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Atrimustine

Atrimustine, also known as bestrabucil or busramustine, is a cytostatic antineoplastic agent which was under development in Japan by Kureha Chemicals 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. It is the benzoate ester of an ester conjugate of estradiol and chlorambucil, which results in targeted/site-directed cytostatic activity toward estrogen receptor–positive tissues such as breast and bone. 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.

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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)acetylestradiol1
Drug classChemotherapeutic agent; Estrogen; Estrogen ester
Identifiers
  • [(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
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC41H47Cl2NO6
Molar mass720.73 g·mol−1
3D model (JSmol)
  • 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=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

Atrimustine (INNTooltip 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.123 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.56 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

See also

See also

References

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): 2115–2124. 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.