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quinacrine (CHEBI:8711)

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ChEBI Name quinacrine
ChEBI ID CHEBI:8711
Definition A member of the class of acridines that is acridine substituted by a chloro group at position 6, a methoxy group at position 2 and a [5-(diethylamino)pentan-2-yl]nitrilo group at position 9.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula Source
C23H30ClN3O KEGG COMPOUND
Net Charge 0
Average Mass 399.95700
InChI
InChI=1S/C23H30ClN3O/c1-5-27(6-2)13-7-8-16(3)25-23-19-11-9-17(24)14-22(19)26-21-12-10-18(28-4)15-20(21)23/h9-12,14-16H,5-8,13H2,1-4H3,(H,25,26)
InChIKey
GPKJTRJOBQGKQK-UHFFFAOYSA-N
SMILES
CCN(CC)CCCC(C)Nc1c2ccc(Cl)cc2nc2ccc(OC)cc12
Roles Classification
Chemical Role(s): EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor
An EC 1.8.1.* (oxidoreductase acting on sulfur group of donors, NAD+ or NADP+ as acceptor) inhibitor that interferes with the action of trypanothione-disulfide reductase (EC 1.8.1.12).
Biological Role(s): antimalarial
A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor
An EC 1.8.1.* (oxidoreductase acting on sulfur group of donors, NAD+ or NADP+ as acceptor) inhibitor that interferes with the action of trypanothione-disulfide reductase (EC 1.8.1.12).
Application(s): antimalarial
A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
View more on the ChEBI Ontology
ChEBI Ontology
Outgoing quinacrine (CHEBI:8711) has parent hydride acridine (CHEBI:36420)
quinacrine (CHEBI:8711) has role antimalarial (CHEBI:38068)
quinacrine (CHEBI:8711) has role EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor (CHEBI:77402)
quinacrine (CHEBI:8711) is a acridines (CHEBI:22213)
quinacrine (CHEBI:8711) is a aromatic ether (CHEBI:35618)
quinacrine (CHEBI:8711) is a organochlorine compound (CHEBI:36683)
quinacrine (CHEBI:8711) is a tertiary amino compound (CHEBI:50996)
Incoming quinacrine mustard (CHEBI:37595) has functional parent quinacrine (CHEBI:8711)
(R)-quinacrine (CHEBI:49845) is a quinacrine (CHEBI:8711)
(S)-quinacrine (CHEBI:37597) is a quinacrine (CHEBI:8711)
IUPAC Name
4-N-(6-chloro-2-methoxyacridin-9-yl)-1-N,1-N-diethylpentane-1,4-diamine
Synonyms Sources
2-methoxy-6-chloro-9-diethylaminopentylaminoacridine ChemIDplus
3-chloro-7-methoxy-9-(1-methyl-4-diethylaminobutylamino)acridine ChemIDplus
6-chloro-9-((4-(diethylamino)-1-methylbutyl)amino)-2-methoxyacridine ChemIDplus
mepacrine ChemIDplus
N4-(6-chloro-2-methoxy-9-acridinyl)-N1,N1-diethyl-1,4-pentanediamine ChemIDplus
Quinacrine KEGG COMPOUND
Database Links Databases
ATABRINE MetaCyc
C07339 KEGG COMPOUND
DB01103 DrugBank
HMDB15235 HMDB
Quinacrine Wikipedia
View more database links
Registry Numbers Types Sources
497807 Beilstein Registry Number Beilstein
83-89-6 CAS Registry Number ChemIDplus
95500 Beilstein Registry Number Beilstein
95500 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11339632 PubMed citation CiteXplore
11908878 PubMed citation CiteXplore
19747949 PubMed citation CiteXplore
Last Modified
24 marzo 2014

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