atrimustine

{{short description|Chemical compound}}

{{Drugbox

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| IUPAC_name = [(8R,9S,13S,14S,17S)-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

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| class = Chemotherapeutic agent; Estrogen; Estrogen ester

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| CAS_number = 75219-46-4

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| PubChem = 6917688

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| 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

| 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

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| 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

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| StdInChIKey = IFJUINDAXYAPTO-UUBSBJJBSA-N

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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.{{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}}{{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–}}{{cite web |url=https://adisinsight.springer.com/drugs/800000756 |title=Atrimustine – AdisInsight}} It is the benzoate ester of an ester conjugate of estradiol and chlorambucil,{{cite book |title=The Cancer Bulletin |url=https://books.google.com/books?id=mZMVAQAAMAAJ |year=1987 |publisher=Medical Arts Publishing Foundation |page=245}} which results in targeted/site-directed cytostatic activity toward estrogen receptor–positive tissues such as breast and bone.{{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}}{{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}} It reached preregistration for the treatment of cancer but was ultimately discontinued. Estrogenicic side effects of atrimustine in clinical trials included vaginal bleeding and gynecomastia. The drug was first patented in 1980.