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-UHFFFAOYSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
PlaquenilTablet200 mg/1OralCovis Pharmaceuticals, Inc.2013-06-282017-12-31Us
PlaquenilTablet200 mgOralSanofi Aventis1957-12-31Not applicableCanada
PlaquenilTablet200 mg/1OralConcordia Pharmaceuticals, Inc2013-06-28Not applicableUs
PlaquenilTablet200 mg/1OralAphena Pharma Solutions Tennessee, Inc.2013-06-28Not applicableUs
PlaquenilTablet, film coated200 mg/1OralSanofi Aventis1955-04-182013-05-31Us
PlaquenilTablet200 mg/1OralCarilion Materials Management2013-06-28Not applicableUs
PlaquenilTablet200 mg/1OralAv Kare, Inc.2016-07-14Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-hydroxyquineTablet200 mgOralApotex Corporation2002-12-13Not applicableCanada
Hydroxychloroquine SulfateTablet200 mg/1OralAphena Pharma Solutions Tennessee, Inc.2014-12-12Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralNorth Star Rx Llc2015-12-18Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralAv Kare, Inc.2014-01-282015-02-20Us
Hydroxychloroquine sulfateTablet, film coated200 mg/1OralZydus Pharmaceuticals (USA) Inc.2008-01-03Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralAidarex Pharmaceuticals LLC2009-01-07Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralNorth Star Rx Llc2015-12-18Not applicableUs
Hydroxychloroquine sulfateTablet, film coated200 mg/1OralCardinal Health2008-08-05Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralA-S Medication Solutions2009-01-07Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralCardinal Health1995-11-302012-03-31Us
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.

Associated Conditions
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
DrugInteraction
2-MethoxyethanolThe risk or severity of adverse effects can be increased when 2-Methoxyethanol is combined with Hydroxychloroquine.
9-(N-methyl-L-isoleucine)-cyclosporin AThe risk or severity of adverse effects can be increased when 9-(N-methyl-L-isoleucine)-cyclosporin A is combined with Hydroxychloroquine.
AbataceptThe risk or severity of adverse effects can be increased when Abatacept is combined with Hydroxychloroquine.
AbemaciclibThe serum concentration of Abemaciclib can be increased when it is combined with Hydroxychloroquine.
AbetimusThe risk or severity of adverse effects can be increased when Abetimus is combined with Hydroxychloroquine.
AbexinostatThe risk or severity of QTc prolongation can be increased when Hydroxychloroquine is combined with Abexinostat.
AcebutololThe risk or severity of QTc prolongation can be decreased when Hydroxychloroquine is combined with Acebutolol.
AcepromazineThe risk or severity of QTc prolongation can be increased when Hydroxychloroquine is combined with Acepromazine.
AceprometazineThe risk or severity of QTc prolongation can be increased when Hydroxychloroquine is combined with Aceprometazine.
AcetophenazineThe risk or severity of QTc prolongation can be increased when Hydroxychloroquine is combined with Acetophenazine.
Food Interactions
Not Available

References

Synthesis Reference

U.S. Patent 2,546,658.

General References
Not Available
External Links
Human Metabolome Database
HMDB0015549
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 / Hormone-Resistant Prostate Carcinoma / 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 Prostate Cancer AJCC v7 / Stage IV Renal Cell Cancer / Stage IV Renal Cell Cancer AJCC V7 / Stage IV Skin Melanoma1
1Active Not RecruitingTreatmentAdvanced Cancers1
1Active Not RecruitingTreatmentMalignant Solid Tumours1
1Active Not RecruitingTreatmentTumors, Solid1
1Active Not RecruitingTreatmentUnspecified Adult Solid Tumor, Protocol Specific1
1CompletedTreatmentCystic Fibrosis (CF)1
1CompletedTreatmentImmunosuppression / Rheumatism1
1CompletedTreatmentMelanoma1
1CompletedTreatmentRecurrent Plasma Cell Myeloma / Refractory Plasma Cell Myeloma1
1CompletedTreatmentUnspecified Adult Solid Tumor, Protocol Specific1
1RecruitingTreatmentTumors, Solid1
1TerminatedTreatmentAcute Myelogenous Leukaemia (AML)1
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 RecruitingTreatmentAdvanced Adenocarcinoma / Metastatic Adenocarcinoma1
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, 2Active Not RecruitingTreatmentMetastatic Renal Cell Carcinoma1
1, 2CompletedDiagnosticSystemic Lupus Erythematosus (SLE)1
1, 2CompletedTreatmentAcute HIV Infection1
1, 2CompletedTreatmentAdenocarcinomas / Malignant Neoplasm of Colon / Metastasis / Rectal Carcinoma1
1, 2Not Yet RecruitingTreatmentRecurrent Osteosarcoma / Refractory Osteosarcoma1
1, 2Not Yet RecruitingTreatmentType 2 Diabetes Mellitus1
1, 2RecruitingTreatmentAcne Inversa / Follicular Occlusion Tetrad / Follicular Occlusion Triad / Furuncle / Hidradenitis / Hidradenitis Suppurativa (HS)1
1, 2RecruitingTreatmentAdvanced BRAF Mutant Melanoma1
1, 2RecruitingTreatmentColorectal Cancers1
1, 2RecruitingTreatmentDisseminated Sclerosis1
1, 2RecruitingTreatmentPlatinum-resistant Epithelial Ovarian Cancer1
1, 2RecruitingTreatmentProstate Cancer1
1, 2TerminatedTreatmentCancer, Breast1
1, 2TerminatedTreatmentHepatitis C Viral 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 RecruitingTreatmentLung Cancer Non-Small Cell Cancer (NSCLC)1
2Active Not RecruitingTreatmentMalignant Neoplasm of Pancreas3
2Active Not RecruitingTreatmentProstate Cancer1
2CompletedTreatmentAdvanced Non-Small Cell Lung Cancer / Lung Cancer Non-Small Cell Cancer (NSCLC) / Non-Small Cell Lung Cancer Recurrent1
2CompletedTreatmentColorectal Cancers1
2CompletedTreatmentGlioblastomas1
2CompletedTreatmentHydroxychloroquine / IgA Patients1
2CompletedTreatmentKnee Osteoarthritis (Knee OA)1
2CompletedTreatmentLichen Planus, Oral1
2CompletedTreatmentProstate Cancer1
2Not Yet RecruitingTreatmentAortic Stiffness / Atherosclerosis / Cardiovascular Disease (CVD) / Chronic Kidney Disease (CKD) / Inflammatory Reaction1
2RecruitingPreventionAutoantibody-Associated Heart Block / Congenital Heart Block / Neonatal Lupus1
2RecruitingPreventionHealthy Participants / Healthy Volunteers / Rheumatoid Arthritis (RA) Prevention / Rheumatoid Arthritis Prevention1
2RecruitingPreventionSystemic Lupus Erythematosus (SLE) / Systemic Lupus Erythematosus Encephalitis1
2RecruitingPreventionType1 Diabetes Mellitus1
2RecruitingTreatmentAntiphospholipid Syndrome (APS)1
2RecruitingTreatmentBreast Cancer Stage IIB1
2RecruitingTreatmentChildren´s Interstitial Lung Disease / Diffuse Parenchymal Lung Diseases / Interstitial Lung Disease (ILD)1
2RecruitingTreatmentColorectal Cancers1
2RecruitingTreatmentCrohn's Disease (CD)1
2RecruitingTreatmentDiabetes Mellitus Type 2 With Hyperglycemia1
2RecruitingTreatmentHepatocellular Cancer1
2RecruitingTreatmentInsulin Dependent Diabetes / Pancreatitis, Chronic1
2RecruitingTreatmentLung Cancer Small Cell Lung Cancer (SCLC)1
2RecruitingTreatmentMultiple Sclerosis, Primary Progressive1
2RecruitingTreatmentPancreatic Cancer Resectable / Pancreatic Cancer, Resectable Adenocarcinoma of the Pancreas1
2RecruitingTreatmentPorphyria Cutanea Tarda1
2TerminatedTreatmentArteriosclerosis / Cardiovascular Disease (CVD) / Chronic Renal Failure (CRF)1
2TerminatedTreatmentB-Cell Chronic Lymphocytic Leukemia1
2TerminatedTreatmentProstate Cancer1
2TerminatedTreatmentSarcomas1
2Unknown StatusPreventionFlu caused by Influenza1
2Unknown StatusTreatmentCancer, Breast1
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
3CompletedTreatmentOsteoarthritis (OA)1
3CompletedTreatmentPrimary Sjögren's Syndrome1
3CompletedTreatmentRheumatoid Arthritis4
3CompletedTreatmentSarcoidosis, Pulmonary1
3CompletedTreatmentSeronegative Spondyloarthropathies1
3RecruitingTreatmentFirst Trimester Abortion / Recurrent Miscarriages1
3RecruitingTreatmentRecurrent Pregnancy Losses1
3RecruitingTreatmentThrombocytopenias1
3TerminatedPreventionAntiphospholipid Syndrome1
4CompletedBasic SciencePre-Diabetic1
4CompletedTreatmentAlopecia Areata (AA)1
4CompletedTreatmentBorrelia Infection / Lyme Disease1
4CompletedTreatmentImmune Thrombocytopenia1
4CompletedTreatmentPrimary IgA Nephropathy1
4CompletedTreatmentRheumatoid Arthritis3
4Not Yet RecruitingTreatmentInsufficient Response to Methotrexate / Rheumatoid Arthritis1
4RecruitingPreventionNonvalvular Atrial Fibrillation1
4RecruitingTreatmentAcute Coronary Syndromes (ACS) / Antirheumatic Agents / Cardiovascular Disease (CVD) / Hydroxychloroquine / Inflammatory Reaction / Myocardial Infarction / Unstable Angina (UA)1
4RecruitingTreatmentAnkylosing Spondylitis (AS)1
4RecruitingTreatmentCoronary Artery Disease1
4RecruitingTreatmentCutaneous Lupus / Juvenile SLE / Systemic Lupus Erythematosus (SLE)1
4RecruitingTreatmentIndividuals Undergoing Cardiac and General Surgery1
4RecruitingTreatmentPrimary IgA Nephropathy1
4RecruitingTreatmentRheumatoid Arthritis4
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 AvailableNot Yet RecruitingTreatmentRecurrent Pregnancy Losses / Undifferentiated Connective Tissue Disease1
Not AvailableRecruitingNot AvailableChloroquine Retinopathy / Proliferative Nephritis1
Not AvailableRecruitingBasic ScienceInsulin Resistance1
Not AvailableRecruitingOtherType 2 Diabetes Mellitus1
Not AvailableRecruitingTreatmentSystemic Lupus Erythematosus (SLE)1
Not AvailableUnknown StatusTreatmentHashimoto's Thyroiditis1
Not AvailableWithdrawnTreatmentChronic Urticaria1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Amerisource Health Services Corp.
  • Amneal Pharmaceuticals
  • Apotheca Inc.
  • A-S Medication Solutions LLC
  • Cadila Healthcare Ltd.
  • Cardinal Health
  • Caremark LLC
  • Comprehensive Consultant Services Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Ipca Laboratories Ltd.
  • Kaiser Foundation Hospital
  • Major Pharmaceuticals
  • Mallinckrodt Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mylan
  • Nucare Pharmaceuticals Inc.
  • Ohm Laboratories Inc.
  • Pharmedix
  • Physicians Total Care Inc.
  • Professional Co.
  • Qualitest
  • Ranbaxy Laboratories
  • Resource Optimization and Innovation LLC
  • Sandoz
  • Sanofi-Aventis Inc.
  • Southwood Pharmaceuticals
  • Teva Pharmaceutical Industries Ltd.
  • United Research Laboratories Inc.
  • Watson Pharmaceuticals
  • West-Ward Pharmaceuticals
  • Winthrop Us
  • Zydus Pharmaceuticals
Dosage forms
FormRouteStrength
Tablet, film coatedEnteral200 mg/1
Tablet, film coatedOral200 mg/1
TabletOral200 mg
TabletOral200 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]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Crowe A, Ilett KF, Karunajeewa HA, Batty KT, Davis TM: Role of P glycoprotein in absorption of novel antimalarial drugs. Antimicrob Agents Chemother. 2006 Oct;50(10):3504-6. doi: 10.1128/AAC.00708-06. Epub 2006 Aug 17. [PubMed:16917012]
  2. Plaquenil (hydroxychloroquine sulfate) - Drug Summary [Link]

Drug created on August 29, 2007 14:00 / Updated on October 16, 2018 08:37