| Identification | Back Directory | [Name]
Amsacrine hydrochloride | [CAS]
54301-15-4 | [Synonyms]
nsc141549
nci-c03190
M-Amsacrine
M-AMSA, HCL
META-AMSACRINE
AMSA hydrochloride
M-AMSA HYDROCHLORIDE
AMSACRINE HYDROCHLORIDE
acridinyl anisidide hydrochloride
AMine hydrochloride benzene acridine
Amsacrine hydrochloride, ≥98% (HPLC)
Methanesulfon-m-anisidide 4'-(9-acridinylamino)-
4’-((9-acridinyl)amino)-methanesulfon-m-anisidinhydrochloride
4’-(9-acridinylamino)methanesulfon-m-anisidemonohydrochloride
4’-(9-acridinylamino)-methanesulfon-m-anisididmonohydrochloride
Methanesulfone-m-anisidine-4'-[(9-acridinyl)amino] hydrochloride
Methansulfon-m-aniside, 4'-(9-acridinylamino)-, monohydrochloride
4’-(9-acridinylamino)-methanesulfonyl-m-anisidinmonohydrochloride
4-[9-ACRIDINYLAMINO]-N-[METHANE-SULFONYL]-M-ANISIDINE HYDROCHLORIDE
n-(4-(9-acridinylamino)-3-methoxyphenyl)-methanesulfonamidmonohydrochlor
N-(4-(acridin-9-ylaMino)-3-Methoxyphenyl)MethanesulfonaMide hydrochloride
m-AMSA, 4-(9-Acridinylamino)-N-(methanesulfonyl)-m-anisidine hydrochloride
Methanesulfonamide, N-4-(9-acridinylamino)-3-methoxyphenyl-, monohydrochloride
MethanesulfonaMide,N-[4-(9-acridinylaMino)-3-Methoxyphenyl]-, hydrochloride (1:1)
Amsacrine Hydrochloride, 4-(9-Acridinylamino)-N-(Methanesulfonyl)-M-Anisidine Hydrochloride | [EINECS(EC#)]
637-255-8 | [Molecular Formula]
C21H20ClN3O3S | [MDL Number]
MFCD07799963 | [MOL File]
54301-15-4.mol | [Molecular Weight]
429.92 |
| Chemical Properties | Back Directory | [Melting point ]
197-199 °C(lit.)
| [storage temp. ]
Refrigerator | [solubility ]
DMSO: 10 mg/mL with heat and sonication
| [form ]
powder
| [color ]
red to brown
| [InChI]
1S/C21H19N3O3S.ClH/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);1H | [InChIKey]
WDISRLXRMMTXEV-UHFFFAOYSA-N | [SMILES]
Cl.COc1cc(NS(C)(=O)=O)ccc1Nc2c3ccccc3nc4ccccc24 |
| Safety Data | Back Directory | [Hazard Codes ]
T | [Risk Statements ]
25-36/37/38 | [Safety Statements ]
26-45 | [RIDADR ]
UN 2811 6.1/PG 3
| [WGK Germany ]
3
| [RTECS ]
PB1081000
| [HS Code ]
2933.99.8290 | [HazardClass ]
6.1(b) | [PackingGroup ]
III | [Storage Class]
6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects | [Hazard Classifications]
Acute Tox. 3 Oral
Carc. 2
Muta. 2
Repr. 2
Skin Sens. 1 |
| Hazard Information | Back Directory | [Uses]
Amsacrine hydrochloride has been used:
- as a topoisomerase poison in bacteriophage T4 topoisomerase assay
- as a topoisomerase inhibitor in Drosophila cell line, Kc167
- as an antileukemia drug to test its effect on p53 transcriptional activity in tumor xenografts
- as a topoisomerase II poison in dose-response assays in C elegans
| [Biological Activity]
amsacrine hydrochloride (amsidine, m-amsa) is an inhibitor of topoisomerase 2 [1].amsacrine hydrochloride is a chemotherapy drug of antineoplastic, used to treat some types of lymphoma and acute leukaemia. in addition, amsacrine hydrochloride has shown the sensitivities to the cancer cell lines with the ic50 values of 190.2±27.4ng/ml, 46.1±3.9ng/ml,22.6±3.1ng/ml, 11.8±2.0ng/ml, 5.0±0.4ng/ml, and 11.7±1.5ng/ml for three bladder cancer cell lines (ht1376,rt112, rt4) and three testis cancer cell lines(833k, susa, gh), respectively. and it has been found that the testis tumor cell lines are more sensitive to inhibiting by amsacrine hydrochloride than the bladder cell lines [1]. | [Biochem/physiol Actions]
Amsacrine (m-AMSA) is a derivative of acridine and an antileukemia drug. It is an anticancer drug with antineoplastic activity that targets topoisomerase II. AMSA is an apoptosis inducer and favors the accumulation of double-stranded breaks (DSBs). It also inhibits the expression of matrix metallopeptidase 2 (MMP-2) and MMP-9 expression in leukemia cells by generating reactive oxygen species (ROS). AMSA serves as an adjuvant in trabeculectomy surgery. | [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 (mAMSA) 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]. | [IC 50]
Topoisomerase II | [References]
[1] nelson em, tewey km, liu lf. mechanism of antitumor drug action: poisoning of mammalian dna topoisomerase ii on dna by 4'-(9-acridinylamino)-methanesulfon-m-anisidide. proc natl acad sci u s a. 1984 mar;81(5):1361-5. |
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Jia Xing Isenchem Co.,Ltd
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Sigma-Aldrich
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SPIRO PHARMA
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