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51264-14-3

51264-14-3 structure
51264-14-3 structure
  • Name: Amsacrine
  • Chemical Name: amsacrine
  • CAS Number: 51264-14-3
  • Molecular Formula: C21H19N3O3S
  • Molecular Weight: 393.459
  • Catalog: API Antineoplastic agents Antimetabolite antineoplastic
  • Create Date: 2018-08-29 11:04:36
  • Modify Date: 2024-01-02 15:19:58
  • Amsacrine is an inhibitor of topoisomerase II, and acts as an antineoplastic agent which can intercalates into the DNA of tumor cells.
Name amsacrine
Synonyms m-AMSA
meta-Amsacrine
Methanesulfonamide, N-[4-(9-acridinylamino)-3-methoxyphenyl]-
Amsacrine
4'-(Acridinylamino)methanesulfon-m-anisidide
Amsidyl
AMSA P-D
Amekrin
EINECS 257-094-3
AMSA, M-
Methanesulfonamide, N-(4-(9-acridinylamino)-3-methoxyphenyl)-
Amsine
Amsidine
N-[4-(9-Acridinylamino)-3-methoxuphenyl]methanesulfonamide
N-[4-(9-Acridinylamino)-3-methoxyphenyl]methanesulfonamide
N-[4-(acridin-9-ylamino)-3-(methyloxy)phenyl]methanesulfonamide
N-[4-(acridin-9-ylamino)-3-methoxyphenyl]methanesulfonamide
Description Amsacrine is an inhibitor of topoisomerase II, and acts as an antineoplastic agent which can intercalates into the DNA of tumor cells.
Related Catalog
Target

Topoisomerase II

In Vitro Amsacrine blocks HERG currents in HEK 293 cells and Xenopus oocytes in a concentration-dependent manner, with IC50 values of 209.4 nm and 2.0 μM, respectively. Amsacrine causes a negative shift in the voltage dependence of both activation (−7.6 mV) and inactivation (−7.6 mV). HERG current block by amsacrine is not frequency dependent[1]. In vitro studies of normal human lymphocytes with various concentrations of m-AMSA, show both increased levels of chromosomal aberrations, ranging from 8% to 100%, and increase SCEs, ranging from 1.5 times the normal at the lowest concentration studied (0.005 μg/mL) to 12 times the normal (0.25 μg/mL)[3]. Amsacrine-induced apoptosis of U937 cells is characterized by caspase-9 and caspase-3 activation, increased intracellular Ca2+ concentration, mitochondrial depolarization, and MCL1 down-regulation. Amsacrine induces MCL1 down-regulation by decreasing its stability. Further, amsacrine-treated U937 cells show AKT degradation and Ca2+-mediated ERK inactivation[4].
In Vivo In animals treated with different doses of amsacrine (0.5-12 mg/kg), the frequencies of micronucleated polychromatic erythrocytes increase significantly after treatment with 9 and 12 mg/kg. Furthermore, the present study demonstrates for the first time that amsacrine has high incidences of clastogenicity and low incidences of aneugenicity whereas nocodazole has high incidences of aneugenicity and low incidences of clastogenicity during mitotic phases in vivo[2].
Animal Admin Amsacrine is investigated in three separated experiments. In the first experiment, animals are treated by intraperitoneal injection with 0.5, 1.5 and 4.5 mg/kg of amsacrine and bone marrow is sampled 24 h after treatment. Preliminary negative MN results at this sampling time lead to the use of 30 h sampling time for amsacrine. Thus, in the second experiment, mice are treated with 0.5, 1.5 and 4.5 mg/kg of amsacrine and bone marrow is sampled 30 h after treatment. The doses and sampling times for amsacrine are chosen by reference to earlier studies and the selected doses are within the dose range used for human chemotherapy. The results again show that the micronuclei frequency in the bone marrow of mice is not affected by treatment with any of the selected doses of the test agent, at 30 h sampling time, thus, in the third experiment, mice are treated with 6, 9 and 12 mg/kg of amsacrine and bone marrow is sampled 24 and 30 h after treatment.
References

[1]. Thomas D, et al. Inhibition of cardiac HERG currents by the DNA topoisomerase II inhibitor amsacrine: mode of action. Br J Pharmacol. 2004 Jun;142(3):485-94.

[2]. Attia SM. Molecular cytogenetic evaluation of the mechanism of genotoxic potential of amsacrine and nocodazole in mouse bone marrow cells. J Appl Toxicol. 2013 Jun;33(6):426-33.

[3]. Kao-Shan CS, et al. Cytogenetic effects of amsacrine on human lymphocytes in vivo and in vitro. Cancer Treat Rep. 1984 Jul-Aug;68(7-8):989-97.

[4]. Lee YC, et al. Amsacrine-induced apoptosis of human leukemia U937 cells is mediated by the inhibition of AKT- and ERK-induced stabilization of MCL1. Apoptosis. 2016 Oct 19
Density 1.4±0.1 g/cm3
Boiling Point 563.0±60.0 °C at 760 mmHg
Melting Point 230-240ºC
Molecular Formula C21H19N3O3S
Molecular Weight 393.459
Flash Point 294.3±32.9 °C
Exact Mass 393.114716
PSA 88.70000
LogP 2.12
Vapour Pressure 0.0±1.5 mmHg at 25°C
Index of Refraction 1.723

CHEMICAL IDENTIFICATION

RTECS NUMBER :
PB1080000
CHEMICAL NAME :
Methanesulfon-m-anisidide, 4'-(9-acridinylamino)-
CAS REGISTRY NUMBER :
51264-14-3
BEILSTEIN REFERENCE NO. :
0500176
LAST UPDATED :
199801
DATA ITEMS CITED :
58
MOLECULAR FORMULA :
C21-H19-N3-O3-S
MOLECULAR WEIGHT :
393.49
WISWESSER LINE NOTATION :
T C666 BNJ IMR BO1 DMSW1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
5405 ug/kg/3H-C
TOXIC EFFECTS :
Blood - changes in bone marrow (not otherwise specified)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human
DOSE/DURATION :
12 mg/kg
TOXIC EFFECTS :
Vascular - thrombosis distant from injection site Gastrointestinal - nausea or vomiting Blood - other changes
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
53420 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
15470 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
110 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
33700 ug/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - dyspnea
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
50 mg/kg
TOXIC EFFECTS :
Behavioral - food intake (animal) Gastrointestinal - hypermotility, diarrhea Gastrointestinal - nausea or vomiting
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
6250 ug/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - dyspnea Nutritional and Gross Metabolic - weight loss or decreased weight gain
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Primate - monkey
DOSE/DURATION :
10400 ug/kg
TOXIC EFFECTS :
Blood - changes in bone marrow (not otherwise specified)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
546 mg/kg/13W-I
TOXIC EFFECTS :
Blood - changes in bone marrow (not otherwise specified) Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
90 mg/kg/24W-I
TOXIC EFFECTS :
Blood - changes in bone marrow (not otherwise specified) Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - changes in testicular weight
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
69250 ug/kg/5D-I
TOXIC EFFECTS :
Behavioral - muscle contraction or spasticity Blood - pigmented or nucleated red blood cells Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
125 mg/kg/5D-I
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Blood - changes in bone marrow (not otherwise specified) Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
1950 ug/kg/5D-I
TOXIC EFFECTS :
Blood - hemorrhage Blood - changes in bone marrow (not otherwise specified) Blood - changes in leukocyte (WBC) count
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Primate - monkey
DOSE/DURATION :
13 mg/kg/5D-I
TOXIC EFFECTS :
Blood - changes in bone marrow (not otherwise specified) Blood - changes in leukocyte (WBC) count
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
30 mg/kg/24W-I
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Gastrointestinal - tumors Skin and Appendages - tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
DOSE :
6486 ug/kg
SEX/DURATION :
male 3 week(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
8 mg/kg
SEX/DURATION :
female 6-9 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
15 mg/kg
SEX/DURATION :
male 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)
TYPE OF TEST :
Micronucleus test
TYPE OF TEST :
DNA damage
TYPE OF TEST :
Cytogenetic analysis

MUTATION DATA

TYPE OF TEST :
DNA damage
TEST SYSTEM :
Mammal - species unspecified Lymphocyte
DOSE/DURATION :
54 umol/L
REFERENCE :
CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut Sts., Philadelphia, PA 19106) V.1- 1941- Volume(issue)/page/year: 38,1300,1978 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X6337 No. of Facilities: 7 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 14 (estimated) No. of Female Employees: 14 (estimated)
RIDADR UN 3249
Packaging Group III
Hazard Class 6.1(b)
HS Code 2935009090
HS Code 2935009090
Summary 2935009090 other sulphonamides VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:35.0%

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