Estradiol pivalate explained

Iupac Name:[(8''R'',9''S'',13''S'',14''S'',17''S'')-3-Hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[''a'']phenanthren-17-yl] 2,2-dimethylpropanoate
Width:250px
Tradename:Estrotate, Estrotate with Progesterone, Menotrope
Routes Of Administration:By mouth, intramuscular injection
Class:Estrogen
Estrogen ester
Cas Number:24894-50-6
Pubchem:10522263
Chemspiderid:8697659
Unii:I12U06L6S4
Synonyms:E2-TMA; Estradiol trimethyl acetate; Trimethyl estradiol acetate; Estradiol 17-(2,2-dimethylpropanoate)
C:23
H:32
O:3
Smiles:CC(C)(C)C(=O)O[C@H]1CC[C@H]2[C@@H]3CCc4cc(O)ccc4[C@H]3CC[C@]12C
Stdinchi: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
Stdinchikey: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] or at the C17β position. It was marketed as an oil solution for intramuscular injection in the 1940s and 1950s. A combination of estradiol pivalate (1 mg/mL) and progesterone (10 mg/mL) in oil solution for intramuscular injection was available in 1949.[5] [6] [7] An aqueous suspension of estradiol pivalate was also developed by 1950 although whether it was ever marketed is unclear.[8]

The duration of biological effect of estradiol pivalate in women has been studied.[9] 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. 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.

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.[10] [11] [12] [13]

See also

Notes and References

  1. Book: Elks J . The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. 14 November 2014. Springer. 978-1-4757-2085-3. 898.
  2. Book: Negwer M . Organic-chemical Drugs and Their Synonyms: (an International Survey). 1994. Akademie Verlag. 978-3-05-500156-7. 2235.
  3. Book: Wilson CO, Gisvold O . Textbook of Organic Medicinal and Pharmaceutical Chemistry. 1956. Lippincott. 578. A trimethylacetic acid ester of α-estradiol in sesame oil solution [...].
  4. Book: Medical Times. 1952. Romaine Pierson Pub.. 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..
  5. New Drugs and Instruments . Postgraduate Medicine . 5 . 5 . 434–436 . 1949 . McGraw-Hill . 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..
  6. Book: Howard ME . Modern Drug Encyclopedia and Therapeutic Index. 1949. 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 [...].
  7. Tyler ET . Use and misuse of endocrine therapy in sterility . Journal of the American Medical Association . 139 . 9 . 560–564 . February 1949 . 18123546 . 10.1001/jama.1949.02900260006002 . 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. .
  8. Book: New York State Journal of Medicine. 1950. Medical Society of the State of New York. 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..
  9. Brown WE, Bradbury JT . The use of the human vaginal smear in the assay of estrogens . The Journal of Clinical Endocrinology and Metabolism . 9 . 8 . 725–735 . August 1949 . 18133489 . 10.1210/jcem-9-8-725 .
  10. Book: Unlisted Drugs. 1952. Unlisted Drugs. 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.. 58.
  11. Book: American Practitioner and Digest of Treatment. July 1952. Lippincott.. 604.
  12. Book: Medical Economics. 1952. Medical Economics, Incorporated. 61.
  13. Book: American Professional Pharmacist. 1952. American Professional Pharmacist, Incorporated. 633, 780.

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