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Substance Name: Amsacrine [USAN:INN:BAN]
RN: 51264-14-3
UNII: 00DPD30SOY
InChIKey: XCPGHVQEEXUHNC-UHFFFAOYSA-N

Note

  • An aminoacridine derivative that intercalates into DNA and is used as an antineoplastic agent.

Molecular Formula

  • C21-H19-N3-O3-S

Molecular Weight

  • 393.4651
 

Classification Codes

  • Antineoplastic
  • Antineoplastic Agents
  • DNA Topoisomerase II Inhibitor
  • Drug / Therapeutic Agent
  • Human Data
  • Indicators and Reagents
  • Intercalating Agents
  • Mutation Data
  • Reproductive Effect
  • Tumor Data
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Names and Synonyms

Name of Substance

  • Amsacrine
  • Amsacrine [USAN:INN:BAN]

MeSH Heading

  • Amsacrine

Synonyms

  • 4'-(9-Acridinylamino)-3'-methoxymethanesulfonanilide
  • 4'-(9-Acridinylamino)methanesulfon-m-anisidide
  • 4'-(9-Acridinylamino)methanesulfon-meta-anisidide
  • 4'-(9-Acridinylamino)methanesulphon-m-anisidide
  • 5-22-11-00030 (Beilstein Handbook Reference)
  • Acridinylanisidide
  • AMSA
  • Amsacrina
  • Amsacrina [INN-Spanish]
  • Amsacrine
  • Amsacrinum
  • Amsacrinum [INN-Latin]
  • Amsidine
  • Amsidyl
  • BRN 0500176
  • CCRIS 1027
  • CI 880
  • CI-880
  • EINECS 257-094-3
  • HSDB 7087
  • m-AMSA
  • meta-Amsacrine
  • Methanesulfonamide, N-(4-(9-acridinylamino)-3-methoxyphenyl)-
  • Methanesulfonanilide, 4'-(9-acridinylamino)-3'-methoxy-
  • N-(4-(9-Acridinylamino)-3-methoxyphenyl)methanesulfonamide
  • NSC 156303
  • NSC 249992
  • SN 21429
  • UNII-00DPD30SOY

Systematic Names

  • Amsacrine
  • Methanesulfon-m-anisidide, 4'-(9-acridinylamino)-
  • Methanesulfonamide, N-(4-(9-acridinylamino)-3-methoxyphenyl)-

Superlist Name

  • Amsacrine

Registry Numbers

CAS Registry Number

  • 51264-14-3

FDA UNII

  • 00DPD30SOY

System Generated Number

  • 0051264143

Structure Descriptors

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)

InChIKey

XCPGHVQEEXUHNC-UHFFFAOYSA-N

Smiles

COc1cc(ccc1Nc2c3ccccc3nc4c2cccc4)NS(=O)(=O)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous 6250ug/kg (6.25mg/kg)   Cancer Treatment Reports. Vol. 64, Pg. 855, 1980.
dog LD50 intravenous 6250ug/kg (6.25mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Cancer Treatment Reports. Vol. 64, Pg. 855, 1980.
dog LD50 oral 50mg/kg (50mg/kg) BEHAVIORAL: FOOD INTAKE (ANIMAL)

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

GASTROINTESTINAL: NAUSEA OR VOMITING
Cancer Treatment Reports. Vol. 66, Pg. 1939, 1982.
human TDLo intravenous 12mg/kg (12mg/kg) BLOOD: OTHER CHANGES

GASTROINTESTINAL: NAUSEA OR VOMITING

VASCULAR: THROMBOSIS DISTANT FROM INJECTION SITE
Cancer Research. Vol. 38, Pg. 3712, 1978.
man LDLo intravenous 5405ug/kg/3H- (5.405mg/kg) BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE Archives of Internal Medicine. Vol. 143, Pg. 165, 1983.
monkey LDLo intravenous 10400ug/kg (10.4mg/kg) BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE Pharmacy International. Vol. 7, Pg. 3, 1986.
mouse LD50 intraperitoneal 15470ug/kg (15.47mg/kg)   National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986,
mouse LD50 intravenous 33700ug/kg (33.7mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Cancer Treatment Reports. Vol. 64, Pg. 855, 1980.
mouse LD50 oral 53420ug/kg (53.42mg/kg)   National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986,
mouse LD50 subcutaneous 110mg/kg (110mg/kg)   National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986,

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) 3.890 (none)   EST
Atmospheric OH Rate Constant 4.02E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.