CHEBI:5801 - hydroxychloroquine

ChEBI IDCHEBI:5801
ChEBI Namehydroxychloroquine
Stars
DefinitionAn 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.
Last Modified30 April 2020
DownloadsMolfile
FormulaC18H26ClN3O
Net Charge0
Average Mass335.879
Monoisotopic Mass335.17644
SMILESCCN(CCO)CCCC(C)Nc1ccnc2cc(Cl)ccc12
InChIInChI=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)
InChIKeyXXSMGPRMXLTPCZ-UHFFFAOYSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
anti-HIV agent  An antiviral agent that destroys or inhibits the replication of the human immunodeficiency virus.
anticoronaviral agent  Any antiviral agent which inhibits the activity of coronaviruses.
antiviral agent  A substance that destroys or inhibits replication of viruses.
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
insulin-sensitizing drug  An agent which overcomes insulin resistance by activation of the peroxisome proliferator activated receptor gamma (PPAR-gamma).
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.
immunosuppressive agent  An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
Applications:
antirheumatic drug  A drug used to treat rheumatoid arthritis.
antiinfective agent  A substance used in the prophylaxis or therapy of infectious diseases.
insulin-sensitizing drug  An agent which overcomes insulin resistance by activation of the peroxisome proliferator activated receptor gamma (PPAR-gamma).
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.
hypoglycemic agent  A drug which lowers the blood glucose level.
immunosuppressive agent  An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
dermatologic drug  A drug used to treat or prevent skin disorders or for the routine care of skin.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
anti-inflammatory agent  Any compound that has anti-inflammatory effects.
ChEBI Ontology
Outgoing Relation(s)
hydroxychloroquine (CHEBI:5801) has functional parent chloroquine (CHEBI:3638)
hydroxychloroquine (CHEBI:5801) has role anti-HIV agent (CHEBI:64946)
hydroxychloroquine (CHEBI:5801) has role anti-inflammatory agent (CHEBI:67079)
hydroxychloroquine (CHEBI:5801) has role anticoronaviral agent (CHEBI:149553)
hydroxychloroquine (CHEBI:5801) has role antifungal agent (CHEBI:35718)
hydroxychloroquine (CHEBI:5801) has role antiinfective agent (CHEBI:35441)
hydroxychloroquine (CHEBI:5801) has role antimalarial (CHEBI:38068)
hydroxychloroquine (CHEBI:5801) has role antimicrobial agent (CHEBI:33281)
hydroxychloroquine (CHEBI:5801) has role antineoplastic agent (CHEBI:35610)
hydroxychloroquine (CHEBI:5801) has role antirheumatic drug (CHEBI:35842)
hydroxychloroquine (CHEBI:5801) has role antiviral agent (CHEBI:22587)
hydroxychloroquine (CHEBI:5801) has role dermatologic drug (CHEBI:50177)
hydroxychloroquine (CHEBI:5801) has role hypoglycemic agent (CHEBI:35526)
hydroxychloroquine (CHEBI:5801) has role immunosuppressive agent (CHEBI:35705)
hydroxychloroquine (CHEBI:5801) has role insulin-sensitizing drug (CHEBI:50864)
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 Relation(s)
hydroxychloroquine(2+) (CHEBI:149564) is conjugate acid of hydroxychloroquine (CHEBI:5801)
IUPAC Name 
2-[{4-[(7-chloroquinolin-4-yl)amino]pentyl}(ethyl)amino]ethanol
INNs  Source
hidroxicloroquinaChemIDplus
hydroxychloroquineChemIDplus
hydroxychloroquineWHO MedNet
hydroxychloroquinumChemIDplus
Synonyms  Source
2-((4-((7-chloro-4-quinolyl)amino)pentyl)ethylamino)ethanolChemIDplus
2-(N-(4-(7-chlor-4-chinolylamino)-4-methylbutyl)ethylamino)ethanolChemIDplus
7-chloro-4-(4-(N-ethyl-N-β-hydroxyethylamino)-1-methylbutylamino)quinolineChemIDplus
7-chloro-4-[4-(N-ethyl-N-β-hydroxyethylamino)-1-methylbutylamino]quinolineChEBI
7-chloro-4-(4-(ethyl(2-hydroxyethyl)amino)-1-methylbutylamino)quinolineChemIDplus
7-chloro-4-[5-(N-ethyl-N-2-hydroxyethylamino)-2-pentyl]aminoquinolineChEBI
Brand Name  Source
PolirreuminKEGG DRUG
Manual XrefsDatabases
1395DrugCentral
C07043KEGG COMPOUND
D08050KEGG DRUG
DB01611DrugBank
HMDB0015549HMDB
HydroxychloroquineWikipedia
LSM-5193LINCS
US2546658Patent
Registry NumbersSources
Reaxys:253894Reaxys
CAS:118-42-3NIST Chemistry WebBook
CAS:118-42-3KEGG COMPOUND
CAS:118-42-3ChemIDplus
Citations