51264-14-3

Basic information

• Product Name: Amsacrine
• Synonyms: M-AMSA, HCL;M-AMSA HYDROCHLORIDE;4'-(9-Acridinylamino)methanesulfon-m-anisidide;AMSIDINE;META-AMSA;Amsacrine/Amsacrine hydrochloride;N-[4-(Acridin-9-ylamino)-3-(methyloxy)phenyl]methanesulfonamide;Amekrin
• CAS NO: 51264-14-3
• Molecular Formula: C21H19N3O3S
• Molecular Weight: 393.46
• EINECS: 257-094-3
• Product Categories: Pharmaceutical material and intermeidates
• Mol File: 51264-14-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 230-240 °C
• Boiling Point: 563 °C at 760 mmHg
• Flash Point: 294.3 °C
• Appearance: white solid
• Density: 1.2205 (rough estimate)
• Vapor Pressure: 4.07E-14mmHg at 25°C
• Refractive Index: 1.6740 (estimate)
• Storage Temp.: 2-8°C(protect from light)
• Solubility: Soluble in DMSO
• PKA: 8.55±0.10(Predicted)
• CAS DataBase Reference: Amsacrine(CAS DataBase Reference)
• NIST Chemistry Reference: Amsacrine(51264-14-3)
• EPA Substance Registry System: Amsacrine(51264-14-3)

Safety Data

• RIDADR: 3249
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 51264-14-3(Hazardous Substances Data)

Usage

Description

Amsacrine, also known as Amsidyl, is a sulfonamide-based cytostatic drug with antineoplastic activity. It is characterized by its N-phenylmethanesulfonamide structure, which is substituted by a methoxy group at position 3 and an acridin-9-ylamino group at position 4. Amsacrine is particularly effective against adult lymphoblastic leukemia that has failed primary treatment or become resistant. However, its clinical use is associated with significant neuro-, gastro-, and hepatotoxicity.

Uses

Used in Oncology:
Amsacrine is used as an antineoplastic agent for the treatment of severe leukemia and lymphoma. It functions as a cytotoxic drug that binds with DNA, showing expressed specificity to the adenosine-tyrosine pair, thereby inhibiting DNA synthesis. This action makes it a potential therapeutic option for patients with severe leukemia.
Used in Investigational Drug Research:
Amsacrine is also used as an investigational drug, undergoing intensive trials to further explore its potential applications and effectiveness in treating various types of cancer. Its antineoplastic properties and DNA-binding specificity make it a valuable compound for research in the field of oncology.
Used in Drug Development:
The antineoplastic activity of Amsacrine has led to its use in the development of novel drug delivery systems and therapeutic strategies. Researchers are working on enhancing its delivery, bioavailability, and therapeutic outcomes by employing various organic and metallic nanoparticles as carriers for Amsacrine delivery.

Originator

Auckland Cancer Chemotherapy Lab (New Zealand)

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).

InChI:InChI=1/C22H20N2O3S/c1-27-22-14-16(24-28(2,25)26)12-11-15(22)13-19-17-7-3-5-9-20(17)23-21-10-6-4-8-18(19)21/h3-12,14,24H,13H2,1-2H3

Upstream product

• 132445-56-8 N-(2-methoxy-4-nitrophenyl)acridin-9-amine 
• 1207-69-8 9-Chloroacridine 
• 97-52-9 2-methoxy-4-nitrophenylamine 
• 124-63-0 methanesulfonyl chloride 
• 74-93-1 methylthiol 
• 117252-49-0 N(1')-(methylsulfonyl)-N(4')-(9-acridynyl)-3'-methoxy-2',5'-cyclohexadiene-1',4'-diimine 
• 57165-06-7 N-(4-amino-3-methoxyphenyl)methanesulfonamide 

Downstream Products

• 57165-06-7 N-(4-amino-3-methoxyphenyl)methanesulfonamide 
• 77273-65-5 4-[2-(Acridin-9-ylsulfanyl)-1-(carboxymethyl-carbamoyl)-ethylcarbamoyl]-2-amino-butyric acid 

Relevant articles and documents

With tumor-responsive release drug compound or its pharmaceutically acceptable salts and its preparation, application

The invention discloses a compound with a tumor responsive drug release function, or a pharmaceutical salt of the compound, as well as preparation and application of the compound, and belongs to the technical field of drug targeting release. The structural formula of the compound is as shown in the Specifications. The designed and synthesized novel tumor cell-sensitive compound disclosed by the invention can stably exist in the normal physiological environment, can release amsacrine drug when entering into tumor cells and performing a cascade reaction under a high-concentration glutathione environment in the tumor cells, and can be used for prepare a novel targeting antitumor drug. In addition, the preparation method of the compound disclosed by the invention is simple and convenient to operate, moderate in conditions, and high in reaction yield.

Reactivity of Quinone Imine and Quinone Diimine Metabolites of the Antitumor Drug Amsacrine and Related Compounds to Nucleophiles

The quinone diimine AQDI (7) and the quinone imine AQI (10) (products of oxidative metabolism of the clinical antileukemia drug amsacrine (1)) and related compounds were prepared, and their reactions with a variety of nucleophiles were studied.Reaction of

Multi-step process for the production of methanesulfon-m-anisidide, 4'-(9-acridinylamino)-

A multi-step method of producing the compound methanesulfon-m-anisidide, 4''-(9-acridinylamino)-, acetate (VII), which may be in free base form and designated NSC 249992, also known as AMSA. This compound is produced by an elegant process from a starting material, 4-butyrylamino-3-methoxy-nitrobenzene, which is later transformed to methanesulfon-m-anisidide, 4''-amino- (IV) and is coupled or joined to 9-chloro-acridine, producing the chloride salt which is later converted to the acetate.