Atrimustine

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.^[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]

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

CAS Number

• 75219-46-4

PubChem CID

• 6917688

Quick facts Clinical data, Other names ...

Atrimustine

Clinical data
Other names	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[1]
Drug class	Chemotherapeutic 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	75219-46-4
PubChem CID	6917688
ChemSpider	5292918
UNII	XC0K09B7K4
ChEMBL	ChEMBL2106381
CompTox Dashboard (EPA)	DTXSID501046416
Chemical and physical data
Formula	C41H47Cl2NO6
Molar mass	720.73 g·mol−1
3D model (JSmol)	Interactive image
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

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