Estradiol pivalate

Estradiol pivalate
Clinical data
Trade names	Estrotate
Other names	Estradiol trimethyl acetate; Trimethyl estradiol acetate; Estradiol 17-(2,2-dimethylpropanoate)
Routes of; administration	Intramuscular injection
Drug class	Estrogen; Estrogen ester
Identifiers
	IUPAC name [(8R,9S,13S,14S,17S)-3-Hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] 2,2-dimethylpropanoate;
CAS Number	24894-50-6;
PubChem CID	10522263;
ChemSpider	8697659;
UNII	I12U06L6S4;
CompTox Dashboard (EPA)	DTXSID40179603 ;
Chemical and physical data
Formula	C23H32O3
Molar mass	356.506 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(C)(C)C(=O)O[C@H]1CC[C@H]2[C@@H]3CCc4cc(O)ccc4[C@H]3CC[C@]12C;
	InChI InChI=1S/C23H32O3/c1-22(2,3)21(25)26-20-10-9-19-18-7-5-14-13-15(24)6-8-16(14)17(18)11-12-23(19,20)4/h6,8,13,17-20,24H,5,7,9-12H2,1-4H3/t17-,18-,19+,20+,23+/m1/s1; Key:SLOFBKMZOOTTDZ-WCZGSDDISA-N;

Estradiol pivalate, also known as estradiol trimethyl acetate and sold under the brand name Estrotate, is an estrogen medication and an estrogen ester; specifically, the C3 pivalic acid (trimethylacetic acid) ester of estradiol.[1] It was marketed in the 1940s.[1] A combination of estradiol pivalate (1 mg/mL) and progesterone (10 mg/mL) in oil solution was available in 1949.[2][3][4] The duration of biological effect of estradiol pivalate in women has been studied.[5]

References

J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. p. 898. ISBN 978-1-4757-2085-3.
Postgraduate Medicine. McGraw-Hill. 1949. ESTROTATE AND ESTROTATE WITH PROGESTERONE purpose: Steroid hormone therapy. composition: Estrotate is the trimethyl acetic acid ester of alpha-estradiol. indications for use: Control of menopausal syndrome, functional uterine [...]
Marion E. Howard (1949). Modern Drug Encyclopedia and Therapeutic Index. Drug Publications. [...] Supply: ESTROTATE—Vials, multi dose 10 cc. Combination: ESTROTATE WITH PROGESTERONE—Each cc contains 1 mg estradiol trimethyl acetate and 10 mg progesterone. For the simultaneous administration where both natural ovarian [...]
Tyler, Edward T. (1949). "Use and misuse of endocrine therapy in sterility". Journal of the American Medical Association. 139 (9): 560. doi:10.1001/jama.1949.02900260006002. ISSN 0002-9955. Both hormones may be given in one injection with a preparation which contains 10 mg. of progesterone and 1 mg. of [estradiol] trimethyl acetate per cubic centimeter.15 One cubic centimeter is given three times weekly. [...] Supplied as Estrotate® (trimethyl acetic acid ester of alpha [estradiol] in sesame oil) with progesterone.
Brown, Willis E.; Bradbury, James T. (1949). "The use of the human vaginal smear in the assay of estrogens". The Journal of Clinical Endocrinology & Metabolism. 9 (8): 725–735. doi:10.1210/jcem-9-8-725. ISSN 0021-972X. PMID 18133489.

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[Elks2014-1] J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. p. 898. ISBN 978-1-4757-2085-3.

[McGraw-Hill1949-2] Postgraduate Medicine. McGraw-Hill. 1949. ESTROTATE AND ESTROTATE WITH PROGESTERONE purpose: Steroid hormone therapy. composition: Estrotate is the trimethyl acetic acid ester of alpha-estradiol. indications for use: Control of menopausal syndrome, functional uterine [...]

[Howard1949-3] Marion E. Howard (1949). Modern Drug Encyclopedia and Therapeutic Index. Drug Publications. [...] Supply: ESTROTATE—Vials, multi dose 10 cc. Combination: ESTROTATE WITH PROGESTERONE—Each cc contains 1 mg estradiol trimethyl acetate and 10 mg progesterone. For the simultaneous administration where both natural ovarian [...]

[Tyler1949-4] Tyler, Edward T. (1949). "Use and misuse of endocrine therapy in sterility". Journal of the American Medical Association. 139 (9): 560. doi:10.1001/jama.1949.02900260006002. ISSN 0002-9955. Both hormones may be given in one injection with a preparation which contains 10 mg. of progesterone and 1 mg. of [estradiol] trimethyl acetate per cubic centimeter.15 One cubic centimeter is given three times weekly. [...] Supplied as Estrotate® (trimethyl acetic acid ester of alpha [estradiol] in sesame oil) with progesterone.

[pmid18133489-5] Brown, Willis E.; Bradbury, James T. (1949). "The use of the human vaginal smear in the assay of estrogens". The Journal of Clinical Endocrinology & Metabolism. 9 (8): 725–735. doi:10.1210/jcem-9-8-725. ISSN 0021-972X. PMID 18133489.

Estradiol pivalate

See also

References