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51264-14-3 molecular structure
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N-{4-[(acridin-9-yl)amino]-3-methoxyphenyl}methanesulfonamide

ChemBase ID: 161
Molecular Formular: C21H19N3O3S
Molecular Mass: 393.45886
Monoisotopic Mass: 393.11471248
SMILES and InChIs

SMILES:
S(=O)(=O)(Nc1cc(OC)c(Nc2c3c(nc4c2cccc4)cccc3)cc1)C
Canonical SMILES:
COc1cc(ccc1Nc1c2ccccc2nc2c1cccc2)NS(=O)(=O)C
InChI:
InChI=1S/C21H19N3O3S/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/h3-13,24H,1-2H3,(H,22,23)
InChIKey:
XCPGHVQEEXUHNC-UHFFFAOYSA-N

Cite this record

CBID:161 http://www.chembase.cn/molecule-161.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
N-{4-[(acridin-9-yl)amino]-3-methoxyphenyl}methanesulfonamide
IUPAC Traditional name
amsacrine
Brand Name
Amsidine
Amsidyl
Amsine
AMSA P-D
Synonyms
Acridinyl Anisidide
M-AMSA
MAMSA
Amsacrine
CAS Number
51264-14-3
PubChem SID
46507539
160963624
PubChem CID
2179

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
DrugBank DB00276 external link
PubChem 2179 external link
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 10.824813  H Acceptors
H Donor LogD (pH = 5.5) 1.4867606 
LogD (pH = 7.4) 2.164806  Log P 3.1616213 
Molar Refractivity 107.6901 cm3 Polarizability 44.860916 Å3
Polar Surface Area 80.32 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 4.66  LOG S -5.09 
Solubility (Water) 3.17e-03 g/l 

PROPERTIES

PROPERTIES

Physical Property Bioassay(PubChem)
Solubility
<1 mg/mL expand Show data source
Hydrophobicity(logP)
3.8 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00276 external link
Item Information
Drug Groups approved
Description Aminoacridine derivative that is a potent intercalating antineoplastic agent. It is effective in the treatment of acute leukemias and malignant lymphomas, but has poor activity in the treatment of solid tumors. It is frequently used in combination with other antineoplastic agents in chemotherapy protocols. It produces consistent but acceptable myelosuppression and cardiotoxic effects. [PubChem]
Indication For treatment of acute myeloid leukaemia.
Pharmacology Amsacrine is an aminoacridine derivative that is a potent intercalating antineoplastic agent. It is effective in the treatment of acute leukemias and malignant lymphomas, but has poor activity in the treatment of solid tumors. It is frequently used in combination with other antineoplastic agents in chemotherapy protocols. It produces consistent but acceptable myelosuppression and cardiotoxic effects.
Toxicity Symptoms of overdose include nausea and vomiting, diarrhea, some cardiotoxicity (rarely).
Affected Organisms
Humans and other mammals
Biotransformation Extensive, primarily hepatic, converted to glutathione conjugate.
Absorption Poorly absorbed
Half Life 8-9 hours
Protein Binding 96-98%
References
[Link]
External Links
Wikipedia

REFERENCES

REFERENCES

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PATENTS

PATENTS

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