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Amsacrine hydrochloride

pharmaceutical raw materials
Amsacrine hydrochloride structure

Amsacrine hydrochloride 

structure
  • CAS No:

    54301-15-4

  • Formula:

    C21H19N3O3S.ClH

  • Chemical Name:

    Amsacrine hydrochloride

  • Synonyms:

    Methanesulfonamide,N-[4-(9-acridinylamino)-3-methoxyphenyl]-,hydrochloride (1:1);Methanesulfonamide,N-[4-(9-acridinylamino)-3-methoxyphenyl]-,monohydrochloride;NSC 141549;4′-(Acridin-9-ylamino)-3′-methoxymethanesulfonanilide hydrochloride;N-[4-(9-Acridinylamino)-3-methoxyphenyl]methanesulfonamide hydrochloride;AMSA hydrochloride;m-AMSA hydrochloride;Amsacrine hydrochloride;76095-44-8

Description

Amsacrine is an inhibitor of topoisomerase II, and acts as an antineoplastic agent which can intercalates into the DNA of tumor cells.


An aminoacridine derivative that intercalates into DNA and is used as an antineoplastic agent.

Amsacrine hydrochloride Basic Attributes

429.92

429.09100

257-094-3

U66HX4K4CO

141549

DTXSID2037186

2935009090

Characteristics

88.7

2.85 @ pH 7.4

red to brown powder

197-199 °C

563ºC at 760 mmHg

294.3ºC

DMSO: 10 mg/mL with heat and sonication

Storage site should be as close as practical to lab in which carcinogens are to be used, so that only small quantities required for expt need to be carried. Carcinogens should be kept in only one section of cupboard, an explosion-proof refrigerator or freezer (depending on chemicophysical properties ) that bears appropriate label. An inventory should be kept, showing quantity of carcinogen & date it was acquired Facilities for dispensing should be contiguous to storage area.

Oral-mouse LD50: 181 mg/kg; intraperitoneal-mouse LD50: 20.56 mg/kg

Combustible; Decomposes by heating to release toxic nitrogen oxides, sulfur oxides and hydrogen chloride fumes

Safety Information

III

6.1(b)

UN 2811 6.1/PG 3

3

25-36/37/38

26-45

PB1081000

T

Warehouse ventilated, low temperature and dry

Physical stability is not significantly affected by normal temp ranges. The drug is light-sensitive. After dilution in 5% glucose at a final concn of 150 ug/ml, amsacrine is stable during exposure to diffuse daylight or fluorescent light over a 48 hr period.

P261-P301 + P310-P305 + P351 + P338

H301-H315-H319-H335

|Danger|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 39 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

highly toxic

Drug Information

Agents that are capable of inserting themselves between the successive bases in DNA, thus kinking, uncoiling or otherwise deforming it and therefore preventing its proper functioning. They are used in the study of DNA. (See all compounds classified as Intercalating Agents.)|Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)

AMSA

Amsacrine hydrochloride Use and Manufacturing

Used as an antitumor drug

Computed Properties

Molecular Weight:429.9
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:5
Exact Mass:429.0913904
Monoisotopic Mass:429.0913904
Topological Polar Surface Area:88.7
Heavy Atom Count:29
Complexity:601
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes

Drug Function and Efficacy

Amsacrine has a broad spectrum of anti-tumor activity, and its mechanism of action is similar to that of anthracyclines. Amsacrine binds to DNA and affects the pairing of adenine and thymine base pairs. It mainly inhibits DNA synthesis, and has a more obvious inhibitory effect on cells in the S and G2 phases, but has less effect on RNA synthesis.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

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