Androstanolone

Androstanolone
Clinical data
Trade names	Andractim, others
Other names	Stanolone; 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 class	Androgen; Anabolic steroid
ATC code	A14AA01 (WHO) ;
Legal status
Legal status	BR: Class C5 (Anabolic steroids);
Pharmacokinetic data
Bioavailability	Oral: Very low; Transdermal: 10%; IM injection: 100%
Metabolism	Liver
Elimination half-life	Transdermal: 2.8 hours
Excretion	Urine
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	521-18-6 ;
PubChem CID	10635;
IUPHAR/BPS	2856;
DrugBank	DB02901 ;
ChemSpider	10189 ;
UNII	08J2K08A3Y;
ChEBI	CHEBI:16330 ;
ChEMBL	ChEMBL27769 ;
Chemical and physical data
Formula	C19H30O2
Molar mass	290.447 g·mol−1
3D model (JSmol)	Interactive image;
	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 ; Key:NVKAWKQGWWIWPM-ABEVXSGRSA-N ;
	(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. It is also used to treat breast development and small penis in males. 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.

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

Side effects of androstanolone include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire. 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.

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

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.