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Estradiol pivalate Trade names Estrotate, Estrotate with Progesterone, Menotrope Other names E2-TMA; Estradiol trimethyl acetate; Trimethyl estradiol acetate; Estradiol 17-(2,2-dimethylpropanoate) Routes of administration By mouth , intramuscular injection Drug class Estrogen ; Estrogen ester
[(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 ) Formula C 23 H 32 O 3 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, the C3 pivalic acid (trimethylacetic acid) ester of estradiol .[1] [2] [3] 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] [5] [6]
The duration of biological effect of estradiol pivalate in women has been studied.[7] 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.[7] 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.[7]
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 .[8] [9] [10] [11] [12]
Mean change in vaginal smear test grade with different doses of estradiol pivalate (Estrotate) in oil solution by intramuscular injection in women.[7] There were 10 to 20 women in each dose group.[7]
See also
References
^ a b 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 .
^ Negwer, Martin (1994). Organic-chemical Drugs and Their Synonyms: (an International Survey) . Akademie Verlag. p. 2235. ISBN 978-3-05-500156-7 .
^ a b Wilson, Charles Owens; Gisvold, Ole (1956). Textbook of Organic Medicinal and Pharmaceutical Chemistry . Lippincott. p. 578. A trimethylacetic acid ester of α-estradiol in sesame oil solution [...]
^ "New Drugs and Instruments" . Postgraduate Medicine . 5 (5). McGraw-Hill: 434–6. 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 [...]
^ Howard, Marion E. (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): 560–4. 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.
^ a b c d e 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): 725–35. doi :10.1210/jcem-9-8-725 . PMID 18133489 .
^ Unlisted Drugs . Unlisted Drugs. 1952. p. 58. a Menotrope C. each tablet contains: choline bitartrate, 80 mg ; Estrota te (estradiol 3 -trimethylacetate j , 0,33 mg . ; folic acid, 0.46 mg.; and vitamin B12 U.S. P., 1.25 micrograms N. Lakeside Labs , A. for menopausal therapy R.
^ American Practitioner and Digest of Treatment . Lippincott. July 1952. p. 604.
^ Medical Times . Romaine Pierson Pub. 1952. pp. 390, 514.
^ Medical Economics . Medical Economics, Incorporated. 1952. p. 61.
^ American Professional Pharmacist . American Professional Pharmacist, Incorporated. 1952. pp. 633, 780.
Estrogens
ER Tooltip Estrogen receptor agonists
Steroidal: Alfatradiol
Certain androgens /anabolic steroids (e.g., testosterone , testosterone esters , methyltestosterone , metandienone , nandrolone esters ) (via estrogenic metabolites)
Certain progestins (e.g., norethisterone , noretynodrel , etynodiol diacetate , tibolone )
Clomestrone
Cloxestradiol acetate
Conjugated estriol
Conjugated estrogens
Epiestriol
Epimestrol
Esterified estrogens
Estetrol †
Estradiol
Estradiol esters (e.g., estradiol acetate , estradiol benzoate , estradiol cypionate , estradiol enanthate , estradiol undecylate , estradiol valerate , polyestradiol phosphate , estradiol ester mixtures (Climacteron ))
Estramustine phosphate
Estriol
Estriol esters (e.g., estriol succinate , polyestriol phosphate )
Estrogenic substances
Estrone
Estrone esters
Ethinylestradiol #
Hydroxyestrone diacetate
Mestranol
Methylestradiol
Moxestrol
Nilestriol
Prasterone (dehydroepiandrosterone; DHEA)
Promestriene
Quinestradol
Quinestrol
Progonadotropins
Antiestrogens
ER Tooltip Estrogen receptor antagonists (incl. SERMs Tooltip selective estrogen receptor modulators /SERDs Tooltip selective estrogen receptor downregulators )Aromatase inhibitors Antigonadotropins
Androgens /anabolic steroids (e.g., testosterone , testosterone esters , nandrolone esters , oxandrolone , fluoxymesterone )
D2 receptor antagonists (prolactin releasers) (e.g., domperidone , metoclopramide , risperidone , haloperidol , chlorpromazine , sulpiride )
GnRH agonists (e.g., leuprorelin , goserelin )
GnRH antagonists (e.g., cetrorelix , elagolix )
Progestogens (e.g., chlormadinone acetate , cyproterone acetate , gestonorone caproate , hydroxyprogesterone caproate , medroxyprogesterone acetate , megestrol acetate )
Others
ER Tooltip Estrogen receptor
Agonists
Steroidal: 2-Hydroxyestradiol
2-Hydroxyestrone
3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol
3α-Androstanediol
3α,5α-Dihydrolevonorgestrel
3β,5α-Dihydrolevonorgestrel
3α-Hydroxytibolone
3β-Hydroxytibolone
3β-Androstanediol
4-Androstenediol
4-Androstenedione
4-Fluoroestradiol
4-Hydroxyestradiol
4-Hydroxyestrone
4-Methoxyestradiol
4-Methoxyestrone
5-Androstenediol
7-Oxo-DHEA
7α-Hydroxy-DHEA
7α-Methylestradiol
7β-Hydroxyepiandrosterone
8,9-Dehydroestradiol
8,9-Dehydroestrone
8β-VE2
10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED)
11β-Chloromethylestradiol
11β-Methoxyestradiol
15α-Hydroxyestradiol
16-Ketoestradiol
16-Ketoestrone
16α-Fluoroestradiol
16α-Hydroxy-DHEA
16α-Hydroxyestrone
16α-Iodoestradiol
16α-LE2
16β-Hydroxyestrone
16β,17α-Epiestriol (16β-hydroxy-17α-estradiol)
17α-Estradiol (alfatradiol )
17α-Dihydroequilenin
17α-Dihydroequilin
17α-Epiestriol (16α-hydroxy-17α-estradiol)
17α-Ethynyl-3α-androstanediol
17α-Ethynyl-3β-androstanediol
17β-Dihydroequilenin
17β-Dihydroequilin
17β-Methyl-17α-dihydroequilenin
Abiraterone
Abiraterone acetate
Alestramustine
Almestrone
Anabolic steroids (e.g., testosterone and esters , methyltestosterone , metandienone (methandrostenolone) , nandrolone and esters , many others; via estrogenic metabolites)
Atrimustine
Bolandiol
Bolandiol dipropionate
Butolame
Clomestrone
Cloxestradiol
Conjugated estriol
Conjugated estrogens
Cyclodiol
Cyclotriol
DHEA
DHEA-S
ent -Estradiol
Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol)
Epimestrol
Equilenin
Equilin
ERA-63 (ORG-37663)
Esterified estrogens
Estetrol
Estradiol
Estramustine
Estramustine phosphate
Estrapronicate
Estrazinol
Estriol
Estrofurate
Estrogenic substances
Estromustine
Estrone
Etamestrol (eptamestrol)
Ethinylandrostenediol
Ethinylestradiol
Ethinylestriol
Ethylestradiol
Etynodiol
Etynodiol diacetate
Hexolame
Hippulin
Hydroxyestrone diacetate
Lynestrenol
Lynestrenol phenylpropionate
Mestranol
Methylestradiol
Moxestrol
Mytatrienediol
Nilestriol
Norethisterone
Noretynodrel
Orestrate
Pentolame
Prodiame
Prolame
Promestriene
RU-16117
Quinestradol
Quinestrol
Tibolone
Xenoestrogens: Anise -related (e.g., anethole , anol , dianethole , dianol , photoanethole )
Chalconoids (e.g., isoliquiritigenin , phloretin , phlorizin (phloridzin) , wedelolactone )
Coumestans (e.g., coumestrol , psoralidin )
Flavonoids (incl. 7,8-DHF , 8-prenylnaringenin , apigenin , baicalein , baicalin , biochanin A , calycosin , catechin , daidzein , daidzin , ECG , EGCG , epicatechin , equol , formononetin , glabrene , glabridin , genistein , genistin , glycitein , kaempferol , liquiritigenin , mirificin , myricetin , naringenin , penduletin , pinocembrin , prunetin , puerarin , quercetin , tectoridin , tectorigenin )
Lavender oil
Lignans (e.g., enterodiol , enterolactone , nyasol (cis -hinokiresinol) )
Metalloestrogens (e.g., cadmium )
Pesticides (e.g., alternariol , dieldrin , endosulfan , fenarimol , HPTE , methiocarb , methoxychlor , triclocarban , triclosan )
Phytosteroids (e.g., digitoxin (digitalis ), diosgenin , guggulsterone )
Phytosterols (e.g., β-sitosterol , campesterol , stigmasterol )
Resorcylic acid lactones (e.g., zearalanone , α-zearalenol , β-zearalenol , zearalenone , zeranol (α-zearalanol) , taleranol (teranol, β-zearalanol) )
Steroid -like (e.g., deoxymiroestrol , miroestrol )
Stilbenoids (e.g., resveratrol , rhaponticin )
Synthetic xenoestrogens (e.g., alkylphenols , bisphenols (e.g., BPA , BPF , BPS ), DDT , parabens , PBBs , PHBA , phthalates , PCBs )
Others (e.g., agnuside , rotundifuran )
Mixed (SERMs Tooltip Selective estrogen receptor modulators ) Antagonists
Coregulator-binding modulators: ERX-11
GPER Tooltip G protein-coupled estrogen receptor
Agonists Antagonists Unknown