CHEBI:5801 - hydroxychloroquine

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ChEBI Name hydroxychloroquine
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 335.17644
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)
SMILES CCN(CCO)CCCC(C)Nc1ccnc2cc(Cl)ccc12
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): anticoronaviral agent
Any antiviral agent which inhibits the activity of coronaviruses.
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.
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 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 hydroxychloroquine(2+) (CHEBI:149564) is conjugate acid of hydroxychloroquine (CHEBI:5801)
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
oxichlorochine ChEBI
oxichloroquine ChEBI
Brand Name Source
Polirreumin KEGG DRUG
Manual Xrefs Databases
1395 DrugCentral
DB01611 DrugBank
HMDB0015549 HMDB
Hydroxychloroquine Wikipedia
US2546658 Patent
View more database links
Registry Numbers Types Sources
118-42-3 CAS Registry Number KEGG COMPOUND
118-42-3 CAS Registry Number NIST Chemistry WebBook
118-42-3 CAS Registry Number ChemIDplus
253894 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
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PMC7122276 PubMed Central citation Europe PMC
Last Modified
30 April 2020