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

References

1. Gooren LJ, van der Veen EA, van Kessel H, Harmsen-Louman W, Wiegel AR (February 1984). "Prolactin secretion in the human male is increased by endogenous oestrogens and decreased by exogenous/endogenous androgens". Int. J. Androl. 7 (1): 53–60. doi:10.1111/j.1365-2605.1984.tb00759.x. PMID 6715064.
2. Swerdloff RS, Dudley RE, Page ST, Wang C, Salameh WA (June 2017). "Dihydrotestosterone: Biochemistry, Physiology, and Clinical Implications of Elevated Blood Levels". Endocr. Rev. 38 (3): 220–254. doi:10.1210/er.2016-1067. PMC 6459338. PMID 28472278.
3. Gooren LJ, van der Veen EA, van Kessel H, Harmsen-Louman W, Wiegel AR (1984). "Androgens in the feedback regulation of gonadotropin secretion in men: effects of administration of dihydrotestosterone to eugonadal and agonadal subjects and of spironolactone to eugonadal subjects". Andrologia. 16 (4): 289–98. doi:10.1111/j.1439-0272.1984.tb00286.x. PMID 6433746.
4. Gooren LJ (December 1985). "Human male sexual functions do not require aromatization of testosterone: a study using tamoxifen, testolactone, and dihydrotestosterone". Arch Sex Behav. 14 (6): 539–48. doi:10.1007/BF01541754. PMID 4084053.
5. Lachance S, Dhingra O, Bernstein J, Gagnon S, Savard C, Pelletier N, Boudreau N, Lévesque A (November 2015). "Importance of measuring testosterone in enzyme-inhibited plasma for oral testosterone undecanoate androgen replacement therapy clinical trials". Future Sci OA. 1 (4): FSO55. doi:10.4155/fso.15.55. PMC 5137954. PMID 28031910.
6. Valentino Stella; Ronald Borchardt; Michael Hageman; Reza Oliyai, Hans Maag, Jefferson Tilley (26 August 2007). Prodrugs: Challenges and Rewards. Springer Science & Business Media. pp. 668–. ISBN 978-0-387-49785-3.CS1 maint: multiple names: authors list (link)
7. Hirschhäuser C, Hopkinson CR, Sturm G, Coert A (September 1975). "Testosterone undecanoate: a new orally active androgen". Acta Endocrinol. 80 (1): 179–87. doi:10.1530/acta.0.0800179. PMID 1098350.
8. Horst HJ, Höltje WJ, Dennis M, Coert A, Geelen J, Voigt KD (September 1976). "Lymphatic absorption and metabolism of orally administered testosterone undecanoate in man". Klin. Wochenschr. 54 (18): 875–9. doi:10.1007/bf01483589. PMID 966635.
9. Roth MY, Dudley RE, Hull L, Leung A, Christenson P, Wang C, Swerdloff R, Amory JK (December 2011). "Steady-state pharmacokinetics of oral testosterone undecanoate with concomitant inhibition of 5α-reductase by finasteride". Int. J. Androl. 34 (6 Pt 1): 541–7. doi:10.1111/j.1365-2605.2010.01120.x. PMC 4269219. PMID 20969601.