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CHEBI:2687 - amsacrine

Default Structure
ChEBI IDCHEBI:2687
ChEBI Nameamsacrine
Stars
DefinitionA sulfonamide that is N-phenylmethanesulfonamide substituted by a methoxy group at position 3 and an acridin-9-ylamino group at position 4. It exhibits antineoplastic activity.
Last Modified22 February 2017
DownloadsMolfile
FormulaC21H19N3O3S
Net Charge0
Average Mass393.468
Monoisotopic Mass393.11471
SMILESCOc1cc(NS(C)(=O)=O)ccc1Nc1c2ccccc2nc2ccccc12
InChIInChI=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)
InChIKeyXCPGHVQEEXUHNC-UHFFFAOYSA-N
Wikipedia
Roles Classification
Biological Role:
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor  A topoisomerase inhibitor that inhibits DNA topoisomerase (ATP-hydrolysing), EC 5.99.1.3 (also known as topoisomerase II and as DNA gyrase), which catalyses ATP-dependent breakage of both strands of DNA, passage of the unbroken strands through the breaks, and rejoining of the broken strands.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
amsacrine (CHEBI:2687) has role antineoplastic agent (CHEBI:35610)
amsacrine (CHEBI:2687) has role EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor (CHEBI:50750)
amsacrine (CHEBI:2687) is a acridines (CHEBI:22213)
amsacrine (CHEBI:2687) is a aromatic ether (CHEBI:35618)
amsacrine (CHEBI:2687) is a sulfonamide (CHEBI:35358)
IUPAC Name 
N-[4-(acridin-9-ylamino)-3-methoxyphenyl]methanesulfonamide
INNs  Source
amsacrinaChemIDplus
amsacrinumChemIDplus
Synonyms  Source
4'-(9-Acridinylamino)-3'-methoxymethanesulfonanilideKEGG COMPOUND
4'-(9-Acridinylamino)methanesulfon-m-anisidideChemIDplus
4'-(9-Acridinylamino)methanesulfon-meta-anisidideChemIDplus
4'-(9-Acridinylamino)methanesulphon-m-anisidideChemIDplus
AmsacrineKEGG COMPOUND
mAMSAKEGG COMPOUND
Manual XrefsDatabases
203DrugCentral
AmsacrineWikipedia
C01553KEGG COMPOUND
D02321KEGG DRUG
DB00276DrugBank
HMDB0014421HMDB
Registry NumbersSources
Reaxys:500176Reaxys
CAS:51264-14-3KEGG COMPOUND
CAS:51264-14-3ChemIDplus
Citations