chloroquine (CHEBI:3638)

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ChEBI Name	chloroquine

ChEBI ID	CHEBI:3638

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

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)

InChIKey

WHTVZRBIWZFKQO-UHFFFAOYSA-N

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. 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	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)

IUPAC Name

N⁴-(7-chloroquinolin-4-yl)-N¹,N¹-diethylpentane-1,4-diamine

Synonyms	Sources
Chlorochin	ChemIDplus
Chloroquine	KEGG COMPOUND
N⁴-(7-chloro-4-quinolinyl)-N¹,N¹-diethyl-1,4-pentanediamine	NIST Chemistry WebBook

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.