{{short description|Chemical compound}} {{Drugbox | Verifiedfields = | Watchedfields = | verifiedrevid = | IUPAC_name = [(8''R'',9''S'',13''S'',14''S'',17''S'')-17-[2-[4-[4-[''bis''(2-chloroethyl)amino]phenyl]butanoyloxy]acetyl]oxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[''a'']phenanthren-3-yl] benzoate | image = Atrimustine.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 = | excretion =
<!--Identifiers--> | CAS_number_Ref = | CAS_number = 75219-46-4 | CAS_supplemental = | ATC_prefix = | ATC_suffix = | PubChem = 6917688 | DrugBank_Ref = | DrugBank = | ChemSpiderID_Ref = | ChemSpiderID = 5292918 | UNII = XC0K09B7K4 | ChEMBL = 2106381 | synonyms = Bestrabucil; Busramustine; KM-2210; Kregan; Estradiol 3-benzoate 17β-((4-(4-(bis(2-chloroethyl)amino)phenyl)-1-oxobutoxy)acetate; 3-Benzoyl-17β-((4-(4-(bis(2-chloroethyl)amino)phenyl)-1-oxobutoxy)acetylestradiol<ref name="Elks2014" />
<!--Chemical data--> | C=41 | H=47 | Cl=2 | N=1 | O=6 | SMILES = C[C@]12CC[C@H]3[C@@H](CCc4cc(OC(=O)c5ccccc5)ccc34)[C@@H]1CC[C@@H]2OC(=O)COC(=O)CCCc6ccc(cc6)N(CCCl)CCCl | StdInChI_Ref = | StdInChI = 1S/C41H47Cl2NO6/c1-41-21-20-34-33-17-15-32(49-40(47)29-7-3-2-4-8-29)26-30(33)12-16-35(34)36(41)18-19-37(41)50-39(46)27-48-38(45)9-5-6-28-10-13-31(14-11-28)44(24-22-42)25-23-43/h2-4,7-8,10-11,13-15,17,26,34-37H,5-6,9,12,16,18-25,27H2,1H3/t34-,35-,36+,37+,41+/m1/s1 | StdInChIKey_Ref = | StdInChIKey = IFJUINDAXYAPTO-UUBSBJJBSA-N }}
'''Atrimustine''' ({{abbrlink|INN|International Nonproprietary Name}}) (developmental code name '''KM-2210'''; former tentative brand name '''Kregan'''), also known as '''bestrabucil''' or '''busramustine''', is a cytostatic antineoplastic agent which was under development in Japan by Kureha Chemicals (now Kureha Corporation) for the treatment of breast cancer and non-Hodgkin's lymphoma as well as for the prevention of graft-versus-host disease in bone marrow transplant recipients.<ref name="Elks2014">{{cite book |author=J. Elks |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies |url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PR2 |date=14 November 2014 |publisher=Springer |isbn=978-1-4757-2085-3 |pages=897–898}}</ref><ref name="Publishing2013">{{cite book |author=William Andrew Publishing |title=Pharmaceutical Manufacturing Encyclopedia, 3rd Edition |url=https://books.google.com/books?id=_J2ti4EkYpkC&pg=PA438 |date=22 October 2013 |publisher=Elsevier |isbn=978-0-8155-1856-3 |pages=438–}}</ref><ref name="AdisInsight">{{cite web |url=https://adisinsight.springer.com/drugs/800000756 |title=Atrimustine – AdisInsight}}</ref> It is the benzoate ester of an ester conjugate of estradiol and chlorambucil,<ref>{{cite book |title=The Cancer Bulletin |url=https://books.google.com/books?id=mZMVAQAAMAAJ |year=1987 |publisher=Medical Arts Publishing Foundation |page=245}}</ref> which results in targeted/site-directed cytostatic activity toward estrogen receptor–positive tissues such as breast and bone.<ref name="pmid6548354">{{cite journal |vauthors=Ohsawa N, Yamazaki Z, Wagatsuma T, Isurugi K |title=[Bestrabacil: a possible target-oriented anticancer agent] |language=ja |journal=Gan to Kagaku Ryoho |volume=11 |issue=10 |pages=2115–2124 |year=1984 |pmid=6548354}}</ref><ref name="Ishigami1985">{{cite book |author=Joji Ishigami |title=Recent Advances in Chemotherapy: Proceedings of the 14th Internat. Congress of Chemotherapy, Kyoto, 1985. Antimicrobial section; 1. 1 ,1 |url=https://books.google.com/books?id=AKQTAQAAMAAJ |year=1985 |publisher=University of Tokyo Press |isbn=978-0-86008-385-6 |page=52,54,471}}</ref> It reached preregistration for the treatment of cancer but was ultimately discontinued.<ref name="AdisInsight" /> Estrogenicic side effects of atrimustine in clinical trials included vaginal bleeding and gynecomastia.<ref name="AdisInsight" /> The drug was first patented in 1980.<ref name="Elks2014" />
==See also== * List of hormonal cytostatic antineoplastic agents * List of estrogen esters § Estradiol esters
==References== {{reflist}}
{{Estrogen receptor modulators}}
Category:Abandoned drugs Category:Antineoplastic drugs Category:Chloroethyl compounds Category:Estradiol esters Category:Estranes Category:Estrogens Category:Hormonal antineoplastic drugs Category:Nitrogen mustards
{{Antineoplastic-drug-stub}} {{Genito-urinary-drug-stub}} {{Estrane-stub}}