Estradiol pivalate

Last updated
Estradiol pivalate
Estradiol pivalate structure.svg
Clinical data
Trade names Estrotate, Estrotate with Progesterone, Menotrope
Other namesE2-TMA; Estradiol trimethyl acetate; Trimethyl estradiol acetate; Estradiol 17-(2,2-dimethylpropanoate)
Routes of
administration 		By mouth, intramuscular injection
Drug class Estrogen; Estrogen ester
Identifiers
  • [(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
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C23H32O3
Molar mass 356.506 g·mol−1
3D model (JSmol)
  • CC(C)(C)C(=O)O[C@H]1CC[C@H]2[C@@H]3CCc4cc(O)ccc4[C@H]3CC[C@]12C
  • 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 (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. There were 10 to 20 women in each dose group. Vaginal changes with estradiol pivalate in oil solution by intramuscular injection in women.png
Mean change in vaginal smear test grade with different doses of estradiol pivalate (Estrotate) in oil solution by intramuscular injection in women. There were 10 to 20 women in each dose group.

See also

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<span class="mw-page-title-main">Estradiol benzoate/estradiol dienanthate/testosterone enanthate benzilic acid hydrazone</span> Combination drug

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<span class="mw-page-title-main">Estradiol pivalate/progesterone</span> Combination drug

Estradiol pivalate/progesterone (ETMA/P4), sold under the brand name Estrotate with Progesterone, is a combination medication of estradiol pivalate, an estrogen, and progesterone (P4), a progestogen, which was used in menopausal hormone therapy and the treatment of gynecological disorders but is no longer available. It contained 1 mg/mL ETMA and 10 mg/mL P4 in oil solution provided in vials and was administered by intramuscular injection at regular intervals.

References

  1. 1 2 3 Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. p. 898. ISBN   978-1-4757-2085-3.
  2. 1 2 Negwer M (1994). Organic-chemical Drugs and Their Synonyms: (an International Survey). Akademie Verlag. p. 2235. ISBN   978-3-05-500156-7.
  3. 1 2 Wilson 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 [...]
  4. 1 2 "New Drugs and Instruments". Postgraduate Medicine. McGraw-Hill. 5 (5): 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.
  5. 1 2 New 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.
  6. 1 2 Unlisted 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.
  7. 1 2 Medical Times. Romaine Pierson Pub. 1952. pp. 388–390, 514. formula: Each tablet of MENOTROPE contains Choline Bitartrate 80.00 mg. Estrotate (estradiol-3-trimethylacetate) 0.33 mg.; Folic Acid 0.46 mg.; Vitamin B12 U.S.P. 125 mcg.
  8. ↑ 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 [...]
  9. ↑ 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.
  10. 1 2 3 4 5 Brown 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.
  11. ↑ American Practitioner and Digest of Treatment. Lippincott. July 1952. p. 604.
  12. ↑ Medical Economics. Medical Economics, Incorporated. 1952. p. 61.
  13. ↑ American Professional Pharmacist. American Professional Pharmacist, Incorporated. 1952. pp. 633, 780.


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