminohydroxytoremifene0.82–2.630.59–1.22 ? ?SERM
Bazedoxifene – ? ?0.053 ?SERM
Etacstil GW-56384.3011.5 ? ?SERM
ICI-164,384 –63.5 (3.70–97.7)1660.20.08Antiestrogen
Fulvestrant ICI-182,78043.5 (9.4–325)21.65 (2.05–40.5)0.421.3Antiestrogen
Propylpyrazoletriol PPT49 (10.0–89.1)0.120.4092.8ERα agonist
16α-LE2 16α-Lactone-17β-estradiol14.6–570.0890.27131ERα agonist
16α-Iodo-E2 16α-Iodo-17β-estradiol30.22.30 ? ?ERα agonist
Methylpiperidinopyrazole MPP110.05 ? ?ERα antagonist
Diarylpropionitrile DPN0.12–0.256.6–1832.41.7ERβ agonist
8β-VE2 8β-Vinyl-17β-estradiol0.3522.0–8312.90.50ERβ agonist
Prinaberel ERB-041; WAY-202,0410.2767–72 ? ?ERβ agonist
ERB-196 WAY-202,196 ?180 ? ?ERβ agonist
Erteberel SERBA-1; LY-500,307 ? ?2.680.19ERβ agonist
SERBA-2 – ? ?14.51.54ERβ agonist
Coumestrol –9.225 (0.0117–94)64.125 (0.41–185)0.14–80.00.07–27.0Xenoestrogen
Genistein –0.445 (0.0012–16)33.42 (0.86–87)2.6–1260.3–12.8Xenoestrogen
Equol –0.2–0.2870.85 (0.10–2.85) ? ?Xenoestrogen
Daidzein –0.07 (0.0018–9.3)0.7865 (0.04–17.1)2.085.3Xenoestrogen
Biochanin A –0.04 (0.022–0.15)0.6225 (0.010–1.2)1748.9Xenoestrogen
Kaempferol –0.07 (0.029–0.10)2.2 (0.002–3.00) ? ?Xenoestrogen
Naringenin –0.0054 (<0.001–0.01)0.15 (0.11–0.33) ? ?Xenoestrogen
8-Prenylnaringenin 8-PN4.4 ? ? ?Xenoestrogen
Quercetin –<0.001–0.010.002–0.040 ? ?Xenoestrogen
Ipriflavone –<0.01<0.01 ? ?Xenoestrogen
Miroestrol –0.39 ? ? ?Xenoestrogen
Deoxymiroestrol –2.0 ? ? ?Xenoestrogen
β-Sitosterol –<0.001–0.0875<0.001–0.016 ? ?Xenoestrogen
Resveratrol –<0.001–0.0032 ? ? ?Xenoestrogen
α-Zearalenol –48 (13–52.5) ? ? ?Xenoestrogen
β-Zearalenol –0.6 (0.032–13) ? ? ?Xenoestrogen
Zeranol α-Zearalanol48–111 ? ? ?Xenoestrogen
Taleranol β-Zearalanol16 (13–17.8)140.80.9Xenoestrogen
Zearalenone ZEN7.68 (2.04–28)9.45 (2.43–31.5) ? ?Xenoestrogen
Zearalanone ZAN0.51 ? ? ?Xenoestrogen
Bisphenol A BPA0.0315 (0.008–1.0)0.135 (0.002–4.23)19535Xenoestrogen
Endosulfan EDS<0.001–<0.01<0.01 ? ?Xenoestrogen
Kepone Chlordecone0.0069–0.2 ? ? ?Xenoestrogen
o,p'-DDT –0.0073–0.4 ? ? ?Xenoestrogen
p,p'-DDT –0.03 ? ? ?Xenoestrogen
Methoxychlor p,p'-Dimethoxy-DDT0.01 (<0.001–0.02)0.01–0.13 ? ?Xenoestrogen
HPTE Hydroxychlor; p,p'-OH-DDT1.2–1.7 ? ? ?Xenoestrogen
Testosterone T; 4-Androstenolone<0.0001–<0.01<0.002–0.040>5000>5000Androgen
Dihydrotestosterone DHT; 5α-Androstanolone0.01 (<0.001–0.05)0.0059–0.17221–>500073–1688Androgen
Nandrolone 19-Nortestosterone; 19-NT0.010.2376553Androgen
Dehydroepiandrosterone DHEA; Prasterone0.038 (<0.001–0.04)0.019–0.07245–1053163–515Androgen
5-AndrostenediolA5; Androstenediol6173.60.9Androgen
4-Androstenediol –0.50.62319Androgen
4-Androstenedione A4; Androstenedione<0.01<0.01>10000>10000Androgen
3α-Androstanediol 3α-Adiol0.070.326048Androgen
3β-Androstanediol 3β-Adiol3762Androgen
Androstanedione 5α-Androstanedione<0.01<0.01>10000>10000Androgen
Etiocholanedione 5β-Androstanedione<0.01<0.01>10000>10000Androgen
Methyltestosterone 17α-Methyltestosterone<0.0001 ? ? ?Androgen
Ethinyl-3α-androstanediol 17α-Ethynyl-3α-adiol4.0<0.07 ? ?Estrogen
Ethinyl-3β-androstanediol 17α-Ethynyl-3β-adiol505.6 ? ?Estrogen
Progesterone P4; 4-Pregnenedione<0.001–0.6<0.001–0.010 ? ?Progestogen
Norethisterone NET; 17α-Ethynyl-19-NT0.085 (0.0015–<0.1)0.1 (0.01–0.3)1521084Progestogen
Norethynodrel 5(10)-Norethisterone0.5 (0.3–0.7)<0.1–0.221453Progestogen
Tibolone 7α-Methylnorethynodrel0.5 (0.45–2.0)0.2–0.076 ? ?Progestogen
Δ4-Tibolone 7α-Methylnorethisterone0.069–<0.10.027–<0.1 ? ?Progestogen
3α-Hydroxytibolone –2.5 (1.06–5.0)0.6–0.8 ? ?Progestogen
3β-Hydroxytibolone –1.6 (0.75–1.9)0.070–0.1 ? ?Progestogen
Footnotes:a = (1) Binding affinity values are of the format "median (range)" (# (#–#)), "range" (#–#), or "value" (#) depending on the values available. The full sets of values within the ranges can be found in the Wiki code. (2) Binding affinities were determined via displacement studies in a variety of in-vitro systems with labeled estradiol and human ERα and ERβ proteins (except the ERβ values from Kuiper et al. (1997), which are rat ERβ). Sources: See template page.

Chemistry

Androstenediol, also known as androst-5-ene-3β,17β-diol, is a naturally occurring androstane steroid. [5] It is closely related structurally to androstenedione (A4; androst-4-ene-3,17-dione), dehydroepiandrosterone (DHEA; androst-5-en-3β-ol-17-one), and testosterone (androst-4-en-17β-ol-3-one), as well as to 3β-androstanediol (5α-androstane-3β,17β-diol). [5]

Derivatives and analogues of androstenediol, such as the 17α-substituted methandriol (17α-methylandrostenediol) and ethinylandrostenediol (17α-ethynylandrostenediol) as well as the naturally occurring 19-norandrostane derivative norandostenediol (19-nor-5-androstenediol), have been synthesized and studied. Methandriol and its esters are androgens and anabolic steroids while ethinylandrostenediol is an estrogen.

Research

Radiation countermeasure

Androstenediol has been investigated for use as a radiation countermeasure. Its value as a radiation countermeasure is based mainly on its stimulation of production of white blood cells and platelets. [6] Its potential use as a radiation countermeasure was developed by the Armed Forces Radiobiology Research Institute (AFRRI) and subsequently studied by AFRRI and Hollis-Eden Pharmaceuticals under the proposed brand name Neumune for the treatment of acute radiation syndrome. [6] [7]

The clinical trials with 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. [8]

Hollis-Eden had applied for a contract from the U.S. 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". [9] [10] No further explanation was given. As a result, Hollis-Eden has now withdrawn from the radiation countermeasure field.

Additional images

Steroidogenesis, with androstenediol at bottom left. Steroidogenesis.svg
Steroidogenesis, with androstenediol at bottom left.

Related Research Articles

An androgen prohormone, or proandrogen, is a prohormone of an anabolic-androgenic steroid (AAS). They can be prohormones of testosterone or of synthetic AAS, for example, nandrolone (19-nortestosterone). Dehydroepiandrosterone (DHEA), DHEA sulfate (DHEA-S), and androstenedione may all be considered proandrogens of testosterone.

<span class="mw-page-title-main">Androstenedione</span> Endogenous weak androgen

Androstenedione, or 4-androstenedione, also known as androst-4-ene-3,17-dione, is an endogenous weak androgen steroid hormone and intermediate in the biosynthesis of estrone and of testosterone from dehydroepiandrosterone (DHEA). It is closely related to androstenediol (androst-5-ene-3β,17β-diol).

Androstenediol may refer to:

<span class="mw-page-title-main">1-Testosterone</span> Chemical compound

1-Testosterone, also known as δ1-dihydrotestosterone (δ1-DHT), as well as dihydroboldenone, is a synthetic anabolic–androgenic steroid (AAS) and a 5α-reduced derivative of boldenone (Δ1-testosterone). It differs from testosterone by having a 1(2)-double bond instead of a 4(5)-double bond in its A ring. It was legally sold online in the United States until 2005, when it was reclassified as a Schedule III drug.

<span class="mw-page-title-main">4-Androstenediol</span> Chemical compound

4-Androstenediol, also known as androst-4-ene-3β,17β-diol, is an androstenediol that is converted to testosterone. The conversion rate is about 15.76%, almost triple that of 4-androstenedione, due to utilization of a different enzymatic pathway. There is also some conversion into estrogen, since testosterone is the metabolic precursor of the estrogens.

<span class="mw-page-title-main">Methandriol</span> Chemical compound

Methandriol, also known as methylandrostenediol, is an androgen and anabolic steroid (AAS) medication which was developed by Organon and is used in both oral and injectable formulations. It is an orally active 17α-alkylated AAS and a derivative of the endogenous androgen prohormone androstenediol.

<span class="mw-page-title-main">3β-Androstanediol</span> Chemical compound

3β-Androstanediol, also known as 5α-androstane-3β,17β-diol, and sometimes shortened in the literature to 3β-diol, is an endogenous steroid hormone and a metabolite of androgens like dehydroepiandrosterone (DHEA) and dihydrotestosterone (DHT).

Androstenedione may refer to:

Androstenolone may refer to:

Methandriol bisenanthoyl acetate, or methylandrostenediol bisenanthoyl acetate, also known as 17α-methylandrost-5-ene-3β,17β-diol 3β,17β-di(3-oxononanoate), is a synthetic, injected anabolic–androgenic steroid (AAS) and a 17α-alkylated derivative of 5-androstenediol. It is an androgen ester—specifically, the C3β,17β di(3-oxononanoate) ester of methandriol (17α-methyl-5-androstenediol)—and acts as a prodrug of methandriol in the body. Methandriol bisenanthoyl acetate is administered by intramuscular injection and, relative to methandriol, has an extended duration via this route due to a depot effect afforded by its ester.

<span class="mw-page-title-main">Methandriol diacetate</span> Chemical compound

Methandriol diacetate, or methylandrostenediol diacetate, also known as 17α-methylandrost-5-ene-3β,17β-diol 3β,17β-diacetate, is a synthetic, injected anabolic–androgenic steroid (AAS) and a 17α-alkylated derivative of 5-androstenediol that was never marketed. It is an androgen ester – specifically, the C3,17β diacetate ester of methandriol (17α-methyl-5-androstenediol) – and acts as a prodrug of methandriol in the body.

<span class="mw-page-title-main">19-Nor-5-androstenediol</span> Chemical compound

19-Nor-5-androstenediol, also known as estr-5-ene-3β,17β-diol, is a synthetic, orally active anabolic-androgenic steroid (AAS) and a derivative of 19-nortestosterone (nandrolone) that was never introduced for medical use. It is an androgen prohormone of nandrolone and of other 19-norandrostanes.

<span class="mw-page-title-main">17α-Ethynyl-3α-androstanediol</span> Chemical compound

17α-Ethynyl-3α-androstanediol, also known as 17α-ethynyl-5α-androstane-3α,17β-diol, is a synthetic androstane steroid and a 17α-substituted derivative of 3α-androstanediol which was never marketed. It was under development for the treatment of prostate cancer but was discontinued.

<span class="mw-page-title-main">Testosterone dipropionate</span> Chemical compound

Testosterone dipropionate, or testosterone 3β,17β-dipropanoate, also known as 4-androstenediol dipropionate, as well as androst-4-ene-3β,17β-diol 3β,17β-dipropanoate, is a synthetic anabolic-androgenic steroid and an androgen ester which was never marketed. It is the 3β,17β-dipropionate (dipropanoate) diester of testosterone (androst-4-en-17β-ol-3-one), or, more accurately, of 4-androstenediol (androst-4-ene-3β,17β-diol).

<span class="mw-page-title-main">Testosterone diacetate</span> Chemical compound

Testosterone diacetate, or testosterone 3β,17β-diacetate, also known as 4-androstenediol diacetate, as well as androst-4-ene-3β,17β-diol 3β,17β-diacetate, is a synthetic anabolic-androgenic steroid and an androgen ester which was never marketed. It is the 3β,17β-diacetate diester of testosterone (androst-4-en-17β-ol-3-one), or, more accurately, of 4-androstenediol (androst-4-ene-3β,17β-diol).

<span class="mw-page-title-main">Testosterone acetate butyrate</span> Chemical compound

Testosterone acetate butyrate, or testosterone 3β-acetate 17β-butanoate, also known as 4-androstenediol acetate butyrate, as well as androst-4-ene-3β,17β-diol 3β-acetate 17β-butanoate, is a synthetic anabolic-androgenic steroid and an androgen ester which was never marketed. It is the 3β-acetate, 17β-butyrate (butanoate) diester of testosterone (androst-4-en-17β-ol-3-one), or, more accurately, of 4-androstenediol (androst-4-ene-3β,17β-diol).

<span class="mw-page-title-main">Testosterone acetate propionate</span> Chemical compound

Testosterone acetate propionate, or testosterone 3β-acetate 17β-propanoate, also known as 4-androstenediol acetate propionate, as well as androst-4-ene-3β,17β-diol 3β-acetate 17β-propanoate, is a synthetic anabolic-androgenic steroid and an androgen ester which was never marketed. It is the 3β-acetate, 17β-propionate (propanoate) diester of testosterone (androst-4-en-17β-ol-3-one), or, more accurately, of 4-androstenediol (androst-4-ene-3β,17β-diol).

<span class="mw-page-title-main">17α-Ethynyl-3β-androstanediol</span> Chemical compound

17α-Ethynyl-3β-androstanediol is a synthetic estrogen and a 17α-substituted derivative of 3β-androstanediol which was never marketed.

<span class="mw-page-title-main">Ethinylandrostenediol</span> Chemical compound

Ethinylandrostenediol, also known as 17α-ethynyl-5-androstenediol, is a synthetic estrogen, progestogen, and androgen which was never marketed. It is the C17α ethynyl derivative of the androgen precursor and prohormone 5-androstenediol.

References

  1. ↑ Coffey DS (1988). "Androgen action and the sex accessory tissues". In Knobil E, Neill J (eds.). The Physiology of Reproduction. New York: Raven Press. pp. 1081–1119.
  2. ↑ Hackenberg R, Turgetto I, Filmer A, Schulz KD (November 1993). "Estrogen and androgen receptor mediated stimulation and inhibition of proliferation by androst-5-ene-3 beta,17 beta-diol in human mammary cancer cells". The Journal of Steroid Biochemistry and Molecular Biology. 46 (5): 597–603. doi:10.1016/0960-0760(93)90187-2. PMID   8240982. S2CID   54256515.
  3. ↑ Kuiper GG, Carlsson B, Grandien K, Enmark E, Häggblad J, Nilsson S, Gustafsson JA (March 1997). "Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta". Endocrinology. 138 (3): 863–870. doi: 10.1210/endo.138.3.4979 . PMID   9048584.
  4. ↑ Bradbury R (30 January 2007). Cancer. Springer Science & Business Media. pp. 43–. ISBN   978-3-540-33120-9.
  5. 1 2 Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 86–. ISBN   978-1-4757-2085-3.
  6. 1 2 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.
  7. ↑ 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. PMC   3483857 . PMID   22843381.
  8. ↑ 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.
  9. ↑ Government Nukes Hollis-Eden's Radiation Drug, by Val Brickates Kennedy and Angela Moore, March 8, 2007
  10. ↑ US cancels radiation contract with Hollis-Eden Archived 2007-09-12 at archive.today , March 9, 2007


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