CHEBI:2687 - amsacrine

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ChEBI Name amsacrine
ChEBI ID CHEBI:2687
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C21H19N3O3S
Net Charge 0
Average Mass 393.45900
Monoisotopic Mass 393.11471
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
SMILES COc1cc(NS(C)(=O)=O)ccc1Nc1c2ccccc2nc2ccccc12
Roles Classification
Biological Role(s): 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(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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ChEBI Ontology
Outgoing 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 Sources
amsacrina ChemIDplus
amsacrinum ChemIDplus
Synonyms Sources
4'-(9-Acridinylamino)-3'-methoxymethanesulfonanilide KEGG COMPOUND
4'-(9-Acridinylamino)methanesulfon-m-anisidide ChemIDplus
4'-(9-Acridinylamino)methanesulfon-meta-anisidide ChemIDplus
4'-(9-Acridinylamino)methanesulphon-m-anisidide ChemIDplus
Amsacrine KEGG COMPOUND
mAMSA KEGG COMPOUND
Manual Xrefs Databases
203 DrugCentral
Amsacrine Wikipedia
C01553 KEGG COMPOUND
D02321 KEGG DRUG
DB00276 DrugBank
HMDB0014421 HMDB
View more database links
Registry Numbers Types Sources
500176 Reaxys Registry Number Reaxys
500176 Beilstein Registry Number Beilstein
51264-14-3 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
17675230 PubMed citation Europe PMC
9625435 PubMed citation Europe PMC
Last Modified
22 February 2017