4-Androstenediol

4-Androstenediol
Names


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-cyclopenta[a]phenanthrene-3,17-diol
Other names Androst-4-ene-3β,17β-diol
Identifiers
CAS Number	1156-92-9^N
ChEMBL	ChEMBL195836^Y
ChemSpider	120071^Y
DrugBank	DB01526^Y
Jmol interactive 3D	Image Image
PubChem	136297
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^Y Key: BTTWKVFKBPAFDK-LOVVWNRFSA-N^Y 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/h11,13-17,20-21H,3-10H2,1-2H3/t13-,14-,15-,16-,17-,18-,19-/m0/s1 Key: BTTWKVFKBPAFDK-LOVVWNRFBP
SMILES C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=C[C@H](CC[C@]34C)O O[C@@H]4/C=C2\[C@]([C@H]1CC[C@@]3([C@@H](O)CC[C@H]3[C@@H]1CC2)C)(C)CC4
Properties
Chemical formula	C₁₉H₃₀O₂
Molar mass	290.44 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is ^YN ?)
Infobox references

Δ⁴-Androstenediol is an androstenediol that is converted to testosterone. The conversion rate is about 15.76%, almost triple that of Δ⁴-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.

Δ⁴-Androstenediol is closer to testosterone structurally than Δ⁵-androstenediol, and has androgenic effects, acting as a weak partial agonist of the androgen receptor.^[1] However, due to its lower intrinsic activity in comparison, in the presence of full agonists like testosterone or dihydrotestosterone (DHT), Δ⁴-androstenediol has antagonistic actions, behaving more like an antiandrogen.^[1]

Medical and commercial use

Patrick Arnold holds a 1999 patent on "Use of 4-androstenediol to increase testosterone levels in humans".^[2]

References

1 2 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.
↑ http://www.patentstorm.us/patents/5880117/description.html

Androgens and antiandrogens

Androgens

Agonists	Anabolic steroids (see here instead) Androgenic progestins (e.g., norethisterone, levonorgestrel, medroxyprogesterone acetate) Androstanolone Androstenediol Androstenedione DHEA DHEA sulfate Dihydrotestosterone Fluoxymesterone Mesterolone Methyltestosterone Testosterone^# Testosterone acetate Testosterone capropate Testosterone cypionate Testosterone decanoate Testosterone enanthate Testosterone isocaproate Testosterone phenylpropionate Testosterone propionate Testosterone undecanoate Tibolone

SARMs	AC-262,356^§ Andarine^§ BMS-564,929^§ Enobosarm (ostarine)^§ LGD-2226^§ LGD-3303^§ S-23^§ S-40503^§

Antiandrogens

Antagonists

Enzyme inhibitors

5α-Reductase	Alfatradiol Chlormadinone acetate Dutasteride Finasteride Saw palmetto extract

CYP17A1	Abiraterone acetate Cyproterone acetate Danazol Galeterone^† Gestrinone Ketoconazole Orteronel^† Spironolactone VT-464^†

Others	Abiraterone acetate Aminoglutethimide Cyproterone acetate Danazol Gestrinone Ketoconazole Mitotane Trilostane

Antigonadotropins

Anabolic steroids (e.g., nandrolone, oxandrolone)
Estrogens (e.g., estradiol)
GnRH agonists (e.g., leuprorelin)
GnRH antagonists (e.g., cetrorelix)
Progestogens (incl. allylestrenol, chlormadinone acetate, cyproterone acetate, delmadinone acetate, dydrogesterone, medroxyprogesterone acetate, megestrol acetate, nomegestrol acetate, norethisterone acetate, progesterone, spironolactone)

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

Androgenics

Receptor
(ligands)

Agonists	4-Chlordehydromethyltestosterone 4-Hydroxytestosterone 5α-Androst-1-ene-3,17-dione 7β-Hydroxyepiandrosterone 11-Ketotestosterone 17-((1-Oxoheptyl)oxy)androstan-3-one 17-((1-Oxopentyl)oxy)androstan-3-one 17-(1-Oxopropoxy)androstan-3-one 17β-Hydroxyandrost-2-ene-2-carbonitrile 19-Norandrostenediol 19-Norandrostenedione 19-Norandrosterone 19-Nordehydrotestosterone Δ¹-Androstenediol Δ¹-Testosterone Δ^1,4-Androstenedione Δ⁴-Androstenediol Δ⁴-Androstenedione Δ^4-Tibolone Δ⁴-Androstenediol Δ⁴-Androstenedione Adrenosterone Androisoxazole Androstanolone Bolandiol Bolasterone Bolazine Boldenone Boldione Bolenol Bolmantalate Calusterone Cl-4AS-1 Clostebol Cloxotestosterone Cortexolone 17α-propionate Danazol Desogestrel Desoxymethyltestosterone DHEA DHEA sulfate Dihydrotestosterone Drostanolone Enestebol Epitiostanol Ethisterone Ethyldienolone Ethylestrenol Fluoxymesterone Formebolone Furazabol Hexabolan Hydroxystenozole Levonorgestrel Mebolazine Medroxyprogesterone acetate Mepitiostane Mesabolone Mestanolone Mesterolone Metandienone/Methandrostenolone Metenolone Metenolone acetate Metenolone enanthate Methandriol Methandriol propionate Methasterone Methylestrenolone Methyltestosterone Metribolone Mibolerone Nandrolone Nandrolone caproate Nandrolone cypionate Nandrolone cyclohexane carboxylate Nandrolone cyclohexylpropionate Nandrolone cyclotate Nandrolone decanoate Nandrolone furylpropionate Nandrolone hexyloxyphenylpropionate Nandrolone hydrogen succinate Nandrolone laurate Nandrolone phenylpropionate Nandrolone propionate Nandrolone undecyclate Norboletone Norclostebol Norethandrolone Norethisterone Norgestrel Oxabolone Oxabolone cypionate Oxandrolone Oxendolone Oxymesterone Oxymetholone Penmesterol Propetandrol Quinbolone Quingestanol acetate Roxibolone Silandrone Stanozolol Stenbolone Stenbolone acetate Testolactone Testosterone Testosterone acetate Testosterone capropate Testosterone cypionate Testosterone decanoate Testosterone enanthate Testosterone isocaproate Testosterone ketolaurate Testosterone nicotinate Testosterone phenylpropionate Testosterone propionate Testosterone undecanoate Tetrahydrogestrinone Thiomesterone Tibolone Tiomesterone Trenboloneca Trenbolone acetate Trestolone

Mixed (SARMs)	AC-262,356 Andarine BMS-564,929 Enobosarm (ostarine) LGD-2226 LGD-3303 LGD-4033 RAD140 S-23 S-40503 TFM-4AS-1

Antagonists	3α-Hydroxytibolone 3β-Hydroxytibolone Abiraterone Abiraterone acetate Apalutamide AZD-3514 Bisphenols (e.g., BADGE, BFDGE, bisphenol A, bisphenol F, bisphenol S) Benorterone Bicalutamide BMS-641,988 BOMT Canrenoic acid Canrenone Chlormadinone acetate Cimetidine Cioteronel Clometerone Cyproterone Cyproterone acetate Delanterone DDT (via metabolite p,p’-DDE) Dieldrin Dienogest Drospirenone Endosulfan Enzalutamide EPI-001 Epitestosterone Fenarimol Flutamide Galeterone Guggulsterone Hydroxyflutamide Inocoterone Ketoconazole Lavender oil Linuron Megestrol acetate Mespirenone Methiocarb Metogest Mifepristone Nilutamide Nomegestrol Nordinone Norgestimate ODM-201 ONC1-13B ORM-15341 Osaterone Oxendolone PF-998425 Potassium canrenoate Prochloraz Procymidone R-2956 Rosterolone RU-58642 RU-58841 Spironolactone Topilutamide (fluridil) Topterone Valproic acid Vinclozolin VT-464 Zanoterone

Enzyme

Modulators	See here instead (modulators of 20,22-desmolase, 17α-hydroxylase/17,20-lyase, 3β-HSD, 17β-HSD, 5α-reductase, and aromatase).

Others

Precursors/prohormones	Cholesterol 22R-Hydroxycholesterol 20α,22R-Dihydroxycholesterol Pregnenolone Pregnenolone sulfate 17-Hydroxypregnenolone Progesterone 17-Hydroxyprogesterone 11-Deoxycortisol (cortodoxone) DHEA DHEA sulfate Δ⁵-Androstenediol Δ⁴-Androstenedione

Indirect	Antigonadotropins (e.g., estrogens, progestogens, prolactin) GnRH agonists (e,g, GnRH, leuprorelin) GnRH antagonists (e.g., cetrorelix) Gonadotropins (e.g., FSH, hCG, LH) Kisspeptin Plasma proteins (ABP, albumin, SHBG)

See also: Estrogenics • Glucocorticoids • Mineralocorticoids • Progestogenics

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