Identification

Name
Hydroxychloroquine
Accession Number
DB01611
Type
Small Molecule
Groups
Approved
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
Product Ingredients
IngredientUNIICASInChI Key
Hydroxychloroquine sulfate8Q2869CNVH747-36-4JCBIVZZPXRZKTI-UHFFFAOYNA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Hydroxychloroquine SulfateTablet200 mg/1OralPrasco, Laboratories2014-12-12Not applicableUs
Hydroxychloroquine SulfateTablet200 mg/1OralAphena Pharma Solutions Tennessee, Inc.2014-12-12Not applicableUs
Hydroxychloroquine SulfateTablet200 mg/1OralAvera Mc Kennan Hospital2015-03-24Not 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/1OralConcordia Pharmaceuticals, Inc2013-06-28Not applicableUs
PlaquenilTablet200 mgOralSanofi Aventis1957-12-31Not applicableCanada
PlaquenilTablet200 mg/1OralCovis Pharmaceuticals, Inc.2013-06-282017-12-31Us
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-hydroxyquineTablet200 mgOralApotex Corporation2002-12-13Not applicableCanada
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralCardinal Health1995-11-30Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1EnteralMylan Institutional2016-03-28Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralWest Ward Pharmaceutical2007-08-15Not applicableUs
Hydroxychloroquine SulfateTablet200 mg/1OralAv Kare, Inc.2012-02-292015-12-29Us
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralA S Medication Solutions2016-03-242017-06-20Us
Hydroxychloroquine SulfateTablet200 mg/1OralRemedy Repack2011-04-132016-10-13Us
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralA S Medication Solutions2009-01-072017-06-20Us
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralBlenheim Pharmacal, Inc.2013-12-20Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralActavis Pharma Company2016-03-24Not applicableUs
International/Other Brands
Axokine (AstraZeneca) / Dolquine (Inmunosyn) / HCQS (Medigroup) / Polirreumin (TRB) / Quensyl (Sanofi)
Categories
UNII
4QWG6N8QKH
CAS number
118-42-3
Weight
Average: 335.872
Monoisotopic: 335.176440176
Chemical Formula
C18H26ClN3O
InChI Key
XXSMGPRMXLTPCZ-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.

TargetActionsOrganism
ADNA
cross-linking/alkylation
Human
AToll-like receptor 7
antagonist
Human
AToll-like receptor 9
antagonist
Human
Absorption

Very rapidly and completely absorbed following oral administration.

Volume of distribution
Not Available
Protein binding

Approximately 45%.

Metabolism

Partially hepatic, to active de-ethylated metabolites.

Route of elimination
Not Available
Half life

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

Clearance
Not 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
Pathways
Not 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
AcetyldigoxinThe serum concentration of Acetyldigoxin can be increased when it is combined with Hydroxychloroquine.Experimental
AlbendazoleThe serum concentration of Albendazole can be decreased when it is combined with Hydroxychloroquine.Approved, Vet Approved
Albendazole oxideThe serum concentration of Albendazole oxide can be decreased when it is combined with Hydroxychloroquine.Experimental
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
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
ArtemotilThe serum concentration of Artemotil can be decreased when it is combined with Hydroxychloroquine.Experimental
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
BepheniumThe serum concentration of Bephenium 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
CarbendazimThe serum concentration of Carbendazim can be decreased when it is combined with Hydroxychloroquine.Investigational
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
ChlorproethazineThe serum concentration of Chlorproethazine can be increased when it is combined with Hydroxychloroquine.Experimental
ChlorpromazineThe serum concentration of Chlorpromazine can be increased when it is combined with Hydroxychloroquine.Approved, Vet Approved
CiclobendazoleThe serum concentration of Ciclobendazole can be decreased when it is combined with Hydroxychloroquine.Experimental
CloranololThe metabolism of Cloranolol can be decreased when combined with Hydroxychloroquine.Experimental
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
CymarinThe serum concentration of Cymarin can be increased when it is combined with Hydroxychloroquine.Experimental
DapsoneThe risk or severity of adverse effects can be increased when Hydroxychloroquine is combined with Dapsone.Approved, Investigational
DesaspidinThe serum concentration of Desaspidin can be decreased when it is combined with Hydroxychloroquine.Experimental
DeslanosideThe serum concentration of Deslanoside can be increased when it is combined with Hydroxychloroquine.Approved
DichloropheneThe serum concentration of Dichlorophene can be decreased when it is combined with Hydroxychloroquine.Vet 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
EmetineThe serum concentration of Emetine can be decreased when it is combined with Hydroxychloroquine.Experimental
EpanololThe metabolism of Epanolol can be decreased when combined with Hydroxychloroquine.Experimental
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
GitoformateThe serum concentration of Gitoformate can be increased when it is combined with Hydroxychloroquine.Experimental
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
LabetalolThe metabolism of Labetalol can be decreased when combined with Hydroxychloroquine.Approved
Lanatoside CThe serum concentration of Lanatoside C can be increased when it is combined with Hydroxychloroquine.Experimental
LandiololThe metabolism of Landiolol can be decreased when combined with Hydroxychloroquine.Investigational
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
MepindololThe metabolism of Mepindolol can be decreased when combined with Hydroxychloroquine.Experimental
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
MetildigoxinThe serum concentration of Metildigoxin can be increased when it is combined with Hydroxychloroquine.Experimental
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
NiridazoleThe serum concentration of Niridazole can be decreased when it is combined with Hydroxychloroquine.Experimental
OleandrinThe serum concentration of Oleandrin can be increased when it is combined with Hydroxychloroquine.Experimental
OltiprazThe serum concentration of Oltipraz can be decreased when it is combined with Hydroxychloroquine.Investigational
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
OxantelThe serum concentration of Oxantel can be decreased when it is combined with Hydroxychloroquine.Experimental
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
PeruvosideThe serum concentration of Peruvoside can be increased when it is combined with Hydroxychloroquine.Experimental
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
ProscillaridinThe serum concentration of Proscillaridin can be increased when it is combined with Hydroxychloroquine.Experimental
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
StibophenThe serum concentration of Stibophen can be decreased when it is combined with Hydroxychloroquine.Experimental
SuraminThe serum concentration of Suramin can be decreased when it is combined with Hydroxychloroquine.Approved
TalinololThe metabolism of Talinolol can be decreased when combined with Hydroxychloroquine.Investigational
TertatololThe metabolism of Tertatolol can be decreased when combined with Hydroxychloroquine.Experimental
ThiabendazoleThe serum concentration of Thiabendazole can be decreased when it is combined with Hydroxychloroquine.Approved, Vet Approved
ThiazinamThe serum concentration of Thiazinam can be increased when it is combined with Hydroxychloroquine.Experimental
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
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 Interactions
Not Available

References

Synthesis Reference

U.S. Patent 2,546,658.

General References
Not Available
External Links
Human Metabolome Database
HMDB15549
KEGG Drug
D08050
KEGG Compound
C07043
PubChem Compound
3652
PubChem Substance
46508459
ChemSpider
3526
ChEBI
5801
ChEMBL
CHEMBL1535
Therapeutic Targets Database
DAP000878
PharmGKB
PA164777036
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Hydroxychloroquine
ATC Codes
P01BA02 — Hydroxychloroquine
AHFS Codes
  • 08:30.08 — Antimalarials

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedSupportive CareLiver Cirrhosis / Muscle Cramps1
0CompletedTreatmentMelanoma (Skin)1
0CompletedTreatmentPlasma Cell Myeloma1
0TerminatedTreatmentProstate Cancer1
1Active Not RecruitingTreatmentAdult Solid Neoplasm1
1Active Not RecruitingTreatmentAdult Solid Neoplasm / Hormone-Resistant Prostate Cancer / Recurrent Melanoma / Recurrent Prostate Carcinoma / Renal Cell Carcinoma Recurrent / Stage IIIA Cutaneous Melanoma AJCC v7 / Stage IIIA Skin Melanoma / Stage IIIB Cutaneous Melanoma AJCC v7 / Stage IIIB Skin Melanoma / Stage IIIC Cutaneous Melanoma AJCC v7 / Stage IIIC Skin Melanoma / Stage IV Cutaneous Melanoma AJCC v6 and v7 / Stage IV Prostate Cancer / Stage IV Renal Cell Cancer / Stage IV Skin Melanoma1
1Active Not RecruitingTreatmentAdvanced Cancers1
1Active Not RecruitingTreatmentMelanoma1
1Active Not RecruitingTreatmentUnspecified Adult Solid Tumor, Protocol Specific1
1CompletedTreatmentCystic Fibrosis (CF)1
1CompletedTreatmentImmunosuppression / Rheumatism1
1CompletedTreatmentLymphangioleiomyomatosis1
1CompletedTreatmentRecurrent Plasma Cell Myeloma / Refractory Plasma Cell Myeloma1
1CompletedTreatmentUnspecified Adult Solid Tumor, Protocol Specific1
1Not Yet RecruitingTreatmentTumors, Solid1
1RecruitingTreatmentAcute Myelogenous Leukaemia (AML)1
1RecruitingTreatmentMalignant Solid Tumours1
1RecruitingTreatmentTumors, Solid1
1TerminatedTreatmentBone Metastases / Unspecified Adult Solid Tumor, Protocol Specific1
1TerminatedTreatmentEstrogen Receptor Positive Breast Cancer1
1TerminatedTreatmentLung Cancer Non-Small Cell Cancer (NSCLC)1
1TerminatedTreatmentRenal Cell Adenocarcinoma1
1Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections1
1, 2Active Not RecruitingTreatmentAdenocarcinomas / Malignant Neoplasm of Colon / Metastasis / Rectal Carcinoma1
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 Erythematosus (SLE)1
1, 2CompletedTreatmentAcute HIV Infection1
1, 2Not Yet RecruitingTreatmentColorectal Cancers1
1, 2Not Yet RecruitingTreatmentDiabetes Type Two1
1, 2Not Yet RecruitingTreatmentPlatinum-resistant Epithelial Ovarian Cancer1
1, 2RecruitingTreatmentAcne Inversa / Follicular Occlusion Tetrad / Follicular Occlusion Triad / Furuncle / Hidradenitis / Hidradenitis Suppurativa (HS)1
1, 2RecruitingTreatmentAdvanced Adenocarcinoma / Metastatic Adenocarcinoma1
1, 2RecruitingTreatmentAdvanced BRAF Mutant Melanoma1
1, 2RecruitingTreatmentDisseminated Sclerosis1
1, 2RecruitingTreatmentMetastatic Renal Cell Carcinoma1
1, 2TerminatedTreatmentCancer, Breast1
1, 2TerminatedTreatmentChronic Hepatitis C Infection1
1, 2TerminatedTreatmentLung Cancers1
1, 2Unknown StatusTreatmentBrain and Central Nervous System Tumors1
1, 2Unknown StatusTreatmentLung Cancer Non-Small Cell Cancer (NSCLC)1
1, 2Unknown StatusTreatmentMalignant Neoplasm of Pancreas1
1, 2Unknown StatusTreatmentMultiple Myeloma and Plasma Cell Neoplasm1
2Active Not RecruitingTreatmentGlioblastomas1
2Active Not RecruitingTreatmentLung Cancer Non-Small Cell Cancer (NSCLC)1
2Active Not RecruitingTreatmentMalignant Neoplasm of Pancreas2
2Active Not RecruitingTreatmentProstate Cancer1
2CompletedTreatmentAdvanced Non-Small Cell Lung Cancer / Lung Cancer Non-Small Cell Cancer (NSCLC) / Recurrent Non-small Cell Lung Cancer1
2CompletedTreatmentColorectal Cancers1
2CompletedTreatmentLichen Planus, Oral1
2CompletedTreatmentOsteoarthritis of the Knees1
2CompletedTreatmentProstate Cancer1
2Not Yet RecruitingPreventionSystemic Lupus Erythematosus Encephalitis1
2Not Yet RecruitingTreatmentHepatocellular Cancer1
2Not Yet RecruitingTreatmentInsulin Dependent Diabetes / Pancreatitis, Chronic1
2Not Yet RecruitingTreatmentLung Cancer Small 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
2RecruitingTreatmentMalignant Neoplasm of Pancreas1
2RecruitingTreatmentMultiple Sclerosis, Primary Progressive1
2RecruitingTreatmentPorphyria Cutanea Tarda1
2TerminatedTreatmentArteriosclerosis / Cardiovascular Disease (CVD) / Kidney Failure,Chronic1
2TerminatedTreatmentB-Cell Chronic Lymphocytic Leukemia1
2TerminatedTreatmentProstate Cancer1
2TerminatedTreatmentSarcomas1
2Unknown StatusPreventionFlu caused by Influenza1
2Unknown StatusTreatmentCancer, Breast1
2Unknown StatusTreatmentCrohn's Disease (CD)1
2Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections1
2Unknown StatusTreatmentLeukemias1
2WithdrawnTreatmentAbortions spontaneous / Recurrent Pregnancy Losses1
3CompletedSupportive CareGraft Versus Host Disease (GVHD)1
3CompletedTreatmentAutoimmune Diseases / Eye Dryness / Sjögren's Syndrome1
3CompletedTreatmentCutaneous Lupus Erythematosus-Systemic Lupus Erythematosus1
3CompletedTreatmentGiant Cells Arteritis1
3CompletedTreatmentInsulin Resistance / Rheumatoid Arthritis1
3CompletedTreatmentPrimary Sjögren's Syndrome1
3CompletedTreatmentRheumatoid Arthritis4
3CompletedTreatmentSarcoidosis, Pulmonary1
3CompletedTreatmentSeronegative Spondyloarthropathies1
3CompletedTreatmentSynovitis of osteoarthritis1
3Not Yet RecruitingTreatmentFirst Trimester Abortion / Recurrent Miscarriages1
3Not Yet RecruitingTreatmentRecurrent Pregnancy Losses1
3RecruitingTreatmentThrombocytopenias1
3TerminatedPreventionAntiphospholipid Syndrome1
4CompletedBasic SciencePre-Diabetic1
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 RecruitingTreatmentImmune Thrombocytopenia1
4Not Yet RecruitingTreatmentInsufficient Response to Methotrexate / Rheumatoid Arthritis1
4RecruitingTreatmentAcute Coronary Syndromes (ACS) / Antirheumatic Agents / Cardiovascular Disease (CVD) / Hydroxychloroquine / Inflammatory Reaction / Myocardial Infarction (MI) / Unstable Angina (UA)1
4RecruitingTreatmentIndividuals Undergoing Cardiac and General Surgery1
4RecruitingTreatmentPrimary IgA Nephropathy1
4RecruitingTreatmentRheumatoid Arthritis3
Not AvailableActive Not RecruitingBasic ScienceHuman Immunodeficiency Virus (HIV)1
Not AvailableCompletedNot AvailableSjögren's Syndrome / Xerostomia1
Not AvailableCompletedTreatmentHashimoto's Thyroiditis1
Not AvailableCompletedTreatmentRheumatoid Arthritis2
Not AvailableNot Yet RecruitingNot AvailableAutoimmune Diseases1
Not AvailableRecruitingNot AvailableType 2 Diabetes Mellitus1
Not AvailableRecruitingBasic ScienceInsulin Resistance1
Not AvailableRecruitingTreatmentSystemic Lupus Erythematosus (SLE)1
Not AvailableUnknown StatusTreatmentHashimoto's Thyroiditis1
Not AvailableWithdrawnTreatmentChronic Urticaria1

Pharmacoeconomics

Manufacturers
Not 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.
Patents
Not Available

Properties

State
Solid
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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-0f6t-3972000000-7c193125680c0c9e276f
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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 / 1,2-aminoalcohols / Azacyclic compounds / Primary alcohols
show 3 more
Substituents
Chloroquinoline / 4-aminoquinoline / Haloquinoline / Aminopyridine / Secondary aliphatic/aromatic amine / Aryl chloride / Aryl halide / Pyridine / Benzenoid / Heteroaromatic compound
show 18 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
tertiary amino compound, organochlorine compound, secondary amino compound, primary alcohol, aminoquinoline (CHEBI:5801)

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 i...
Gene Name
TLR7
Uniprot ID
Q9NYK1
Uniprot Name
Toll-like receptor 7
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 i...
Gene Name
TLR9
Uniprot ID
Q9NR96
Uniprot Name
Toll-like receptor 9
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...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
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 October 21, 2017 19:30