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

• ChemBase ID: 161
• Molecular Formular: C21H19N3O3S
• Molecular Mass: 393.45886
• Monoisotopic Mass: 393.11471248
• 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

NAMES AND DATABASE IDS

Names

• 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

Database IDs

• CAS Number: 51264-14-3
• PubChem SID: 160963624; 46507539
• PubChem CID: 2179

CALCULATED PROPERTIES

JChem

• Acid pKa: 10.824813
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.4867606
• LogD (pH = 7.4): 2.164806
• Log P: 3.1616213
• Molar Refractivity: 107.6901 cm^3
• Polarizability: 44.860916 Å^3
• Polar Surface Area: 80.32 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.66
• LOG S: -5.09
• Solubility (Water): 3.17e-03 g/l

PROPERTIES

Physical Property

• Solubility: <1 mg/mL
• Hydrophobicity(logP): 3.8

DETAILS

DrugBank - DB00276

• 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

• Link