Atrimustine

Atrimustine (INN) (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.[1][2][3] It is the benzoate ester of an ester conjugate of estradiol and chlorambucil,[4] which results in targeted/site-directed cytostatic activity toward estrogen receptor-positive tissues such as breast and bone.[5][6] It reached preregistration for the treatment of cancer but was ultimately discontinued.[3] Estrogenicic side effects of atrimustine in clinical trials included vaginal bleeding and gynecomastia.[3] The drug was first patented in 1980.[1]

Atrimustine
Clinical data
Other namesBestrabucil; 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[1]
Drug classChemotherapeutic agent; Estrogen; Estrogen ester
Identifiers
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
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC41H47Cl2NO6
Molar mass720.73 g·mol−1
3D model (JSmol)
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
InChI
  • InChI=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
  • Key:IFJUINDAXYAPTO-UUBSBJJBSA-N

See also

References
  1. J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 897–898. ISBN 978-1-4757-2085-3.
  2. William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. Elsevier. pp. 438–. ISBN 978-0-8155-1856-3.
  3. "Atrimustine - AdisInsight".
  4. The Cancer Bulletin. Medical Arts Publishing Foundation. 1987. p. 245.
  5. Ohsawa N, Yamazaki Z, Wagatsuma T, Isurugi K (1984). "[Bestrabacil: a possible target-oriented anticancer agent]". Gan to Kagaku Ryoho (in Japanese). 11 (10): 2115–24. PMID 6548354.
  6. Joji Ishigami (1985). Recent Advances in Chemotherapy: Proceedings of the 14th Internat. Congress of Chemotherapy, Kyoto, 1985. Antimicrobial section; 1. 1 ,1. University of Tokyo Press. p. 52,54,471. ISBN 978-0-86008-385-6.



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