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Properties

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Taxonomy

Hydroxychloroquine

Targets (3)Enzymes (1)Transporters (1)Biointeractions (4)

Identification

Name

Hydroxychloroquine

Accession Number

DB01611

Type

Small Molecule

Groups

Approved

Description

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

Structure

Similar Structures

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

Ingredient	UNII	CAS	InChI Key
Hydroxychloroquine sulfate	8Q2869CNVH	747-36-4	JCBIVZZPXRZKTI-UHFFFAOYSA-N

Product Images

Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Plaquenil	Tablet	200 mg/1	Oral	Covis Pharmaceuticals, Inc.	2013-06-28	2017-12-31
Plaquenil	Tablet	200 mg	Oral	Sanofi Aventis	1957-12-31	Not applicable
Plaquenil	Tablet	200 mg/1	Oral	Concordia Pharmaceuticals, Inc	2013-06-28	Not applicable
Plaquenil	Tablet	200 mg/1	Oral	Aphena Pharma Solutions Tennessee, Inc.	2013-06-28	Not applicable
Plaquenil	Tablet, film coated	200 mg/1	Oral	Sanofi Aventis	1955-04-18	2013-05-31
Plaquenil	Tablet	200 mg/1	Oral	Carilion Materials Management	2013-06-28	Not applicable
Plaquenil	Tablet	200 mg/1	Oral	Av Kare, Inc.	2016-07-14	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Apo-hydroxyquine	Tablet	200 mg	Oral	Apotex Corporation	2002-12-13	Not applicable
Hydroxychloroquine Sulfate	Tablet, film coated	200 mg/1	Oral	Av Kare, Inc.	2014-01-28	2015-02-20
Hydroxychloroquine Sulfate	Tablet	200 mg/1	Oral	Aphena Pharma Solutions Tennessee, Inc.	2014-12-12	Not applicable
Hydroxychloroquine Sulfate	Tablet, film coated	200 mg/1	Oral	Amneal Pharmaceuticals	2018-05-17	Not applicable
Hydroxychloroquine Sulfate	Tablet, film coated	200 mg/1	Oral	American Health Packaging	2008-07-24	Not applicable
Hydroxychloroquine Sulfate	Tablet, film coated	200 mg/1	Oral	A-S Medication Solutions	2016-03-30	Not applicable
Hydroxychloroquine sulfate	Tablet, film coated	200 mg/1	Oral	Cardinal Health	2008-08-05	Not applicable
Hydroxychloroquine Sulfate	Tablet, film coated	200 mg/1	Oral	Aidarex Pharmaceuticals LLC	2009-01-07	Not applicable
Hydroxychloroquine Sulfate	Tablet, film coated	200 mg/1	Oral	North Star Rx Llc	2015-12-18	Not applicable
Hydroxychloroquine Sulfate	Tablet, film coated	200 mg/1	Oral	Teva	1995-09-01	2013-09-30

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.

Target	Actions	Organism
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

Drug	Interaction
2-Methoxyethanol	The risk or severity of adverse effects can be increased when Hydroxychloroquine is combined with 2-Methoxyethanol.
4-Methoxyamphetamine	The metabolism of 4-Methoxyamphetamine can be decreased when combined with Hydroxychloroquine.
9-(N-methyl-L-isoleucine)-cyclosporin A	The risk or severity of adverse effects can be increased when Hydroxychloroquine is combined with 9-(N-methyl-L-isoleucine)-cyclosporin A.
Abatacept	The risk or severity of adverse effects can be increased when Abatacept is combined with Hydroxychloroquine.
Abemaciclib	The serum concentration of Abemaciclib can be increased when it is combined with Hydroxychloroquine.
Abetimus	The risk or severity of adverse effects can be increased when Hydroxychloroquine is combined with Abetimus.
Abexinostat	The risk or severity of QTc prolongation can be increased when Hydroxychloroquine is combined with Abexinostat.
Acebutolol	The risk or severity of QTc prolongation can be decreased when Hydroxychloroquine is combined with Acebutolol.
Acepromazine	The risk or severity of QTc prolongation can be increased when Hydroxychloroquine is combined with Acepromazine.
Aceprometazine	The risk or severity of QTc prolongation can be increased when Hydroxychloroquine is combined with Aceprometazine.

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

Phase	Status	Purpose	Conditions	Count
0	Completed	Supportive Care	Liver Cirrhosis / Muscle Cramps	1
0	Completed	Treatment	Melanoma (Skin)	1
0	Completed	Treatment	Plasma Cell Myeloma	1
0	Terminated	Treatment	Prostate Cancer	1
1	Active Not Recruiting	Treatment	Adult Solid Neoplasm	1
1	Active Not Recruiting	Treatment	Adult 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 Melanoma	1
1	Active Not Recruiting	Treatment	Advanced Cancers	1
1	Active Not Recruiting	Treatment	Malignant Solid Tumours	1
1	Active Not Recruiting	Treatment	Tumors, Solid	1
1	Active Not Recruiting	Treatment	Unspecified Adult Solid Tumor, Protocol Specific	1
1	Completed	Treatment	Cystic Fibrosis (CF)	1
1	Completed	Treatment	Immunosuppression / Rheumatism	1
1	Completed	Treatment	Melanoma	1
1	Completed	Treatment	Recurrent Plasma Cell Myeloma / Refractory Plasma Cell Myeloma	1
1	Completed	Treatment	Unspecified Adult Solid Tumor, Protocol Specific	1
1	Recruiting	Treatment	Tumors, Solid	1
1	Terminated	Treatment	Acute Myelogenous Leukaemia (AML)	1
1	Terminated	Treatment	Bone Metastases / Unspecified Adult Solid Tumor, Protocol Specific	1
1	Terminated	Treatment	Estrogen Receptor Positive Breast Cancer	1
1	Terminated	Treatment	Lung Cancer Non-Small Cell Cancer (NSCLC)	1
1	Terminated	Treatment	Renal Cell Adenocarcinoma	1
1	Unknown Status	Treatment	Human Immunodeficiency Virus (HIV) Infections	1
1, 2	Active Not Recruiting	Treatment	Advanced Adenocarcinoma / Metastatic Adenocarcinoma	1
1, 2	Active Not Recruiting	Treatment	Histological 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 Months	1
1, 2	Active Not Recruiting	Treatment	Metastatic Renal Cell Carcinoma	1
1, 2	Completed	Diagnostic	Systemic Lupus Erythematosus (SLE)	1
1, 2	Completed	Treatment	Acute HIV Infection	1
1, 2	Completed	Treatment	Adenocarcinomas / Malignant Neoplasm of Colon / Metastasis / Rectal Carcinoma	1
1, 2	Not Yet Recruiting	Treatment	Recurrent Osteosarcoma / Refractory Osteosarcoma	1
1, 2	Not Yet Recruiting	Treatment	Type 2 Diabetes Mellitus	1
1, 2	Recruiting	Treatment	Acne Inversa / Follicular Occlusion Tetrad / Follicular Occlusion Triad / Furuncle / Hidradenitis / Hidradenitis Suppurativa (HS)	1
1, 2	Recruiting	Treatment	Advanced BRAF Mutant Melanoma	1
1, 2	Recruiting	Treatment	Colorectal Cancers	1
1, 2	Recruiting	Treatment	Disseminated Sclerosis	1
1, 2	Recruiting	Treatment	Platinum-resistant Epithelial Ovarian Cancer	1
1, 2	Recruiting	Treatment	Prostate Cancer	1
1, 2	Terminated	Treatment	Cancer, Breast	1
1, 2	Terminated	Treatment	Hepatitis C Viral Infection	1
1, 2	Terminated	Treatment	Lung Cancers	1
1, 2	Unknown Status	Treatment	Brain and Central Nervous System Tumors	1
1, 2	Unknown Status	Treatment	Lung Cancer Non-Small Cell Cancer (NSCLC)	1
1, 2	Unknown Status	Treatment	Malignant Neoplasm of Pancreas	1
1, 2	Unknown Status	Treatment	Multiple Myeloma and Plasma Cell Neoplasm	1
2	Active Not Recruiting	Treatment	Lung Cancer Non-Small Cell Cancer (NSCLC)	1
2	Active Not Recruiting	Treatment	Malignant Neoplasm of Pancreas	3
2	Active Not Recruiting	Treatment	Prostate Cancer	1
2	Completed	Treatment	Advanced Non-Small Cell Lung Cancer / Lung Cancer Non-Small Cell Cancer (NSCLC) / Non-Small Cell Lung Cancer Recurrent	1
2	Completed	Treatment	Colorectal Cancers	1
2	Completed	Treatment	Glioblastomas	1
2	Completed	Treatment	Hydroxychloroquine / IgA Patients	1
2	Completed	Treatment	Knee Osteoarthritis (Knee OA)	1
2	Completed	Treatment	Lichen Planus, Oral	1
2	Completed	Treatment	Prostate Cancer	1
2	Not Yet Recruiting	Treatment	Aortic Stiffness / Atherosclerosis / Cardiovascular Disease (CVD) / Chronic Kidney Disease (CKD) / Inflammatory Reaction	1
2	Recruiting	Prevention	Autoantibody-Associated Heart Block / Congenital Heart Block / Neonatal Lupus	1
2	Recruiting	Prevention	Healthy Participants / Healthy Volunteers / Rheumatoid Arthritis (RA) Prevention / Rheumatoid Arthritis Prevention	1
2	Recruiting	Prevention	Systemic Lupus Erythematosus (SLE) / Systemic Lupus Erythematosus Encephalitis	1
2	Recruiting	Prevention	Type1 Diabetes Mellitus	1
2	Recruiting	Treatment	Antiphospholipid Syndrome (APS)	1
2	Recruiting	Treatment	Breast Cancer Stage IIB	1
2	Recruiting	Treatment	Children´s Interstitial Lung Disease / Diffuse Parenchymal Lung Diseases / Interstitial Lung Disease (ILD)	1
2	Recruiting	Treatment	Colorectal Cancers	1
2	Recruiting	Treatment	Crohn's Disease (CD)	1
2	Recruiting	Treatment	Diabetes Mellitus Type 2 With Hyperglycemia	1
2	Recruiting	Treatment	Hepatocellular Cancer	1
2	Recruiting	Treatment	Insulin Dependent Diabetes / Pancreatitis, Chronic	1
2	Recruiting	Treatment	Lung Cancer Small Cell Lung Cancer (SCLC)	1
2	Recruiting	Treatment	Multiple Sclerosis, Primary Progressive	1
2	Recruiting	Treatment	Pancreatic Cancer Resectable / Pancreatic Cancer, Resectable Adenocarcinoma of the Pancreas	1
2	Recruiting	Treatment	Porphyria Cutanea Tarda	1
2	Terminated	Treatment	Arteriosclerosis / Cardiovascular Disease (CVD) / Chronic Renal Failure (CRF)	1
2	Terminated	Treatment	B-Cell Chronic Lymphocytic Leukemia	1
2	Terminated	Treatment	Prostate Cancer	1
2	Terminated	Treatment	Sarcomas	1
2	Unknown Status	Prevention	Flu caused by Influenza	1
2	Unknown Status	Treatment	Cancer, Breast	1
2	Unknown Status	Treatment	Human Immunodeficiency Virus (HIV) Infections	1
2	Unknown Status	Treatment	Leukemias	1
2	Withdrawn	Treatment	Abortions spontaneous / Recurrent Pregnancy Losses	1
3	Completed	Supportive Care	Graft Versus Host Disease (GVHD)	1
3	Completed	Treatment	Autoimmune Diseases / Eye Dryness / Sjögren's Syndrome	1
3	Completed	Treatment	Cutaneous Lupus Erythematosus-Systemic Lupus Erythematosus	1
3	Completed	Treatment	Giant Cells Arteritis	1
3	Completed	Treatment	Insulin Resistance / Rheumatoid Arthritis	1
3	Completed	Treatment	Osteoarthritis (OA)	1
3	Completed	Treatment	Primary Sjögren's Syndrome	1
3	Completed	Treatment	Rheumatoid Arthritis	4
3	Completed	Treatment	Sarcoidosis, Pulmonary	1
3	Completed	Treatment	Seronegative Spondyloarthropathies	1
3	Recruiting	Treatment	First Trimester Abortion / Recurrent Miscarriages	1
3	Recruiting	Treatment	Recurrent Pregnancy Losses	1
3	Recruiting	Treatment	Thrombocytopenias	1
3	Terminated	Prevention	Antiphospholipid Syndrome	1
4	Completed	Basic Science	Pre-Diabetic	1
4	Completed	Treatment	Alopecia Areata (AA)	1
4	Completed	Treatment	Borrelia Infection / Lyme Disease	1
4	Completed	Treatment	Immune Thrombocytopenia	1
4	Completed	Treatment	Primary IgA Nephropathy	1
4	Completed	Treatment	Rheumatoid Arthritis	3
4	Not Yet Recruiting	Treatment	Insufficient Response to Methotrexate / Rheumatoid Arthritis	1
4	Recruiting	Prevention	Nonvalvular Atrial Fibrillation	1
4	Recruiting	Treatment	Acute Coronary Syndromes (ACS) / Antirheumatic Agents / Cardiovascular Disease (CVD) / Hydroxychloroquine / Inflammatory Reaction / Myocardial Infarction / Unstable Angina (UA)	1
4	Recruiting	Treatment	Ankylosing Spondylitis (AS)	1
4	Recruiting	Treatment	Coronary Artery Disease	1
4	Recruiting	Treatment	Cutaneous Lupus / Juvenile SLE / Systemic Lupus Erythematosus (SLE)	1
4	Recruiting	Treatment	Individuals Undergoing Cardiac and General Surgery	1
4	Recruiting	Treatment	Primary IgA Nephropathy	1
4	Recruiting	Treatment	Rheumatoid Arthritis	4
Not Available	Active Not Recruiting	Basic Science	Human Immunodeficiency Virus (HIV)	1
Not Available	Completed	Not Available	Sjögren's Syndrome / Xerostomia	1
Not Available	Completed	Treatment	Hashimoto's Thyroiditis	1
Not Available	Completed	Treatment	Rheumatoid Arthritis	2
Not Available	Not Yet Recruiting	Not Available	Autoimmune Diseases	1
Not Available	Not Yet Recruiting	Treatment	Recurrent Pregnancy Losses / Undifferentiated Connective Tissue Disease	1
Not Available	Recruiting	Not Available	Chloroquine Retinopathy / Proliferative Nephritis	1
Not Available	Recruiting	Basic Science	Insulin Resistance	1
Not Available	Recruiting	Other	Type 2 Diabetes Mellitus	1
Not Available	Recruiting	Treatment	Systemic Lupus Erythematosus (SLE)	1
Not Available	Unknown Status	Treatment	Hashimoto's Thyroiditis	1
Not Available	Withdrawn	Treatment	Chronic Urticaria	1

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

Form	Route	Strength
Tablet, film coated	Enteral	200 mg/1
Tablet, film coated	Oral	200 mg/1
Tablet	Oral	200 mg
Tablet	Oral	200 mg/1

Prices

Unit description	Cost	Unit
Hydroxychloroquine sulf powder	4.8USD	g
Plaquenil 200 mg tablet	3.14USD	tablet
Hydroxychloroquine Sulfate 200 mg tablet	1.28USD	tablet
Hydroxychloroquine 200 mg tablet	1.17USD	tablet
Plaquenil Sulfate 200 mg Tablet	0.66USD	tablet
Apo-Hydroxyquine 200 mg Tablet	0.35USD	tablet
Mylan-Hydroxychloroquine 200 mg Tablet	0.35USD	tablet

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	89-91	U.S. Patent 2,546,658.

Predicted Properties

Property	Value	Source
Water Solubility	0.0261 mg/mL	ALOGPS
logP	3.87	ALOGPS
logP	2.89	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	15.59	ChemAxon
pKa (Strongest Basic)	9.76	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	48.39 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	97.97 m³·mol^-1	ChemAxon
Polarizability	38.3 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET features

Property	Value	Probability
Human Intestinal Absorption	+	0.9892
Blood Brain Barrier	+	0.5602
Caco-2 permeable	-	0.5154
P-glycoprotein substrate	Substrate	0.8348
P-glycoprotein inhibitor I	Non-inhibitor	0.7297
P-glycoprotein inhibitor II	Inhibitor	0.5106
Renal organic cation transporter	Non-inhibitor	0.5742
CYP450 2C9 substrate	Non-substrate	0.8239
CYP450 2D6 substrate	Non-substrate	0.9117
CYP450 3A4 substrate	Non-substrate	0.5384
CYP450 1A2 substrate	Non-inhibitor	0.5864
CYP450 2C9 inhibitor	Non-inhibitor	0.8457
CYP450 2D6 inhibitor	Non-inhibitor	0.6111
CYP450 2C19 inhibitor	Non-inhibitor	0.8782
CYP450 3A4 inhibitor	Non-inhibitor	0.6287
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.7058
Ames test	AMES toxic	0.6907
Carcinogenicity	Non-carcinogens	0.837
Biodegradation	Not ready biodegradable	1.0
Rat acute toxicity	2.6348 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.6798
hERG inhibition (predictor II)	Inhibitor	0.7173

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Mass Spectrum (Electron Ionization)	MS	splash10-0f6t-3972000000-7c193125680c0c9e276f
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not 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

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]
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]
Koranda FC: Antimalarials. J Am Acad Dermatol. 1981 Jun;4(6):650-5. [PubMed:6165744]

Details2. Toll-like receptor 7

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

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]
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]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Details3. Toll-like receptor 9

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

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]
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

Details1. Cytochrome P450 2D6

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

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]
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

Details1. Multidrug resistance protein 1

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

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]
Plaquenil (hydroxychloroquine sulfate) - Drug Summary [Link]

Drug created on August 29, 2007 14:00 / Updated on November 17, 2018 07:19

Hydroxychloroquine

Identification

Structure for Hydroxychloroquine (DB01611)

Pharmacology

Interactions

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Taxonomy

Targets

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References

References

Enzymes

References

Transporters

References