Movatterモバイル変換


[0]ホーム

URL:


Jump to content
WikipediaThe Free Encyclopedia
Search

4-Androstenediol

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
4-Androstenediol
Clinical data
Other namesAndrost-4-ene-3β,17β-diol
Routes of
administration
Oral
Identifiers
  • (3S,8R,9S,10R,13S,14S,17S)-10,13-dimethyl-2,3,6,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol
CAS Number
PubChemCID
DrugBank
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC19H30O2
Molar mass290.447 g·mol−1
3D model (JSmol)
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=C[C@H](CC[C@]34C)O
  • 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/h11,13-17,20-21H,3-10H2,1-2H3/t13-,14-,15-,16-,17-,18-,19-/m0/s1 checkY
  • Key:BTTWKVFKBPAFDK-LOVVWNRFSA-N checkY
 ☒NcheckY (what is this?)  (verify)

4-Androstenediol, also known asandrost-4-ene-3β,17β-diol, is anandrostenediol that is converted totestosterone. The conversion rate is about 15.76%, almost triple that of4-androstenedione, due to utilization of a different enzymatic pathway. There is also some conversion intoestrogen, since testosterone is the metabolic precursor of the estrogens.

4-Androstenediol is closer totestosterone structurally than5-androstenediol, and hasandrogenic effects, acting as a weakpartial agonist of theandrogen receptor.[1] However, due to its lowerintrinsic activity in comparison, in the presence offull agonists like testosterone ordihydrotestosterone (DHT), 4-androstenediol hasantagonistic actions, behaving more like anantiandrogen.[1]

4-Androstenediol is very weaklyestrogenic. It has approximately 0.5% and 0.6% of theaffinity of estradiol at theERα andERβ, respectively.[2]

Medical and commercial use

[edit]

Patrick Arnold holds a 1999 patent on "Use of 4-androstenediol to increase testosterone levels in humans".[3]

References

[edit]
  1. ^abChen F, Knecht K, Leu C, et al. (August 2004). "Partial agonist/antagonist properties of androstenedione and 4-androsten-3beta,17beta-diol".The Journal of Steroid Biochemistry and Molecular Biology.91 (4–5):247–57.doi:10.1016/j.jsbmb.2004.04.009.PMID 15336702.S2CID 53267316.
  2. ^Kuiper GG, Carlsson B, Grandien K, Enmark E, Häggblad J, Nilsson S, Gustafsson JA (1997)."Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta".Endocrinology.138 (3):863–70.doi:10.1210/endo.138.3.4979.PMID 9048584.
  3. ^"Use of 4-androstenediol to increase testosterone levels in humans". Archived fromthe original on 2011-03-18. Retrieved2011-03-18.


ARTooltip Androgen receptor
Agonists
SARMsTooltip Selective androgen receptor modulator
Antagonists
GPRC6A
Agonists
ERTooltip Estrogen receptor
Agonists
Mixed
(SERMsTooltip Selective estrogen receptor modulators)
Antagonists
GPERTooltip G protein-coupled estrogen receptor
Agonists
Antagonists
Unknown

This article about anAndrogen is astub. You can help Wikipedia byexpanding it.

Stub icon

Thisdrug article relating to thegenito-urinary system is astub. You can help Wikipedia byexpanding it.

Retrieved from "https://en.wikipedia.org/w/index.php?title=4-Androstenediol&oldid=1308580081"
Categories:
Hidden categories:

[8]ページ先頭

©2009-2025 Movatter.jp