Amsacrine

Amsacrine (synonyms: m-AMSA, acridinyl anisidide) is an antineoplastic agent.

Amsacrine

Clinical data
ATC code	L01XX01 (WHO)
Legal status
Legal status	US: a
Pharmacokinetic data
Protein binding	96 to 98%
Elimination half-life	8–9 hours
Identifiers
IUPAC name N-(4-(acridin-9-ylamino)-3-methoxyphenyl)methanesulfonamide
CAS Number	51264-14-3 Y
PubChem CID	2179
DrugBank	DB00276 Y
ChemSpider	2094 Y
UNII	00DPD30SOY
KEGG	D02321 Y
ChEBI	CHEBI:2687 Y
ChEMBL	ChEMBL43 Y
CompTox Dashboard (EPA)	DTXSID4022604
ECHA InfoCard	100.051.887
Chemical and physical data
Formula	C21H19N3O3S
Molar mass	393.46 g·mol−1
3D model (JSmol)	Interactive image
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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It has been used in acute lymphoblastic leukemia.^[1]

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.^[2] In contrast, the structurally similar o-AMSA, which differs only in the position of the methoxy substituent on the anilino ring, exhibits limited ability to poison topoisomerase II despite its intercalative properties. This suggests that intercalation alone is insufficient to stabilize topoisomerase II as a covalent complex on DNA.^[3][4][5]