Revision as of 01:37, 30 April 2012 editVanished 45kd09la13 (talk | contribs)26,505 editsNo edit summary← Previous edit | Latest revision as of 11:08, 12 February 2024 edit undoGraeme Bartlett (talk | contribs)Administrators249,468 edits drugbank | ||
(84 intermediate revisions by 39 users not shown) | |||
Line 1: | Line 1: | ||
{{Short description|Chemical compound}} | |||
{{About|androstenediol the hormone|other uses|Androstenediol (disambiguation)}} | |||
{{Distinguish|androstanedione|androstanediol|androstenedione|androstadienol}} | |||
{{Drugbox | {{Drugbox | ||
⚫ | | verifiedrevid = 477224050 | ||
| Watchedfields = changed | |||
⚫ | | IUPAC_name = (3''S'',8''R'',9''S'',10''R'',13''S'',14''S'',17''S'')-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1''H''-cyclopentaphenanthrene-3,17-diol | ||
⚫ | | verifiedrevid = |
||
| image = Androstendiol.svg | |||
⚫ | | IUPAC_name = (3''S'',8''R'',9''S'',10''R'',13''S'',14''S'',17''S'')-10,13- |
||
| width = 225px | |||
| image = 5-Androstenediol.png | |||
| image2 = |
| image2 = Androstenediol molecule ball.png | ||
| width2 = 235px | |||
<!--Clinical data--> | <!--Clinical data--> | ||
| tradename = |
| tradename = | ||
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | ||
| pregnancy_US = <!-- A / B |
| pregnancy_US = <!-- A / B / C / D / X --> | ||
| pregnancy_category = |
| pregnancy_category = | ||
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> | | legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> | ||
| legal_CA = <!-- |
| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> | ||
| legal_UK = <!-- GSL |
| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C --> | ||
| legal_US = <!-- OTC |
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> | ||
| legal_status = |
| legal_status = | ||
| routes_of_administration = | | routes_of_administration = ] | ||
| class = ]; ] | |||
<!--Pharmacokinetic data--> | <!--Pharmacokinetic data--> | ||
| bioavailability = |
| bioavailability = | ||
| protein_bound = |
| protein_bound = | ||
| metabolism = |
| metabolism = | ||
| elimination_half-life = |
| elimination_half-life = | ||
| excretion = |
| excretion = | ||
<!--Identifiers--> | <!--Identifiers--> | ||
| |
| CAS_number_Ref = {{cascite|correct|CAS}} | ||
| CAS_number = 521-17-5 | | CAS_number = 521-17-5 | ||
| |
| CAS_supplemental = | ||
| |
| ATC_prefix = | ||
| ATC_suffix = | |||
| PubChem = 10634 | | PubChem = 10634 | ||
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | ||
| DrugBank = |
| DrugBank = DB01524 | ||
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ||
| ChemSpiderID = 10188 | | ChemSpiderID = 10188 | ||
| UNII_Ref = {{fdacite|correct|FDA}} | | UNII_Ref = {{fdacite|correct|FDA}} | ||
| UNII = 95PS51EMXY | | UNII = 95PS51EMXY | ||
| KEGG = C04295 | |||
| ChEBI_Ref = {{ebicite|correct|EBI}} | | ChEBI_Ref = {{ebicite|correct|EBI}} | ||
| ChEBI = 2710 | | ChEBI = 2710 | ||
| ChEMBL_Ref = {{ebicite|correct|EBI}} | | ChEMBL_Ref = {{ebicite|correct|EBI}} | ||
| ChEMBL = 440283 | | ChEMBL = 440283 | ||
| synonyms = A5; Δ<sup>5</sup>-Diol; Androstenediol; Androst-5-ene-3β,17β-diol; Hermaphrodiol; HE2100 | |||
<!--Chemical data--> | <!--Chemical data--> | ||
| C=19 | H=30 | O=2 |
| C=19 | H=30 | O=2 | ||
⚫ | | SMILES = O4C/C3=C/C1(CC2((O)CC12)C)3(C)CC4 | ||
| molecular_weight = 290.44 | |||
⚫ | | |
||
| InChI = 1/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 | |||
| InChIKey = QADHLRWLCPCEKT-LOVVWNRFBV | |||
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | ||
| StdInChI = 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 | | StdInChI = 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 | ||
Line 54: | Line 59: | ||
}} | }} | ||
'''Androstenediol''', or '''5-androstenediol''' (abbreviated as '''A5''' or '''Δ<sup>5</sup>-diol'''), also known as '''androst-5-ene-3β,17β-diol''', is an ] weak ] and ] ] and ] in the ] of ] from ] (DHEA). It is closely related to ] (androst-4-ene-3,17-dione). | |||
'''5-Androstenediol''' ('''androst'''-5-'''ene'''-3β,17β-'''diol''' or 5-AED) is one of two ]. | |||
==Biological activity== | |||
Its potential use as a ] countermeasure was introduced by the ] (AFRRI) and subsequently studied by AFRRI and ] under the tradename Neumune for the treatment of ].<ref name="IJI">{{cite journal |author=Whitnall MH |title=Androstenediol stimulates myelopoiesis and enhances resistance to infection in gamma-irradiated mice |journal=Int. J. Immunopharmacol. |volume=22 |issue=1 |pages=1–14 |year=2000 |pmid=10684984 |doi=10.1016/S0192-0561(99)00059-4 |author-separator=, |author2=Elliott TB |author3=Harding RA |display-authors=3 |last4=Inal |first4=CE |last5=Landauer |first5=MR |last6=Wilhelmsen |first6=CL |last7=McKinney |first7=L |last8=Miner |first8=VL |last9=Jackson |first9=WE3rd}}</ref> | |||
⚫ | Androstenediol is a direct ] of the most abundant ] produced by the human ], DHEA. It is less ]ic than the related compound, ], and has been found to stimulate the ]. When administered to ]s, androstenediol, '']'', has approximately 1.4% of the ]icity of DHEA, 0.54% of the androgenicity of ], and 0.21% of the androgenicity of testosterone.<ref>{{cite book | vauthors = Coffey DS | date = 1988 | chapter = Androgen action and the sex accessory tissues | veditors = Knobil E, Neill J | title = The Physiology of Reproduction. | publisher = Raven Press | location = New York | pages = 1081–1119 }}</ref> | ||
Androstenediol possesses potent ]ic activity, similarly to DHEA and ].<ref name="HackenbergTurgetto1993">{{cite journal | vauthors = Hackenberg R, Turgetto I, Filmer A, Schulz KD | title = Estrogen and androgen receptor mediated stimulation and inhibition of proliferation by androst-5-ene-3 beta,17 beta-diol in human mammary cancer cells | journal = The Journal of Steroid Biochemistry and Molecular Biology | volume = 46 | issue = 5 | pages = 597–603 | date = November 1993 | pmid = 8240982 | doi = 10.1016/0960-0760(93)90187-2 | s2cid = 54256515 }}</ref> It has approximately 6% and 17% of the ] of estradiol at the ] and ], respectively.<ref name="pmid9048584">{{cite journal | vauthors = Kuiper GG, Carlsson B, Grandien K, Enmark E, Häggblad J, Nilsson S, Gustafsson JA | title = Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta | journal = Endocrinology | volume = 138 | issue = 3 | pages = 863–870 | date = March 1997 | pmid = 9048584 | doi = 10.1210/endo.138.3.4979 | doi-access = free }}</ref> Although androstenediol has far lower affinity for the ERs compared to the major estrogen ], it circulates at approximately 100-fold higher concentrations, and so is thought may play a significant role as an estrogen in the body.<ref name="Bradbury2007">{{cite book| vauthors = Bradbury R |title=Cancer|url=https://books.google.com/books?id=fdtDAAAAQBAJ&pg=PA43|date=30 January 2007|publisher=Springer Science & Business Media|isbn=978-3-540-33120-9|pages=43–}}</ref> | |||
⚫ | The clinical |
||
{{Affinities of estrogen receptor ligands for the ERα and ERβ}} | |||
⚫ | Hollis-Eden had applied for a contract from the |
||
==Chemistry== | |||
⚫ | ], with |
||
{{See also|List of androgens/anabolic steroids#Testosterone derivatives|List of androgen esters#Esters of other natural AAS}} | |||
⚫ | |||
Androstenediol, also known as androst-5-ene-3β,17β-diol, is a ] ] ].<ref name="Elks2014">{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA86|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=86–}}</ref> It is closely related structurally to ] (A4; androst-4-ene-3,17-dione), ] (DHEA; androst-5-en-3β-ol-17-one), and ] (androst-4-en-17β-ol-3-one), as well as to ] (5α-androstane-3β,17β-diol).<ref name="Elks2014" /> | |||
==See also== | |||
* ] | |||
]s and ]s of androstenediol, such as the ] ] (17α-methylandrostenediol) and ] (17α-ethynylandrostenediol) as well as the naturally occurring ] derivative ] (19-nor-5-androstenediol), have been ] and studied. Methandriol and its ]s are ]s and ]s while ethinylandrostenediol is an estrogen. | |||
⚫ | ==References== | ||
⚫ | {{Reflist}} | ||
== |
==Research== | ||
* - Official Hollis-Eden Pharmaceuticals website | |||
* | |||
===Radiation countermeasure=== | |||
{{Cholesterol and steroid intermediates}} | |||
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 ]s and ]s.<ref name="IJI" /> Its potential use as a ] countermeasure was developed by the ] (AFRRI) and subsequently studied by AFRRI and Hollis-Eden Pharmaceuticals under the proposed brand name Neumune for the treatment of ].<ref name="IJI">{{cite journal | vauthors = 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 | year = 2000 | title = Androstenediol stimulates myelopoiesis and enhances resistance to infection in gamma-irradiated mice | journal = Int. J. Immunopharmacol. | volume = 22 | issue = 1 | pages = 1–14 | pmid = 10684984 | doi=10.1016/s0192-0561(99)00059-4}}</ref><ref>{{cite journal | vauthors = Grace MB, Singh VK, Rhee JG, Jackson WE 3rd, Kao TC, Whitnall MH | year = 2012 | title = 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 | journal = J. Radiat. Res. | volume = 53 | issue = 6 | pages = 840–853 | pmid = 22843381 | doi = 10.1093/jrr/rrs060 | pmc=3483857}}</ref> | |||
⚫ | The ]s with ]s were successful. According to the Hollis-Eden report, only 12.5% of the 40 Neumune-treated animals died versus 32.5% in the ] group.<ref>, February 26, 2007.</ref> | ||
{{DEFAULTSORT:Androstenediol, 5-}} | |||
⚫ | ] | ||
⚫ | 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 ]. According to HHS, "the product was no longer in the competitive range".<ref>, by Val Brickates Kennedy and Angela Moore, March 8, 2007</ref><ref> {{webarchive|url=https://archive.today/20070912210559/http://new.quote.com/stocks/story.action?id=DTM068x6797 |date=2007-09-12 }}, March 9, 2007</ref> No further explanation was given. As a result, Hollis-Eden has now withdrawn from the radiation countermeasure field. | ||
==Additional images== | |||
⚫ | ], with androstenediol at bottom left.]] | ||
{{Clear}} | |||
⚫ | ==References== | ||
⚫ | {{Reflist|30em}} | ||
{{Endogenous steroids}} | |||
{{Navboxes | |||
| title = ] | |||
| titlestyle = background:#ccccff | |||
| list1 = | |||
{{Androgen receptor modulators}} | |||
{{Estrogen receptor modulators}} | |||
{{Xenobiotic-sensing receptor modulators}} | |||
}} | |||
] | |||
] | |||
] | ] | ||
⚫ | ] | ||
] | |||
] |
Latest revision as of 11:08, 12 February 2024
Chemical compound This article is about androstenediol the hormone. For other uses, see Androstenediol (disambiguation). Not to be confused with androstanedione, androstanediol, androstenedione, or androstadienol. Pharmaceutical compoundClinical data | |
---|---|
Other names | A5; Δ-Diol; Androstenediol; Androst-5-ene-3β,17β-diol; Hermaphrodiol; HE2100 |
Routes of administration | By mouth |
Drug class | Androgen; Anabolic steroid |
Identifiers | |
IUPAC name
| |
CAS Number | |
PubChem CID | |
DrugBank | |
ChemSpider | |
UNII | |
KEGG | |
ChEBI | |
ChEMBL | |
CompTox Dashboard (EPA) | |
ECHA InfoCard | 100.007.553 |
Chemical and physical data | |
Formula | C19H30O2 |
Molar mass | 290.447 g·mol |
3D model (JSmol) | |
SMILES
| |
InChI
| |
(verify) |
Androstenediol, or 5-androstenediol (abbreviated as A5 or Δ-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).
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, Δ-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.
Androstenediol possesses potent estrogenic activity, similarly to DHEA and 3β-androstanediol. It has approximately 6% and 17% of the affinity of estradiol at the ERα and ERβ, respectively. 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.
Ligand | Other names | Relative binding affinities (RBA, %) | Absolute binding affinities (Ki, nM) | Action | ||
---|---|---|---|---|---|---|
ERα | ERβ | ERα | ERβ | |||
Estradiol | E2; 17β-Estradiol | 100 | 100 | 0.115 (0.04–0.24) | 0.15 (0.10–2.08) | Estrogen |
Estrone | E1; 17-Ketoestradiol | 16.39 (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-E2 | 12.65 (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-E2 | 4.0 | 3.0 | 4.9 | 19 | Estrogen |
Alfatradiol | 17α-Estradiol | 20.5 (7–80.1) | 8.195 (2–42) | 0.2–0.52 | 0.43–1.2 | Metabolite |
16-Epiestriol | 16β-Hydroxy-17β-estradiol | 7.795 (4.94–63) | 50 | ? | ? | Metabolite |
17-Epiestriol | 16α-Hydroxy-17α-estradiol | 55.45 (29–103) | 79–80 | ? | ? | Metabolite |
16,17-Epiestriol | 16β-Hydroxy-17α-estradiol | 1.0 | 13 | ? | ? | Metabolite |
2-Hydroxyestradiol | 2-OH-E2 | 22 (7–81) | 11–35 | 2.5 | 1.3 | Metabolite |
2-Methoxyestradiol | 2-MeO-E2 | 0.0027–2.0 | 1.0 | ? | ? | Metabolite |
4-Hydroxyestradiol | 4-OH-E2 | 13 (8–70) | 7–56 | 1.0 | 1.9 | Metabolite |
4-Methoxyestradiol | 4-MeO-E2 | 2.0 | 1.0 | ? | ? | Metabolite |
2-Hydroxyestrone | 2-OH-E1 | 2.0–4.0 | 0.2–0.4 | ? | ? | Metabolite |
2-Methoxyestrone | 2-MeO-E1 | <0.001–<1 | <1 | ? | ? | Metabolite |
4-Hydroxyestrone | 4-OH-E1 | 1.0–2.0 | 1.0 | ? | ? | Metabolite |
4-Methoxyestrone | 4-MeO-E1 | <1 | <1 | ? | ? | Metabolite |
16α-Hydroxyestrone | 16α-OH-E1; 17-Ketoestriol | 2.0–6.5 | 35 | ? | ? | Metabolite |
2-Hydroxyestriol | 2-OH-E3 | 2.0 | 1.0 | ? | ? | Metabolite |
4-Methoxyestriol | 4-MeO-E3 | 1.0 | 1.0 | ? | ? | Metabolite |
Estradiol sulfate | E2S; Estradiol 3-sulfate | <1 | <1 | ? | ? | Metabolite |
Estradiol disulfate | Estradiol 3,17β-disulfate | 0.0004 | ? | ? | ? | Metabolite |
Estradiol 3-glucuronide | E2-3G | 0.0079 | ? | ? | ? | Metabolite |
Estradiol 17β-glucuronide | E2-17G | 0.0015 | ? | ? | ? | Metabolite |
Estradiol 3-gluc. 17β-sulfate | E2-3G-17S | 0.0001 | ? | ? | ? | Metabolite |
Estrone sulfate | E1S; Estrone 3-sulfate | <1 | <1 | >10 | >10 | Metabolite |
Estradiol benzoate | EB; Estradiol 3-benzoate | 10 | ? | ? | ? | Estrogen |
Estradiol 17β-benzoate | E2-17B | 11.3 | 32.6 | ? | ? | Estrogen |
Estrone methyl ether | Estrone 3-methyl ether | 0.145 | ? | ? | ? | Estrogen |
ent-Estradiol | 1-Estradiol | 1.31–12.34 | 9.44–80.07 | ? | ? | Estrogen |
Equilin | 7-Dehydroestrone | 13 (4.0–28.9) | 13.0–49 | 0.79 | 0.36 | Estrogen |
Equilenin | 6,8-Didehydroestrone | 2.0–15 | 7.0–20 | 0.64 | 0.62 | Estrogen |
17β-Dihydroequilin | 7-Dehydro-17β-estradiol | 7.9–113 | 7.9–108 | 0.09 | 0.17 | Estrogen |
17α-Dihydroequilin | 7-Dehydro-17α-estradiol | 18.6 (18–41) | 14–32 | 0.24 | 0.57 | Estrogen |
17β-Dihydroequilenin | 6,8-Didehydro-17β-estradiol | 35–68 | 90–100 | 0.15 | 0.20 | Estrogen |
17α-Dihydroequilenin | 6,8-Didehydro-17α-estradiol | 20 | 49 | 0.50 | 0.37 | Estrogen |
Δ-Estradiol | 8,9-Dehydro-17β-estradiol | 68 | 72 | 0.15 | 0.25 | Estrogen |
Δ-Estrone | 8,9-Dehydroestrone | 19 | 32 | 0.52 | 0.57 | Estrogen |
Ethinylestradiol | EE; 17α-Ethynyl-17β-E2 | 120.9 (68.8–480) | 44.4 (2.0–144) | 0.02–0.05 | 0.29–0.81 | Estrogen |
Mestranol | EE 3-methyl ether | ? | 2.5 | ? | ? | Estrogen |
Moxestrol | RU-2858; 11β-Methoxy-EE | 35–43 | 5–20 | 0.5 | 2.6 | Estrogen |
Methylestradiol | 17α-Methyl-17β-estradiol | 70 | 44 | ? | ? | Estrogen |
Diethylstilbestrol | DES; Stilbestrol | 129.5 (89.1–468) | 219.63 (61.2–295) | 0.04 | 0.05 | Estrogen |
Hexestrol | Dihydrodiethylstilbestrol | 153.6 (31–302) | 60–234 | 0.06 | 0.06 | Estrogen |
Dienestrol | Dehydrostilbestrol | 37 (20.4–223) | 56–404 | 0.05 | 0.03 | Estrogen |
Benzestrol (B2) | – | 114 | ? | ? | ? | Estrogen |
Chlorotrianisene | TACE | 1.74 | ? | 15.30 | ? | Estrogen |
Triphenylethylene | TPE | 0.074 | ? | ? | ? | Estrogen |
Triphenylbromoethylene | TPBE | 2.69 | ? | ? | ? | Estrogen |
Tamoxifen | ICI-46,474 | 3 (0.1–47) | 3.33 (0.28–6) | 3.4–9.69 | 2.5 | SERM |
Afimoxifene | 4-Hydroxytamoxifen; 4-OHT | 100.1 (1.7–257) | 10 (0.98–339) | 2.3 (0.1–3.61) | 0.04–4.8 | SERM |
Toremifene | 4-Chlorotamoxifen; 4-CT | ? | ? | 7.14–20.3 | 15.4 | SERM |
Clomifene | MRL-41 | 25 (19.2–37.2) | 12 | 0.9 | 1.2 | SERM |
Cyclofenil | F-6066; Sexovid | 151–152 | 243 | ? | ? | SERM |
Nafoxidine | U-11,000A | 30.9–44 | 16 | 0.3 | 0.8 | SERM |
Raloxifene | – | 41.2 (7.8–69) | 5.34 (0.54–16) | 0.188–0.52 | 20.2 | SERM |
Arzoxifene | LY-353,381 | ? | ? | 0.179 | ? | SERM |
Lasofoxifene | CP-336,156 | 10.2–166 | 19.0 | 0.229 | ? | SERM |
Ormeloxifene | Centchroman | ? | ? | 0.313 | ? | SERM |
Levormeloxifene | 6720-CDRI; NNC-460,020 | 1.55 | 1.88 | ? | ? | SERM |
Ospemifene | Deaminohydroxytoremifene | 0.82–2.63 | 0.59–1.22 | ? | ? | SERM |
Bazedoxifene | – | ? | ? | 0.053 | ? | SERM |
Etacstil | GW-5638 | 4.30 | 11.5 | ? | ? | SERM |
ICI-164,384 | – | 63.5 (3.70–97.7) | 166 | 0.2 | 0.08 | Antiestrogen |
Fulvestrant | ICI-182,780 | 43.5 (9.4–325) | 21.65 (2.05–40.5) | 0.42 | 1.3 | Antiestrogen |
Propylpyrazoletriol | PPT | 49 (10.0–89.1) | 0.12 | 0.40 | 92.8 | ERα agonist |
16α-LE2 | 16α-Lactone-17β-estradiol | 14.6–57 | 0.089 | 0.27 | 131 | ERα agonist |
16α-Iodo-E2 | 16α-Iodo-17β-estradiol | 30.2 | 2.30 | ? | ? | ERα agonist |
Methylpiperidinopyrazole | MPP | 11 | 0.05 | ? | ? | ERα antagonist |
Diarylpropionitrile | DPN | 0.12–0.25 | 6.6–18 | 32.4 | 1.7 | ERβ agonist |
8β-VE2 | 8β-Vinyl-17β-estradiol | 0.35 | 22.0–83 | 12.9 | 0.50 | ERβ agonist |
Prinaberel | ERB-041; WAY-202,041 | 0.27 | 67–72 | ? | ? | ERβ agonist |
ERB-196 | WAY-202,196 | ? | 180 | ? | ? | ERβ agonist |
Erteberel | SERBA-1; LY-500,307 | ? | ? | 2.68 | 0.19 | ERβ agonist |
SERBA-2 | – | ? | ? | 14.5 | 1.54 | ERβ agonist |
Coumestrol | – | 9.225 (0.0117–94) | 64.125 (0.41–185) | 0.14–80.0 | 0.07–27.0 | Xenoestrogen |
Genistein | – | 0.445 (0.0012–16) | 33.42 (0.86–87) | 2.6–126 | 0.3–12.8 | Xenoestrogen |
Equol | – | 0.2–0.287 | 0.85 (0.10–2.85) | ? | ? | Xenoestrogen |
Daidzein | – | 0.07 (0.0018–9.3) | 0.7865 (0.04–17.1) | 2.0 | 85.3 | Xenoestrogen |
Biochanin A | – | 0.04 (0.022–0.15) | 0.6225 (0.010–1.2) | 174 | 8.9 | Xenoestrogen |
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-PN | 4.4 | ? | ? | ? | Xenoestrogen |
Quercetin | – | <0.001–0.01 | 0.002–0.040 | ? | ? | 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-Zearalanol | 48–111 | ? | ? | ? | Xenoestrogen |
Taleranol | β-Zearalanol | 16 (13–17.8) | 14 | 0.8 | 0.9 | Xenoestrogen |
Zearalenone | ZEN | 7.68 (2.04–28) | 9.45 (2.43–31.5) | ? | ? | Xenoestrogen |
Zearalanone | ZAN | 0.51 | ? | ? | ? | Xenoestrogen |
Bisphenol A | BPA | 0.0315 (0.008–1.0) | 0.135 (0.002–4.23) | 195 | 35 | Xenoestrogen |
Endosulfan | EDS | <0.001–<0.01 | <0.01 | ? | ? | Xenoestrogen |
Kepone | Chlordecone | 0.0069–0.2 | ? | ? | ? | Xenoestrogen |
o,p'-DDT | – | 0.0073–0.4 | ? | ? | ? | Xenoestrogen |
p,p'-DDT | – | 0.03 | ? | ? | ? | Xenoestrogen |
Methoxychlor | p,p'-Dimethoxy-DDT | 0.01 (<0.001–0.02) | 0.01–0.13 | ? | ? | Xenoestrogen |
HPTE | Hydroxychlor; p,p'-OH-DDT | 1.2–1.7 | ? | ? | ? | Xenoestrogen |
Testosterone | T; 4-Androstenolone | <0.0001–<0.01 | <0.002–0.040 | >5000 | >5000 | Androgen |
Dihydrotestosterone | DHT; 5α-Androstanolone | 0.01 (<0.001–0.05) | 0.0059–0.17 | 221–>5000 | 73–1688 | Androgen |
Nandrolone | 19-Nortestosterone; 19-NT | 0.01 | 0.23 | 765 | 53 | Androgen |
Dehydroepiandrosterone | DHEA; Prasterone | 0.038 (<0.001–0.04) | 0.019–0.07 | 245–1053 | 163–515 | Androgen |
5-Androstenediol | A5; Androstenediol | 6 | 17 | 3.6 | 0.9 | Androgen |
4-Androstenediol | – | 0.5 | 0.6 | 23 | 19 | Androgen |
4-Androstenedione | A4; Androstenedione | <0.01 | <0.01 | >10000 | >10000 | Androgen |
3α-Androstanediol | 3α-Adiol | 0.07 | 0.3 | 260 | 48 | Androgen |
3β-Androstanediol | 3β-Adiol | 3 | 7 | 6 | 2 | Androgen |
Androstanedione | 5α-Androstanedione | <0.01 | <0.01 | >10000 | >10000 | Androgen |
Etiocholanedione | 5β-Androstanedione | <0.01 | <0.01 | >10000 | >10000 | Androgen |
Methyltestosterone | 17α-Methyltestosterone | <0.0001 | ? | ? | ? | Androgen |
Ethinyl-3α-androstanediol | 17α-Ethynyl-3α-adiol | 4.0 | <0.07 | ? | ? | Estrogen |
Ethinyl-3β-androstanediol | 17α-Ethynyl-3β-adiol | 50 | 5.6 | ? | ? | Estrogen |
Progesterone | P4; 4-Pregnenedione | <0.001–0.6 | <0.001–0.010 | ? | ? | Progestogen |
Norethisterone | NET; 17α-Ethynyl-19-NT | 0.085 (0.0015–<0.1) | 0.1 (0.01–0.3) | 152 | 1084 | Progestogen |
Norethynodrel | 5(10)-Norethisterone | 0.5 (0.3–0.7) | <0.1–0.22 | 14 | 53 | Progestogen |
Tibolone | 7α-Methylnorethynodrel | 0.5 (0.45–2.0) | 0.2–0.076 | ? | ? | Progestogen |
Δ-Tibolone | 7α-Methylnorethisterone | 0.069–<0.1 | 0.027–<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: = (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
See also: List of androgens/anabolic steroids § Testosterone derivatives, and List of androgen esters § Esters of other natural AASAndrostenediol, also known as androst-5-ene-3β,17β-diol, is a naturally occurring androstane steroid. 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).
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. 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.
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.
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". No further explanation was given. As a result, Hollis-Eden has now withdrawn from the radiation countermeasure field.
Additional images
References
- 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.
- 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.
- 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.
- Bradbury R (30 January 2007). Cancer. Springer Science & Business Media. pp. 43–. ISBN 978-3-540-33120-9.
- ^ 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.
- ^ 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.
- 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.
- 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.
- Government Nukes Hollis-Eden's Radiation Drug, by Val Brickates Kennedy and Angela Moore, March 8, 2007
- US cancels radiation contract with Hollis-Eden Archived 2007-09-12 at archive.today, March 9, 2007
Biological activity | |||||||||||||||||||||||||||||||||||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
|