AMSACRINE GLUCONATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H19N3O3S.C6H12O7
Molecular Weight	589.614
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O.COC1=CC(NS(C)(=O)=O)=CC=C1NC2=C3C=CC=CC3=NC4=CC=CC=C24

InChI

InChIKey=XXNAQBNJPZNRSZ-IFWQJVLJSA-N

InChI=1S/C21H19N3O3S.C6H12O7/c1-27-20-13-14(24-28(2,25)26)11-12-19(20)23-21-15-7-3-5-9-17(15)22-18-10-6-4-8-16(18)21;7-1-2(8)3(9)4(10)5(11)6(12)13/h3-13,24H,1-2H3,(H,22,23);2-5,7-11H,1H2,(H,12,13)/t;2-,3-,4+,5-/m.1/s1

HIDE SMILES / InChI

Molecular Formula	C21H19N3O3S
Molecular Weight	393.459
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C6H12O7
Molecular Weight	196.1553
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6580948
Curator's Comment: description was created based on several sources, including: https://www.ncbi.nlm.nih.gov/pubmed/3884748 | https://www.ncbi.nlm.nih.gov/pubmed/2752503

The gluconate formulation of amsacrine (AMSA) has better water solubility then DMA formulation. It was thus developed and investigated to determine if it would be less cardiotoxic than the widely used N,N-dimethylacetamide (DMA) formulation. Amsacrine gluconate is the anticancer agent, which was tested against refractory leukemia. Moreover, their cytotoxic activity was demonstrated in the in vitro studies on 48 specimens of 9 histologically different types of human malignancy. The use of the gluconate formulation of AMSA, which contains no dimethylacetamide, has been associated with three cases of cardiomyopathy. Also, paresthesia was found in one patient among 26 treated with AMSA gluconate. This preparation has no apparent advantage when compared with amsacrine lactate.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA 282 Target ID: CHEMBL2311221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2602146	Binding Agent 1076
DNA topoisomerase II alpha 37 Target ID: CHEMBL1806 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10691026	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Acute non-lymphocytic leukemia 10 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6580948 https://www.ncbi.nlm.nih.gov/pubmed/3884748	Primary	Phase II 1147	Unknown Approved Use Unknown
Acute lymphocytic leukemia 4 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6580948 https://www.ncbi.nlm.nih.gov/pubmed/3884748	Primary	Phase II 1147	Unknown Approved Use Unknown
Chronic myeloid leukemia in blast crisis 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6580948 https://www.ncbi.nlm.nih.gov/pubmed/3884748	Primary	Phase II 1147	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
Chemieliva Pharmaceutical Co., Ltd	PBCM1421215
Smolecule	S518821	http://www.smolecule.com/products/s518821
THE BioTek	bt-259867	https://www.thebiotek.com/product/inhibitors/bt-259867

PubMed

Title	Date	PubMed
Evaluation of an amsacrine analog in a human tumor cloning system.	1989	2752503
Phase II study of amsacrine gluconate in refractory leukemia.	1983-12	6580948

Patents

Sample Use Guides

In Vivo Use Guide

120 mg/m2 daily for 5 days

Route of Administration: Intravenous

In Vitro Use Guide

A total of 128 human tumors were placed in culture and tested against amsacrine. At 10 ug/ml amsacrine gluconate showed cytotoxic activity against breast, colon, and lung cancer as well as melanoma with an overall activity of 37%.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:00:17 GMT 2025` Edited by `admin` on `Mon Mar 31 18:00:17 GMT 2025`
Record UNII	M4P91439UZ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-334213

Preferred Name

English

AMSACRINE GLUCONATE

Common Name

English

METHANESULFONAMIDE, N-(4-(9-ACRIDINYLAMINO)-3-METHOXYPHENYL)-, MONO-D-GLUCONATE

Common Name

English

D-GLUCONIC ACID, COMPD. WITH N-(4-(9-ACRIDINYLAMINO)-3-METHOXYPHENYL)METHANESULFONAMIDE (1:1)

Common Name

English

Code System Code Type Description

PUBCHEM

22824017