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
SMILES
OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O.COC1=C(NC2=C3C=CC=CC3=NC4=C2C=CC=C4)C=CC(NS(C)(=O)=O)=C1
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
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/6580948Curator'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
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1177257
Curator's Comment: Amsacrine preparation
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2311221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2602146 |
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Target ID: CHEMBL1806 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10691026 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6580948
120 mg/m2 daily for 5 days
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2752503
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%.
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80277-07-2
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DBSALT002301
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PARENT (SALT/SOLVATE)
PARENT (SALT/SOLVATE)
SUBSTANCE RECORD