Description
Amsacrine is a cytostatic reported to be active against adult lymphoblastic leukemia
which has failed primary treatment or become resistant. Its clinical use, however, is
associated with significant neuro-, gastro- and hepatotoxicity.
Chemical Properties
Acute toxicity LD50 male mice, female mice (mg/m2): 810, 729 oral. Amsacrine Hydrochloride (Amsacrine Hydrochloride): C2Lh19N3O3SHCl. crystalline, melting point 197-199°C. Acute toxicity LD50 mice (mg/kg): about 60 intraperitoneally. Amsacrine Methanesulfonate (Amsacrine Methanesulfonate): C21H19N3O3SCH3SO3H. crystallization, melting point 292-293 ℃. Acute toxicity LD50 mice (mg/kg): about 24 intraperitoneal injection.
Originator
Auckland Cancer Chemotherapy Lab (New Zealand)
Uses
Amsacrine (Amsidyl) is used as an Investigational drug.
Uses
Amsacrine is a drug undergoing intensive trials for severe leukemia and lymphoma. It is a
cytotoxic drug that binds with DNA with expressed specificity to the adenosine–tyrosine
pair, thus inhibiting DNA synthesis. It has been suggested to be used for severe leukemia.
A synonym of this drug is amsidyl.
Definition
ChEBI: A sulfonamide that is N-phenylmethanesulfonamide substituted by a methoxy group at position 3 and an acridin-9-ylamino group at position 4. It exhibits antineoplastic activity.
brand name
Amsidyl (Parke-Davis);Amsakrin.
Synthesis
Amsacrine, 4-(9-acridinylamino)-3-methoxyphenyl-N-methansulfonamide
(30.6.11), is made by sulfonating 4-nitro-m-anisidine with methanesulfonyl chloride,
which forms a sulfonyl amide 30.6.9, and the nitro group is reduced to an amino group by
hydrogen, forming 4-amino-3-methoxyphenyl-N-methansulfonamide (30.6.10). Reacting
this with 9-chloroacridine gives amsacrine (30.6.11).
References
[1] nelson em, tewey km, liu lf. mechanism of antitumor drug action: poisoning of mammalian dna topoisomerase ii on dna by 4'-(9-acridinylamino)-methanesulfon-m-anisidide. proc natl acad sci u s a. 1984 mar;81(5):1361-5.
