Amsacrine (CHEM003632)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (3)XML
Record Information
Version1.0
Creation Date2014-09-11 02:04:22 UTC
Update Date2026-03-31 16:56:33 UTC
Accession NumberCHEM003632
Identification
Common NameAmsacrine
ClassSmall Molecule
DescriptionAminoacridine 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.
Contaminant Sources
  • HMDB Contaminants - Urine
  • IARC Carcinogens Group 2B
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Amide
  • Antineoplastic Agent
  • Drug
  • Ether
  • Intercalating Agent
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4'-(9-Acridinylamino)-3'-methoxymethanesulfonanilideChEBI
4'-(9-Acridinylamino)methanesulfon-m-anisidideChEBI
4'-(9-Acridinylamino)methanesulfon-meta-anisidideChEBI
4'-(9-Acridinylamino)methanesulphon-m-anisidideChEBI
AmsacrinaChEBI
AmsacrinumChEBI
MAMSAChEBI
AmsidylKegg
4'-(9-Acridinylamino)-3'-methoxymethanesulphonanilideGenerator
4'-(9-Acridinylamino)methanesulphon-meta-anisidideGenerator
Acridinyl anisidideHMDB
m-AMSAHMDB
AMSAHMDB
Cain acridineHMDB
Meta amsaHMDB
AMSA p DHMDB
AmsidineHMDB
Cains acridineHMDB
Meta-amsaHMDB
AMSA PDHMDB
Cain's acridineHMDB
AMSA p-DHMDB
Chemical FormulaC21H19N3O3S
Average Molecular Mass393.459 g/mol
Monoisotopic Mass393.115 g/mol
CAS Registry Number51264-14-3
IUPAC NameN-{4-[(acridin-9-yl)amino]-3-methoxyphenyl}methanesulfonamide
Traditional Nameamsacrine
SMILESCOC1=C(NC2=C3C=CC=CC3=NC3=CC=CC=C23)C=CC(NS(C)(=O)=O)=C1
InChI IdentifierInChI=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)
InChI KeyXCPGHVQEEXUHNC-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as acridines. These are organic compounds containing the acridine moiety, a linear tricyclic heterocycle which consists of two benzene rings joined by a pyridine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassBenzoquinolines
Direct ParentAcridines
Alternative Parents
Substituents
  • Acridine
  • 4-aminoquinoline
  • Aminoquinoline
  • Sulfanilide
  • Aminophenyl ether
  • Methoxyaniline
  • Phenoxy compound
  • Anisole
  • Phenol ether
  • Methoxybenzene
  • Aniline or substituted anilines
  • Alkyl aryl ether
  • Aminopyridine
  • Benzenoid
  • Pyridine
  • Monocyclic benzene moiety
  • Organosulfonic acid amide
  • Organic sulfonic acid amide
  • Heteroaromatic compound
  • Aminosulfonyl compound
  • Sulfonyl
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Azacycle
  • Ether
  • Secondary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Amine
  • Organopnictogen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point235°C
Boiling PointNot Available
Solubility<1 mg/mL
Predicted Properties
PropertyValueSource
Water Solubility0.0032 g/LALOGPS
logP4.66ALOGPS
logP3.16ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)10.82ChemAxon
pKa (Strongest Basic)8.44ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area80.32 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity107.69 m³·mol⁻¹ChemAxon
Polarizability41.65 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-02di-0019000000-7fcad477b7be59278713Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0007-0039000000-a2af4673e9da0eaf5858Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0092000000-8a23bcbe428e91081693Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000t-0090000000-3aca95179e2c583051c0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002f-5009000000-746720e7c744fadf4763Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9013000000-3e03298b63d7bfc80bf0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-630f95bbb2b03fc262f6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0009000000-e9cf7bbf444e4e4947d9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0009000000-998445f6c8ead946b587Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01pt-0898000000-b5849c315c2f06cf19a9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-4dca3821da1c28bc99c3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-4019000000-c3abc35c5eb7fd25ce6eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-9264000000-0de95adfd752b07865e4Spectrum
Toxicity Profile
Route of ExposurePoorly absorbed.
Mechanism of ToxicityAmsacrine binds to DNA through intercalation and external binding. It has a base specificity for A-T pairs. Rapidly dividing cells are two to four times more sensitive to amsacrine than are resting cells. Amsacrine appears to cleave DNA by inducing double stranded breaks. Amsacrine also targets and inhibits topoisomerase II. Cytotoxicity is greatest during the S phase of the cell cycle when topoisomerase levels are at a maximum.
MetabolismExtensive, primarily hepatic, converted to glutathione conjugate. Half Life: 8-9 hours
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (2)
Uses/SourcesFor treatment of acute myeloid leukaemia.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsSymptoms of overdose include nausea and vomiting, diarrhea, some cardiotoxicity (rarely).
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00276
HMDB IDHMDB0014421
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAmsacrine
Chemspider ID2094
ChEBI ID2687
PubChem Compound ID2179
Kegg Compound IDC01553
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSLink
General References
1. BC Cancer Agency: http://www.bccancer.bc.ca/HPI/DrugDatabase/DrugIndexPro/Amsacrine.htm
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=17675230
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=9625435