hydroxychloroquine (CHEBI:5801)

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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

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)

InChIKey

XXSMGPRMXLTPCZ-UHFFFAOYSA-N

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. 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.

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)

IUPAC Name

2-[{4-[(7-chloroquinolin-4-yl)amino]pentyl}(ethyl)amino]ethanol

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

Last Modified

30 April 2020