Chloroquine

Identification

Summary

Chloroquine is an antimalarial drug used to treat susceptible infections with P. vivax, P. malariae, P. ovale, and P. falciparum. It is also used for second line treatment for rheumatoid arthritis.

Generic Name
Chloroquine
DrugBank Accession Number
DB00608
Background

Chloroquine is an aminoquinolone derivative first developed in the 1940s for the treatment of malaria.4 It was the drug of choice to treat malaria until the development of newer antimalarials such as pyrimethamine, artemisinin, and mefloquine.17 Chloroquine and its derivative hydroxychloroquine have since been repurposed for the treatment of a number of other conditions including HIV, systemic lupus erythematosus, and rheumatoid arthritis.18

The FDA emergency use authorization for hydroxychloroquine and chloroquine in the treatment of COVID-19 was revoked on 15 June 2020.21

Chloroquine was granted FDA Approval on 31 October 1949.20

Type
Small Molecule
Groups
Approved, Investigational, Vet approved
Structure
Weight
Average: 319.872
Monoisotopic: 319.181525554
Chemical Formula
C18H26ClN3
Synonyms
  • Chloraquine
  • Chlorochin
  • Chloroquina
  • Chloroquine
  • Chloroquinium
  • Chloroquinum
  • Cloroquina
  • N4-(7-chloro-4-quinolinyl)-N1,N1-diethyl-1,4-pentanediamine

Pharmacology

Indication

Chloroquine is indicated to treat infections of P. vivax, P. malariae, P. ovale, and susceptible strains of P. falciparum.19 It is also used to treat extraintestinal amebiasis.19

Chloroquine is also used off label for the treatment of rheumatic diseases,4 as well as treatment and prophylaxis of Zika virus.1,2 Chloroquine is currently undergoing clinical trials for the treatment of COVID-19.3

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofAmebiasis of the extraintestinal••••••••••••
Treatment ofDiscoid lupus erythematosus••• •••••
Prophylaxis ofMalaria••••••••••••
Used in combination to treatPlasmodium infectionsCombination Product in combination with: Lidocaine (DB00281)•••••••••••••••••••••• ••••••••
Treatment ofPolymorphous light eruption••• •••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Chloroquine inhibits the action of heme polymerase, which causes the buildup of toxic heme in Plasmodium species.11 It has a long duration of action as the half life is 20-60 days.10 Patients should be counselled regarding the risk of retinopathy with long term usage or high dosage, muscle weakness, and toxicity in children.19

Mechanism of action

Chloroquine inhibits the action of heme polymerase in malarial trophozoites, preventing the conversion of heme to hemazoin.11,15,16 Plasmodium species continue to accumulate toxic heme, killing the parasite.11

Chloroquine passively diffuses through cell membranes and into endosomes, lysosomes, and Golgi vesicles; where it becomes protonated, trapping the chloroquine in the organelle and raising the surrounding pH.10,13 The raised pH in endosomes, prevent virus particles from utilizing their activity for fusion and entry into the cell.14

Chloroquine does not affect the level of ACE2 expression on cell surfaces, but inhibits terminal glycosylation of ACE2, the receptor that SARS-CoV and SARS-CoV-2 target for cell entry.13,14 ACE2 that is not in the glycosylated state may less efficiently interact with the SARS-CoV-2 spike protein, further inhibiting viral entry.14

TargetActionsOrganism
UGlutathione S-transferase A2
inhibitor
Humans
UTumor necrosis factor
inhibitor
Humans
UToll-like receptor 9
inhibitor
Humans
UGlutathione S-transferase
inhibitor
Plasmodium falciparum
UHigh mobility group protein B1
inhibitor
Humans
UGlutathione S-transferase Mu 1
inhibitor
Humans
UAngiotensin-converting enzyme 2
modulator
Humans
Absorption

Chloroquine oral solution has a bioavailability of 52-102% and oral tablets have a bioavailability of 67-114%.10 Intravenous chloroquine reaches a Cmax of 650-1300µg/L and oral chloroquine reaches a Cmax of 65-128µg/L with a Tmax of 0.5h.10

Volume of distribution

The volume of distribution of chloroquine is 200-800L/kg.10

Protein binding

Chloroquine is 46-74% bound to plasma proteins.9 (-)-chloroquine binds more strongly to alpha-1-acid glycoprotein and (+)-chloroquine binds more strongly to serum albumin.8

Metabolism

Chloroquine is N-dealkylated primarily by CYP2C8 and CYP3A4 to N-desethylchloroquine.5,6,7,10 It is N-dealkylated to a lesser extent by CYP3A5, CYP2D6, and to an ever lesser extent by CYP1A1.5,6,7,10 N-desethylchloroquine can be further N-dealkylated to N-bidesethylchloroquine, which is further N-dealkylated to 7-chloro-4-aminoquinoline.10

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Route of elimination

Chloroquine is predominantly eliminated in the urine.10 50% of a dose is recovered in the urine as unchanged chloroquine, with 10% of the dose recovered in the urine as desethylchloroquine.10

Half-life

The half life of chloroquine is 20-60 days.10

Clearance

Chloroquine has a total plasma clearance of 0.35-1L/h/kg.10

Adverse Effects
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Toxicity

Patients experiencing an overdose may present with headache, drowsiness, visual disturbances, nausea, vomiting, cardiovascular collapse, shock, convulsions, respiratory arrest, cardiac arrest, and hypokalemia.19 Overdose should be managed with symptomatic and supportive treatment which may include prompt emesis, gastric lavage, and activated charcoal.19

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Glucose-6-phosphate 1-dehydrogenaseVilleurbanneNot Available1000_1002delACCADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseTorunNot Available1006A->GADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseSunderlandNot Available105_107delCATADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseIwatsukiNot Available1081G->AADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseSerresNot Available1082C->TADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseTondelaNot Available1084_1101delCTGAACGAGCGCAAGGCCADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseLoma LindaNot Available1089C->AADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseAachenNot Available1089C->GADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseTenriNot Available1096A->GADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseMontpellierNot Available1132G>AADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseCalvo MackennaNot Available1138A->GADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseRileyNot Available1139T->CADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseOlomoucNot Available1141T->CADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseTomahNot Available1153T->CADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseLynwoodNot Available1154G->TADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseMadridNot Available1155C->GADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseIowa, Walter Reed, SpringfieldNot Available1156A->GADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseBeverly Hills, Genova, Iwate, Niigata, YamaguchiNot Available1160G->AADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseHartfordNot Available1162A->GADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenasePrahaNot Available1166A->GADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseKrakowNot Available1175T>CADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseWisconsinNot Available1177C->GADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseNashville, Anaheim, PorticiNot Available1178G->AADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseAlhambraNot Available1180G->CADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseBariNot Available1187C->TADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenasePuerto LimonNot Available1192G->AADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseCovao do LoboNot Available1205C>AADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseClinicNot Available1215G->AADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseUtrechtNot Available1225C->TADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseSuwalkiNot Available1226C->GADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseRiversideNot Available1228G->TADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseJapan, ShinagawaNot Available1229G->AADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseKawasakiNot Available1229G->CADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseMunichNot Available1231A->GADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseGeorgiaNot Available1284C->AADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseSumareNot Available1292T->GADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseTelti/KobeNot Available1318C->TADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseSantiago de Cuba, MoriokaNot Available1339G->AADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseHarimaNot Available1358T->AADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseFiguera da FozNot Available1366G->CADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseAmiensNot Available1367A>TADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseBangkok NoiNot Available1376G->T, 1502T->GADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseFukayaNot Available1462G->AADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseCampinasNot Available1463G->TADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseBuenos AiresNot Available1465C>TADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseArakawaNot Available1466C->TADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseBrightonNot Available1488_1490delGAAADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseKozukataNot Available159G->CADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseAmsterdamNot Available180_182delTCTADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseNo nameNot Available202G->A, 376A->G, 1264C>GADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseSwanseaNot Available224T->CADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseUrayasuNot Available281_283delAGAADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseVancouverNot Available317C->G544C->T592C->TADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseMt SinaiNot Available376A->G, 1159C->TADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenasePlymouthNot Available488G->AADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseVolendamNot Available514C->TADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseShinshuNot Available527A->GADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseChikugoNot Available535A->TADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseTsukuiNot Available561_563delCTCADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenasePedoplis-CkaroNot Available573C>GADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseSantiagoNot Available593G->CADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseMinnesota, Marion, Gastonia, LeJeuneNot Available637G->TADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseCincinnatiNot Available637G->T, 1037A->TADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseHarilaouNot Available648T->GADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseNorth DallasNot Available683_685delACAADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseAsahikawaNot Available695G->AADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseDurhamNot Available713A->GADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseStonybrookNot Available724_729delGGCACTADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseWayneNot Available769C->GADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseAveiroNot Available806G->AADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseCleveland CorumNot Available820G->AADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseLilleNot Available821A>TADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseBangkokNot Available825G>CADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseSugaoNot Available826C->TADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseLa JollaNot Available832T->CADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseWexhamNot Available833C->TADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenasePiotrkowNot Available851T>CADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseWest VirginiaNot Available910G->TADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseOmiyaNot Available921G->CADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseNaraNot Available953_976delCCACCAAAGGGTACCTGGAC GACCADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseManhattanNot Available962G->AADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseRehevotNot Available964T->CADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseHoniaraNot Available99A->G / 1360C->TADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseTokyo, FukushimaNot Available1246G->AADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseChathamNot Available1003G->AADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseFushanNot Available1004C->AADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenasePartenopeNot Available1052G->TADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseIerapetraNot Available1057C->TADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseAnadiaNot Available1193A->GADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseAbenoNot Available1220A->CADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseSurabayaNot Available1291G->AADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenasePawneeNot Available1316G->CADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseS. AntiocoNot Available1342A->GADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseCassanoNot Available1347G->CADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseHermoupolisNot Available1347G->C / 1360C->TADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseUnion,Maewo, Chinese-2, KaloNot Available1360C->TADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseAndalusNot Available1361G->AADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseCosenzaNot Available1376G->CADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseCanton, Taiwan- Hakka, Gifu-like, Agrigento-likeNot Available1376G->TADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseFloresNot Available1387C->AADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseKaiping, Anant, Dhon, Sapporo-like, WoseraNot Available1388G->AADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseKamogawaNot Available169C->TADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseCostanzoNot Available179T>CADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseAmazoniaNot Available185C->AADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseSongklanagarindNot Available196T->AADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseHechiNot Available202G->A / 871G->AADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseNamouruNot Available208T->CADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseBao LocNot Available352T>CADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseCrispimNot Available375G->T, 379G->T383T->C384C>TADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseAcrokorinthosNot Available376A->G / 463C->GADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseSanta MariaNot Available376A->G / 542A->TADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseAnanindeuaNot Available376A->G / 871G->AADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseVanua LavaNot Available383T->CADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseValladolidNot Available406C->TADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseBelemNot Available409C->TADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseLiuzhouNot Available442G->AADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseShenzenNot Available473G>AADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseTaipei “Chinese- 3”Not Available493A->GADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseToledoNot Available496C>TADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseNaoneNot Available497G->AADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseNankangNot Available517T->CADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseMiaoliNot Available519C->GADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseMediterranean, Dallas, Panama‚ Sassari, Cagliari, BirminghamNot Available563C->TADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseCoimbra ShundeNot Available592C->TADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseNilgiriNot Available593G>AADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseRadlowoNot Available679C->TADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseRoubaixNot Available811G>CADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseHaikouNot Available835A->GADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseChinese-1Not Available835A->TADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseMizushimaNot Available848A>GADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseOsakaNot Available853C->TADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseViangchan, JammuNot Available871G->AADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseSeoulNot Available916G->AADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseLudhianaNot Available929G->AADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseFarroupilhaNot Available977C->AADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseChinese-5Not Available1024C->TADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseRignanoNot Available130G>AADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseOrissaNot Available131C->GADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseG6PDNiceNot Available1380G>CADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseKamiube, KeelungNot Available1387C->TADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseNeapolisNot Available1400C->GADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseAuresNot Available143T->CADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseSplitNot Available1442C->GADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseKambosNot Available148C->TADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenasePalestrinaNot Available170G>AADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseMetapontoNot Available172G->AADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseMusashinoNot Available185C->TADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseAsahiNot Available202G->AADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseA- (202), Ferrara INot Available202G->A / 376A->GADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseMurcia OristanoNot Available209A->GADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseUbe KonanNot Available241C->TADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseLagosantoNot Available242G->AADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseGuangzhouNot Available274C->TADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseHammersmithNot Available323T->AADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseSinnaiNot Available34G->TADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseA- (680)Not Available376A->G / 680G->TADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseA- (968), Betica,Selma, GuantanamoNot Available376A->G / 968T->CADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseSalerno PyrgosNot Available383T>GADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseQuing YanNot Available392G->TADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseLagesNot Available40G->AADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseIleshaNot Available466G->AADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseMahidolNot Available487G->AADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseMalagaNot Available542A->TADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseSibariNot Available634A->GADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseMexico CityNot Available680G->AADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseNanningNot Available703C->TADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseSeattle, Lodi, Modena, Ferrara II, Athens-likeNot Available844G->CADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseBajo MaumereNot Available844G->TADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseMontalbanoNot Available854G->AADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseKalyan-Kerala, Jamnaga, RohiniNot Available949G->AADR InferredIncreased risk of hematological effects.Details
Glucose-6-phosphate 1-dehydrogenaseGaoheNot Available95A->GADR InferredIncreased risk of hematological effects.Details

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirChloroquine may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbametapirThe serum concentration of Chloroquine can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Chloroquine can be increased when combined with Abatacept.
AbirateroneThe metabolism of Chloroquine can be decreased when combined with Abiraterone.
AcalabrutinibThe metabolism of Chloroquine can be decreased when combined with Acalabrutinib.
Food Interactions
  • Take with food. Food reduces irritation and increases bioavailability.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Chloroquine hydrochlorideNT0J0815S53545-67-3PCFGECQRSMVKCC-UHFFFAOYSA-N
Chloroquine phosphate7FY24HE2G350-63-5AEUAEICGCMSYCQ-UHFFFAOYSA-N
Chloroquine sulfateOE48649K6N132-73-0OJPWHUOVKVKBQB-UHFFFAOYSA-N
Product Images
International/Other Brands
Artrichin / Bemaphate / Capquin / Malarex (Actavis) / Nivaquine B (Sanofi) / Resoquine / Reumachlor / Sanoquin
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AralenTablet, film coated500 mg/1OralSanofi Aventis1972-12-142013-02-28US flag
AralenTablet250 mgOralSanofi Synthelabo1951-12-312005-08-01Canada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
ChloroquineTablet250 mg/1OralHikma Pharmaceuticals USA Inc.1975-07-092015-10-31US flag
ChloroquineTablet, coated500 mg/1OralGolden State Medical Supply1999-09-172017-01-02US flag
ChloroquineTablet250 mg/1OralPhysicians Total Care, Inc.1975-07-092012-06-30US flag
ChloroquineTablet, coated500 mg/1OralPD-Rx Pharmaceuticals, Inc.1999-09-172019-06-17US flag
ChloroquineTablet250 mg/1OralGolden State Medical Supply1975-07-092017-01-02US flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
CHLOROQUINE TABLETS 250 mgTablet, film coated250 mgOralBEACONS PHARMACEUTICALS PTE. LTD.1988-05-26Not applicableSingapore flag

Categories

ATC Codes
P01BB52 — Chloroquine and proguanilP01BA01 — Chloroquine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as 4-aminoquinolines. These are organic compounds containing an amino group attached to the 4-position of a quinoline ring system.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Quinolines and derivatives
Sub Class
Aminoquinolines and derivatives
Direct Parent
4-aminoquinolines
Alternative Parents
Chloroquinolines / Secondary alkylarylamines / Aminopyridines and derivatives / Benzenoids / Aryl chlorides / Heteroaromatic compounds / Trialkylamines / Azacyclic compounds / Organopnictogen compounds / Organochlorides
show 1 more
Substituents
4-aminoquinoline / Amine / Aminopyridine / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle / Benzenoid / Chloroquinoline / Haloquinoline
show 12 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
tertiary amino compound, organochlorine compound, secondary amino compound, aminoquinoline (CHEBI:3638)
Affected organisms
  • Plasmodium
  • SARS-CoV-2

Chemical Identifiers

UNII
886U3H6UFF
CAS number
54-05-7
InChI Key
WHTVZRBIWZFKQO-UHFFFAOYSA-N
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)
IUPAC Name
7-chloro-N-[5-(diethylamino)pentan-2-yl]quinolin-4-amine
SMILES
CCN(CC)CCCC(C)NC1=CC=NC2=CC(Cl)=CC=C12

References

Synthesis Reference

Andersag, H., Breitner, S.and Jung, H.; U S . Patent 2,233,970; March 4,1941; assigned to Winthrop Chemical Company, Inc.

US2233970
General References
  1. Li C, Zhu X, Ji X, Quanquin N, Deng YQ, Tian M, Aliyari R, Zuo X, Yuan L, Afridi SK, Li XF, Jung JU, Nielsen-Saines K, Qin FX, Qin CF, Xu Z, Cheng G: Chloroquine, a FDA-approved Drug, Prevents Zika Virus Infection and its Associated Congenital Microcephaly in Mice. EBioMedicine. 2017 Oct;24:189-194. doi: 10.1016/j.ebiom.2017.09.034. Epub 2017 Sep 28. [Article]
  2. Shiryaev SA, Mesci P, Pinto A, Fernandes I, Sheets N, Shresta S, Farhy C, Huang CT, Strongin AY, Muotri AR, Terskikh AV: Repurposing of the anti-malaria drug chloroquine for Zika Virus treatment and prophylaxis. Sci Rep. 2017 Nov 17;7(1):15771. doi: 10.1038/s41598-017-15467-6. [Article]
  3. Gao J, Tian Z, Yang X: Breakthrough: Chloroquine phosphate has shown apparent efficacy in treatment of COVID-19 associated pneumonia in clinical studies. Biosci Trends. 2020 Feb 19. doi: 10.5582/bst.2020.01047. [Article]
  4. Authors unspecified: Chloroquine . [Article]
  5. Kim KA, Park JY, Lee JS, Lim S: Cytochrome P450 2C8 and CYP3A4/5 are involved in chloroquine metabolism in human liver microsomes. Arch Pharm Res. 2003 Aug;26(8):631-7. [Article]
  6. Kaewkhao K, Chotivanich K, Winterberg M, Day NP, Tarning J, Blessborn D: High sensitivity methods to quantify chloroquine and its metabolite in human blood samples using LC-MS/MS. Bioanalysis. 2019 Mar;11(5):333-347. doi: 10.4155/bio-2018-0202. Epub 2019 Mar 15. [Article]
  7. Projean D, Baune B, Farinotti R, Flinois JP, Beaune P, Taburet AM, Ducharme J: In vitro metabolism of chloroquine: identification of CYP2C8, CYP3A4, and CYP2D6 as the main isoforms catalyzing N-desethylchloroquine formation. Drug Metab Dispos. 2003 Jun;31(6):748-54. [Article]
  8. Ofori-Adjei D, Ericsson O, Lindstrom B, Sjoqvist F: Protein binding of chloroquine enantiomers and desethylchloroquine. Br J Clin Pharmacol. 1986 Sep;22(3):356-8. doi: 10.1111/j.1365-2125.1986.tb02900.x. [Article]
  9. Walker O, Birkett DJ, Alvan G, Gustafsson LL, Sjoqvist F: Characterization of chloroquine plasma protein binding in man. Br J Clin Pharmacol. 1983 Mar;15(3):375-7. doi: 10.1111/j.1365-2125.1983.tb01513.x. [Article]
  10. Ducharme J, Farinotti R: Clinical pharmacokinetics and metabolism of chloroquine. Focus on recent advancements. Clin Pharmacokinet. 1996 Oct;31(4):257-74. doi: 10.2165/00003088-199631040-00003. [Article]
  11. Coronado LM, Nadovich CT, Spadafora C: Malarial hemozoin: from target to tool. Biochim Biophys Acta. 2014 Jun;1840(6):2032-41. doi: 10.1016/j.bbagen.2014.02.009. Epub 2014 Feb 17. [Article]
  12. Colson P, Rolain JM, Raoult D: Chloroquine for the 2019 novel coronavirus SARS-CoV-2. Int J Antimicrob Agents. 2020 Feb 15:105923. doi: 10.1016/j.ijantimicag.2020.105923. [Article]
  13. Wang M, Cao R, Zhang L, Yang X, Liu J, Xu M, Shi Z, Hu Z, Zhong W, Xiao G: Remdesivir and chloroquine effectively inhibit the recently emerged novel coronavirus (2019-nCoV) in vitro. Cell Res. 2020 Mar;30(3):269-271. doi: 10.1038/s41422-020-0282-0. Epub 2020 Feb 4. [Article]
  14. Vincent MJ, Bergeron E, Benjannet S, Erickson BR, Rollin PE, Ksiazek TG, Seidah NG, Nichol ST: Chloroquine is a potent inhibitor of SARS coronavirus infection and spread. Virol J. 2005 Aug 22;2:69. doi: 10.1186/1743-422X-2-69. [Article]
  15. Chou AC, Fitch CD: Heme polymerase: modulation by chloroquine treatment of a rodent malaria. Life Sci. 1992;51(26):2073-8. doi: 10.1016/0024-3205(92)90158-l. [Article]
  16. Slater AF, Cerami A: Inhibition by chloroquine of a novel haem polymerase enzyme activity in malaria trophozoites. Nature. 1992 Jan 9;355(6356):167-9. doi: 10.1038/355167a0. [Article]
  17. Vandekerckhove S, D'hooghe M: Quinoline-based antimalarial hybrid compounds. Bioorg Med Chem. 2015 Aug 15;23(16):5098-119. doi: 10.1016/j.bmc.2014.12.018. Epub 2014 Dec 19. [Article]
  18. Plantone D, Koudriavtseva T: Current and Future Use of Chloroquine and Hydroxychloroquine in Infectious, Immune, Neoplastic, and Neurological Diseases: A Mini-Review. Clin Drug Investig. 2018 Aug;38(8):653-671. doi: 10.1007/s40261-018-0656-y. [Article]
  19. FDA Approved Drug Products: Chloroquine Phosphate Oral Tablets [Link]
  20. FDA Approved Drug Products: Aralen Chloroquine Oral Tablets (Discontinued) [Link]
  21. FDA: Emergency use Authorization for Hydroxychloroquine and Chloroquine Revoked [Link]
Human Metabolome Database
HMDB0014746
KEGG Drug
D02366
KEGG Compound
C07625
PubChem Compound
2719
PubChem Substance
46506925
ChemSpider
2618
BindingDB
22985
RxNav
2393
ChEBI
3638
ChEMBL
CHEMBL76
Therapeutic Targets Database
DAP001357
PharmGKB
PA448948
PDBe Ligand
CLQ
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Chloroquine
FDA label
Download (153 KB)
MSDS
Download (74.9 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Pharmacoeconomics

Manufacturers
  • Sanofi aventis us llc
  • Impax laboratories inc
  • Ipca laboratories ltd
  • Md pharmaceutical inc
  • Purepac pharmaceutical co
  • Teva pharmaceuticals usa inc
  • Watson laboratories inc
  • West ward pharmaceutical corp
Packagers
  • A-S Medication Solutions LLC
  • Bayer Healthcare
  • Consolidated Midland Corp.
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • Gallipot
  • Global Pharmaceuticals
  • Impax Laboratories Inc.
  • Nucare Pharmaceuticals Inc.
  • PD-Rx Pharmaceuticals Inc.
  • Physicians Total Care Inc.
  • Sanofi-Aventis Inc.
  • West-Ward Pharmaceuticals
Dosage Forms
FormRouteStrength
TabletOral250.000 mg
Tablet, film coatedOral500 mg/1
SolutionOral0.666 g
TabletOral250 mg/1
Tablet, coatedOral500 mg/1
TabletOral
TabletOral500 mg/1
Tablet, film coatedOral250 mg/1
Tablet, coatedOral
Injection, solutionIntravenous250 mg/5ml
TabletOral150.000 mg
Injection, solutionIntravenous40 mg/1ml
Capsule250 mg
TabletOral250 mg
Tablet, film coatedOral250 mg
SolutionOral40 mg/1ml
Syrup50 mg/5mL
Tablet, coatedOral100 mg
Tablet, coatedOral250 mg
Prices
Unit descriptionCostUnit
Aralen 500 mg tablet7.85USD tablet
Aralen phosphate 500 mg tablet7.78USD tablet
Chloroquine ph 500 mg tablet5.64USD tablet
Chloroquine Phosphate 500 mg tablet5.42USD tablet
Chloroquine phosphate powdr4.29USD g
Plaquenil 200 mg tablet3.14USD tablet
Chloroquine Phosphate 250 mg tablet2.57USD tablet
Chloroquine ph 250 mg tablet2.49USD tablet
Novo-Chloroquine 250 mg Tablet0.35USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)87-89.5ChemSpider
logP4.63HANSCH,C ET AL. (1995)
pKa10.1SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.0175 mg/mLALOGPS
logP5.28ALOGPS
logP3.93Chemaxon
logS-4.3ALOGPS
pKa (Strongest Basic)10.32Chemaxon
Physiological Charge2Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area28.16 Å2Chemaxon
Rotatable Bond Count8Chemaxon
Refractivity96.42 m3·mol-1Chemaxon
Polarizability37.29 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9939
Blood Brain Barrier+0.7421
Caco-2 permeable+0.5804
P-glycoprotein substrateSubstrate0.8
P-glycoprotein inhibitor IInhibitor0.622
P-glycoprotein inhibitor IIInhibitor0.7773
Renal organic cation transporterInhibitor0.6046
CYP450 2C9 substrateNon-substrate0.8422
CYP450 2D6 substrateSubstrate0.8804
CYP450 3A4 substrateSubstrate0.6009
CYP450 1A2 substrateNon-inhibitor0.8586
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9218
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8308
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5496
Ames testAMES toxic0.9106
CarcinogenicityNon-carcinogens0.8374
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.9547 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6959
hERG inhibition (predictor II)Inhibitor0.8293
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (8.47 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0pbi-9242000000-6cd79ce1c8a9ada4550d
GC-MS Spectrum - CI-BGC-MSsplash10-00di-0009000000-d54119d64cfc341cee7d
Mass Spectrum (Electron Ionization)MSsplash10-000i-9320000000-2663c398ede2e502ca34
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0039000000-b8e27c4b7ee82554febf
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9014000000-41004bc1106976d93630
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9003000000-6a2427c77158670aa876
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00dj-1279000000-3f218533051b20a20adf
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0059-4900000000-6b3aeedfe5fcbe681065
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0zi9-4791000000-80f2f07d067969922d2b
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-178.501672
predicted
DarkChem Lite v0.1.0
[M-H]-178.12596
predicted
DeepCCS 1.0 (2019)
[M+H]+178.855072
predicted
DarkChem Lite v0.1.0
[M+H]+180.48396
predicted
DeepCCS 1.0 (2019)
[M+Na]+178.697872
predicted
DarkChem Lite v0.1.0
[M+Na]+186.57709
predicted
DeepCCS 1.0 (2019)

Targets

Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Glutathione transferase activity
Specific Function
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
Gene Name
GSTA2
Uniprot ID
P09210
Uniprot Name
Glutathione S-transferase A2
Molecular Weight
25663.675 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
  2. Mukanganyama S, Masimirembwa CM, Naik YS, Hasler JA: Phenotyping of the glutathione S-transferase M1 polymorphism in Zimbabweans and the effects of chloroquine on blood glutathione S-transferases M1 and A. Clin Chim Acta. 1997 Sep 30;265(2):145-55. doi: 10.1016/s0009-8981(97)00104-6. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Tumor necrosis factor receptor binding
Specific Function
Cytokine that binds to TNFRSF1A/TNFR1 and TNFRSF1B/TNFBR. It is mainly secreted by macrophages and can induce cell death of certain tumor cell lines. It is potent pyrogen causing fever by direct ac...
Gene Name
TNF
Uniprot ID
P01375
Uniprot Name
Tumor necrosis factor
Molecular Weight
25644.15 Da
References
  1. Jang CH, Choi JH, Byun MS, Jue DM: Chloroquine inhibits production of TNF-alpha, IL-1beta and IL-6 from lipopolysaccharide-stimulated human monocytes/macrophages by different modes. Rheumatology (Oxford). 2006 Jun;45(6):703-10. Epub 2006 Jan 17. [Article]
  2. Rachmilewitz D, Karmeli F, Shteingart S, Lee J, Takabayashi K, Raz E: Immunostimulatory oligonucleotides inhibit colonic proinflammatory cytokine production in ulcerative colitis. Inflamm Bowel Dis. 2006 May;12(5):339-45. [Article]
  3. Wozniacka A, Lesiak A, Narbutt J, McCauliffe DP, Sysa-Jedrzejowska A: Chloroquine treatment influences proinflammatory cytokine levels in systemic lupus erythematosus patients. Lupus. 2006;15(5):268-75. [Article]
  4. Lim EJ, Lee SH, Lee JG, Chin BR, Bae YS, Kim JR, Lee CH, Baek SH: Activation of toll-like receptor-9 induces matrix metalloproteinase-9 expression through Akt and tumor necrosis factor-alpha signaling. FEBS Lett. 2006 Aug 7;580(18):4533-8. Epub 2006 Jul 17. [Article]
  5. Dias-Melicio LA, Calvi SA, Bordon AP, Golim MA, Peracoli MT, Soares AM: Chloroquine is therapeutic in murine experimental model of paracoccidioidomycosis. FEMS Immunol Med Microbiol. 2007 Jun;50(1):133-43. Epub 2007 Apr 23. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Transmembrane signaling receptor activity
Specific Function
Key component of innate and adaptive immunity. TLRs (Toll-like receptors) control host immune response against pathogens through recognition of molecular patterns specific to microorganisms. TLR9 i...
Gene Name
TLR9
Uniprot ID
Q9NR96
Uniprot Name
Toll-like receptor 9
Molecular Weight
115858.665 Da
References
  1. Trevani AS, Chorny A, Salamone G, Vermeulen M, Gamberale R, Schettini J, Raiden S, Geffner J: Bacterial DNA activates human neutrophils by a CpG-independent pathway. Eur J Immunol. 2003 Nov;33(11):3164-74. [Article]
  2. Rutz M, Metzger J, Gellert T, Luppa P, Lipford GB, Wagner H, Bauer S: Toll-like receptor 9 binds single-stranded CpG-DNA in a sequence- and pH-dependent manner. Eur J Immunol. 2004 Sep;34(9):2541-50. [Article]
  3. Lenert P: Inhibitory oligodeoxynucleotides - therapeutic promise for systemic autoimmune diseases? Clin Exp Immunol. 2005 Apr;140(1):1-10. [Article]
  4. Huang LY, Ishii KJ, Akira S, Aliberti J, Golding B: Th1-like cytokine induction by heat-killed Brucella abortus is dependent on triggering of TLR9. J Immunol. 2005 Sep 15;175(6):3964-70. [Article]
  5. Merrell MA, Ilvesaro JM, Lehtonen N, Sorsa T, Gehrs B, Rosenthal E, Chen D, Shackley B, Harris KW, Selander KS: Toll-like receptor 9 agonists promote cellular invasion by increasing matrix metalloproteinase activity. Mol Cancer Res. 2006 Jul;4(7):437-47. [Article]
Kind
Protein
Organism
Plasmodium falciparum
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Glutathione transferase activity
Specific Function
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. May also function as a storage protein or ligandin for parasitotoxic ferriprotoporphyrin I...
Gene Name
GST
Uniprot ID
Q8ILQ7
Uniprot Name
Glutathione S-transferase
Molecular Weight
24788.9 Da
References
  1. Hiller N, Fritz-Wolf K, Deponte M, Wende W, Zimmermann H, Becker K: Plasmodium falciparum glutathione S-transferase--structural and mechanistic studies on ligand binding and enzyme inhibition. Protein Sci. 2006 Feb;15(2):281-9. Epub 2005 Dec 29. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Transcription factor binding
Specific Function
Multifunctional redox sensitive protein with various roles in different cellular compartments. In the nucleus is one of the major chromatin-associated non-histone proteins and acts as a DNA chapero...
Gene Name
HMGB1
Uniprot ID
P09429
Uniprot Name
High mobility group protein B1
Molecular Weight
24893.58 Da
References
  1. Yang M, Cao L, Xie M, Yu Y, Kang R, Yang L, Zhao M, Tang D: Chloroquine inhibits HMGB1 inflammatory signaling and protects mice from lethal sepsis. Biochem Pharmacol. 2013 Aug 1;86(3):410-8. doi: 10.1016/j.bcp.2013.05.013. Epub 2013 May 22. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Protein homodimerization activity
Specific Function
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
Gene Name
GSTM1
Uniprot ID
P09488
Uniprot Name
Glutathione S-transferase Mu 1
Molecular Weight
25711.555 Da
References
  1. Mukanganyama S, Masimirembwa CM, Naik YS, Hasler JA: Phenotyping of the glutathione S-transferase M1 polymorphism in Zimbabweans and the effects of chloroquine on blood glutathione S-transferases M1 and A. Clin Chim Acta. 1997 Sep 30;265(2):145-55. doi: 10.1016/s0009-8981(97)00104-6. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Modulator
General Function
Zinc ion binding
Specific Function
Carboxypeptidase which converts angiotensin I to angiotensin 1-9, a peptide of unknown function, and angiotensin II to angiotensin 1-7, a vasodilator. Also able to hydrolyze apelin-13 and dynorphin...
Gene Name
ACE2
Uniprot ID
Q9BYF1
Uniprot Name
Angiotensin-converting enzyme 2
Molecular Weight
92462.4 Da
References
  1. Vincent MJ, Bergeron E, Benjannet S, Erickson BR, Rollin PE, Ksiazek TG, Seidah NG, Nichol ST: Chloroquine is a potent inhibitor of SARS coronavirus infection and spread. Virol J. 2005 Aug 22;2:69. doi: 10.1186/1743-422X-2-69. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Kim KA, Park JY, Lee JS, Lim S: Cytochrome P450 2C8 and CYP3A4/5 are involved in chloroquine metabolism in human liver microsomes. Arch Pharm Res. 2003 Aug;26(8):631-7. [Article]
  2. Li XQ, Bjorkman A, Andersson TB, Gustafsson LL, Masimirembwa CM: Identification of human cytochrome P(450)s that metabolise anti-parasitic drugs and predictions of in vivo drug hepatic clearance from in vitro data. Eur J Clin Pharmacol. 2003 Sep;59(5-6):429-42. Epub 2003 Aug 12. [Article]
  3. Projean D, Baune B, Farinotti R, Flinois JP, Beaune P, Taburet AM, Ducharme J: In vitro metabolism of chloroquine: identification of CYP2C8, CYP3A4, and CYP2D6 as the main isoforms catalyzing N-desethylchloroquine formation. Drug Metab Dispos. 2003 Jun;31(6):748-54. [Article]
  4. Kaewkhao K, Chotivanich K, Winterberg M, Day NP, Tarning J, Blessborn D: High sensitivity methods to quantify chloroquine and its metabolite in human blood samples using LC-MS/MS. Bioanalysis. 2019 Mar;11(5):333-347. doi: 10.4155/bio-2018-0202. Epub 2019 Mar 15. [Article]
Details
2. Cytochrome P450 3A4
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Kim KA, Park JY, Lee JS, Lim S: Cytochrome P450 2C8 and CYP3A4/5 are involved in chloroquine metabolism in human liver microsomes. Arch Pharm Res. 2003 Aug;26(8):631-7. [Article]
  2. Li XQ, Bjorkman A, Andersson TB, Gustafsson LL, Masimirembwa CM: Identification of human cytochrome P(450)s that metabolise anti-parasitic drugs and predictions of in vivo drug hepatic clearance from in vitro data. Eur J Clin Pharmacol. 2003 Sep;59(5-6):429-42. Epub 2003 Aug 12. [Article]
  3. Projean D, Baune B, Farinotti R, Flinois JP, Beaune P, Taburet AM, Ducharme J: In vitro metabolism of chloroquine: identification of CYP2C8, CYP3A4, and CYP2D6 as the main isoforms catalyzing N-desethylchloroquine formation. Drug Metab Dispos. 2003 Jun;31(6):748-54. [Article]
  4. Kaewkhao K, Chotivanich K, Winterberg M, Day NP, Tarning J, Blessborn D: High sensitivity methods to quantify chloroquine and its metabolite in human blood samples using LC-MS/MS. Bioanalysis. 2019 Mar;11(5):333-347. doi: 10.4155/bio-2018-0202. Epub 2019 Mar 15. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Kim KA, Park JY, Lee JS, Lim S: Cytochrome P450 2C8 and CYP3A4/5 are involved in chloroquine metabolism in human liver microsomes. Arch Pharm Res. 2003 Aug;26(8):631-7. [Article]
  2. Lee JY, Vinayagamoorthy N, Han K, Kwok SK, Ju JH, Park KS, Jung SH, Park SW, Chung YJ, Park SH: Association of Polymorphisms of Cytochrome P450 2D6 With Blood Hydroxychloroquine Levels in Patients With Systemic Lupus Erythematosus. Arthritis Rheumatol. 2016 Jan;68(1):184-90. doi: 10.1002/art.39402. [Article]
  3. Kaewkhao K, Chotivanich K, Winterberg M, Day NP, Tarning J, Blessborn D: High sensitivity methods to quantify chloroquine and its metabolite in human blood samples using LC-MS/MS. Bioanalysis. 2019 Mar;11(5):333-347. doi: 10.4155/bio-2018-0202. Epub 2019 Mar 15. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Projean D, Baune B, Farinotti R, Flinois JP, Beaune P, Taburet AM, Ducharme J: In vitro metabolism of chloroquine: identification of CYP2C8, CYP3A4, and CYP2D6 as the main isoforms catalyzing N-desethylchloroquine formation. Drug Metab Dispos. 2003 Jun;31(6):748-54. [Article]
  2. Adedoyin A, Frye RF, Mauro K, Branch RA: Chloroquine modulation of specific metabolizing enzymes activities: investigation with selective five drug cocktail. Br J Clin Pharmacol. 1998 Sep;46(3):215-9. [Article]
  3. Simooya OO, Sijumbil G, Lennard MS, Tucker GT: Halofantrine and chloroquine inhibit CYP2D6 activity in healthy Zambians. Br J Clin Pharmacol. 1998 Mar;45(3):315-7. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d 24-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A1
Uniprot ID
P04798
Uniprot Name
Cytochrome P450 1A1
Molecular Weight
58164.815 Da
References
  1. Projean D, Baune B, Farinotti R, Flinois JP, Beaune P, Taburet AM, Ducharme J: In vitro metabolism of chloroquine: identification of CYP2C8, CYP3A4, and CYP2D6 as the main isoforms catalyzing N-desethylchloroquine formation. Drug Metab Dispos. 2003 Jun;31(6):748-54. [Article]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Ofori-Adjei D, Ericsson O, Lindstrom B, Sjoqvist F: Protein binding of chloroquine enantiomers and desethylchloroquine. Br J Clin Pharmacol. 1986 Sep;22(3):356-8. doi: 10.1111/j.1365-2125.1986.tb02900.x. [Article]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Not Available
Specific Function
Functions as transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in...

Components:
References
  1. Ofori-Adjei D, Ericsson O, Lindstrom B, Sjoqvist F: Protein binding of chloroquine enantiomers and desethylchloroquine. Br J Clin Pharmacol. 1986 Sep;22(3):356-8. doi: 10.1111/j.1365-2125.1986.tb02900.x. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Crowe A, Ilett KF, Karunajeewa HA, Batty KT, Davis TM: Role of P glycoprotein in absorption of novel antimalarial drugs. Antimicrob Agents Chemother. 2006 Oct;50(10):3504-6. doi: 10.1128/AAC.00708-06. Epub 2006 Aug 17. [Article]

Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:54