CHEBI:5801 - hydroxychloroquine

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ChEBI Name hydroxychloroquine
ChEBI ID CHEBI:5801
Definition An 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C18H26ClN3O
Net Charge 0
Average Mass 335.87200
Monoisotopic Mass 335.176
InChI InChI=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)
InChIKey XXSMGPRMXLTPCZ-UHFFFAOYSA-N
SMILES CCN(CCO)CCCC(C)Nc1ccnc2cc(Cl)ccc12
Roles Classification
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.
Application(s): 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.
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.
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ChEBI Ontology
Outgoing hydroxychloroquine (CHEBI:5801) has functional parent chloroquine (CHEBI:3638)
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)
IUPAC Name
2-[{4-[(7-chloroquinolin-4-yl)amino]pentyl}(ethyl)amino]ethanol
INNs Sources
hidroxicloroquina ChemIDplus
hydroxychloroquine WHO MedNet
hydroxychloroquine ChemIDplus
hydroxychloroquinum ChemIDplus
Synonyms Sources
(±)-hydroxychloroquine ChemIDplus
2-((4-((7-chloro-4-quinolyl)amino)pentyl)ethylamino)ethanol ChemIDplus
2-(N-(4-(7-chlor-4-chinolylamino)-4-methylbutyl)ethylamino)ethanol ChemIDplus
7-chloro-4-(4-(ethyl(2-hydroxyethyl)amino)-1-methylbutylamino)quinoline ChemIDplus
7-chloro-4-(4-(N-ethyl-N-β-hydroxyethylamino)-1-methylbutylamino)quinoline ChemIDplus
7-chloro-4-[4-(N-ethyl-N-β-hydroxyethylamino)-1-methylbutylamino]quinoline ChEBI
7-chloro-4-[5-(N-ethyl-N-2-hydroxyethylamino)-2-pentyl]aminoquinoline ChEBI
NSC4375 ChEBI
oxichlorochine ChEBI
oxichloroquine ChEBI
Brand Name Source
Polirreumin KEGG DRUG
Database Links Databases
C07043 KEGG COMPOUND
D08050 KEGG DRUG
DB01611 DrugBank
HMDB15549 HMDB
Hydroxychloroquine Wikipedia
LSM-5193 LINCS
US2546658 Patent
View more database links
Registry Numbers Types Sources
118-42-3 CAS Registry Number ChemIDplus
118-42-3 CAS Registry Number NIST Chemistry WebBook
253894 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
23216212 PubMed citation Europe PMC
23218706 PubMed citation Europe PMC
23481418 PubMed citation Europe PMC
23485647 PubMed citation Europe PMC
23581274 PubMed citation Europe PMC
23778483 PubMed citation Europe PMC
23887202 PubMed citation Europe PMC
23902281 PubMed citation Europe PMC
Last Modified
25 February 2016