Misplaced Pages

4-Androstenediol

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
(Redirected from 4-androstenediol) Chemical compound Pharmaceutical compound
4-Androstenediol
Clinical data
Other namesAndrost-4-ene-3β,17β-diol
Routes of
administration		Oral
Identifiers
IUPAC name
  • (3S,8R,9S,10R,13S,14S,17S)-10,13-dimethyl-2,3,6,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopentaphenanthrene-3,17-diol
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H30O2
Molar mass290.447 g·mol
3D model (JSmol)
SMILES
  • C12CC3(1CC2O)CCC4=C(CC34C)O
InChI
  • 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
  • Key:BTTWKVFKBPAFDK-LOVVWNRFSA-N
  (what is this?)  (verify)

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.

4-Androstenediol is closer to testosterone structurally than 5-androstenediol, and has androgenic effects, acting as a weak partial agonist of the androgen receptor. However, due to its lower intrinsic activity in comparison, in the presence of full agonists like testosterone or dihydrotestosterone (DHT), 4-androstenediol has antagonistic actions, behaving more like an antiandrogen.

4-Androstenediol is very weakly estrogenic. It has approximately 0.5% and 0.6% of the affinity of estradiol at the ERα and ERβ, respectively.

Medical and commercial use

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

References

  1. ^ Chen 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 from the original on 2011-03-18. Retrieved 2011-03-18.


Androgen receptor modulators
ARTooltip Androgen receptor
Agonists
SARMsTooltip Selective androgen receptor modulator
Antagonists
GPRC6A
Agonists
See also
Receptor/signaling modulators
Androgens and antiandrogens
Estrogen receptor modulators
Progesterone receptor modulators
List of androgens and anabolic steroids
Estrogen receptor modulators
ERTooltip Estrogen receptor
Agonists
Mixed
(SERMsTooltip Selective estrogen receptor modulators)
Antagonists
  • Coregulator-binding modulators: ERX-11
GPERTooltip G protein-coupled estrogen receptor
Agonists
Antagonists
Unknown
See also
Receptor/signaling modulators
Estrogens and antiestrogens
Androgen receptor modulators
Progesterone receptor modulators
List of estrogens
Stub icon

This article about a steroid is a stub. You can help Misplaced Pages by expanding it.

Stub icon

This drug article relating to the genito-urinary system is a stub. You can help Misplaced Pages by expanding it.

Categories: