CHEBI:3638 - chloroquine

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ChEBI Name chloroquine
Definition An aminoquinoline that is quinoline which is substituted at position 4 by a [5-(diethylamino)pentan-2-yl]amino group at at position 7 by chlorine. It is used for the treatment of malaria, hepatic amoebiasis, lupus erythematosus, light-sensitive skin eruptions, and rheumatoid arthritis.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C18H26ClN3
Net Charge 0
Average Mass 319.87200
Monoisotopic Mass 319.18153
InChI InChI=1S/C18H26ClN3/c1-4-22(5-2)12-6-7-14(3)21-17-10-11-20-18-13-15(19)8-9-16(17)18/h8-11,13-14H,4-7,12H2,1-3H3,(H,20,21)
SMILES CCN(CC)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): autophagy inhibitor
Any compound that inhibits the process of autophagy (the self-digestion of one or more components of a cell through the action of enzymes originating within the same cell).
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 chloroquine (CHEBI:3638) has role anticoronaviral agent (CHEBI:149553)
chloroquine (CHEBI:3638) has role antimalarial (CHEBI:38068)
chloroquine (CHEBI:3638) has role antirheumatic drug (CHEBI:35842)
chloroquine (CHEBI:3638) has role autophagy inhibitor (CHEBI:88230)
chloroquine (CHEBI:3638) has role dermatologic drug (CHEBI:50177)
chloroquine (CHEBI:3638) is a aminoquinoline (CHEBI:36709)
chloroquine (CHEBI:3638) is a organochlorine compound (CHEBI:36683)
chloroquine (CHEBI:3638) is a secondary amino compound (CHEBI:50995)
chloroquine (CHEBI:3638) is a tertiary amino compound (CHEBI:50996)
chloroquine (CHEBI:3638) is conjugate base of chloroquine(2+) (CHEBI:149484)
Incoming hydroxychloroquine (CHEBI:5801) has functional parent chloroquine (CHEBI:3638)
chloroquine sulfate (CHEBI:50178) has part chloroquine (CHEBI:3638)
(R)-chloroquine (CHEBI:48811) is a chloroquine (CHEBI:3638)
(S)-chloroquine (CHEBI:39254) is a chloroquine (CHEBI:3638)
chloroquine(2+) (CHEBI:149484) is conjugate acid of chloroquine (CHEBI:3638)
INNs Sources
chloroquine WHO MedNet
chloroquine ChemIDplus
chloroquinum ChemIDplus
cloroquina ChemIDplus
Synonyms Sources
Chlorochin ChemIDplus
N4-(7-chloro-4-quinolinyl)-N1,N1-diethyl-1,4-pentanediamine NIST Chemistry WebBook
Brand Names Sources
Aralen DrugBank
Artrichin DrugBank
Bemaphate DrugBank
Capquin DrugBank
Nivaquine B DrugBank
Resoquine DrugBank
Reumachlor DrugBank
Sanoquin DrugBank
Manual Xrefs Databases
607 DrugCentral
Chloroquine Wikipedia
DB00608 DrugBank
DE683692 Patent
HMDB0014746 HMDB
US2233970 Patent
View more database links
Registry Numbers Types Sources
482809 Reaxys Registry Number Reaxys
482809 Beilstein Registry Number Beilstein
54-05-7 CAS Registry Number KEGG COMPOUND
54-05-7 CAS Registry Number NIST Chemistry WebBook
54-05-7 CAS Registry Number ChemIDplus
781126 Gmelin Registry Number Gmelin
Citations Waiting for Citations Types Sources
11198399 PubMed citation Europe PMC
17594118 PubMed citation Europe PMC
18052874 PubMed citation Europe PMC
19426658 PubMed citation Europe PMC
23288916 PubMed citation Europe PMC
23580861 PubMed citation Europe PMC
23635029 PubMed citation Europe PMC
23644906 PubMed citation Europe PMC
23706562 PubMed citation Europe PMC
23852712 PubMed citation Europe PMC
23891850 PubMed citation Europe PMC
25285162 PubMed citation Europe PMC
Last Modified
23 April 2020
General Comment
2014-07-14 Chloroquine can be found in blood and urine samples of individuals who have taken this drug.