Testosterone enantate benzilic acid hydrazone

Testosterone enantate
benzilic acid hydrazone
Clinical data
Trade namesClimacteron, Lactimex, Lactostat
Other namesTestosterone enantate benziloylhydrazone; Testosterone 17β-enantate 3-benzilic acid hydrazone; TEBH; TEBAH; TEBaH
Routes of
administration		Intramuscular injection[1][2]
Identifiers
  • [(3Z,8R,9S,10R,13S,14S)-3-[(2-Hydroxy-2,2-diphenylacetyl)hydrazinylidene]-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl] heptanoate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
Chemical and physical data
FormulaC40H52N2O4
Molar mass624.866 g·mol−1
3D model (JSmol)
  • CCCCCCC(=O)OC1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=C/C(=N\NC(=O)C(C5=CC=CC=C5)(C6=CC=CC=C6)O)/CC[C@]34C)C
  • InChI=1S/C40H52N2O4/c1-4-5-6-13-18-36(43)46-35-22-21-33-32-20-19-30-27-31(23-25-38(30,2)34(32)24-26-39(33,35)3)41-42-37(44)40(45,28-14-9-7-10-15-28)29-16-11-8-12-17-29/h7-12,14-17,27,32-35,45H,4-6,13,18-26H2,1-3H3,(H,42,44)/b41-31-/t32-,33-,34-,35?,38-,39-/m0/s1
  • Key:PTVXYACXDYZNID-JKNBFTAXSA-N

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]

Androgen replacement therapy formulations and dosages used in women
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

[edit]

Chemical synthesis of TEBH has been described.[16]

See also

[edit]

References

[edit]
  1. ^ a b 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.
  2. ^ a b c d Al-Imari L, Wolfman WL (September 2012). "The safety of testosterone therapy in women". J Obstet Gynaecol Can. 34 (9): 859–865. doi:10.1016/S1701-2163(16)35385-3. PMID 22971455.
  3. ^ Geburtshilfe und Frauenheilkunde: Ergebnisse der Forschung für die Praxis. Georg Thieme Verlag. 1969.
  4. ^ Zentralblatt für Gynäkologie. J. A. Barth. 1971.
  5. ^ Sherwin BB, Gelfand MM (March 1984). "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. doi:10.1016/0002-9378(84)90746-4. PMID 6367474.
  6. ^ Sherwin BB, Gelfand MM (January 1985). "Differential symptom response to parenteral estrogen and/or androgen administration in the surgical menopause". Am. J. Obstet. Gynecol. 151 (2): 153–60. doi:10.1016/0002-9378(85)90001-8. PMID 3881960.
  7. ^ Sherwin BB (September 1985). "Changes in sexual behavior as a function of plasma sex steroid levels in post-menopausal women". Maturitas. 7 (3): 225–33. doi:10.1016/0378-5122(85)90044-1. PMID 4079822.
  8. ^ Sherwin BB, Gelfand MM (1985). "Sex steroids and affect in the surgical menopause: a double-blind, cross-over study". Psychoneuroendocrinology. 10 (3): 325–35. doi:10.1016/0306-4530(85)90009-5. PMID 3903822. S2CID 40861936.
  9. ^ Sherwin BB, Gelfand MM, Schucher R, Gabor J (February 1987). "Postmenopausal estrogen and androgen replacement and lipoprotein lipid concentrations". Am. J. Obstet. Gynecol. 156 (2): 414–9. doi:10.1016/0002-9378(87)90295-X. PMID 3826177.
  10. ^ Sherwin BB (1988). "Affective changes with estrogen and androgen replacement therapy in surgically menopausal women". J Affect Disord. 14 (2): 177–87. doi:10.1016/0165-0327(88)90061-4. PMID 2966832.
  11. ^ Sherwin BB (1988). "Estrogen and/or androgen replacement therapy and cognitive functioning in surgically menopausal women". Psychoneuroendocrinology. 13 (4): 345–57. doi:10.1016/0306-4530(88)90060-1. PMID 3067252. S2CID 24695692.
  12. ^ Gleason CH, Parker JM (September 1959). "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. doi:10.1210/endo-65-3-508. PMID 13828402.
  13. ^ Dodek SM (December 1960). "The hormonal control of lactation". Clin Obstet Gynecol. 3 (4): 1099–108. doi:10.1097/00003081-196003040-00022. PMID 13723335.
  14. ^ Greenblatt RB, Barfield WE, Jungck EC (January 1962). "The treatment of the menopause". Can Med Assoc J. 86 (3): 113–4. PMC 1848811. PMID 13901504.
  15. ^ Kelly MJ, Primrose T (December 1960). "Evaluation of a new preparation for the suppression of lactation". Can Med Assoc J. 83 (24): 1240–2. PMC 1938994. PMID 13752392.
  16. ^ Gleason CH (July 1964). "Testosterone 17-Heptanoate 3-Benziloylhydrazone". J. Med. Chem. 7 (4): 573. doi:10.1021/jm00334a042. PMID 14221154.



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