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CAS No 51264-14-3 , N-[4-(acridin-9-ylamino)-3-methoxyphenyl]methanesulfonamide

  • Name: N-[4-(acridin-9-ylamino)-3-methoxyphenyl]methanesulfonamide
  • Synonyms: m-AMSA; Amsidyl;Amsidine; AMSA P-D; Amsine; mAMSA;N-[4-(acridin-9-ylamino)-3-methoxyphenyl]methanesulfonamide; Acridinylanisidide; 51264-14-3; meta-Amsacrine;
  • CAS Registry Number:
  • Transport: 3249
  • Melting Point: 230-240 deg C
  • Density: 1.398 g/cm3
  • Refractive index: 1.688
  • Safety Statements: Poison by ingestion, intravenous, subcutaneous, and intraperitoneal routes. Human systemic effects by intravenous route: nausea or vomiting, thrombosis distant from injection site, and bone marrow changes. An experimental teratogen. Other experimental reproductive effects. Mutation data reported. When heated to decomposition it emits very toxic fumes of NOx and SOx.
  • EINECS: 257-094-3
  • Molecular Weight: 393.45886
  • InchiKey: XCPGHVQEEXUHNC-UHFFFAOYSA-N
  • 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)
  • Molecular Formula: C21H19N3O3S
  • Molecular Structure:CAS No:51264-14-3 N-[4-(acridin-9-ylamino)-3-methoxyphenyl]methanesulfonamide

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References of N-[4-(acridin-9-ylamino)-3-methoxyphenyl]methanesulfonamide
Title: Amsacrine
CAS Registry Number: 51264-14-3
CAS Name: N-[4-(9-Acridinylamino)-3-methoxyphenyl]methanesulfonamide
Synonyms: 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.