Dihydrotestosterone undecanoate

Dihydrotestosterone undecanoate (DHTU), also known as androstanolone undecanoate or stanolone undecanoate, is a synthetic androgen and anabolic steroid (AAS) which was never marketed.^[2][1][3][4] It is an androgen ester; specifically, it is the C17β undecanoate (undecylate) ester of dihydrotestosterone (DHT).^{[2][1][3][4][5]} DHTU is a prodrug of DHT.^[2][5][4] Similarly to testosterone undecanoate (TU), DHTU is orally active.^[1][3][4] It occurs as an important active metabolite of oral TU.^{[6][2][5][7][8]} The 5α-reductase inhibitor finasteride in combination with oral TU has no effect on the first-pass transformation of TU into DHTU or DHT, probably because of its unique lymphatic route of absorption.^[9] Oral DHTU may be absorbed by the lymphatic system similarly to TU, and this may explain its oral bioavailability.^[2][1][3][4]

Dihydrotestosterone undecanoate

Clinical data
Other names	DHTU; 5α-Dihydrotestosterone 17β-undecanoate; Androstanolone undecanoate; Stanolone undecanoate; 5α-Androstan-17β-ol-3-one 17β-undecanoate; 3-Oxo-5α-androstan-17β-yl undecanoate
Routes of administration	By mouth[1]
Drug class	Androgen; Anabolic steroid; Androgen ester
Identifiers
IUPAC name [(5S,8R,9S,10S,13S,14S,17S)-10,13-Dimethyl-3-oxo-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl] undecanoate
CAS Number	6804-12-2 Y
PubChem CID	56614500
ChemSpider	31046138
UNII	8DVD393EG2
CompTox Dashboard (EPA)	DTXSID90718066
Chemical and physical data
Formula	C30H50O3
Molar mass	458.727 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCCCCCCCCCC(=O)O[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@@H]4[C@@]3(CCC(=O)C4)C)C
InChI InChI=1S/C30H50O3/c1-4-5-6-7-8-9-10-11-12-28(32)33-27-16-15-25-24-14-13-22-21-23(31)17-19-29(22,2)26(24)18-20-30(25,27)3/h22,24-27H,4-21H2,1-3H3/t22-,24-,25-,26-,27-,29-,30-/m0/s1 Key:AOQIVBOEDICQDB-KNWHVVHCSA-N

See also

• List of androgen esters § Dihydrotestosterone esters
• 3α-Hydroxysteroid dehydrogenase