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HomeProduct name listAmsacrine

Amsacrine

  • CAS NO.:51264-14-3
  • Empirical Formula: C21H19N3O3S
  • Molecular Weight: 393.46
  • MDL number: MFCD00242748
  • EINECS: 257-094-3
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-19 20:33:22
Amsacrine Structural

What is Amsacrine?

Absorption

Poorly absorbed

Toxicity

Symptoms of overdose include nausea and vomiting, diarrhea, some cardiotoxicity (rarely).

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)

The Uses of Amsacrine

Amsacrine (Amsidyl) is used as an Investigational drug.

The Uses of Amsacrine

Antineoplastic.

The Uses of Amsacrine

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.

Indications

For treatment of acute myeloid leukaemia.

Background

Aminoacridine derivative that is a potent intercalating antineoplastic agent. It is effective in the treatment of acute leukemias and malignant lymphomas, but has poor activity in the treatment of solid tumors. It is frequently used in combination with other antineoplastic agents in chemotherapy protocols. It produces consistent but acceptable myelosuppression and cardiotoxic effects.

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.

Pharmacokinetics

Amsacrine is an aminoacridine derivative that is a potent intercalating antineoplastic agent. It is effective in the treatment of acute leukemias and malignant lymphomas, but has poor activity in the treatment of solid tumors. It is frequently used in combination with other antineoplastic agents in chemotherapy protocols. It produces consistent but acceptable myelosuppression and cardiotoxic effects.

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).

Synthesis_51264-14-3

Metabolism

Extensive, primarily hepatic, converted to glutathione conjugate.

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.

Properties of Amsacrine

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 for Amsacrine

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H227:Flammable liquids
H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
Precautionary Statement Codes P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking.
P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P332+P313:IF SKIN irritation occurs: Get medical advice/attention.
P337+P313:IF eye irritation persists: Get medical advice/attention.
P370+P378:In case of fire: Use … for extinction.
P403+P235:Store in a well-ventilated place. Keep cool.

Computed Descriptors for Amsacrine

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