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Abandoned drugs
Testosterone enantate benzilic acid hydrazone
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    Testosterone enantate benzilic acid hydrazone

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    Testosterone enantate
    benzilic acid hydrazone
    Testosterone enanthate benziloylhydrazone.svg
    Clinical data
    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
    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
    Formula C40H52N2O4
    Molar mass 624.866 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. It was previously marketed in combination with estradiol benzoate and estradiol dienantate under the brand names Climacteron, Lactimex, and Lactostat. Clinical studies have assessed this formulation. TEBH was first described in the scientific literature in 1959. It is a very long-lasting prodrug of testosterone when administered in oil via intramuscular injection.

    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

    Chemical synthesis of TEBH has been described.

    See also




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