{{Short description|Chemical compound}} {{About|a non-clinically used compound|the pharmaceutical drug|Estramustine phosphate}} {{cs1 config|name-list-style=vanc|display-authors=6}} {{Drugbox | Verifiedfields = verified | Watchedfields = verified | verifiedrevid = | IUPAC_name = [(8''R'',9''S'',13''S'',14''S'',17''S'')-17-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[''a'']phenanthren-3-yl] ''N'',''N''-bis(2-chloroethyl)carbamate | image = Estramustine.svg | image_class = skin-invert-image | alt = Skeletal formula of estramustine | width = 250px | image2 = Estramustine 3D ball.png | image_class2 = bg-transparent | alt2 = Ball-and-stick model of the estramustine molecule | width2 = 250px
<!--Clinical data--> | tradename = Emcyt, Estracyt | 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 = | excretion =
<!-- Identifiers --> | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 2998-57-4 | CAS_supplemental = | ATC_prefix = L01 | ATC_suffix = XX11 | ATC_supplemental = | PubChem = 259331 | IUPHAR_ligand = | DrugBank_Ref = {{drugbankcite|changed|drugbank}} | DrugBank = | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 227635 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 35LT29625A | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = D04066 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 4868 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 1575 | synonyms = EM; EaM; Leo 275; Ro 21-8837; Estradiol 3-(bis(2-chloroethyl)carbamate) ester; Estra-1,3,5(10)-triene-3,17β-diol 3-(bis(2-chloroethyl)carbamate) ester
<!--Chemical data--> | C=23 | H=31 | Cl=2 | N=1 | O=3 | SMILES = C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=C3C=CC(=C4)OC(=O)N(CCCl)CCCl | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C23H31Cl2NO3/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/h3,5,14,18-21,27H,2,4,6-13H2,1H3/t18-,19-,20+,21+,23+/m1/s1 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = FRPJXPJMRWBBIH-RBRWEJTLSA-N }}
'''Estramustine''' ({{abbrlink|INN|International Nonproprietary Name}}, {{abbrlink|USAN|United States Adopted Name}}, {{abbrlink|BAN|British Approved Name}}) is an estrogen and cytostatic antineoplastic agent which was never marketed.<ref name="Elks2014">{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA502|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=502–}}</ref><ref name="IndexNominum2000">{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA406|date=January 2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=406–}}</ref> It is a carbamate derivative of estradiol and acts in part as a prodrug of estradiol in the body.<ref name="Elks2014" /><ref name="IndexNominum2000" /> Estramustine phosphate, the C17β phosphate ester of estramustine and a prodrug of estramustine, estromustine, estradiol, and estrone, is marketed and used in the treatment of prostate cancer.<ref name="Elks2014" /><ref name="IndexNominum2000" /> ==Synthesis== Estramustine is a carbamate derivative of the natural hormone, estradiol. The amine {{chem2|(ClCH2CH2)2NH}} is treated with phosgene to give the acid chloride of normustine. This reacts with the phenolic hydroxyl group of estradiol in the presence of a base to give estramustine.<ref>{{cite journal | vauthors = Niculescu-Duvăz I, Cambanis A, Tărnăuceanu E | title = Potential anticancer agents. II. Urethan-type nitrogen mustards of some natural sex hormones | journal = Journal of Medicinal Chemistry | volume = 10 | issue = 2 | pages = 172–174 | date = March 1967 | pmid = 6034059 | doi = 10.1021/jm00314a009 }}</ref><ref>{{cite journal | vauthors = Sk UH, Dixit D, Sen E | title = Comparative study of microtubule inhibitors--estramustine and natural podophyllotoxin conjugated PAMAM dendrimer on glioma cell proliferation | journal = European Journal of Medicinal Chemistry | volume = 68 | pages = 47–57 | date = October 2013 | pmid = 23954240 | doi = 10.1016/j.ejmech.2013.07.007 }}</ref>
== See also == * Estradiol mustard * List of hormonal cytostatic antineoplastic agents * List of estrogen esters § Estradiol esters
== References == {{Reflist}}
{{Chemotherapeutic agents}} {{Estrogen receptor modulators}} {{Androgen receptor modulators}}
Category:Abandoned drugs Category:Antiandrogens Category:Antigonadotropins Category:Antineoplastic drugs Category:Carbamates Category:Chloroethyl compounds Category:Secondary alcohols Category:Estradiol esters Category:Estranes Category:Estrogens Category:Hormonal antineoplastic drugs Category:Human drug metabolites Category:Mitotic inhibitors Category:Nitrogen mustards Category:Drugs developed by Pfizer
{{Estrane-stub}} {{Antineoplastic-drug-stub}}