Amsacrine

Amsacrine

Systematic (IUPAC) name
N-(4-(acridin-9-ylamino)-3-methoxyphenyl)methanesulfonamide
Pharmacokinetic data
Protein binding	96 to 98%
Biological half-life	8-9 hours
Identifiers
CAS Number	51264-14-3 Y
ATC code	L01XX01 (WHO)
PubChem	CID: 2179
DrugBank	DB00276 Y
ChemSpider	2094 Y
UNII	00DPD30SOY Y
KEGG	D02321 Y
ChEBI	CHEBI:2687 Y
ChEMBL	CHEMBL43 Y
Chemical data
Formula	C21H19N3O3S
Molecular mass	393.46 g/mol
SMILES O=S(=O)(Nc1ccc(c(OC)c1)Nc2c4c(nc3c2cccc3)cccc4)C
InChI InChI=1S/C21H19N3O3S/c1-27-20-13-14(24-28(2,25)26)11-12-19(20)23-21-15-7-3-5-9-17(15)22-18-10-6-4-8-16(18)21/h3-13,24H,1-2H3,(H,22,23) Y Key:XCPGHVQEEXUHNC-UHFFFAOYSA-N Y
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Amsacrine (synonyms: m-AMSA, acridinyl anisidide) is an antineoplastic agent.

It has been used in acute lymphoblastic leukemia.

Mechanism

Its planar fused ring system can intercalate into the DNA of tumor cells, thereby altering the major and minor groove proportions. These alterations to DNA structure inhibit both DNA replication and transcription by reducing association between the affected DNA and: DNA polymerase, RNA polymerase and transcription factors.

Amsacrine also expresses topoisomerase inhibitor activity, specifically inhibiting topoisomerase II (compares with the better known agent etoposide). In contrast, the structurally similar o-AMSA differing in the position of the methoxy substituent group on the anilino-ring have little ability to poison topoisomerase II despite of its intercalative behavior, suggesting that intercalation of the molecule in itself is insufficient to trap topoisomerase II as a covalent complex on DNA.