Testosterone enantate benzilic acid hydrazone

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]

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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.

Testosterone enantate
benzilic acid hydrazone

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[1][2]
Identifiers
IUPAC name [(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	18625-33-7
PubChem CID	101982710
DrugBank	DB13947
ChemSpider	21160607
UNII	X8Z8A2G2Y4
Chemical and physical data
Formula	C40H52N2O4
Molar mass	624.866 g·mol−1
3D model (JSmol)	Interactive image
SMILES 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 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

Chemistry

Chemical synthesis of TEBH has been described.^[16]

See also

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