| Identification | Back Directory | [Name]
Amsacrine | [CAS]
51264-14-3 | [Synonyms]
AMSA
CI-880
m-AMSA
C01553
Amsidyl
Amekrin
Amsakrin
AMSIDINE
Lamasine
SN 11841
Amsacrine
META-AMSA
NSC-156303
NSC-249992
M-AMSA, HCL
m-AMSA Solution
NSC-249992：SN-11841
M-AMSA HYDROCHLORIDE
Amsacrine/Amsacrine hydrochloride
4'-(9-Acridinylamino)methanesulfon-m-anisidide
4'-(9-Acridinylamino)-3'-methoxymethanesulfonanilide
N-[4-(9-Acridinylamino)-3-methoxyphenyl]methanesulfonamide
N-[4-(Acridin-9-yl)amino-3-methoxyphenyl]methanesulfonamide
MethanesulfonaMide,N-[4-(9-acridinylaMino)-3-Methoxyphenyl]-
N-[4-(acridin-9-ylmethyl)-3-methoxyphenyl]methanesulfonamide
N-[4-(Acridin-9-ylamino)-3-(methyloxy)phenyl]methanesulfonamide | [EINECS(EC#)]
257-094-3 | [Molecular Formula]
C21H19N3O3S | [MDL Number]
MFCD07799963 | [MOL File]
51264-14-3.mol | [Molecular Weight]
393.46 |
| Chemical Properties | Back Directory | [Melting point ]
230-240 °C | [Boiling point ]
563.0±60.0 °C(Predicted) | [density ]
1.2205 (rough estimate) | [refractive index ]
1.6740 (estimate) | [storage temp. ]
2-8°C(protect from light) | [solubility ]
Soluble in DMSO | [form ]
Powder | [pka]
8.55±0.10(Predicted) | [color ]
Orange to red | [CAS DataBase Reference]
51264-14-3 | [IARC]
2B (Vol. 76) 2000 |
| Hazard Information | Back Directory | [Description]
Amsacrine is a cytostatic reported to be active against adult lymphoblastic leukemia
which has failed primary treatment or become resistant. Its clinical use, however, is
associated with significant neuro-, gastro- and hepatotoxicity. | [Chemical Properties]
Acute toxicity LD50 for male and female mice (mg/m2): 810, 729, oral administration. Amsacrine Hydrochloride: C2Lh19N3O3S·HCl. Crystalline, melting point 197-199°C. Acute toxicity LD50 for mice (mg/kg): approximately 60, intraperitoneal injection. Amsacrine Methanesulfonate: C21H19N3O3S·CH3SO3H. Crystalline, melting point 292-293°C. Acute toxicity LD50 for mice (mg/kg): approximately 24, intraperitoneal injection. | [Originator]
Auckland Cancer Chemotherapy Lab (New Zealand) | [Uses]
Amsacrine (Amsidyl) is used as an Investigational drug. | [Uses]
Amsacrine is a drug undergoing intensive trials for severe leukemia and lymphoma. It is a
cytotoxic drug that binds with DNA with expressed specificity to the adenosine–tyrosine
pair, thus inhibiting DNA synthesis. It has been suggested to be used for severe leukemia.
A synonym of this drug is amsidyl. | [Uses]
Antineoplastic. | [Definition]
ChEBI: A sulfonamide that is N-phenylmethanesulfonamide substituted by a methoxy group at position 3 and an acridin-9-ylamino group at position 4. It exhibits antineoplastic activity. | [Brand name]
Amsidyl (Parke-Davis);Amsakrin. | [Synthesis]
Amsacrine, 4-(9-acridinylamino)-3-methoxyphenyl-N-methansulfonamide
(30.6.11), is made by sulfonating 4-nitro-m-anisidine with methanesulfonyl chloride,
which forms a sulfonyl amide 30.6.9, and the nitro group is reduced to an amino group by
hydrogen, forming 4-amino-3-methoxyphenyl-N-methansulfonamide (30.6.10). Reacting
this with 9-chloroacridine gives amsacrine (30.6.11). 
| [storage]
Store at -20°C | [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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