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 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

Different sources of media describe the Uses of 51264-14-3 differently. You can refer to the following data:
1. Amsacrine (Amsidyl) is used as an Investigational drug.
2. 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.
3. 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).

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.