Amsacrine

Title: Amsacrine
CAS Registry Number: 51264-14-3
CAS Name: N-[4-(9-Acridinylamino)-3-methoxyphenyl]methanesulfonamide
Additional Names: 4¢-(9-acridinylamino)methanesulfon-m-anisidide; m-AMSA
Manufacturers' Codes: CI-880; NSC-249992; SN-11841
Trademarks: Amekrin (Warner-Lambert); Amsidine (Parke-Davis); Amsidyl (Pfizer)
Molecular Formula: C21H19N3O3S
Molecular Weight: 393.46
Percent Composition: C 64.10%, H 4.87%, N 10.68%, O 12.20%, S 8.15%
Literature References: Cytostatic agent with antiviral and immunosuppressive properties. Prepn: B. F. Cain et al., J. Med. Chem. 18, 1110 (1975). Synthesis and biological properties of spin-labeled amsacrine: B. K. Sinha et al., ibid. 19, 994 (1976). Mechanism of action: W. R. Wilson, Chem. N. Z. 37, 148 (1973). Pharmacologic disposition: R. L. Cysyk et al., Drug Metab. Dispos. 5, 579 (1977). Antiviral activity: D. M. Byrd, Ann. N.Y. Acad. Sci. 284, 463 (1977). Immunosuppressive properties: B. C. Baguley et al., Eur. J. Cancer 10, 169 (1974). Exptl antitumor properties: B. F. Cain, G. J. Atwell, ibid. 539. Efficacy in adult acute leukemia: S. S. Legha et al., Ann. Intern. Med. 93, 17 (1980). Toxicologic studies: K. L. Pavkov et al., U.S. NTIS Report PB-298106 (1979) 284 pp, C.A. 92, 34335c (1980). Review of pharmacology and clinical efficacy: J. Hornedo, D. A. Van Echo, Pharmacotherapy 5, 78-90 (1985).
Properties: LD50 in male, female CDF1 mice: 810 mg/m2; 729 mg/m2 orally (Pavkov).
Toxicity data: LD50 in male, female CDF1 mice: 810 mg/m2; 729 mg/m2 orally (Pavkov)
Derivative Type: Hydrochloride
Manufacturers' Codes: NSC-141549
Molecular Formula: C21H19N3O3S.HCl
Molecular Weight: 429.92
Percent Composition: C 58.67%, H 4.69%, N 9.77%, O 11.16%, S 7.46%, Cl 8.25%
Properties: Crystals, mp 197-199°. LD50 i.p. in mice: ~60 mg/kg (Byrd).
Melting point: mp 197-199°
Toxicity data: LD50 i.p. in mice: ~60 mg/kg (Byrd)
Derivative Type: Methanesulfonate
Manufacturers' Codes: NSC-156303
Molecular Formula: C21H19N3O3S.CH3SO3H
Molecular Weight: 489.56
Percent Composition: C 53.97%, H 4.74%, N 8.58%, O 19.61%, S 13.10%
Properties: Crystals, mp 292-293°. LD50 i.p. in mice: ~24 mg/kg (Byrd).
Melting point: mp 292-293°
Toxicity data: LD50 i.p. in mice: ~24 mg/kg (Byrd)
Therap-Cat: Antineoplastic.
Keywords: Antineoplastic; Topoisomerase II Inhibitor.
Amsonic Acid Amtolmetin Guacil Amygdalin Amyl Chloride Amyl Nitrite

Amsacrine
Amsacrine.svg
Systematic (IUPAC) name
N-(4-(acridin-9-ylamino)-3-methoxyphenyl)methanesulfonamide
Clinical data
Legal status  ?
Pharmacokinetic data
Protein binding 96 to 98%
Half-life 8-9 hours
Identifiers
CAS number 51264-14-3 YesY
ATC code L01XX01
PubChem CID 2179
DrugBank DB00276
ChemSpider 2094 YesY
UNII 00DPD30SOY YesY
KEGG D02321 YesY
ChEBI CHEBI:2687 YesY
ChEMBL CHEMBL43 YesY
Chemical data
Formula C21H19N3O3S 
Mol. mass 393.46 g/mol
 YesY (what is this?)  (verify)

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

It has been used in acute lymphoblastic leukemia.[1]