Identification
NameHydroxychloroquine
Accession NumberDB01611
TypeSmall Molecule
GroupsApproved
Description

A chemotherapeutic agent that acts against erythrocytic forms of malarial parasites.

Structure
Thumb
Synonyms
(+-)-Hydroxychloroquine
(±)-hydroxychloroquine
2-((4-((7-chloro-4-Quinolyl)amino)pentyl)ethylamino)ethanol
2-(N-(4-(7-Chlor-4-chinolylamino)-4-methylbutyl)ethylamino)ethanol
7-chloro-4-(4-(Ethyl(2-hydroxyethyl)amino)-1-methylbutylamino)quinoline
7-chloro-4-(4-(N-Ethyl-N-beta-hydroxyethylamino)-1-methylbutylamino)quinoline
7-chloro-4-[4-(N-Ethyl-N-beta-hydroxyethylamino)-1-methylbutylamino]quinoline
7-chloro-4-[5-(N-Ethyl-N-2-hydroxyethylamino)-2-pentyl]aminoquinoline
Hidroxicloroquina
Hydroxychloroquinum
NSC4375
Oxichlorochine
Oxichloroquine
Polirreumin
External IDs Not Available
Product Ingredients
IngredientUNIICASInChI KeyDetails
Hydroxychloroquine sulfate8Q2869CNVH 747-36-4JCBIVZZPXRZKTI-UHFFFAOYNA-NDetails
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Hydroxychloroquine SulfateTablet200 mg/1OralAphena Pharma Solutions Tennessee, Inc.2014-12-12Not applicableUs
Hydroxychloroquine SulfateTablet200 mg/1OralAvera Mc Kennan Hospital2015-03-24Not applicableUs
Hydroxychloroquine SulfateTablet200 mg/1OralPrasco, Laboratories2014-12-12Not applicableUs
Mint-hydroxychloroquineTablet200 mgOralMint Pharmaceuticals Inc2014-06-10Not applicableCanada
Mylan-hydroxychloroquineTablet200 mgOralMylan Pharmaceuticals2004-05-21Not applicableCanada
Nu-hydroxyquineTablet200 mgOralNu Pharm IncNot applicableNot applicableCanada
PlaquenilTablet, film coated200 mg/1OralSanofi Aventis1955-04-18Not applicableUs
PlaquenilTablet200 mg/1OralCarilion Materials Management2013-06-28Not applicableUs
PlaquenilTablet200 mg/1OralAphena Pharma Solutions Tennessee, Inc.2013-06-28Not applicableUs
PlaquenilTablet200 mgOralSanofi Aventis1957-12-31Not applicableCanada
PlaquenilTablet200 mg/1OralConcordia Pharmaceuticals, Inc2013-06-28Not applicableUs
PlaquenilTablet200 mg/1OralCovis Pharmaceuticals, Inc.2013-06-282017-12-31Us
PlaquenilTablet200 mg/1OralAv Kare, Inc.2016-07-14Not applicableUs
PMS-hydroxychloroquineTablet200 mgOralPharmascience IncNot applicableNot applicableCanada
Pro-hydroxyquine - 200Tablet200 mgOralPro Doc Limitee2008-07-29Not applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-hydroxyquineTablet200 mgOralApotex Corporation2002-12-13Not applicableCanada
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralRebel Distributors2009-01-07Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralPhysicians Total Care, Inc.1996-07-09Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1EnteralMylan Institutional2016-03-28Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralDirectrx2014-01-01Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralRanbaxy Inc.2009-01-07Not applicableUs
Hydroxychloroquine SulfateTablet200 mg/1OralAv Kare, Inc.2012-02-292015-12-29Us
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralWest Ward Pharmaceutical2007-08-15Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralAidarex Pharmaceuticals LLC2009-01-07Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralAphena Pharma Solutions Tennessee, Inc.1995-11-30Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralAmerincan Health Packaging2008-08-05Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1Oralbryant ranch prepack2009-01-07Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralNorth Star Rx Llc2015-12-18Not applicableUs
Hydroxychloroquine SulfateTablet, coated200 mg/1OralWatson Pharmaceuticals1995-11-302016-03-05Us
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralAv Kare, Inc.2014-05-19Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralAphena Pharma Solutions Tennessee, Inc.2014-05-19Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralA S Medication Solutions2016-03-24Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralMc Kesson Packaging Services A Buisness Unit Of Mc Kesson Corporation2008-01-03Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralSandoz1995-11-30Not applicableUs
Hydroxychloroquine SulfateTablet200 mg/1OralAphena Pharma Solutions Tennessee, Inc.2012-02-29Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralA S Medication Solutions2009-01-07Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1EnteralMylan Pharmaceuticals1998-06-18Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralCardinal Health2008-08-05Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralCadila Pharnmaceuticals2008-01-03Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralMajor1995-11-30Not applicableUs
Hydroxychloroquine SulfateTablet200 mg/1OralRemedy Repack2011-04-132016-10-13Us
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralA S Medication Solutions2009-01-07Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralZydus Pharmaceuticals Usa, Inc.2008-01-03Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralCardinal Health1995-11-30Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralDispensing Solutions, Inc.2009-01-07Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralBlenheim Pharmacal, Inc.2013-12-20Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralOhm Laboratories, Inc.2009-01-07Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralActavis Pharma Company2016-03-24Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralA S Medication Solutions2009-01-07Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralGolden State Medical Supply2007-08-15Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralAvera Mc Kennan Hospital2015-08-31Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AxokineAstraZeneca
DolquineInmunosyn
HCQSMedigroup
PolirreuminTRB
QuensylSanofi
Brand mixturesNot Available
Categories
UNII4QWG6N8QKH
CAS number118-42-3
WeightAverage: 335.872
Monoisotopic: 335.176440176
Chemical FormulaC18H26ClN3O
InChI KeyXXSMGPRMXLTPCZ-UHFFFAOYSA-N
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)
IUPAC Name
2-({4-[(7-chloroquinolin-4-yl)amino]pentyl}(ethyl)amino)ethan-1-ol
SMILES
CCN(CCO)CCCC(C)NC1=C2C=CC(Cl)=CC2=NC=C1
Pharmacology
Indication

For the suppressive treatment and treatment of acute attacks of malaria due to Plasmodium vivax, P. malariae, P. ovale, and susceptible strains of P. falciparum. It is also indicated for the treatment of discoid and systemic lupus erythematosus, and rheumatoid arthritis.

Structured Indications
Pharmacodynamics

Hydroxychloroquine possesses antimalarial properties and also exerts a beneficial effect in lupus erythematosus (chronic discoid or systemic) and acute or chronic rheumatoid arthritis. The precise mechanism of action is not known.

Mechanism of action

Although the exact mechanism of action is unknown, it may be based on ability of hydroxychloroquine to bind to and alter DNA. Hydroxychloroquine has also has been found to be taken up into the acidic food vacuoles of the parasite in the erythrocyte. This increases the pH of the acid vesicles, interfering with vesicle functions and possibly inhibiting phospholipid metabolism. In suppressive treatment, hydroxychloroquine inhibits the erythrocytic stage of development of plasmodia. In acute attacks of malaria, it interrupts erythrocytic schizogony of the parasite. Its ability to concentrate in parasitized erythrocytes may account for their selective toxicity against the erythrocytic stages of plasmodial infection. As an antirheumatic, hydroxychloroquine is thought to act as a mild immunosuppressant, inhibiting the production of rheumatoid factor and acute phase reactants. It also accumulates in white blood cells, stabilizing lysosomal membranes and inhibiting the activity of many enzymes, including collagenase and the proteases that cause cartilage breakdown.

TargetKindPharmacological actionActionsOrganismUniProt ID
DNANucleotideyes
cross-linking/alkylation
Humannot applicabledetails
Toll-like receptor 7Proteinyes
antagonist
HumanQ9NYK1 details
Toll-like receptor 9Proteinyes
antagonist
HumanQ9NR96 details
Related Articles
Absorption

Very rapidly and completely absorbed following oral administration.

Volume of distributionNot Available
Protein binding

Approximately 45%.

Metabolism

Partially hepatic, to active de-ethylated metabolites.

Route of eliminationNot Available
Half life

Terminal elimination half-life In blood is approximately 50 days. In plasma it is approximately 32 days.

ClearanceNot Available
Toxicity

Symptoms of overdose include headache, drowsiness, visual disturbances, cardiovascular collapse, and convulsions, followed by sudden and early respiratory and cardiac arrest. The electrocardiogram may reveal atrial standstill, nodal rhythm, prolonged intraventricular conduction time, and progressive bradycardia leading to ventricular fibrillation and/or arrest.

Affected organisms
  • Plasmodium
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions
DrugInteractionDrug group
AcebutololThe metabolism of Acebutolol can be decreased when combined with Hydroxychloroquine.Approved
AcepromazineThe serum concentration of Acepromazine can be increased when it is combined with Hydroxychloroquine.Approved, Vet Approved
AceprometazineThe serum concentration of Aceprometazine can be increased when it is combined with Hydroxychloroquine.Approved
AcetyldigitoxinThe serum concentration of Acetyldigitoxin can be increased when it is combined with Hydroxychloroquine.Approved
AlbendazoleThe serum concentration of Albendazole can be decreased when it is combined with Hydroxychloroquine.Approved, Vet Approved
AlimemazineThe serum concentration of Alimemazine can be increased when it is combined with Hydroxychloroquine.Approved, Vet Approved
AlprenololThe metabolism of Alprenolol can be decreased when combined with Hydroxychloroquine.Approved, Withdrawn
ArotinololThe metabolism of Arotinolol can be decreased when combined with Hydroxychloroquine.Approved
ArtemetherThe risk or severity of adverse effects can be increased when Artemether is combined with Hydroxychloroquine.Approved
AtenololThe metabolism of Atenolol can be decreased when combined with Hydroxychloroquine.Approved
BefunololThe metabolism of Befunolol can be decreased when combined with Hydroxychloroquine.Experimental
BenzimidazoleThe serum concentration of Benzimidazole can be decreased when it is combined with Hydroxychloroquine.Experimental
BetaxololThe metabolism of Betaxolol can be decreased when combined with Hydroxychloroquine.Approved
BevantololThe metabolism of Bevantolol can be decreased when combined with Hydroxychloroquine.Approved
BisoprololThe metabolism of Bisoprolol can be decreased when combined with Hydroxychloroquine.Approved
BithionolThe serum concentration of Bithionol can be decreased when it is combined with Hydroxychloroquine.Withdrawn
BL-1020The serum concentration of BL-1020 can be increased when it is combined with Hydroxychloroquine.Investigational
BopindololThe metabolism of Bopindolol can be decreased when combined with Hydroxychloroquine.Approved
BufuralolThe metabolism of Bufuralol can be decreased when combined with Hydroxychloroquine.Experimental, Investigational
BupranololThe metabolism of Bupranolol can be decreased when combined with Hydroxychloroquine.Approved
CarteololThe metabolism of Carteolol can be decreased when combined with Hydroxychloroquine.Approved
CarvedilolThe metabolism of Carvedilol can be decreased when combined with Hydroxychloroquine.Approved, Investigational
CeliprololThe metabolism of Celiprolol can be decreased when combined with Hydroxychloroquine.Approved, Investigational
ChloroquineThe serum concentration of Chloroquine can be decreased when it is combined with Hydroxychloroquine.Approved, Vet Approved
ChlorpromazineThe serum concentration of Chlorpromazine can be increased when it is combined with Hydroxychloroquine.Approved, Vet Approved
DapsoneThe risk or severity of adverse effects can be increased when Hydroxychloroquine is combined with Dapsone.Approved, Investigational
DeslanosideThe serum concentration of Deslanoside can be increased when it is combined with Hydroxychloroquine.Approved
DiethylcarbamazineThe serum concentration of Diethylcarbamazine can be decreased when it is combined with Hydroxychloroquine.Approved, Vet Approved
DigitoxinThe serum concentration of Digitoxin can be increased when it is combined with Hydroxychloroquine.Approved
DigoxinThe serum concentration of Digoxin can be increased when it is combined with Hydroxychloroquine.Approved
EsmololThe metabolism of Esmolol can be decreased when combined with Hydroxychloroquine.Approved
FesoterodineThe serum concentration of the active metabolites of Fesoterodine can be increased when Fesoterodine is used in combination with Hydroxychloroquine.Approved
FlubendazoleThe serum concentration of Flubendazole can be decreased when it is combined with Hydroxychloroquine.Approved, Withdrawn
FluphenazineThe serum concentration of Fluphenazine can be increased when it is combined with Hydroxychloroquine.Approved
IndenololThe metabolism of Indenolol can be decreased when combined with Hydroxychloroquine.Withdrawn
IvermectinThe serum concentration of Ivermectin can be decreased when it is combined with Hydroxychloroquine.Approved, Vet Approved
LabetalolThe metabolism of Labetalol can be decreased when combined with Hydroxychloroquine.Approved
LevamisoleThe serum concentration of Levamisole can be decreased when it is combined with Hydroxychloroquine.Vet Approved, Withdrawn
LevobunololThe metabolism of Levobunolol can be decreased when combined with Hydroxychloroquine.Approved
LucanthoneThe serum concentration of Lucanthone can be decreased when it is combined with Hydroxychloroquine.Approved, Investigational
LumefantrineThe risk or severity of adverse effects can be increased when Hydroxychloroquine is combined with Lumefantrine.Approved
MebendazoleThe serum concentration of Mebendazole can be decreased when it is combined with Hydroxychloroquine.Approved, Vet Approved
MefloquineThe risk or severity of adverse effects can be increased when Hydroxychloroquine is combined with Mefloquine.Approved
MesoridazineThe serum concentration of Mesoridazine can be increased when it is combined with Hydroxychloroquine.Approved
MethotrimeprazineThe serum concentration of Methotrimeprazine can be increased when it is combined with Hydroxychloroquine.Approved
Methylene blueThe serum concentration of Methylene blue can be increased when it is combined with Hydroxychloroquine.Investigational
MetipranololThe metabolism of Metipranolol can be decreased when combined with Hydroxychloroquine.Approved
MetoprololThe serum concentration of Metoprolol can be increased when it is combined with Hydroxychloroquine.Approved, Investigational
MoricizineThe serum concentration of Moricizine can be increased when it is combined with Hydroxychloroquine.Approved, Withdrawn
NadololThe metabolism of Nadolol can be decreased when combined with Hydroxychloroquine.Approved
NiclosamideThe serum concentration of Niclosamide can be decreased when it is combined with Hydroxychloroquine.Approved, Vet Approved
OleandrinThe serum concentration of Anvirzel can be increased when it is combined with Hydroxychloroquine.Experimental
OuabainThe serum concentration of Ouabain can be increased when it is combined with Hydroxychloroquine.Approved
OxamniquineThe serum concentration of Oxamniquine can be decreased when it is combined with Hydroxychloroquine.Approved
OxibendazoleThe serum concentration of Oxibendazole can be decreased when it is combined with Hydroxychloroquine.Investigational, Vet Approved
OxprenololThe metabolism of Oxprenolol can be decreased when combined with Hydroxychloroquine.Approved
PenbutololThe metabolism of Penbutolol can be decreased when combined with Hydroxychloroquine.Approved, Investigational
PerphenazineThe serum concentration of Perphenazine can be increased when it is combined with Hydroxychloroquine.Approved
PindololThe metabolism of Pindolol can be decreased when combined with Hydroxychloroquine.Approved
PiperazineThe serum concentration of Piperazine can be decreased when it is combined with Hydroxychloroquine.Approved, Vet Approved
PractololThe metabolism of Practolol can be decreased when combined with Hydroxychloroquine.Approved
PraziquantelThe serum concentration of Praziquantel can be decreased when it is combined with Hydroxychloroquine.Approved, Vet Approved
ProchlorperazineThe serum concentration of Prochlorperazine can be increased when it is combined with Hydroxychloroquine.Approved, Vet Approved
PromazineThe serum concentration of Promazine can be increased when it is combined with Hydroxychloroquine.Approved, Vet Approved
PromethazineThe serum concentration of Promethazine can be increased when it is combined with Hydroxychloroquine.Approved
PropranololThe metabolism of Propranolol can be decreased when combined with Hydroxychloroquine.Approved, Investigational
PyrviniumThe serum concentration of Pyrvinium can be decreased when it is combined with Hydroxychloroquine.Approved
QuinacrineThe serum concentration of Quinacrine can be decreased when it is combined with Hydroxychloroquine.Approved
Sodium stibogluconateThe serum concentration of Sodium stibogluconate can be decreased when it is combined with Hydroxychloroquine.Approved, Investigational
SotalolThe metabolism of Sotalol can be decreased when combined with Hydroxychloroquine.Approved
SuraminThe serum concentration of Suramin can be decreased when it is combined with Hydroxychloroquine.Approved
ThiabendazoleThe serum concentration of Thiabendazole can be decreased when it is combined with Hydroxychloroquine.Approved, Vet Approved
ThiethylperazineThe serum concentration of Thiethylperazine can be increased when it is combined with Hydroxychloroquine.Withdrawn
ThioridazineThe serum concentration of Thioridazine can be increased when it is combined with Hydroxychloroquine.Withdrawn
TimololThe metabolism of Timolol can be decreased when combined with Hydroxychloroquine.Approved
TrifluoperazineThe serum concentration of Trifluoperazine can be increased when it is combined with Hydroxychloroquine.Approved
TriflupromazineThe serum concentration of Triflupromazine can be increased when it is combined with Hydroxychloroquine.Approved, Vet Approved
Food InteractionsNot Available
References
Synthesis Reference

U.S. Patent 2,546,658.

General ReferencesNot Available
External Links
ATC CodesP01BA02
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedSupportive CareLiver Cirrhosis / Muscle Cramps1
0CompletedTreatmentMelanoma (Skin)1
0CompletedTreatmentMyelomas1
0TerminatedTreatmentCarcinoma of the Prostate1
1Active Not RecruitingTreatmentAdult Solid Neoplasm1
1Active Not RecruitingTreatmentAdult Solid Neoplasm / Hormone-Resistant Prostate Cancer / Recurrent Melanoma / Recurrent Prostate Carcinoma / Recurrent Renal Cell Carcinoma / Stage IIIA Skin Melanoma / Stage IIIB Skin Melanoma / Stage IIIC Skin Melanoma / Stage IV Prostate Cancer / Stage IV Renal Cell Cancer / Stage IV Skin Melanoma1
1Active Not RecruitingTreatmentMelanoma1
1Active Not RecruitingTreatmentRecurrent Plasma Cell Myeloma / Refractory Plasma Cell Myeloma1
1Active Not RecruitingTreatmentUnspecified Adult Solid Tumor, Protocol Specific1
1CompletedTreatmentCystic Fibrosis (CF)1
1CompletedTreatmentImmunosuppression / Rheumatism1
1CompletedTreatmentLymphangioleiomyomatosis1
1CompletedTreatmentUnspecified Adult Solid Tumor, Protocol Specific1
1Not Yet RecruitingTreatmentAcute Myelogenous Leukaemia (AML)1
1Not Yet RecruitingTreatmentTumors, Solid1
1RecruitingTreatmentAdvanced Cancers1
1RecruitingTreatmentEstrogen Receptor Positive Breast Cancer1
1RecruitingTreatmentMalignant Solid Tumours1
1RecruitingTreatmentTumors, Solid1
1TerminatedTreatmentBone Metastases / Unspecified Adult Solid Tumor, Protocol Specific1
1TerminatedTreatmentNon-Small-Cell Lung Carcinoma (NSCLC)1
1TerminatedTreatmentRenal Cell Carcinoma (RCC)1
1Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections1
1, 2Active Not RecruitingTreatmentAdenocarcinomas / Colon Cancer / Metastasis / Rectal Cancers1
1, 2Active Not RecruitingTreatmentHistological Evidence of Metastatic Clear Cell Renal Cell Carcinoma / Metastatic Clear Cell Renal Cell Carcinoma / Of Discontinuing Sunitinib, Sorafenib or Pazopanib. Previous / That Has Been Previously Treated With 1-3 Prior Regimens. Phase 1 Only, Any Number of Prior Regimens / Therapy With Bevacizumab, IL2, or Interferon Are Permitted / With Evidence of Progressive Disease on or Within 6 Months1
1, 2CompletedDiagnosticSystemic Lupus Erythematosis1
1, 2CompletedTreatmentAcute HIV Infection1
1, 2Not Yet RecruitingTreatmentDiabetes Type Two1
1, 2Not Yet RecruitingTreatmentPlatinum-resistant Epithelial Ovarian Cancer1
1, 2RecruitingTreatmentAdvanced Adenocarcinoma / Metastatic Adenocarcinoma1
1, 2RecruitingTreatmentAdvanced BRAF Mutant Melanoma1
1, 2RecruitingTreatmentMetastatic Renal Cell Carcinoma1
1, 2RecruitingTreatmentMultiple Sclerosis (MS)1
1, 2TerminatedTreatmentCancer, Breast1
1, 2TerminatedTreatmentHepatitis C1
1, 2TerminatedTreatmentLung Cancers1
1, 2Unknown StatusTreatmentBrain and Central Nervous System Tumors1
1, 2Unknown StatusTreatmentMultiple Myeloma and Plasma Cell Neoplasm1
1, 2Unknown StatusTreatmentNon-Small-Cell Lung Carcinoma (NSCLC)1
1, 2Unknown StatusTreatmentPancreatic Cancers1
2Active Not RecruitingTreatmentCarcinoma of the Prostate1
2Active Not RecruitingTreatmentGlioblastomas1
2Active Not RecruitingTreatmentNon-Small-Cell Lung Carcinoma (NSCLC)1
2Active Not RecruitingTreatmentPancreatic Cancers2
2CompletedTreatmentAdvanced Non-Small Cell Lung Cancer / Non-Small-Cell Lung Carcinoma (NSCLC) / Recurrent Non-small Cell Lung Cancer1
2CompletedTreatmentCarcinoma of the Prostate1
2CompletedTreatmentColorectal Cancers1
2CompletedTreatmentLichen Planus, Oral1
2CompletedTreatmentOsteoarthritis of the Knees1
2Not Yet RecruitingPreventionSystemic Lupus Erythematosus Encephalitis1
2Not Yet RecruitingTreatmentHepatocellular Cancer1
2Not Yet RecruitingTreatmentSmall Cell Lung Cancer (SCLC)1
2RecruitingPreventionAutoantibody-Associated Heart Block / Congenital Heart Block / Neonatal Lupus1
2RecruitingPreventionHealthy Participants / Healthy Volunteers / Rheumatoid Arthritis (RA) Prevention / Rheumatoid Arthritis Prevention1
2RecruitingTreatmentAntiphospholipid Syndrome (APS)1
2RecruitingTreatmentBreast Cancer Stage IIB1
2RecruitingTreatmentChildren´s Interstitial Lung Disease / Diffuse Parenchymal Lung Diseases / Interstitial Lung Disease (ILD)1
2RecruitingTreatmentColorectal Cancers1
2RecruitingTreatmentDiabetes Mellitus Type 2 With Hyperglycemia1
2RecruitingTreatmentHydroxychloroquine / IgA Patients1
2RecruitingTreatmentMultiple Sclerosis, Primary Progressive1
2RecruitingTreatmentPancreatic Cancers1
2RecruitingTreatmentPorphyria Cutanea Tarda1
2TerminatedTreatmentArteriosclerosis / Cardiovascular Disease (CVD) / Kidney Failure,Chronic1
2TerminatedTreatmentB-Cell Chronic Lymphocytic Leukemia1
2TerminatedTreatmentCarcinoma of the Prostate1
2TerminatedTreatmentSarcomas1
2Unknown StatusPreventionFlu caused by Influenza1
2Unknown StatusTreatmentCancer, Breast1
2Unknown StatusTreatmentCrohn's Disease (CD)1
2Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections1
2Unknown StatusTreatmentLeukemias1
2WithdrawnTreatmentMiscarriages / Recurrent Pregnancy Losses1
3CompletedSupportive CareGraft Versus Host Disease (GVHD)1
3CompletedTreatmentAutoimmune Diseases / Dry Eyes / Sjogren's Syndrome1
3CompletedTreatmentCutaneous Lupus Erythematosus-Systemic Lupus Erythematosus1
3CompletedTreatmentGiant Cell Arteritis1
3CompletedTreatmentInsulin Resistance / Rheumatoid Arthritis1
3CompletedTreatmentPrimary Sjögren's Syndrome1
3CompletedTreatmentRheumatoid Arthritis4
3CompletedTreatmentSarcoidosis, Pulmonary1
3CompletedTreatmentSeronegative Spondyloarthropathies1
3CompletedTreatmentSynovitis of osteoarthritis1
3RecruitingTreatmentThrombocytopenias1
3TerminatedPreventionAntiphospholipid Syndrome1
4CompletedBasic SciencePre-Diabetes1
4CompletedTreatmentAlopecia Areata (AA)1
4CompletedTreatmentBorrelia Infection / Lyme Disease1
4CompletedTreatmentPrimary IgA Nephropathy1
4CompletedTreatmentRheumatoid Arthritis3
4Not Yet RecruitingTreatmentCoronary Artery Disease1
4Not Yet RecruitingTreatmentCutaneous Lupus / Juvenile SLE / Systemic Lupus Erythematosus (SLE)1
4Not Yet RecruitingTreatmentIndividuals Undergoing Cardiac and General Surgery1
4Not Yet RecruitingTreatmentInsufficient Response to Methotrexate / Rheumatoid Arthritis1
4RecruitingTreatmentAcute Coronary Syndromes (ACS) / Antirheumatic Agents / Cardiovascular Disease (CVD) / Hydroxychloroquine / Inflammatory processes / Myocardial Infarction (MI) / Unstable Angina1
4RecruitingTreatmentPrimary IgA Nephropathy1
4RecruitingTreatmentRheumatoid Arthritis3
Not AvailableActive Not RecruitingBasic ScienceHIV Disease1
Not AvailableCompletedNot AvailableSjögren's Syndrome / Xerostomia1
Not AvailableCompletedTreatmentHashimoto's Thyroiditis1
Not AvailableCompletedTreatmentRheumatoid Arthritis1
Not AvailableRecruitingNot AvailableType 2 Diabetes Mellitus (T2D)1
Not AvailableRecruitingBasic ScienceInsulin Resistance1
Not AvailableRecruitingTreatmentRheumatoid Arthritis1
Not AvailableRecruitingTreatmentSystemic Lupus Erythematosus (SLE)1
Not AvailableUnknown StatusTreatmentHashimoto's Thyroiditis1
Not AvailableWithdrawnTreatmentChronic Urticaria1
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
TabletOral200 mg/1
Tablet, coatedOral200 mg/1
Tablet, film coatedEnteral200 mg/1
TabletOral200 mg
Tablet, film coatedOral200 mg/1
Prices
Unit descriptionCostUnit
Hydroxychloroquine sulf powder4.8USD g
Plaquenil 200 mg tablet3.14USD tablet
Hydroxychloroquine Sulfate 200 mg tablet1.28USD tablet
Hydroxychloroquine 200 mg tablet1.17USD tablet
Plaquenil Sulfate 200 mg Tablet0.66USD tablet
Apo-Hydroxyquine 200 mg Tablet0.35USD tablet
Mylan-Hydroxychloroquine 200 mg Tablet0.35USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point (°C)89-91U.S. Patent 2,546,658.
Predicted Properties
PropertyValueSource
Water Solubility0.0261 mg/mLALOGPS
logP3.87ALOGPS
logP2.89ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)15.59ChemAxon
pKa (Strongest Basic)9.76ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area48.39 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity97.97 m3·mol-1ChemAxon
Polarizability38.3 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9892
Blood Brain Barrier+0.5602
Caco-2 permeable-0.5154
P-glycoprotein substrateSubstrate0.8348
P-glycoprotein inhibitor INon-inhibitor0.7297
P-glycoprotein inhibitor IIInhibitor0.5106
Renal organic cation transporterNon-inhibitor0.5742
CYP450 2C9 substrateNon-substrate0.8239
CYP450 2D6 substrateNon-substrate0.9117
CYP450 3A4 substrateNon-substrate0.5384
CYP450 1A2 substrateNon-inhibitor0.5864
CYP450 2C9 inhibitorNon-inhibitor0.8457
CYP450 2D6 inhibitorNon-inhibitor0.6111
CYP450 2C19 inhibitorNon-inhibitor0.8782
CYP450 3A4 inhibitorNon-inhibitor0.6287
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7058
Ames testAMES toxic0.6907
CarcinogenicityNon-carcinogens0.837
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.6348 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6798
hERG inhibition (predictor II)Inhibitor0.7173
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-0f6t-3972000000-7c193125680c0c9e276fView in MoNA
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassAminoquinolines and derivatives
Direct Parent4-aminoquinolines
Alternative Parents
Substituents
  • Chloroquinoline
  • 4-aminoquinoline
  • Haloquinoline
  • Aminopyridine
  • Secondary aliphatic/aromatic amine
  • Aryl chloride
  • Aryl halide
  • Pyridine
  • Benzenoid
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • 1,2-aminoalcohol
  • Secondary amine
  • Azacycle
  • Alkanolamine
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Alcohol
  • Primary alcohol
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors

Targets

1. DNA
Kind
Nucleotide
Organism
Human
Pharmacological action
yes
Actions
cross-linking/alkylation
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Koranda FC: Antimalarials. J Am Acad Dermatol. 1981 Jun;4(6):650-5. [PubMed:6165744 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
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. TLR7 is a nucleotide-sensing TLR which is activated by single-stranded RNA. Acts via MYD88 and TRAF6, leading to NF-kappa-B activation, cytokine secretion and the inflammatory response (By similarity).
Gene Name:
TLR7
Uniprot ID:
Q9NYK1
Molecular Weight:
120920.8 Da
References
  1. Sun S, Rao NL, Venable J, Thurmond R, Karlsson L: TLR7/9 antagonists as therapeutics for immune-mediated inflammatory disorders. Inflamm Allergy Drug Targets. 2007 Dec;6(4):223-35. [PubMed:18220957 ]
  2. 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. [PubMed:14579285 ]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
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 is a nucleotide-sensing TLR which is activated by unmethylated cytidine-phosphate-guanosine (CpG) dinucleotides. Acts via MYD88 and TRAF6, leading to NF-kappa-B activation, cytokine secretion and the i...
Gene Name:
TLR9
Uniprot ID:
Q9NR96
Molecular Weight:
115858.665 Da
References
  1. Sun S, Rao NL, Venable J, Thurmond R, Karlsson L: TLR7/9 antagonists as therapeutics for immune-mediated inflammatory disorders. Inflamm Allergy Drug Targets. 2007 Dec;6(4):223-35. [PubMed:18220957 ]
  2. 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. [PubMed:14579285 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
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 antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular Weight:
55768.94 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  2. Somer M, Kallio J, Pesonen U, Pyykko K, Huupponen R, Scheinin M: Influence of hydroxychloroquine on the bioavailability of oral metoprolol. Br J Clin Pharmacol. 2000 Jun;49(6):549-54. [PubMed:10848718 ]
Drug created on August 29, 2007 14:00 / Updated on May 19, 2017 16:56