| 词条 | Estradiol acetate |
| 释义 |
| Verifiedfields = | Watchedfields = | verifiedrevid = | IUPAC_name = [(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 | image = Estradiol 3-acetate.svg | width = 250px | image2 = Estradiol acetate molecule ball.png | width2 = 250px | pronounce = {{IPAc-en|ˌ|ɛ|s|t|r|ə|ˈ|d|aɪ|oʊ|l|_|ˈ|æ|s|ə|t|eɪ|t}} {{respell|ES|trə|DY|ohl|_|ASS|ə|tayt}}[1] | tradename = Femtrace, Femring, Menoring | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = | legal_UK = | legal_US = | legal_status = Rx-only | routes_of_administration = By mouth, vaginal (ring)[2] | class = Estrogen; Estrogen ester | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion = | CAS_number_Ref = | CAS_number = 4245-41-4 | CAS_supplemental = | ATC_prefix = G03 | ATC_suffix = CA03 | ATC_supplemental = | PubChem = 9818306 | IUPHAR_ligand = | DrugBank_Ref = | DrugBank = DB13952 | ChemSpiderID_Ref = | ChemSpiderID = 7994056 | UNII = 5R97F5H93P | KEGG = D04061 | ChEBI = | ChEMBL = 1200430 | synonyms = E2A; E3A; Estradiol 3-acetate | C=20 | H=26 | O=3 | molecular_weight = 314.419 g/mol | SMILES = CC(=O)OC1=CC2=C(C=C1)[C@H]3CC[C@]4([C@H]([C@@H]3CC2)CC[C@@H]4O)C | StdInChI_Ref = | StdInChI = 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 | StdInChIKey_Ref = | StdInChIKey = FHXBMXJMKMWVRG-SLHNCBLASA-N }}Estradiol acetate, sold under the brand names Femtrace, Femring, and Menoring, is an estrogen medication which is used in hormone therapy for the treatment of menopausal symptoms in women.[2][3][4][5] It is taken by mouth or given as a vaginal ring once every three months.[2]Side effects of estradiol acetate include breast tenderness, breast enlargement, nausea, headache, and fluid retention.[8][4][5] Estradiol acetate is a synthetic estrogen and hence is an agonist of the estrogen receptor (ER), the biological target of estrogens like estradiol.[6][12] It is an estrogen ester and a prodrug of estradiol in the body.[12][6] Because of this, it is considered to be a natural and bioidentical form of estrogen.[7][8] Estradiol acetate was introduced for medical use in 2001.[17] It is available in the United States and the United Kingdom.[17][2] The formulation for use by mouth has been discontinued in the United States.[20] {{TOC limit|3}}Medical uses{{Main|Estradiol (medication)#Medical uses}}Estradiol acetate is used as a component of menopausal hormone therapy to treat and prevent menopausal symptoms such as hot flashes and osteoporosis in women.[21][9][10][11] The Women's Health Initiative studies report increased health risks for menopausal women when using unopposed estrogens.[5] 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.[5] {{Estrogen dosages for menopausal hormone therapy}}Available formsEstradiol acetate comes in the form of 0.45, 0.9, and 1.8 mg oral tablets (Femtrace) and in the form of 12.4 or 24.8 mg vaginal rings that release 50 or 100 μg/day estradiol for 3 months (Femring, Menoring).[4][5][12] However, the Femtrace product was discontinued in the United States.[13] {{Available forms of estradiol}}Side effects{{Main|Estradiol (medication)#Side effects}}The side effects of estradiol acetate are the same as those of estradiol. Examples of such side effects include breast tenderness and enlargement, nausea, bloating, edema, headache, and melasma.[14] PharmacologyPharmacodynamics{{See also|Pharmacodynamics of estradiol}}Estradiol acetate is an estradiol ester, or a prodrug of estradiol.[7][6] As such, it is an estrogen, or an agonist of the estrogen receptors.[6][7] Estradiol acetate is of about 15% higher molecular weight than estradiol due to the presence of its C3 acetate ester.[2] Because estradiol acetate is a prodrug of estradiol, it is considered to be a natural and bioidentical form of estrogen.[7][8] Pharmacokinetics{{See also|Pharmacokinetics of estradiol}}Estradiol acetate is converted into estradiol in the body.[7][6] Chemistry{{See also|Estrogen ester|List of estrogen esters}}Estradiol acetate is a synthetic estrane steroid and the C3 acetate ester of estradiol.[2] It is also known as estradiol 3-acetate or as estra-1,3,5(10)-triene-3,17β-diol 3-acetate.[2] Another common ester of estradiol in use for oral administration is estradiol valerate, which is a C17β ester of estradiol.[6][15] {{Structural properties of major estradiol esters}}HistoryEstradiol acetate is relatively recent to the market, having been first approved in a vaginal ring formulation as Menoring in the United Kingdom in 2001,[16] followed by a vaginal ring formulation as Femring in the United States in 2002,[17] and finally as an oral preparation as Femtrace in the United States in 2004.[17][18] Society and cultureGeneric namesEstradiol acetate is the generic name of the drug and its {{abbrlink|USAN|United States Adopted Name}}.[2]Brand namesEstradiol acetate is marketed under the brand names Femtrace, Femring, and Menoring.[2][19][20] AvailabilityEstradiol acetate is available in the United States and the United Kingdom.[18][2] References1. ^https://www.drugs.com/cdi/estradiol-acetate.html {{Estradiol}}{{Estrogens and antiestrogens}}{{Estrogen receptor modulators}}2. ^1 2 3 4 5 6 7 https://www.drugs.com/international/estradiol-acetate.html 3. ^{{cite journal | vauthors = Buckler H, Al-Azzawi F | title = The effect of a novel vaginal ring delivering oestradiol acetate on climacteric symptoms in postmenopausal women | journal = BJOG | volume = 110 | issue = 8 | pages = 753–9 | year = 2003 | pmid = 12892687 | doi = 10.1016/s1470-0328(03)02908-2| url = }} 4. ^1 2 https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021633s005lbl.pdf 5. ^1 2 3 4 {{cite web|title=FEMRING|url=http://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=86b90d68-bfb6-47f6-aa5b-a6642391ff13#i4i_clinical_studies_id_2a230567-d4b8-4161-9dd0-fb082cd301e5|website=DailyMed|publisher=U.S. National Library of Medicine}} 6. ^1 2 3 4 5 {{cite journal | vauthors = Kuhl H | title = Pharmacology of estrogens and progestogens: influence of different routes of administration | journal = Climacteric | volume = 8 Suppl 1 | issue = | pages = 3–63 | year = 2005 | pmid = 16112947 | doi = 10.1080/13697130500148875 | url = http://hormonebalance.org/images/documents/Kuhl%2005%20%20Pharm%20Estro%20Progest%20Climacteric_1313155660.pdf}} 7. ^1 2 3 4 5 6 {{cite book|author1=Michael Oettel|author2=Ekkehard Schillinger|title=Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen|url=https://books.google.com/books?id=wBvyCAAAQBAJ&pg=PA261|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-3-642-60107-1|page=261|quote=Natural estrogens considered here include: [...] Esters of 17β-estradiol, such as estradiol valerate, estradiol benzoate and estradiol cypionate. Esterification aims at either better absorption after oral administration or a sustained release from the depot after intramuscular administration. During absorption, the esters are cleaved by endogenous esterases and the pharmacologically active 17β-estradiol is released; therefore, the esters are considered as natural estrogens.}} 8. ^1 {{cite journal | vauthors = Cirigliano M | title = Bioidentical hormone therapy: a review of the evidence | journal = J Womens Health (Larchmt) | volume = 16 | issue = 5 | pages = 600–31 | date = June 2007 | pmid = 17627398 | doi = 10.1089/jwh.2006.0311 | url = }} 9. ^{{cite journal |vauthors=Al-Azzawi F, Lees B, Thompson J, Stevenson JC | title = Bone mineral density in postmenopausal women treated with a vaginal ring delivering systemic doses of estradiol acetate | journal = Menopause | volume = 12 | issue = 3 | pages = 331–9 | year = 2005 | pmid = 15879923 | doi = 10.1097/01.gme.0000163870.03388.4d| url = http://meta.wkhealth.com/pt/pt-core/template-journal/lwwgateway/media/landingpage.htm?issn=1072-3714&volume=12&issue=3&spage=331}} 10. ^{{cite journal |vauthors=Utian WH, Speroff L, Ellman H, Dart C | title = Comparative controlled trial of a novel oral estrogen therapy, estradiol acetate, for relief of menopause symptoms | journal = Menopause | volume = 12 | issue = 6 | pages = 708–15 | year = 2005 | pmid = 16278614 | doi = 10.1097/01.gme.0000184220.63459.a8 | url = http://meta.wkhealth.com/pt/pt-core/template-journal/lwwgateway/media/landingpage.htm?issn=1072-3714&volume=12&issue=6&spage=708}} 11. ^{{cite journal |vauthors=Speroff L, Haney AF, Gilbert RD, Ellman H | title = Efficacy of a new, oral estradiol acetate formulation for relief of menopause symptoms | journal = Menopause | volume = 13 | issue = 3 | pages = 442–50 | year = 2006 | pmid = 16735941 | doi = 10.1097/01.gme.0000182802.06762.b2 | url = http://meta.wkhealth.com/pt/pt-core/template-journal/lwwgateway/media/landingpage.htm?issn=1072-3714&volume=13&issue=3&spage=442}} 12. ^{{cite book|author1=Deitra Leonard Lowdermilk|author2=Shannon E. Perry|author3=Mary Catherine Cashion|author4=Kathryn Rhodes Alden|title=Maternity and Women's Health Care - E-Book|url=https://books.google.com/books?id=urzuBQAAQBAJ&pg=PA137|date=18 December 2014|publisher=Elsevier Health Sciences|isbn=978-0-323-39019-4|pages=137–}} 13. ^1 https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=021633 14. ^1 {{cite book|author=Amit K. Ghosh|title=Mayo Clinic Internal Medicine Board Review|url=https://books.google.com/books?id=LS65jBzoD40C&pg=PA222|date=23 September 2010|publisher=OUP USA|isbn=978-0-19-975569-1|pages=222–}} 15. ^{{cite journal |vauthors=Düsterberg B, Nishino Y | title = Pharmacokinetic and pharmacological features of oestradiol valerate | journal = Maturitas | volume = 4 | issue = 4 | pages = 315–24 |date=December 1982 | pmid = 7169965 | doi = 10.1016/0378-5122(82)90064-0| url = http://linkinghub.elsevier.com/retrieve/pii/0378-5122(82)90064-0}} 16. ^1 {{cite journal | author = Speroff L | title = Efficacy and tolerability of a novel estradiol vaginal ring for relief of menopausal symptoms | journal = Obstetrics and Gynecology | volume = 102 | issue = 4 | pages = 823–34 |date=October 2003 | pmid = 14551014 | doi = 10.1016/s0029-7844(03)00764-6| url = }} 17. ^1 2 3 {{cite journal |vauthors=Sivanandy MS, Masimasi N, Thacker HL | title = Newer hormonal therapies: lower doses; oral, transdermal, and vaginal formulations | journal = Cleveland Clinic Journal of Medicine | volume = 74 | issue = 5 | pages = 369–75 |date=May 2007 | pmid = 17506242 | doi = 10.3949/ccjm.74.5.369| url = http://www.ccjm.org/cgi/pmidlookup?view=long&pmid=17506242}} 18. ^1 2 3 {{cite journal | vauthors = Ballagh SA | title = Vaginal rings for menopausal symptom relief | journal = Drugs Aging | volume = 21 | issue = 12 | pages = 757–66 | date = 2004 | pmid = 15382956 | doi = 10.2165/00002512-200421120-00001 | url = }} 19. ^{{cite book|author=U.S. Food and Drug Administration|title=Menopause - Medicines to Help You|url=https://books.google.com/books?id=LCajOxNaM_4C&pg=PA3|year=2009|publisher=GPO FCIC|isbn=978-1-61221-026-1|pages=3–}} 20. ^{{cite book|author1=Marc A. Fritz|author2=Leon Speroff|title=Clinical Gynecologic Endocrinology and Infertility|url=https://books.google.com/books?id=KZLubBxJEwEC&pg=PA757|date=28 March 2012|publisher=Lippincott Williams & Wilkins|isbn=978-1-4511-4847-3|pages=757–}} 6 : Acetate esters|Alcohols|Estradiol esters|Estranes|Prodrugs|Synthetic estrogens |
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