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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:37 UTC
HMDB IDHMDB0014421
Secondary Accession Numbers
  • HMDB14421
Metabolite Identification
Common NameAmsacrine
DescriptionAmsacrine, also known as MAMSA or amsacrinum, 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. Amsacrine is a drug which is used for treatment of acute myeloid leukaemia. Amsacrine is a very strong basic compound (based on its pKa). Amsacrine is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound.
Structure
Data?1582753177
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 Weight393.459
Monoisotopic Molecular Weight393.114712179
IUPAC NameN-{4-[(acridin-9-yl)amino]-3-methoxyphenyl}methanesulfonamide
Traditional Nameamsacrine
CAS Registry Number51264-14-3
SMILES
COC1=C(NC2=C3C=CC=CC3=NC3=CC=CC=C23)C=CC(NS(C)(=O)=O)=C1
InChI Identifier
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)
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
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point234 - 236 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0032 g/LNot Available
LogP3.8Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available193.114http://allccs.zhulab.cn/database/detail?ID=AllCCS00001023
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+188.19831661259
DarkChem[M-H]-192.60731661259
DeepCCS[M-2H]-229.37430932474
DeepCCS[M+Na]+204.76730932474
AllCCS[M+H]+193.232859911
AllCCS[M+H-H2O]+190.332859911
AllCCS[M+NH4]+195.932859911
AllCCS[M+Na]+196.632859911
AllCCS[M-H]-191.532859911
AllCCS[M+Na-2H]-191.032859911
AllCCS[M+HCOO]-190.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AmsacrineCOC1=C(NC2=C3C=CC=CC3=NC3=CC=CC=C23)C=CC(NS(C)(=O)=O)=C15381.4Standard polar33892256
AmsacrineCOC1=C(NC2=C3C=CC=CC3=NC3=CC=CC=C23)C=CC(NS(C)(=O)=O)=C13875.8Standard non polar33892256
AmsacrineCOC1=C(NC2=C3C=CC=CC3=NC3=CC=CC=C23)C=CC(NS(C)(=O)=O)=C13795.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Amsacrine,1TMS,isomer #1COC1=CC(NS(C)(=O)=O)=CC=C1N(C1=C2C=CC=CC2=NC2=CC=CC=C12)[Si](C)(C)C3663.6Semi standard non polar33892256
Amsacrine,1TMS,isomer #1COC1=CC(NS(C)(=O)=O)=CC=C1N(C1=C2C=CC=CC2=NC2=CC=CC=C12)[Si](C)(C)C3402.8Standard non polar33892256
Amsacrine,1TMS,isomer #1COC1=CC(NS(C)(=O)=O)=CC=C1N(C1=C2C=CC=CC2=NC2=CC=CC=C12)[Si](C)(C)C4915.9Standard polar33892256
Amsacrine,1TMS,isomer #2COC1=CC(N([Si](C)(C)C)S(C)(=O)=O)=CC=C1NC1=C2C=CC=CC2=NC2=CC=CC=C123663.3Semi standard non polar33892256
Amsacrine,1TMS,isomer #2COC1=CC(N([Si](C)(C)C)S(C)(=O)=O)=CC=C1NC1=C2C=CC=CC2=NC2=CC=CC=C123470.3Standard non polar33892256
Amsacrine,1TMS,isomer #2COC1=CC(N([Si](C)(C)C)S(C)(=O)=O)=CC=C1NC1=C2C=CC=CC2=NC2=CC=CC=C125081.4Standard polar33892256
Amsacrine,2TMS,isomer #1COC1=CC(N([Si](C)(C)C)S(C)(=O)=O)=CC=C1N(C1=C2C=CC=CC2=NC2=CC=CC=C12)[Si](C)(C)C3518.9Semi standard non polar33892256
Amsacrine,2TMS,isomer #1COC1=CC(N([Si](C)(C)C)S(C)(=O)=O)=CC=C1N(C1=C2C=CC=CC2=NC2=CC=CC=C12)[Si](C)(C)C3493.7Standard non polar33892256
Amsacrine,2TMS,isomer #1COC1=CC(N([Si](C)(C)C)S(C)(=O)=O)=CC=C1N(C1=C2C=CC=CC2=NC2=CC=CC=C12)[Si](C)(C)C4531.1Standard polar33892256
Amsacrine,1TBDMS,isomer #1COC1=CC(NS(C)(=O)=O)=CC=C1N(C1=C2C=CC=CC2=NC2=CC=CC=C12)[Si](C)(C)C(C)(C)C3903.5Semi standard non polar33892256
Amsacrine,1TBDMS,isomer #1COC1=CC(NS(C)(=O)=O)=CC=C1N(C1=C2C=CC=CC2=NC2=CC=CC=C12)[Si](C)(C)C(C)(C)C3629.9Standard non polar33892256
Amsacrine,1TBDMS,isomer #1COC1=CC(NS(C)(=O)=O)=CC=C1N(C1=C2C=CC=CC2=NC2=CC=CC=C12)[Si](C)(C)C(C)(C)C4867.0Standard polar33892256
Amsacrine,1TBDMS,isomer #2COC1=CC(N([Si](C)(C)C(C)(C)C)S(C)(=O)=O)=CC=C1NC1=C2C=CC=CC2=NC2=CC=CC=C123902.4Semi standard non polar33892256
Amsacrine,1TBDMS,isomer #2COC1=CC(N([Si](C)(C)C(C)(C)C)S(C)(=O)=O)=CC=C1NC1=C2C=CC=CC2=NC2=CC=CC=C123673.0Standard non polar33892256
Amsacrine,1TBDMS,isomer #2COC1=CC(N([Si](C)(C)C(C)(C)C)S(C)(=O)=O)=CC=C1NC1=C2C=CC=CC2=NC2=CC=CC=C125008.3Standard polar33892256
Amsacrine,2TBDMS,isomer #1COC1=CC(N([Si](C)(C)C(C)(C)C)S(C)(=O)=O)=CC=C1N(C1=C2C=CC=CC2=NC2=CC=CC=C12)[Si](C)(C)C(C)(C)C3969.7Semi standard non polar33892256
Amsacrine,2TBDMS,isomer #1COC1=CC(N([Si](C)(C)C(C)(C)C)S(C)(=O)=O)=CC=C1N(C1=C2C=CC=CC2=NC2=CC=CC=C12)[Si](C)(C)C(C)(C)C3939.9Standard non polar33892256
Amsacrine,2TBDMS,isomer #1COC1=CC(N([Si](C)(C)C(C)(C)C)S(C)(=O)=O)=CC=C1N(C1=C2C=CC=CC2=NC2=CC=CC=C12)[Si](C)(C)C(C)(C)C4528.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Amsacrine GC-MS (Non-derivatized) - 70eV, Positivesplash10-02di-0019000000-7fcad477b7be592787132017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Amsacrine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Amsacrine 10V, Positive-QTOFsplash10-0007-0039000000-a2af4673e9da0eaf58582016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Amsacrine 20V, Positive-QTOFsplash10-0002-0092000000-8a23bcbe428e910816932016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Amsacrine 40V, Positive-QTOFsplash10-000t-0090000000-3aca95179e2c583051c02016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Amsacrine 10V, Negative-QTOFsplash10-002f-5009000000-746720e7c744fadf47632016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Amsacrine 20V, Negative-QTOFsplash10-004i-9013000000-3e03298b63d7bfc80bf02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Amsacrine 40V, Negative-QTOFsplash10-004i-9000000000-630f95bbb2b03fc262f62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Amsacrine 10V, Positive-QTOFsplash10-0006-0009000000-e9cf7bbf444e4e4947d92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Amsacrine 20V, Positive-QTOFsplash10-0006-0009000000-998445f6c8ead946b5872021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Amsacrine 40V, Positive-QTOFsplash10-01pt-0898000000-b5849c315c2f06cf19a92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Amsacrine 10V, Negative-QTOFsplash10-0006-0009000000-4dca3821da1c28bc99c32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Amsacrine 20V, Negative-QTOFsplash10-004l-4019000000-c3abc35c5eb7fd25ce6e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Amsacrine 40V, Negative-QTOFsplash10-057i-9264000000-0de95adfd752b07865e42021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00276 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00276 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00276
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2094
KEGG Compound IDC01553
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAmsacrine
METLIN IDNot Available
PubChem Compound2179
PDB IDNot Available
ChEBI ID2687
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. BC Cancer Agency [Link]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in ion channel activity
Specific function:
Pore-forming (alpha) subunit of voltage-gated inwardly rectifying potassium channel. Channel properties are modulated by cAMP and subunit assembly. Mediates the rapidly activating component of the delayed rectifying potassium current in heart (IKr). Isoform 3 has no channel activity by itself, but modulates channel characteristics when associated with isoform 1
Gene Name:
KCNH2
Uniprot ID:
Q12809
Molecular weight:
126653.5
References
  1. Thomas D, Hammerling BC, Wu K, Wimmer AB, Ficker EK, Kirsch GE, Kochan MC, Wible BA, Scholz EP, Zitron E, Kathofer S, Kreye VA, Katus HA, Schoels W, Karle CA, Kiehn J: Inhibition of cardiac HERG currents by the DNA topoisomerase II inhibitor amsacrine: mode of action. Br J Pharmacol. 2004 Jun;142(3):485-94. Epub 2004 May 17. [PubMed:15148258 ]
General function:
Involved in sequence-specific DNA binding transcription factor activity
Specific function:
Control of topological states of DNA by transient breakage and subsequent rejoining of DNA strands. Topoisomerase II makes double-strand breaks
Gene Name:
TOP2A
Uniprot ID:
P11388
Molecular weight:
174383.9
References
  1. Finlay GJ, Atwell GJ, Baguley BC: Inhibition of the action of the topoisomerase II poison amsacrine by simple aniline derivatives: evidence for drug-protein interactions. Oncol Res. 1999;11(6):249-54. [PubMed:10691026 ]
  2. Ferlin MG, Marzano C, Chiarelotto G, Baccichetti F, Bordin F: Synthesis and antiproliferative activity of some variously substituted acridine and azacridine derivatives. Eur J Med Chem. 2000 Sep;35(9):827-37. [PubMed:11006484 ]
  3. Matsumoto Y, Takano H, Kunishio K, Nagao S, Fojo T: Hypophosphorylation of topoisomerase IIalpha in etoposide (VP-16)-resistant human carcinoma cell lines associated with carboxy-terminal truncation. Jpn J Cancer Res. 2001 Jul;92(7):799-805. [PubMed:11473732 ]
  4. Lee MS, Wang JC, Beran M: Two independent amsacrine-resistant human myeloid leukemia cell lines share an identical point mutation in the 170 kDa form of human topoisomerase II. J Mol Biol. 1992 Feb 20;223(4):837-43. [PubMed:1311390 ]
  5. Nitiss JL, Liu YX, Harbury P, Jannatipour M, Wasserman R, Wang JC: Amsacrine and etoposide hypersensitivity of yeast cells overexpressing DNA topoisomerase II. Cancer Res. 1992 Aug 15;52(16):4467-72. [PubMed:1322791 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  7. Arimondo P, Boukarim C, Bailly C, Dauzonne D, Monneret C: Design of two etoposide-amsacrine conjugates: topoisomerase II and tubuline polymerization inhibition and relation to cytotoxicity. Anticancer Drug Des. 2000 Dec;15(6):413-21. [PubMed:11716434 ]

Transporters

General function:
Involved in ATP binding
Specific function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular weight:
141477.3
References
  1. Nagy H, Goda K, Fenyvesi F, Bacso Z, Szilasi M, Kappelmayer J, Lustyik G, Cianfriglia M, Szabo G Jr: Distinct groups of multidrug resistance modulating agents are distinguished by competition of P-glycoprotein-specific antibodies. Biochem Biophys Res Commun. 2004 Mar 19;315(4):942-9. [PubMed:14985103 ]