Estradiol pivalate, also known as estradiol trimethyl acetate (E2-TMA) and sold under the brand name Estrotate, is an estrogen medication and an estrogen ester; specifically, a pivalic acid (trimethylacetic acid) ester of estradiol.[1][2][3] Literature sources are conflicting as to whether the ester is located at the C3 position[4][5][6][7] or at the C17β position.[1][2] It was marketed as an oil solution for intramuscular injection in the 1940s and 1950s.[1][3] A combination of estradiol pivalate (1 mg/mL) and progesterone (10 mg/mL) in oil solution for intramuscular injection was available in 1949.[4][8][9] An aqueous suspension of estradiol pivalate was also developed by 1950 although whether it was ever marketed is unclear.[5]
The duration of biological effect of estradiol pivalate in women has been studied.[10] It has been found to stimulate the vaginal epithelium in postmenopausal women, with a minimally effective dose of 0.16 mg and a maximally effective dose of 0.5 mg, both by intramuscular injection.[10] Its effect lasted for about 4 weeks at a dose of 0.16 mg and for more than 7 weeks at a dose of 3.3 mg.[10]
Menotrope was an oral tablet that contained 0.33 mg estradiol pivalate, 80 mg choline bitartrate, 0.46 mg folic acid, and 1.25 μg cyanocobalamin (vitamin B12) and was used in menopausal hormone therapy.[6][11][7][12][13]
Mean change in vaginal smear test grade with different doses of estradiol pivalate (Estrotate) in oil solution by intramuscular injection in women.[10] There were 10 to 20 women in each dose group.[10]
^ abcElks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. p. 898. ISBN 978-1-4757-2085-3.
^ abNegwer M (1994). Organic-chemical Drugs and Their Synonyms: (an International Survey). Akademie Verlag. p. 2235. ISBN 978-3-05-500156-7.
^ abWilson CO, Gisvold O (1956). Textbook of Organic Medicinal and Pharmaceutical Chemistry. Lippincott. p. 578. A trimethylacetic acid ester of α-estradiol in sesame oil solution [...]
^ ab"New Drugs and Instruments". Postgraduate Medicine. 5 (5). McGraw-Hill: 434–436. 1949. doi:10.1080/00325481.1949.11693827. 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 [...] HOW SUPPLIED : Estrotate is supplied as the sesame oil solution in multidose 10 cc. vials containing 1.0 mg. alpha estradiol 3-trimethylacetate per cc.
^ abNew York State Journal of Medicine. Medical Society of the State of New York. 1950. p. 835. Booth 74 will feature the lipotropic medications, Methyroid and Lipotropic Capsules, Lakeside, as well as the new Aqueous Suspension of Estrotate (alpha estradiol 3-trimethylacetate). Lanteen Medical Laboratories, Inc., Evanston.
^ abUnlisted Drugs. Unlisted Drugs. 1952. p. 58. Menotrope. C. each tablet contains: choline bitartrate, 80 mg; Estrotate (estradiol 3-trimethylacetate), 0.33 mg; folic acid, 0.46 mg.; and vitamin B12 U.S.P., 1.25 micrograms. M. Lakeside Labs. A. for menopausal therapy.
^Howard ME (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 ET (February 1949). "Use and misuse of endocrine therapy in sterility". Journal of the American Medical Association. 139 (9): 560–564. doi:10.1001/jama.1949.02900260006002. PMID 18123546. 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.
^ abcdeBrown WE, Bradbury JT (August 1949). "The use of the human vaginal smear in the assay of estrogens". The Journal of Clinical Endocrinology and Metabolism. 9 (8): 725–735. doi:10.1210/jcem-9-8-725. PMID 18133489.
^American Practitioner and Digest of Treatment. Lippincott. July 1952. p. 604.
^Medical Economics. Medical Economics, Incorporated. 1952. p. 61.
^American Professional Pharmacist. American Professional Pharmacist, Incorporated. 1952. pp. 633, 780.
and 24 Related for: Estradiol pivalate information
Estradiolpivalate, also known as estradiol trimethyl acetate (E2-TMA) and sold under the brand name Estrotate, is an estrogen medication and an estrogen...
The pharmacology of estradiol, an estrogen medication and naturally occurring steroid hormone, concerns its pharmacodynamics, pharmacokinetics, and various...
Estradiol valerate (EV), sold for use by mouth under the brand name Progynova and for use by injection under the brand names Delestrogen and Progynon...
that have estrogenic hormonal activity: estrone (E1), estradiol (E2), and estriol (E3). Estradiol, an estrane, is the most potent and prevalent. Another...
Estradiol (E2), also spelled oestradiol, is an estrogen steroid hormone and the major female sex hormone. It is involved in the regulation of female reproductive...
women include estradiol, which is the predominant natural estrogen in women, and estradiol esters such as estradiol valerate and estradiol cypionate, which...
Estradiol cypionate (EC), sold under the brand name Depo-Estradiol among others, is an estrogen medication which is used in hormone therapy for menopausal...
Estradiol enantate (EEn or E2-EN), also spelled estradiol enanthate and sold under the brand names Perlutal and Topasel among others, is an estrogen medication...
Estradiol undecylate (EU, EUn, E2U), also known as estradiol undecanoate and formerly sold under the brand names Delestrec and Progynon Depot 100 among...
Estradiol benzoate (EB), sold under the brand name Progynon-B among others, is an estrogen medication which is used in hormone therapy for menopausal...
Instead, other non-oral forms of estradiol such as transdermal estradiol are recommended and may be used. Estradiol injectables are generally well-tolerated...
The pharmacology of estradiol, an estrogen medication and naturally occurring steroid hormone, concerns its pharmacodynamics, pharmacokinetics, and various...
This is a list of currently marketed formulations of estradiol benzoate (EB) throughout the world. Both EB alone and combinations of EB with other medications...
estrogen receptor, the biological target of estrogens like estradiol. Compared to estradiol, certain estrogens in CEEs are more resistant to metabolism...
Estradiol disulfate (also known as E2DS or estradiol 3,17β-disulfate) is an endogenous estrogen conjugate and metabolite of estradiol. It is related to...
An estrogen ester is an ester of an estrogen, most typically of estradiol but also of other estrogens such as estrone, estriol, and even nonsteroidal...
Estradiol dipropionate (EDP), sold under the brand names Agofollin, Di-Ovocylin, and Progynon DP among others, is an estrogen medication which has been...
Estradiol acetate (EA), sold under the brand names Femtrace, Femring, and Menoring, is an estrogen medication which is used in hormone therapy for the...
The hydroxylation of estradiol is one of the major routes of metabolism of the estrogen steroid hormone estradiol. It is hydroxylated into the catechol...
of estrogens like estradiol. It is an estrogen ester in the form of a polymer and is an extremely long-lasting prodrug of estradiol in the body. The biological...
Estradiol glucuronide, or estradiol 17β-D-glucuronide, is a conjugated metabolite of estradiol. It is formed from estradiol in the liver by UDP-glucuronyltransferase...
natural estradiol ester and a long-acting progestin ester, are available for clinical use. Estrogens that are used include estradiol valerate, estradiol cypionate...
Global Information
