Amsacrine Chemical Properties

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

Safety Information

RIDADR 

3249

HazardClass 

6.1(b)

PackingGroup 

III

Hazardous Substances Data

51264-14-3(Hazardous Substances Data)

Toxicity

LD50 in male, female CDF1 mice: 810 mg/m2; 729 mg/m2 orally (Pavkov)

Amsacrine Usage And Synthesis

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.

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).

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.

Amsacrine(51264-14-3)Related Product Information

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• PHENYL VALERATE
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• p-Phenylenediamine
• o-Phenylenediamine
• Phenylacetic acid
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• Amsacrine hydrochloride
• CI 921
• Amsacrine