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CHEBI:5801 - hydroxychloroquine

ChEBI IDCHEBI:5801
ChEBI Namehydroxychloroquine
Stars
DefinitionAn aminoquinoline that is chloroquine in which one of the N-ethyl groups is hydroxylated at position 2. An antimalarial with properties similar to chloroquine that acts against erythrocytic forms of malarial parasites, it is mainly used as the sulfate salt for the treatment of lupus erythematosus, rheumatoid arthritis, and light-sensitive skin eruptions.
Last Modified30 April 2020
DownloadsMolfile
FormulaC18H26ClN3O
Net Charge0
Average Mass335.879
Monoisotopic Mass335.17644
SMILESCCN(CCO)CCCC(C)Nc1ccnc2cc(Cl)ccc12
InChIInChI=1S/C18H26ClN3O/c1-3-22(11-12-23)10-4-5-14(2)21-17-8-9-20-18-13-15(19)6-7-16(17)18/h6-9,13-14,23H,3-5,10-12H2,1-2H3,(H,20,21)
InChIKeyXXSMGPRMXLTPCZ-UHFFFAOYSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
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.
anticoronaviral agent  Any antiviral agent which inhibits the activity of coronaviruses.
Applications:
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.
antirheumatic drug  A drug used to treat rheumatoid arthritis.
dermatologic drug  A drug used to treat or prevent skin disorders or for the routine care of skin.
ChEBI Ontology
Outgoing Relation(s)
hydroxychloroquine (CHEBI:5801) has functional parent chloroquine (CHEBI:3638)
hydroxychloroquine (CHEBI:5801) has role anticoronaviral agent (CHEBI:149553)
hydroxychloroquine (CHEBI:5801) has role antimalarial (CHEBI:38068)
hydroxychloroquine (CHEBI:5801) has role antirheumatic drug (CHEBI:35842)
hydroxychloroquine (CHEBI:5801) has role dermatologic drug (CHEBI:50177)
hydroxychloroquine (CHEBI:5801) is a aminoquinoline (CHEBI:36709)
hydroxychloroquine (CHEBI:5801) is a organochlorine compound (CHEBI:36683)
hydroxychloroquine (CHEBI:5801) is a primary alcohol (CHEBI:15734)
hydroxychloroquine (CHEBI:5801) is a secondary amino compound (CHEBI:50995)
hydroxychloroquine (CHEBI:5801) is a tertiary amino compound (CHEBI:50996)
hydroxychloroquine (CHEBI:5801) is conjugate base of hydroxychloroquine(2+) (CHEBI:149564)
Incoming Relation(s)
hydroxychloroquine(2+) (CHEBI:149564) is conjugate acid of hydroxychloroquine (CHEBI:5801)
IUPAC Name 
2-[{4-[(7-chloroquinolin-4-yl)amino]pentyl}(ethyl)amino]ethanol
INNs  Source
hydroxychloroquineWHO MedNet
hidroxicloroquinaChemIDplus
hydroxychloroquineChemIDplus
hydroxychloroquinumChemIDplus
Synonyms  Source
2-(N-(4-(7-chlor-4-chinolylamino)-4-methylbutyl)ethylamino)ethanolChemIDplus
7-chloro-4-(4-(N-ethyl-N-β-hydroxyethylamino)-1-methylbutylamino)quinolineChemIDplus
7-chloro-4-(4-(ethyl(2-hydroxyethyl)amino)-1-methylbutylamino)quinolineChemIDplus
2-((4-((7-chloro-4-quinolyl)amino)pentyl)ethylamino)ethanolChemIDplus
oxichloroquineChEBI
7-chloro-4-[4-(N-ethyl-N-β-hydroxyethylamino)-1-methylbutylamino]quinolineChEBI
Brand Name  Source
PolirreuminKEGG DRUG
Manual XrefsDatabases
C07043KEGG COMPOUND
D08050KEGG DRUG
US2546658Patent
DB01611DrugBank
HMDB0015549HMDB
HydroxychloroquineWikipedia
LSM-5193LINCS
1395DrugCentral
Registry NumbersSources
Reaxys:253894Reaxys
CAS:118-42-3KEGG COMPOUND
CAS:118-42-3ChemIDplus
CAS:118-42-3NIST Chemistry WebBook
Citations