Dihydrotestosterone undecanoate

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Dihydrotestosterone undecanoate
Dihydrotestosterone undecanoate.svg
Clinical data
Other namesDHTU; 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 classAndrogen; Anabolic steroid; Androgen ester
Identifiers
  • [(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
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC30H50O3
Molar mass458.727 g·mol−1
3D model (JSmol)
  • 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=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

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]

  1. ^ 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". Int. J. Androl. 7 (1): 53–60. doi:10.1111/j.1365-2605.1984.tb00759.x. PMID 6715064.
  2. ^ 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". Endocr. Rev. 38 (3): 220–254. doi:10.1210/er.2016-1067. PMC 6459338. PMID 28472278.
  3. ^ 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): 289–98. doi:10.1111/j.1439-0272.1984.tb00286.x. PMID 6433746. S2CID 32546312.
  4. ^ 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". Arch Sex Behav. 14 (6): 539–48. doi:10.1007/BF01541754. PMID 4084053. S2CID 23059918.
  5. ^ a b c 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.{{cite book}}: 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. S2CID 466234.
  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.