{{Short description|Chemical compound}} {{Distinguish|Estramustine phosphate|Estramustine}} {{Drugbox | Verifiedfields = | Watchedfields = | verifiedrevid = | IUPAC_name = [(8''R'',9''S'',13''S'',14''S'')-13-Methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6''H''-cyclopenta[''a'']phenanthren-3-yl] ''N'',''N''-bis(2-chloroethyl)carbamate | image = Estromustine.svg | image_class = skin-invert-image | width = 250px
<!--Clinical data--> | tradename = | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_US = <!-- A / B / C / D / X --> | pregnancy_category = | legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration = | class = Chemotherapeutic agent; Estrogen; Estrogen ester
<!--Pharmacokinetic data--> | bioavailability = | protein_bound = | metabolism = | elimination_half-life = 14 hours<ref name="ChabnerLongo2011" /> | excretion =
<!-- Identifiers --> | CAS_number_Ref = | CAS_number = 62899-40-5 | CAS_supplemental = | ATC_prefix = | ATC_suffix = | ATC_supplemental = | PubChem = 124946 | IUPHAR_ligand = | DrugBank_Ref = | DrugBank = | ChemSpiderID_Ref = | ChemSpiderID = 111241 | UNII = | KEGG = | ChEBI = | ChEMBL = | synonyms = EoM; Leo 271 f; Estrone 17β-3-N-bis(2-chloroethyl)carbamate; Estrone–cytostatic complex
<!--Chemical data--> | C=23 | H=29 | Cl=2 | N=1 | O=3 | SMILES = C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CCC4=C3C=CC(=C4)OC(=O)N(CCCl)CCCl | StdInChI_Ref = | StdInChI = 1S/C23H29Cl2NO3/c1-23-9-8-18-17-5-3-16(29-22(28)26(12-10-24)13-11-25)14-15(17)2-4-19(18)20(23)6-7-21(23)27/h3,5,14,18-20H,2,4,6-13H2,1H3/t18-,19-,20+,23+/m1/s1 | StdInChIKey_Ref = | StdInChIKey = AXWYROHIFVWHMR-UGTOYMOASA-N }}
'''Estromustine''' (developmental code name '''Leo 271 f'''), also known as '''estrone 17β-3-N-bis(2-chloroethyl)carbamate''' or '''estrone–cytostatic complex''',<ref>{{cite journal | vauthors = Yamanaka H, Kitaura K, Imai K, Yuasa H, Nakai K, Matsumura Y, Uehara H, Shida K | title = In vivo studies of 3H-estramustine in castrated male rat | journal = Acta Urologica Japonica | date = 1981 | volume = 27 | issue = 3 | pages = 243–50 | url = http://repository.kulib.kyoto-u.ac.jp/dspace/handle/2433/122855}}</ref> is a major active metabolite of the cytostatic antineoplastic agent and estrogen estramustine phosphate, a medication used in the treatment of prostate cancer.<ref name="ChabnerLongo2011">{{cite book| vauthors = Chabner BA, Longo DL |title=Cancer Chemotherapy and Biotherapy: Principles and Practice|url=https://books.google.com/books?id=0U4aj4GZWCIC&pg=PA252|date=7 December 2011|publisher=Lippincott Williams & Wilkins|isbn=978-1-4511-4820-6|pages=252–}}</ref><ref>{{cite book|title=Medical Subject Headings: Supplementary chemical records|url=https://books.google.com/books?id=oqttAAAAMAAJ|year=1993|publisher=The Library|page=684}}</ref>
==See also== * List of hormonal cytostatic antineoplastic agents * List of estrogen esters § Estradiol esters
==References== {{Reflist}}
{{Estrogen receptor modulators}} {{Androgen receptor modulators}}
Category:Abandoned drugs Category:Antiandrogens Category:Antigonadotropins Category:Antineoplastic drugs Category:Carbamates Category:Chloroethyl compounds Category:Estradiol esters Category:Estranes Category:Estrogens Category:Human drug metabolites Category:Ketones Category:Mitotic inhibitors Category:Nitrogen mustards Category:Phenol esters
{{Estrane-stub}} {{Antineoplastic-drug-stub}}