# Atrimustine

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Atrimustine
> Markdown URL: https://mediated.wiki/source/Atrimustine.md
> Source: https://en.wikipedia.org/wiki/Atrimustine
> Source revision: 1329018021
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

{{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](/source/Chemotherapeutic_agent); [Estrogen](/source/Estrogen_(medication)); [Estrogen ester](/source/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](/source/cytostatic) [antineoplastic agent](/source/antineoplastic_agent) which was under development in [Japan](/source/Japan) by [Kureha Chemicals](/source/Kureha_Chemical_Industries) (now Kureha Corporation) for the treatment of [breast cancer](/source/breast_cancer) and [non-Hodgkin's lymphoma](/source/non-Hodgkin's_lymphoma) as well as for the prevention of [graft-versus-host disease](/source/graft-versus-host_disease) in [bone marrow transplant](/source/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](/source/benzoate) [ester](/source/ester) of an [ester](/source/ester) [conjugate](/source/conjugated_system) of [estradiol](/source/estradiol_(medication)) and [chlorambucil](/source/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](/source/estrogen_receptor)–positive tissues such as [breast](/source/breast) and [bone](/source/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](/source/marketing_authorization) for the treatment of [cancer](/source/cancer) but was ultimately discontinued.<ref name="AdisInsight" /> [Estrogenic](/source/Estrogen_(medication))ic [side effect](/source/side_effect)s of atrimustine in [clinical trial](/source/clinical_trial)s included [vaginal bleeding](/source/vaginal_bleeding) and [gynecomastia](/source/gynecomastia).<ref name="AdisInsight" /> The drug was first patented in 1980.<ref name="Elks2014" />

==See also==
* [List of hormonal cytostatic antineoplastic agents](/source/List_of_hormonal_cytostatic_antineoplastic_agents)
* [List of estrogen esters § Estradiol esters](/source/List_of_estrogen_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}}

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Adapted from the Wikipedia article [Atrimustine](https://en.wikipedia.org/wiki/Atrimustine) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Atrimustine?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.
