Chemistry:Testosterone enantate benzilic acid hydrazone
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Short description: Chemical compound
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| Clinical data | |
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| Trade names | Climacteron, Lactimex, Lactostat |
| Other names | Testosterone enantate benziloylhydrazone; Testosterone 17β-enantate 3-benzilic acid hydrazone; TEBH; TEBAH; TEBaH |
| Routes of administration | Intramuscular injection[1][2] |
| Identifiers | |
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| CAS Number | |
| PubChem CID | |
| DrugBank | |
| ChemSpider | |
| UNII | |
| Chemical and physical data | |
| Formula | C40H52N2O4 |
| Molar mass | 624.866 g·mol−1 |
| 3D model (JSmol) | |
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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.[2][3][4] Clinical studies have assessed this formulation.[5][6][7][8][9][10][11][2] TEBH was first described in the scientific literature in 1959.[12] It is a very long-lasting prodrug of testosterone when administered in oil via intramuscular injection.[13][14][15]
| Route | Medication | Major brand names | Form | Dosage |
|---|---|---|---|---|
| Oral | Testosterone undecanoate | Andriol, Jatenzo | Capsule | 40–80 mg 1x/1–2 days |
| Methyltestosterone | Metandren, Estratest | Tablet | 0.5–10 mg/day | |
| Fluoxymesterone | Halotestin | Tablet | 1–2.5 mg 1x/1–2 days | |
| Normethandronea | Ginecoside | Tablet | 5 mg/day | |
| Tibolone | Livial | Tablet | 1.25–2.5 mg/day | |
| Prasterone (DHEA)b | – | Tablet | 10–100 mg/day | |
| Sublingual | Methyltestosterone | Metandren | Tablet | 0.25 mg/day |
| Transdermal | Testosterone | Intrinsa | Patch | 150–300 μg/day |
| AndroGel | Gel, cream | 1–10 mg/day | ||
| Vaginal | Prasterone (DHEA) | Intrarosa | Insert | 6.5 mg/day |
| Injection | Testosterone propionatea | Testoviron | Oil solution | 25 mg 1x/1–2 weeks |
| Testosterone enanthate | Delatestryl, Primodian Depot | Oil solution | 25–100 mg 1x/4–6 weeks | |
| Testosterone cypionate | Depo-Testosterone, Depo-Testadiol | Oil solution | 25–100 mg 1x/4–6 weeks | |
| Testosterone isobutyratea | Femandren M, Folivirin | Aqueous suspension | 25–50 mg 1x/4–6 weeks | |
| Mixed testosterone esters | Climacterona | Oil solution | 150 mg 1x/4–8 weeks | |
| Omnadren, Sustanon | Oil solution | 50–100 mg 1x/4–6 weeks | ||
| Nandrolone decanoate | Deca-Durabolin | Oil solution | 25–50 mg 1x/6–12 weeks | |
| Prasterone enanthatea | Gynodian Depot | Oil solution | 200 mg 1x/4–6 weeks | |
| Implant | Testosterone | Testopel | Pellet | 50–100 mg 1x/3–6 months |
| Notes: Premenopausal women produce about 230 ± 70 μg testosterone per day (6.4 ± 2.0 mg testosterone per 4 weeks), with a range of 130 to 330 μg per day (3.6–9.2 mg per 4 weeks). Footnotes: a = Mostly discontinued or unavailable. b = Over-the-counter. Sources: See template. | ||||
Chemistry
Chemical synthesis of TEBH has been described.[16]
See also
- List of androgen esters § Testosterone esters
- Hydroxyprogesterone heptanoate benzilic acid hydrazone
References
- ↑ 1.0 1.1 J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 641–. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA641.
- ↑ 2.0 2.1 2.2 2.3 "The safety of testosterone therapy in women". J Obstet Gynaecol Can 34 (9): 859–865. September 2012. doi:10.1016/S1701-2163(16)35385-3. PMID 22971455.
- ↑ Geburtshilfe und Frauenheilkunde: Ergebnisse der Forschung für die Praxis. Georg Thieme Verlag.. 1969. https://books.google.com/books?id=_-owAAAAIAAJ.
- ↑ Zentralblatt für Gynäkologie. J. A. Barth. 1971. https://books.google.com/books?id=uNkwAAAAIAAJ.
- ↑ "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. doi:10.1016/0002-9378(84)90746-4. PMID 6367474.
- ↑ "Differential symptom response to parenteral estrogen and/or androgen administration in the surgical menopause". Am. J. Obstet. Gynecol. 151 (2): 153–60. January 1985. doi:10.1016/0002-9378(85)90001-8. PMID 3881960.
- ↑ "Changes in sexual behavior as a function of plasma sex steroid levels in post-menopausal women". Maturitas 7 (3): 225–33. September 1985. doi:10.1016/0378-5122(85)90044-1. PMID 4079822.
- ↑ "Sex steroids and affect in the surgical menopause: a double-blind, cross-over study". Psychoneuroendocrinology 10 (3): 325–35. 1985. doi:10.1016/0306-4530(85)90009-5. PMID 3903822.
- ↑ "Postmenopausal estrogen and androgen replacement and lipoprotein lipid concentrations". Am. J. Obstet. Gynecol. 156 (2): 414–9. February 1987. doi:10.1016/0002-9378(87)90295-X. PMID 3826177.
- ↑ "Affective changes with estrogen and androgen replacement therapy in surgically menopausal women". J Affect Disord 14 (2): 177–87. 1988. doi:10.1016/0165-0327(88)90061-4. PMID 2966832.
- ↑ "Estrogen and/or androgen replacement therapy and cognitive functioning in surgically menopausal women". Psychoneuroendocrinology 13 (4): 345–57. 1988. doi:10.1016/0306-4530(88)90060-1. PMID 3067252.
- ↑ "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. doi:10.1210/endo-65-3-508. PMID 13828402.
- ↑ "The hormonal control of lactation". Clin Obstet Gynecol 3 (4): 1099–108. December 1960. doi:10.1097/00003081-196003040-00022. PMID 13723335.
- ↑ "The treatment of the menopause". Can Med Assoc J 86 (3): 113–4. January 1962. PMID 13901504.
- ↑ "Evaluation of a new preparation for the suppression of lactation". Can Med Assoc J 83 (24): 1240–2. December 1960. PMID 13752392.
- ↑ "Testosterone 17-Heptanoate 3-Benziloylhydrazone". J. Med. Chem. 7 (4): 573. July 1964. doi:10.1021/jm00334a042. PMID 14221154.
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