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Estradiol acetate Pronunciation ESS -tra-DYE -ole ASS-uh-tate [ 1] Trade names Femtrace, Femring, Menoring Routes of administration Oral , vaginal (ring )ATC code Legal status
In general: ℞ (Prescription only)
[(8R,9S,13S,14S,17S)-17-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl] acetate
CAS Number PubChem CID DrugBank ChemSpider UNII KEGG ChEMBL CompTox Dashboard (EPA ) ECHA InfoCard 100.167.088 Formula C 20 H 26 O 3 Molar mass 314.419 g/mol g·mol−1 3D model (JSmol )
C(C)(=O)Oc1ccc2[C@@H]3CC[C@@]4([C@H](CC[C@@H]4[C@@H]3CCc2c1)O)C
InChI=1S/C20H26O3/c1-12(21)23-14-4-6-15-13(11-14)3-5-17-16(15)9-10-20(2)18(17)7-8-19(20)22/h4,6,11,16-19,22H,3,5,7-10H2,1-2H3/t16-,17-,18+,19+,20+/m1/s1
Key:FHXBMXJMKMWVRG-SLHNCBLASA-N
Estradiol acetate (INN , USAN , BAN ) (brand names Femtrace , Femring , Menoring ), or estradiol 3-acetate , is a semisynthetic , steroidal estrogen and an estrogen ester – specifically, the 3-acetate ester of estradiol .[ 2] It acts as a prodrug of estradiol, and hence, is considered to be a natural , bioidentical form of estrogen.[ 3] Estradiol acetate is relatively recent to the market, having been first approved in a vaginal ring formulation as Menoring in the United Kingdom in 2001,[ 4] followed by another vaginal ring formulation as Femring in the United States in 2003,[ 5] and finally as an oral preparation as Femtrace in the United States in 2004.[ 5] It is used as a component of hormone replacement therapy to treat and prevent symptoms of menopause such as osteoporosis in postmenopausal women.[ 4] [ 6] [ 7] [ 8]
The Women's Health Initiative studies report increased health risks for postmenopausal women when using unopposed estrogens. Estrogens with or without progestins should be prescribed at the lowest effective doses and for the shortest duration consistent with treatment goals and risks for the individual woman.[ 9]
See also
References
^ https://www.drugs.com/cdi/estradiol-acetate.html
^ Buckler H, Al-Azzawi F (2003). "The effect of a novel vaginal ring delivering oestradiol acetate on climacteric symptoms in postmenopausal women". BJOG . 110 (8): 753–9. PMID 12892687 .
^ Michael Oettel; Ekkehard Schillinger (6 December 2012). Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen . Springer Science & Business Media. pp. 261–. ISBN 978-3-642-60107-1 .
^ a b Speroff L (October 2003). "Efficacy and tolerability of a novel estradiol vaginal ring for relief of menopausal symptoms". Obstetrics and Gynecology . 102 (4): 823–34. doi :10.1016/s0029-7844(03)00764-6 . PMID 14551014 .
^ a b Sivanandy MS, Masimasi N, Thacker HL (May 2007). "Newer hormonal therapies: lower doses; oral, transdermal, and vaginal formulations" . Cleveland Clinic Journal of Medicine . 74 (5): 369–75. doi :10.3949/ccjm.74.5.369 . PMID 17506242 .
^ Al-Azzawi F, Lees B, Thompson J, Stevenson JC (2005). "Bone mineral density in postmenopausal women treated with a vaginal ring delivering systemic doses of estradiol acetate" . Menopause (New York, N.Y.) . 12 (3): 331–9. doi :10.1097/01.gme.0000163870.03388.4d . PMID 15879923 .
^ Utian WH, Speroff L, Ellman H, Dart C (2005). "Comparative controlled trial of a novel oral estrogen therapy, estradiol acetate, for relief of menopause symptoms" . Menopause (New York, N.Y.) . 12 (6): 708–15. doi :10.1097/01.gme.0000184220.63459.a8 . PMID 16278614 .
^ Speroff L, Haney AF, Gilbert RD, Ellman H (2006). "Efficacy of a new, oral estradiol acetate formulation for relief of menopause symptoms" . Menopause (New York, N.Y.) . 13 (3): 442–50. doi :10.1097/01.gme.0000182802.06762.b2 . PMID 16735941 .
^ "FEMRING" . DailyMed . U.S. National Library of Medicine. Retrieved June 2010 .
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