Testosterone enantate benzilic acid hydrazone explained

Testosterone enantate benzilic acid hydrazone (TEBH), or testosterone 17β-enantate 3-benzilic acid hydrazone, is a synthetic, injected androgen/anabolic steroid and an androgen ester – specifically, the C17β enantate (heptanoate) ester and C3 benzilic acid hydrazone of testosterone.^{[1] [2]} It was previously marketed in combination with estradiol benzoate and estradiol dienantate under the brand names Climacteron, Lactimex, and Lactostat.^{[3] [4]} Clinical studies have assessed this formulation.^{[5] [6] [7] [8] [9] [10] [11] [12]} TEBH was first described in the scientific literature in 1959.^[13] It is a very long-lasting prodrug of testosterone when administered in oil via intramuscular injection.^{[14] [15] [16]}

Chemistry

Chemical synthesis of TEBH has been described.^[17]

See also

• List of androgen esters § Testosterone esters
• Hydroxyprogesterone heptanoate benzilic acid hydrazone

Notes and References

1. Book: J. Elks. The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. 14 November 2014. Springer. 978-1-4757-2085-3. 641–.
2. Al-Imari L, Wolfman WL . The safety of testosterone therapy in women . J Obstet Gynaecol Can . 34 . 9 . 859–865 . September 2012 . 22971455 . 10.1016/S1701-2163(16)35385-3 .
3. Book: Geburtshilfe und Frauenheilkunde: Ergebnisse der Forschung für die Praxis. 1969. Georg Thieme Verlag..
4. Book: Zentralblatt für Gynäkologie. 1971. J. A. Barth.
5. Sherwin BB, Gelfand MM . Effects of parenteral administration of estrogen and androgen on plasma hormone levels and hot flushes in the surgical menopause . Am. J. Obstet. Gynecol. . 148 . 5 . 552–7 . March 1984 . 6367474 . 10.1016/0002-9378(84)90746-4 .
6. Sherwin BB, Gelfand MM . Differential symptom response to parenteral estrogen and/or androgen administration in the surgical menopause . Am. J. Obstet. Gynecol. . 151 . 2 . 153–60 . January 1985 . 3881960 . 10.1016/0002-9378(85)90001-8 .
7. Sherwin BB . Changes in sexual behavior as a function of plasma sex steroid levels in post-menopausal women . Maturitas . 7 . 3 . 225–33 . September 1985 . 4079822 . 10.1016/0378-5122(85)90044-1 .
8. Sherwin BB, Gelfand MM . Sex steroids and affect in the surgical menopause: a double-blind, cross-over study . Psychoneuroendocrinology . 10 . 3 . 325–35 . 1985 . 3903822 . 10.1016/0306-4530(85)90009-5 . 40861936 .
9. Sherwin BB, Gelfand MM, Schucher R, Gabor J . Postmenopausal estrogen and androgen replacement and lipoprotein lipid concentrations . Am. J. Obstet. Gynecol. . 156 . 2 . 414–9 . February 1987 . 3826177 . 10.1016/0002-9378(87)90295-X .
10. Sherwin BB . Affective changes with estrogen and androgen replacement therapy in surgically menopausal women . J Affect Disord . 14 . 2 . 177–87 . 1988 . 2966832 . 10.1016/0165-0327(88)90061-4 .
11. Sherwin BB . Estrogen and/or androgen replacement therapy and cognitive functioning in surgically menopausal women . Psychoneuroendocrinology . 13 . 4 . 345–57 . 1988 . 3067252 . 10.1016/0306-4530(88)90060-1 . 24695692 .
12. Al-Imari L, Wolfman WL . The safety of testosterone therapy in women . J Obstet Gynaecol Can . 34 . 9 . 859–865 . September 2012 . 22971455 . 10.1016/S1701-2163(16)35385-3 .
13. Gleason CH, Parker JM . The duration of activity of the benziloyl hydrazones of testosterone-17-heptanoate, estrone-3-heptanoate and 17 alpha-hydroxy-progesterone-17-heptanoate . Endocrinology . 65 . 3. 508–11 . September 1959 . 13828402 . 10.1210/endo-65-3-508 .
14. Dodek SM . The hormonal control of lactation . Clin Obstet Gynecol . 3 . 4. 1099–108 . December 1960 . 13723335 . 10.1097/00003081-196003040-00022.
15. Greenblatt RB, Barfield WE, Jungck EC . The treatment of the menopause . Can Med Assoc J . 86 . 113–4 . January 1962 . 3 . 13901504 . 1848811 .
16. Kelly MJ, Primrose T . Evaluation of a new preparation for the suppression of lactation . Can Med Assoc J . 83 . 1240–2 . December 1960 . 24 . 13752392 . 1938994 .
17. Gleason CH . Testosterone 17-Heptanoate 3-Benziloylhydrazone . J. Med. Chem. . 7 . 4. 573 . July 1964 . 14221154 . 10.1021/jm00334a042 .