Androstanolone

This article is about dihydrotestosterone as a medication. For the natural hormone, see Dihydrotestosterone.
Androstanolone
Clinical data
Trade namesAndractim, others
Other namesStanolone; Dihydrotestosterone; DHT; 5α-Dihydrotestosterone; 5α-DHT
Pregnancy
category
  • X
Routes of
administration		Transdermal (gel), in the cheek, under the tongue, intramuscular injection (as esters)
Drug classAndrogen; Anabolic steroid
ATC code
Legal status
Legal status
  • BR: Class C5 (Anabolic steroids)[1]
Pharmacokinetic data
BioavailabilityOral: Very low[2]
Transdermal: 10%[2][3]
IM injection: 100%[3]
MetabolismLiver
Elimination half-lifeTransdermal: 2.8 hours[4]
ExcretionUrine
Identifiers
IUPAC name
  • (5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
Chemical and physical data
FormulaC19H30O2
Molar mass290.447 g·mol−1
3D model (JSmol)
SMILES
  • O=C4C[C@@H]3CC[C@@H]2[C@H](CC[C@]1(C)[C@@H](O)CC[C@H]12)[C@@]3(C)CC4
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/h12,14-17,21H,3-11H2,1-2H3/t12-,14-,15-,16-,17-,18-,19-/m0/s1 Y
  • Key:NVKAWKQGWWIWPM-ABEVXSGRSA-N Y
  (verify)

Androstanolone, or stanolone, also known as dihydrotestosterone (DHT) and sold under the brand name Andractim among others, is an androgen and anabolic steroid (AAS) medication and hormone which is used mainly in the treatment of low testosterone levels in men.[2] It is also used to treat breast development and small penis in males.[2] Compared to testosterone, androstanolone (DHT) is less likely to aromatize into estrogen, and therefore it shows less pronounced estrogenic side effects, such as gynecomastia and water retention. On the other hand, androstanolone (DHT) show more significant androgenic side effects, such as acne, hair loss and prostate enlargement.

It has strong androgenic effects and muscle-building effects, as well as relatively weak estrogenic effects.[2]

It is typically given as a gel for application to the skin, but can also be used as an ester by injection into muscle.[2][5]

Side effects of androstanolone include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire.[2] The medication is a naturally occurring androgen and anabolic steroid and hence is an agonist of the androgen receptor (AR), the biological target of androgens like testosterone and DHT.[2][6]

Androstanolone was discovered in 1935 and was introduced for medical use in 1953.[2][7][8][9] It is used mostly in France and Belgium.[2][10][11] The drug has been used by weightlifters to increase performance due to its powerful androgenic properties.[12][13] The medication is a controlled substance in many countries and so non-medical use is generally illicit.[2]

  1. ^ Anvisa (31 March 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). Archived from the original on 3 August 2023. Retrieved 15 August 2023.
  2. ^ a b c d e f g h i j k Llewellyn W (2011). Anabolics. Molecular Nutrition Llc. pp. 8, 23–25, 353–359. ISBN 978-0-9828280-1-4.
  3. ^ a b Coutts SB, Kicman AT, Hurst DT, Cowan DA (November 1997). "Intramuscular administration of 5 alpha-dihydrotestosterone heptanoate: changes in urinary hormone profile". Clinical Chemistry. 43 (11): 2091–2098. doi:10.1093/clinchem/43.11.2091. PMID 9365393.
  4. ^ Cite error: The named reference MozayaniRaymon2003 was invoked but never defined (see the help page).
  5. ^ Cite error: The named reference HydeGengenbach2007 was invoked but never defined (see the help page).
  6. ^ Kicman AT (June 2008). "Pharmacology of anabolic steroids". British Journal of Pharmacology. 154 (3): 502–521. doi:10.1038/bjp.2008.165. PMC 2439524. PMID 18500378.
  7. ^ Cite error: The named reference Schnitzer1967 was invoked but never defined (see the help page).
  8. ^ Cite error: The named reference Krüskemper2013 was invoked but never defined (see the help page).
  9. ^ Cite error: The named reference Publishing2007 was invoked but never defined (see the help page).
  10. ^ Cite error: The named reference Drugs.com was invoked but never defined (see the help page).
  11. ^ Cite error: The named reference GoorenBunck2004 was invoked but never defined (see the help page).
  12. ^ "Public Disclosure". 30 May 2018.
  13. ^ "Steroid Use by Chinese Hints at Systematic Doping". Chicago Tribune. 10 December 1994.
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