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Identification
NameHydroxychloroquine
Accession NumberDB01611
TypeSmall Molecule
GroupsApproved
DescriptionA 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 Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Hydroxychloroquine SulfateTablet200 mg/1OralAvera Mc Kennan Hospital2015-03-24Not applicableUs
Hydroxychloroquine SulfateTablet200 mg/1OralPrasco Laboratories2014-12-12Not applicableUs
Hydroxychloroquine SulfateTablet200 mg/1OralAphena Pharma Solutions Tennessee, Llc2014-12-12Not applicableUs
Mint-hydroxychloroquineTablet200 mgOralMint Pharmaceuticals Inc2014-06-10Not applicableCanada
Mylan-hydroxychloroquineTablet200 mgOralMylan Pharmaceuticals Ulc2004-05-21Not applicableCanada
Nu-hydroxyquineTablet200 mgOralNu Pharm IncNot applicableNot applicableCanada
PlaquenilTablet, film coated200 mg/1OralSanofi Aventis U.S. Llc1955-04-18Not applicableUs
PlaquenilTablet200 mg/1OralConcordia Pharmaceuticals Inc.2013-06-28Not applicableUs
PlaquenilTablet200 mg/1OralCovis Pharmaceuticals Inc2013-06-28Not applicableUs
PlaquenilTablet200 mg/1OralAv Kare, Inc.2016-07-14Not applicableUs
PlaquenilTablet200 mgOralSanofi Aventis Canada Inc1957-12-31Not applicableCanada
PlaquenilTablet200 mg/1OralCarilion Materials Management2013-06-28Not applicableUs
PlaquenilTablet200 mg/1OralAphena Pharma Solutions Tennessee, Llc2013-06-28Not 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 Inc2002-12-13Not applicableCanada
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralAvera Mc Kennan Hospital2015-08-31Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralAidarex Pharmaceuticals LLC2009-01-07Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralA S Medication Solutions2009-01-07Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralGolden State Medical Supply, Inc.2007-08-15Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralWest ward Pharmaceutical Corp2007-08-15Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralActavis Pharma, Inc.2016-03-24Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralOhm Laboratories Inc.2009-01-07Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralCadila Healthcare Limited2008-01-03Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralMajor Pharmaceuticals1995-11-30Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralAmerican Health Packaging2008-08-05Not applicableUs
Hydroxychloroquine SulfateTablet200 mg/1OralAv Kare, Inc.2012-02-292015-12-29Us
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralAv Kare, Inc.2014-05-19Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralA S Medication Solutions2009-01-07Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralRanbaxy Pharmaceuticals Inc.2009-01-07Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1EnteralMylan Pharmaceuticals Inc.1998-06-18Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1EnteralMylan Institutional Inc.2016-03-28Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralPhysicians Total Care, Inc.1996-07-09Not 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 SulfateTablet200 mg/1OralAphena Pharma Solutions Tennessee, Llc2012-02-29Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralNorthstar Rx LLC2015-12-18Not applicableUs
Hydroxychloroquine SulfateTablet, coated200 mg/1OralWatson Laboratories, Inc.1995-11-302016-03-05Us
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralA S Medication Solutions2009-01-07Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1Oralbryant ranch prepack2009-01-07Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralAphena Pharma Solutions Tennessee, Llc1995-11-30Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralCardinal Health2008-08-05Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralZydus Pharmaceuticals (USA) Inc.2008-01-03Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralRebel Distributors Corp2009-01-07Not applicableUs
Hydroxychloroquine SulfateTablet200 mg/1OralREMEDYREPACK INC.2011-04-132016-10-13Us
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralSandoz Inc1995-11-30Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralDIRECT RX2014-01-01Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralMc Kesson Packaging Services A Business Unit Of Mc Kesson Corporation2008-01-03Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralAphena Pharma Solutions Tennessee, Llc2014-05-19Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralCardinal Health1995-11-30Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AxokineAstraZeneca
DolquineInmunosyn
HCQSMedigroup
PolirreuminTRB
QuensylSanofi
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Hydroxychloroquine sulfate
Thumb
  • InChI Key: JCBIVZZPXRZKTI-UHFFFAOYNA-N
  • Monoisotopic Mass: 433.143819418
  • Average Mass: 433.95
DBSALT000096
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
IndicationFor 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
PharmacodynamicsHydroxychloroquine 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 actionAlthough 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
AbsorptionVery rapidly and completely absorbed following oral administration.
Volume of distributionNot Available
Protein bindingApproximately 45%.
Metabolism

Partially hepatic, to active de-ethylated metabolites.

Route of eliminationNot Available
Half lifeTerminal elimination half-life In blood is approximately 50 days. In plasma it is approximately 32 days.
ClearanceNot Available
ToxicitySymptoms 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
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot 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
AnvirzelThe serum concentration of Anvirzel can be increased when it is combined with Hydroxychloroquine.Investigational
Aop200704The metabolism of Aop200704 can be decreased when combined with Hydroxychloroquine.Investigational
ArotinololThe metabolism of Arotinolol can be decreased when combined with Hydroxychloroquine.Approved
ArsenamideThe serum concentration of Arsenamide can be decreased when it is combined with Hydroxychloroquine.Vet 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
BucindololThe metabolism of Bucindolol can be decreased when combined with Hydroxychloroquine.Investigational
BufuralolThe metabolism of Bufuralol can be decreased when combined with Hydroxychloroquine.Experimental, Investigational
BunamidineThe serum concentration of Bunamidine can be decreased when it is combined with Hydroxychloroquine.Vet Approved
BupranololThe metabolism of Bupranolol can be decreased when combined with Hydroxychloroquine.Approved
CambendazoleThe serum concentration of Cambendazole can be decreased when it is combined with Hydroxychloroquine.Vet 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
ChloroxylenolThe serum concentration of Chloroxylenol can be decreased when it is combined with Hydroxychloroquine.Approved
ChlorpromazineThe serum concentration of Chlorpromazine can be increased when it is combined with Hydroxychloroquine.Approved, Vet Approved
ClorsulonThe serum concentration of Clorsulon can be decreased when it is combined with Hydroxychloroquine.Vet Approved
CoumaphosThe serum concentration of Coumaphos can be decreased when it is combined with Hydroxychloroquine.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
DichlorvosThe serum concentration of Dichlorvos can be decreased when it is combined with Hydroxychloroquine.Vet 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
DithiazanineThe serum concentration of Dithiazanine can be decreased when it is combined with Hydroxychloroquine.Vet Approved
DoramectinThe serum concentration of Doramectin can be decreased when it is combined with Hydroxychloroquine.Vet Approved
EprinomectinThe serum concentration of Eprinomectin can be decreased when it is combined with Hydroxychloroquine.Vet Approved
EsmololThe metabolism of Esmolol can be decreased when combined with Hydroxychloroquine.Approved
FebantelThe serum concentration of Febantel can be decreased when it is combined with Hydroxychloroquine.Vet Approved
FenbendazoleThe serum concentration of Fenbendazole can be decreased when it is combined with Hydroxychloroquine.Vet 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
HexylresorcinolThe serum concentration of Hexylresorcinol can be decreased when it is combined with Hydroxychloroquine.Approved
Hygromycin BThe serum concentration of Hygromycin B can be decreased when it is combined with Hydroxychloroquine.Vet 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
Milbemycin oximeThe serum concentration of Milbemycin oxime can be decreased when it is combined with Hydroxychloroquine.Vet Approved
MorantelThe serum concentration of Morantel can be decreased when it is combined with Hydroxychloroquine.Vet Approved
MoricizineThe serum concentration of Moricizine can be increased when it is combined with Hydroxychloroquine.Approved, Withdrawn
MoxidectinThe serum concentration of Moxidectin can be decreased when it is combined with Hydroxychloroquine.Vet Approved
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
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
OxfendazoleThe serum concentration of Oxfendazole can be decreased when it is combined with Hydroxychloroquine.Vet 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
PerazineThe serum concentration of Perazine can be increased when it is combined with Hydroxychloroquine.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
PropiopromazineThe serum concentration of Propiopromazine can be increased when it is combined with Hydroxychloroquine.Vet Approved
PropranololThe metabolism of Propranolol can be decreased when combined with Hydroxychloroquine.Approved, Investigational
PyrantelThe serum concentration of Pyrantel can be decreased when it is combined with Hydroxychloroquine.Approved, Vet Approved
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.Approved
TimololThe metabolism of Timolol can be decreased when combined with Hydroxychloroquine.Approved
TrichlorfonThe serum concentration of Trichlorfon can be decreased when it is combined with Hydroxychloroquine.Vet Approved
TriclabendazoleThe serum concentration of Triclabendazole can be decreased when it is combined with Hydroxychloroquine.Investigational
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
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Tablet, coatedOral200 mg/1
Tablet, film coatedEnteral200 mg/1
TabletOral200 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 point89-91U.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
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 aminoquinolines and derivatives. These are organic compounds containing an amino group attached to a quinoline ring system.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassAminoquinolines and derivatives
Direct ParentAminoquinolines and derivatives
Alternative Parents
Substituents
  • Chloroquinoline
  • Aminoquinoline
  • Secondary aliphatic/aromatic amine
  • Chlorobenzene
  • Aminopyridine
  • Benzenoid
  • Pyridine
  • Aryl halide
  • Aryl chloride
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • 1,2-aminoalcohol
  • Azacycle
  • Secondary amine
  • Alkanolamine
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available

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 ]
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Drug created on August 29, 2007 14:00 / Updated on August 17, 2016 12:23