Chemistry:Testosterone enantate benzilic acid hydrazone

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
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;

Short description: Chemical compound

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]

Chemistry

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

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.

{{Navbox

| name = Androgens and antiandrogens
| title = Androgens and antiandrogens
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| group1 = Androgens
(incl. AAS)

| list1 =

| group2 = Antiandrogens
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| groupstyle = text-align:center;
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  | group1 = AR antagonists
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  | group2 = Steroidogenesis
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  | list3 =

D₂ receptor antagonists (prolactin releasers) (e.g., domperidone, metoclopramide, risperidone, haloperidol, chlorpromazine, sulpiride)
Estrogens (e.g., bifluranol, [[diethylstilbestrol, estradiol, estradiol esters, ethinylestradiol, ethinylestradiol sulfonate, paroxypropione)
GnRH agonists (e.g., leuprorelin)
GnRH antagonists (e.g., cetrorelix)
Progestogens (incl., chlormadinone acetate, [[cyproterone acetate, hydroxyprogesterone caproate, gestonorone caproate, [[Chemistry:Medroxyprogesterone medroxyprogesterone acetate, Chemistry:Megestrol acetate|megestrol acetate]])

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Androstenedione immunogens: Androvax (androstenedione albumin)
Ovandrotone albumin (Fecundin)

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^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

See also: Androgen receptor modulators; Estrogens and antiestrogens; Progestogens and antiprogestogens; List of androgens/anabolic steroids

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Original source: https://en.wikipedia.org/wiki/Testosterone enantate benzilic acid hydrazone. Read more

[Elks2014-1] 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.

[pmid22971455-2] 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.

[Thieme1969-3] Geburtshilfe und Frauenheilkunde: Ergebnisse der Forschung für die Praxis. Georg Thieme Verlag.. 1969. https://books.google.com/books?id=_-owAAAAIAAJ.

[Barth1971-4] Zentralblatt für Gynäkologie. J. A. Barth. 1971. https://books.google.com/books?id=uNkwAAAAIAAJ.

[pmid6367474-5] "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.

[pmid3881960-6] "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.

[pmid4079822-7] "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.

[pmid3903822-8] "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.

[pmid3826177-9] "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.

[pmid2966832-10] "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.

[pmid3067252-11] "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.

[pmid13828402-12] "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.

[pmid13723335-13] "The hormonal control of lactation". Clin Obstet Gynecol 3 (4): 1099–108. December 1960. doi:10.1097/00003081-196003040-00022. PMID 13723335.

[pmid13901504-14] "The treatment of the menopause". Can Med Assoc J 86 (3): 113–4. January 1962. PMID 13901504.

[pmid13752392-15] "Evaluation of a new preparation for the suppression of lactation". Can Med Assoc J 83 (24): 1240–2. December 1960. PMID 13752392.

[pmid14221154-16] "Testosterone 17-Heptanoate 3-Benziloylhydrazone". J. Med. Chem. 7 (4): 573. July 1964. doi:10.1021/jm00334a042. PMID 14221154.

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