Dihydrotestosterone undecanoate
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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 |
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Chemical and physical data | |
Formula | C30H50O3 |
Molar mass | 458.727 g·mol−1 |
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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]
See also
[edit]References
[edit]- ^ a b c d e 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". International Journal of Andrology. 7 (1): 53–60. doi:10.1111/j.1365-2605.1984.tb00759.x. PMID 6715064.
- ^ a b c d e Swerdloff RS, Dudley RE, Page ST, Wang C, Salameh WA (June 2017). "Dihydrotestosterone: Biochemistry, Physiology, and Clinical Implications of Elevated Blood Levels". Endocrine Reviews. 38 (3): 220–254. doi:10.1210/er.2016-1067. PMC 6459338. PMID 28472278.
- ^ a b c d 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): 289–298. doi:10.1111/j.1439-0272.1984.tb00286.x. PMID 6433746. S2CID 32546312.
- ^ a b c d e Gooren LJ (December 1985). "Human male sexual functions do not require aromatization of testosterone: a study using tamoxifen, testolactone, and dihydrotestosterone". Archives of Sexual Behavior. 14 (6): 539–548. doi:10.1007/BF01541754. PMID 4084053. S2CID 23059918.
- ^ a b c Lachance S, Dhingra O, Bernstein J, Gagnon S, Savard C, Pelletier N, et al. (November 2015). "Importance of measuring testosterone in enzyme-inhibited plasma for oral testosterone undecanoate androgen replacement therapy clinical trials". Future Science OA. 1 (4): FSO55. doi:10.4155/fso.15.55. PMC 5137954. PMID 28031910.
- ^ Shackleford DM, Porter CJ, Charman WN (26 August 2007). "Lymphatic Adsorption of Orally Administered Prodrugs". In Stella V, Borchardt R, Hageman M, Oliyai R, Maag H, Tilley J (eds.). Prodrugs: Challenges and Rewards. Springer Science & Business Media. pp. 668–. ISBN 978-0-387-49785-3.
- ^ Hirschhäuser C, Hopkinson CR, Sturm G, Coert A (September 1975). "Testosterone undecanoate: a new orally active androgen". Acta Endocrinologica. 80 (1): 179–187. doi:10.1530/acta.0.0800179. PMID 1098350.
- ^ 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". Klinische Wochenschrift. 54 (18): 875–879. doi:10.1007/bf01483589. PMID 966635. S2CID 466234.
- ^ Roth MY, Dudley RE, Hull L, Leung A, Christenson P, Wang C, et al. (December 2011). "Steady-state pharmacokinetics of oral testosterone undecanoate with concomitant inhibition of 5α-reductase by finasteride". International Journal of Andrology. 34 (6 Pt 1): 541–547. doi:10.1111/j.1365-2605.2010.01120.x. PMC 4269219. PMID 20969601.