Hydroxychloroquine

ID Pharmacology Interactions References Trials Economics Properties Spectra Taxonomy

Targets (3)Enzymes (1)

Targets (3)Enzymes (1)Biointeractions (3)

Identification

Name

Hydroxychloroquine

Accession Number

DB01611

Type

Small Molecule

Groups

Approved

Description

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

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

(+-)-Hydroxychloroquine

(±)-hydroxychloroquine

2-((4-((7-chloro-4-Quinolyl)amino)pentyl)ethylamino)ethanol

2-(N-(4-(7-Chlor-4-chinolylamino)-4-methylbutyl)ethylamino)ethanol

7-chloro-4-(4-(Ethyl(2-hydroxyethyl)amino)-1-methylbutylamino)quinoline

7-chloro-4-(4-(N-Ethyl-N-beta-hydroxyethylamino)-1-methylbutylamino)quinoline

7-chloro-4-[4-(N-Ethyl-N-beta-hydroxyethylamino)-1-methylbutylamino]quinoline

7-chloro-4-[5-(N-Ethyl-N-2-hydroxyethylamino)-2-pentyl]aminoquinoline

Hidroxicloroquina

Hydroxychloroquinum

NSC4375

Oxichlorochine

Oxichloroquine

Polirreumin

External IDs

Not Available

Product Ingredients

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

Product Images

Approved Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Hydroxychloroquine Sulfate	Tablet	200 mg/1	Oral	Aphena Pharma Solutions Tennessee, Inc.	2014-12-12	Not applicable	US
Hydroxychloroquine Sulfate	Tablet	200 mg/1	Oral	Avera Mc Kennan Hospital	2015-03-24	Not applicable	US
Hydroxychloroquine Sulfate	Tablet	200 mg/1	Oral	Prasco, Laboratories	2014-12-12	Not applicable	US
Mint-hydroxychloroquine	Tablet	200 mg	Oral	Mint Pharmaceuticals Inc	2014-06-10	Not applicable	Canada
Mylan-hydroxychloroquine	Tablet	200 mg	Oral	Mylan Pharmaceuticals	2004-05-21	Not applicable	Canada
Nu-hydroxyquine	Tablet	200 mg	Oral	Nu Pharm Inc	Not applicable	Not applicable	Canada
Plaquenil	Tablet	200 mg/1	Oral	Aphena Pharma Solutions Tennessee, Inc.	2013-06-28	Not applicable	US
Plaquenil	Tablet, film coated	200 mg/1	Oral	Sanofi Aventis	1955-04-18	Not applicable	US
Plaquenil	Tablet	200 mg	Oral	Sanofi Aventis	1957-12-31	Not applicable	Canada
Plaquenil	Tablet	200 mg/1	Oral	Concordia Pharmaceuticals, Inc	2013-06-28	Not applicable	US
Plaquenil	Tablet	200 mg/1	Oral	Covis Pharmaceuticals, Inc.	2013-06-28	2017-12-31	US
Plaquenil	Tablet	200 mg/1	Oral	Carilion Materials Management	2013-06-28	Not applicable	US
Plaquenil	Tablet	200 mg/1	Oral	Av Kare, Inc.	2016-07-14	Not applicable	US
PMS-hydroxychloroquine	Tablet	200 mg	Oral	Pharmascience Inc	Not applicable	Not applicable	Canada
Pro-hydroxyquine - 200	Tablet	200 mg	Oral	Pro Doc Limitee	2008-07-29	Not applicable	Canada

Approved 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	Canada
Hydroxychloroquine Sulfate	Tablet, film coated	200 mg/1	Oral	Avera Mc Kennan Hospital	2015-08-31	Not applicable	US
Hydroxychloroquine Sulfate	Tablet, film coated	200 mg/1	Oral	Actavis Pharma Company	2016-03-24	Not applicable	US
Hydroxychloroquine Sulfate	Tablet, film coated	200 mg/1	Oral	West Ward Pharmaceutical	2007-08-15	Not applicable	US
Hydroxychloroquine Sulfate	Tablet, film coated	200 mg/1	Oral	Amerincan Health Packaging	2008-08-05	Not applicable	US
Hydroxychloroquine Sulfate	Tablet, film coated	200 mg/1	Oral	Cardinal Health	2008-08-05	Not applicable	US
Hydroxychloroquine Sulfate	Tablet	200 mg/1	Oral	Aphena Pharma Solutions Tennessee, Inc.	2012-02-29	Not applicable	US
Hydroxychloroquine Sulfate	Tablet, film coated	200 mg/1	Oral	Major	1995-11-30	Not applicable	US
Hydroxychloroquine Sulfate	Tablet, film coated	200 mg/1	Oral	Zydus Pharmaceuticals Usa, Inc.	2008-01-03	Not applicable	US
Hydroxychloroquine Sulfate	Tablet, film coated	200 mg/1	Oral	Ranbaxy Inc.	2009-01-07	Not applicable	US
Hydroxychloroquine Sulfate	Tablet, film coated	200 mg/1	Oral	Physicians Total Care, Inc.	1996-07-09	Not applicable	US
Hydroxychloroquine Sulfate	Tablet, film coated	200 mg/1	Oral	Aphena Pharma Solutions Tennessee, Inc.	2014-05-19	Not applicable	US
Hydroxychloroquine Sulfate	Tablet, film coated	200 mg/1	Oral	A S Medication Solutions	2009-01-07	2017-06-20	US
Hydroxychloroquine Sulfate	Tablet, film coated	200 mg/1	Oral	Aidarex Pharmaceuticals LLC	2009-01-07	Not applicable	US
Hydroxychloroquine Sulfate	Tablet, film coated	200 mg/1	Oral	Cadila Pharnmaceuticals	2008-01-03	Not applicable	US
Hydroxychloroquine Sulfate	Tablet	200 mg/1	Oral	Remedy Repack	2011-04-13	2016-10-13	US
Hydroxychloroquine Sulfate	Tablet	200 mg/1	Oral	Av Kare, Inc.	2012-02-29	2015-12-29	US
Hydroxychloroquine Sulfate	Tablet, film coated	200 mg/1	Enteral	Mylan Institutional	2016-03-28	Not applicable	US
Hydroxychloroquine Sulfate	Tablet, coated	200 mg/1	Oral	Watson Pharmaceuticals	1995-11-30	2016-03-05	US
Hydroxychloroquine Sulfate	Tablet, film coated	200 mg/1	Oral	A S Medication Solutions	2016-03-24	2017-06-20	US
Hydroxychloroquine Sulfate	Tablet, film coated	200 mg/1	Oral	Cardinal Health	1995-11-30	Not applicable	US
Hydroxychloroquine Sulfate	Tablet, film coated	200 mg/1	Oral	Blenheim Pharmacal, Inc.	2013-12-20	Not applicable	US
Hydroxychloroquine Sulfate	Tablet, film coated	200 mg/1	Oral	bryant ranch prepack	2009-01-07	Not applicable	US
Hydroxychloroquine Sulfate	Tablet, film coated	200 mg/1	Oral	A S Medication Solutions	2009-01-07	2017-06-20	US
Hydroxychloroquine Sulfate	Tablet, film coated	200 mg/1	Oral	Dispensing Solutions, Inc.	2009-01-07	Not applicable	US
Hydroxychloroquine Sulfate	Tablet, film coated	200 mg/1	Oral	Directrx	2014-01-01	Not applicable	US
Hydroxychloroquine Sulfate	Tablet, film coated	200 mg/1	Oral	Av Kare, Inc.	2014-05-19	Not applicable	US
Hydroxychloroquine Sulfate	Tablet, film coated	200 mg/1	Oral	Golden State Medical Supply	2007-08-15	Not applicable	US
Hydroxychloroquine Sulfate	Tablet, film coated	200 mg/1	Oral	Ohm Laboratories, Inc.	2009-01-07	Not applicable	US
Hydroxychloroquine Sulfate	Tablet, film coated	200 mg/1	Oral	North Star Rx Llc	2015-12-18	Not applicable	US
Hydroxychloroquine Sulfate	Tablet, film coated	200 mg/1	Oral	Aphena Pharma Solutions Tennessee, Inc.	1995-11-30	Not applicable	US
Hydroxychloroquine Sulfate	Tablet, film coated	200 mg/1	Oral	Sandoz	1995-11-30	Not applicable	US
Hydroxychloroquine Sulfate	Tablet, film coated	200 mg/1	Enteral	Mylan Pharmaceuticals	1998-06-18	Not applicable	US
Hydroxychloroquine Sulfate	Tablet, film coated	200 mg/1	Oral	A S Medication Solutions	2009-01-07	2017-06-20	US
Hydroxychloroquine Sulfate	Tablet, film coated	200 mg/1	Oral	Rebel Distributors	2009-01-07	Not applicable	US
Hydroxychloroquine Sulfate	Tablet, film coated	200 mg/1	Oral	Mc Kesson Packaging Services A Buisness Unit Of Mc Kesson Corporation	2008-01-03	Not applicable	US

Approved Over the Counter Products

Not Available

Unapproved/Other Products

Not Available

International Brands

Name	Company
Axokine	AstraZeneca
Dolquine	Inmunosyn
HCQS	Medigroup
Polirreumin	TRB
Quensyl	Sanofi

Brand mixtures

Not Available

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.

Target	Kind	Pharmacological action	Actions	Organism	UniProt ID
DNA	Nucleotide	yes	cross-linking/alkylation	Human	not applicable	details
Toll-like receptor 7	Protein	yes	antagonist	Human	Q9NYK1	details
Toll-like receptor 9	Protein	yes	antagonist	Human	Q9NR96	details

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	Drug group
Acebutolol	The metabolism of Acebutolol can be decreased when combined with Hydroxychloroquine.	Approved
Acepromazine	The serum concentration of Acepromazine can be increased when it is combined with Hydroxychloroquine.	Approved, Vet Approved
Aceprometazine	The serum concentration of Aceprometazine can be increased when it is combined with Hydroxychloroquine.	Approved
Acetyldigitoxin	The serum concentration of Acetyldigitoxin can be increased when it is combined with Hydroxychloroquine.	Approved
Albendazole	The serum concentration of Albendazole can be decreased when it is combined with Hydroxychloroquine.	Approved, Vet Approved
Alimemazine	The serum concentration of Alimemazine can be increased when it is combined with Hydroxychloroquine.	Approved, Vet Approved
Alprenolol	The metabolism of Alprenolol can be decreased when combined with Hydroxychloroquine.	Approved, Withdrawn
Arotinolol	The metabolism of Arotinolol can be decreased when combined with Hydroxychloroquine.	Approved
Artemether	The risk or severity of adverse effects can be increased when Artemether is combined with Hydroxychloroquine.	Approved
Atenolol	The metabolism of Atenolol can be decreased when combined with Hydroxychloroquine.	Approved
Befunolol	The metabolism of Befunolol can be decreased when combined with Hydroxychloroquine.	Experimental
Benzimidazole	The serum concentration of Benzimidazole can be decreased when it is combined with Hydroxychloroquine.	Experimental
Betaxolol	The metabolism of Betaxolol can be decreased when combined with Hydroxychloroquine.	Approved
Bevantolol	The metabolism of Bevantolol can be decreased when combined with Hydroxychloroquine.	Approved
Bisoprolol	The metabolism of Bisoprolol can be decreased when combined with Hydroxychloroquine.	Approved
Bithionol	The serum concentration of Bithionol can be decreased when it is combined with Hydroxychloroquine.	Withdrawn
BL-1020	The serum concentration of BL-1020 can be increased when it is combined with Hydroxychloroquine.	Investigational
Bopindolol	The metabolism of Bopindolol can be decreased when combined with Hydroxychloroquine.	Approved
Bucindolol	The metabolism of Bucindolol can be decreased when combined with Hydroxychloroquine.	Investigational
Bufuralol	The metabolism of Bufuralol can be decreased when combined with Hydroxychloroquine.	Experimental, Investigational
Bupranolol	The metabolism of Bupranolol can be decreased when combined with Hydroxychloroquine.	Approved
Carteolol	The metabolism of Carteolol can be decreased when combined with Hydroxychloroquine.	Approved
Carvedilol	The metabolism of Carvedilol can be decreased when combined with Hydroxychloroquine.	Approved, Investigational
Celiprolol	The metabolism of Celiprolol can be decreased when combined with Hydroxychloroquine.	Approved, Investigational
Chloroquine	The serum concentration of Chloroquine can be decreased when it is combined with Hydroxychloroquine.	Approved, Vet Approved
Chlorpromazine	The serum concentration of Chlorpromazine can be increased when it is combined with Hydroxychloroquine.	Approved, Vet Approved
Dapsone	The risk or severity of adverse effects can be increased when Hydroxychloroquine is combined with Dapsone.	Approved, Investigational
Deslanoside	The serum concentration of Deslanoside can be increased when it is combined with Hydroxychloroquine.	Approved
Diethylcarbamazine	The serum concentration of Diethylcarbamazine can be decreased when it is combined with Hydroxychloroquine.	Approved, Vet Approved
Digitoxin	The serum concentration of Digitoxin can be increased when it is combined with Hydroxychloroquine.	Approved
Digoxin	The serum concentration of Digoxin can be increased when it is combined with Hydroxychloroquine.	Approved
Esmolol	The metabolism of Esmolol can be decreased when combined with Hydroxychloroquine.	Approved
Fesoterodine	The serum concentration of the active metabolites of Fesoterodine can be increased when Fesoterodine is used in combination with Hydroxychloroquine.	Approved
Flubendazole	The serum concentration of Flubendazole can be decreased when it is combined with Hydroxychloroquine.	Approved, Withdrawn
Fluphenazine	The serum concentration of Fluphenazine can be increased when it is combined with Hydroxychloroquine.	Approved
Indenolol	The metabolism of Indenolol can be decreased when combined with Hydroxychloroquine.	Withdrawn
Ivermectin	The serum concentration of Ivermectin can be decreased when it is combined with Hydroxychloroquine.	Approved, Vet Approved
Labetalol	The metabolism of Labetalol can be decreased when combined with Hydroxychloroquine.	Approved
Landiolol	The metabolism of Aop200704 can be decreased when combined with Hydroxychloroquine.	Investigational
Levamisole	The serum concentration of Levamisole can be decreased when it is combined with Hydroxychloroquine.	Vet Approved, Withdrawn
Levobunolol	The metabolism of Levobunolol can be decreased when combined with Hydroxychloroquine.	Approved
Lucanthone	The serum concentration of Lucanthone can be decreased when it is combined with Hydroxychloroquine.	Approved, Investigational
Lumefantrine	The risk or severity of adverse effects can be increased when Hydroxychloroquine is combined with Lumefantrine.	Approved
Mebendazole	The serum concentration of Mebendazole can be decreased when it is combined with Hydroxychloroquine.	Approved, Vet Approved
Mefloquine	The risk or severity of adverse effects can be increased when Hydroxychloroquine is combined with Mefloquine.	Approved
Mesoridazine	The serum concentration of Mesoridazine can be increased when it is combined with Hydroxychloroquine.	Approved
Methotrimeprazine	The serum concentration of Methotrimeprazine can be increased when it is combined with Hydroxychloroquine.	Approved
Methylene blue	The serum concentration of Methylene blue can be increased when it is combined with Hydroxychloroquine.	Investigational
Metipranolol	The metabolism of Metipranolol can be decreased when combined with Hydroxychloroquine.	Approved
Metoprolol	The serum concentration of Metoprolol can be increased when it is combined with Hydroxychloroquine.	Approved, Investigational
Moricizine	The serum concentration of Moricizine can be increased when it is combined with Hydroxychloroquine.	Approved, Withdrawn
Nadolol	The metabolism of Nadolol can be decreased when combined with Hydroxychloroquine.	Approved
Niclosamide	The serum concentration of Niclosamide can be decreased when it is combined with Hydroxychloroquine.	Approved, Vet Approved
Oleandrin	The serum concentration of Anvirzel can be increased when it is combined with Hydroxychloroquine.	Experimental
Ouabain	The serum concentration of Ouabain can be increased when it is combined with Hydroxychloroquine.	Approved
Oxamniquine	The serum concentration of Oxamniquine can be decreased when it is combined with Hydroxychloroquine.	Approved
Oxibendazole	The serum concentration of Oxibendazole can be decreased when it is combined with Hydroxychloroquine.	Investigational, Vet Approved
Oxprenolol	The metabolism of Oxprenolol can be decreased when combined with Hydroxychloroquine.	Approved
Penbutolol	The metabolism of Penbutolol can be decreased when combined with Hydroxychloroquine.	Approved, Investigational
Perazine	The serum concentration of Perazine can be increased when it is combined with Hydroxychloroquine.	Investigational
Perphenazine	The serum concentration of Perphenazine can be increased when it is combined with Hydroxychloroquine.	Approved
Pindolol	The metabolism of Pindolol can be decreased when combined with Hydroxychloroquine.	Approved
Piperazine	The serum concentration of Piperazine can be decreased when it is combined with Hydroxychloroquine.	Approved, Vet Approved
Practolol	The metabolism of Practolol can be decreased when combined with Hydroxychloroquine.	Approved
Praziquantel	The serum concentration of Praziquantel can be decreased when it is combined with Hydroxychloroquine.	Approved, Vet Approved
Prochlorperazine	The serum concentration of Prochlorperazine can be increased when it is combined with Hydroxychloroquine.	Approved, Vet Approved
Promazine	The serum concentration of Promazine can be increased when it is combined with Hydroxychloroquine.	Approved, Vet Approved
Promethazine	The serum concentration of Promethazine can be increased when it is combined with Hydroxychloroquine.	Approved
Propranolol	The metabolism of Propranolol can be decreased when combined with Hydroxychloroquine.	Approved, Investigational
Pyrvinium	The serum concentration of Pyrvinium can be decreased when it is combined with Hydroxychloroquine.	Approved
Quinacrine	The serum concentration of Quinacrine can be decreased when it is combined with Hydroxychloroquine.	Approved
Sodium stibogluconate	The serum concentration of Sodium stibogluconate can be decreased when it is combined with Hydroxychloroquine.	Approved, Investigational
Sotalol	The metabolism of Sotalol can be decreased when combined with Hydroxychloroquine.	Approved
Suramin	The serum concentration of Suramin can be decreased when it is combined with Hydroxychloroquine.	Approved
Thiabendazole	The serum concentration of Thiabendazole can be decreased when it is combined with Hydroxychloroquine.	Approved, Vet Approved
Thiethylperazine	The serum concentration of Thiethylperazine can be increased when it is combined with Hydroxychloroquine.	Withdrawn
Thioridazine	The serum concentration of Thioridazine can be increased when it is combined with Hydroxychloroquine.	Withdrawn
Timolol	The metabolism of Timolol can be decreased when combined with Hydroxychloroquine.	Approved
Triclabendazole	The serum concentration of Triclabendazole can be decreased when it is combined with Hydroxychloroquine.	Investigational
Trifluoperazine	The serum concentration of Trifluoperazine can be increased when it is combined with Hydroxychloroquine.	Approved
Triflupromazine	The 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

Resource	Link
Human Metabolome Database (HMDB)	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
Drug Product Database	6506
RxList	http://www.rxlist.com/cgi/generic/hquine.htm
Drugs.com	http://www.drugs.com/cdi/hydroxychloroquine.html
Wikipedia	Hydroxychloroquine

ATC Codes

P01BA02 — Hydroxychloroquine

AHFS Codes

Not Available

PDB Entries

Not Available

FDA label

Not Available

MSDS

Not Available

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	Malignant Neoplasm of Prostate	1
1	Active Not Recruiting	Treatment	Adult Solid Neoplasm	1
1	Active Not Recruiting	Treatment	Adult Solid Neoplasm / Hormone-Resistant Prostate Cancer / Recurrent Melanoma / Recurrent Prostate Carcinoma / Renal Cell Carcinoma Recurrent / Stage IIIA Skin Melanoma / Stage IIIB Skin Melanoma / Stage IIIC Skin Melanoma / Stage IV Prostate Cancer / Stage IV Renal Cell Cancer / Stage IV Skin Melanoma	1
1	Active Not Recruiting	Treatment	Advanced Cancers	1
1	Active Not Recruiting	Treatment	Melanoma	1
1	Active Not Recruiting	Treatment	Recurrent Plasma Cell Myeloma / Refractory Plasma Cell Myeloma	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	Lymphangioleiomyomatosis	1
1	Completed	Treatment	Unspecified Adult Solid Tumor, Protocol Specific	1
1	Not Yet Recruiting	Treatment	Acute Myelogenous Leukaemia (AML)	1
1	Not Yet Recruiting	Treatment	Tumors, Solid	1
1	Recruiting	Treatment	Estrogen Receptor Positive Breast Cancer	1
1	Recruiting	Treatment	Malignant Solid Tumours	1
1	Recruiting	Treatment	Tumors, Solid	1
1	Terminated	Treatment	Bone Metastases / Unspecified Adult Solid Tumor, Protocol Specific	1
1	Terminated	Treatment	Non-Small-Cell Lung Carcinoma (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	Adenocarcinomas / Malignant Neoplasm of Colon / Metastasis / Rectal Carcinoma	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	Completed	Diagnostic	Systemic Lupus Erythematosus (SLE)	1
1, 2	Completed	Treatment	Acute HIV Infection	1
1, 2	Not Yet Recruiting	Treatment	Diabetes Type Two	1
1, 2	Not Yet Recruiting	Treatment	Platinum-resistant Epithelial Ovarian Cancer	1
1, 2	Recruiting	Treatment	Advanced Adenocarcinoma / Metastatic Adenocarcinoma	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	Metastatic Renal Cell Carcinoma	1
1, 2	Terminated	Treatment	Cancer, Breast	1
1, 2	Terminated	Treatment	Chronic Hepatitis C 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	Malignant Neoplasm of Pancreas	1
1, 2	Unknown Status	Treatment	Multiple Myeloma and Plasma Cell Neoplasm	1
1, 2	Unknown Status	Treatment	Non-Small-Cell Lung Carcinoma (NSCLC)	1
2	Active Not Recruiting	Treatment	Glioblastomas	1
2	Active Not Recruiting	Treatment	Malignant Neoplasm of Pancreas	2
2	Active Not Recruiting	Treatment	Malignant Neoplasm of Prostate	1
2	Active Not Recruiting	Treatment	Non-Small-Cell Lung Carcinoma (NSCLC)	1
2	Completed	Treatment	Advanced Non-Small Cell Lung Cancer / Non-Small-Cell Lung Carcinoma (NSCLC) / Recurrent Non-small Cell Lung Cancer	1
2	Completed	Treatment	Colorectal Cancers	1
2	Completed	Treatment	Lichen Planus, Oral	1
2	Completed	Treatment	Malignant Neoplasm of Prostate	1
2	Completed	Treatment	Osteoarthritis of the Knees	1
2	Not Yet Recruiting	Prevention	Systemic Lupus Erythematosus Encephalitis	1
2	Not Yet Recruiting	Treatment	Hepatocellular Cancer	1
2	Not Yet Recruiting	Treatment	Lung Cancer Small Cell Lung Cancer (SCLC)	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	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	Diabetes Mellitus Type 2 With Hyperglycemia	1
2	Recruiting	Treatment	Hydroxychloroquine / IgA Patients	1
2	Recruiting	Treatment	Malignant Neoplasm of Pancreas	1
2	Recruiting	Treatment	Multiple Sclerosis, Primary Progressive	1
2	Recruiting	Treatment	Porphyria Cutanea Tarda	1
2	Terminated	Treatment	Arteriosclerosis / Cardiovascular Disease (CVD) / Kidney Failure,Chronic	1
2	Terminated	Treatment	B-Cell Chronic Lymphocytic Leukemia	1
2	Terminated	Treatment	Malignant Neoplasm of Prostate	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	Crohn's Disease (CD)	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 / Sjogren'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	Primary Sjögren's Syndrome	1
3	Completed	Treatment	Rheumatoid Arthritis	4
3	Completed	Treatment	Sarcoidosis, Pulmonary	1
3	Completed	Treatment	Seronegative Spondyloarthropathies	1
3	Completed	Treatment	Synovitis of osteoarthritis	1
3	Not Yet Recruiting	Treatment	First Trimester Abortion / Recurrent Miscarriages	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	Primary IgA Nephropathy	1
4	Completed	Treatment	Rheumatoid Arthritis	3
4	Not Yet Recruiting	Treatment	Coronary Artery Disease	1
4	Not Yet Recruiting	Treatment	Cutaneous Lupus / Juvenile SLE / Systemic Lupus Erythematosus (SLE)	1
4	Not Yet Recruiting	Treatment	Individuals Undergoing Cardiac and General Surgery	1
4	Not Yet Recruiting	Treatment	Insufficient Response to Methotrexate / Rheumatoid Arthritis	1
4	Recruiting	Treatment	Acute Coronary Syndromes (ACS) / Antirheumatic Agents / Cardiovascular Disease (CVD) / Hydroxychloroquine / Inflammatory Reaction / Myocardial Infarction (MI) / Unstable Angina (UA)	1
4	Recruiting	Treatment	Primary IgA Nephropathy	1
4	Recruiting	Treatment	Rheumatoid Arthritis	3
Not Available	Active Not Recruiting	Basic Science	HIV Disease	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	1
Not Available	Not Yet Recruiting	Not Available	Autoimmune Diseases	1
Not Available	Recruiting	Not Available	Type 2 Diabetes Mellitus	1
Not Available	Recruiting	Basic Science	Insulin Resistance	1
Not Available	Recruiting	Treatment	Rheumatoid Arthritis	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	Oral	200 mg/1
Tablet, coated	Oral	200 mg/1
Tablet, film coated	Enteral	200 mg/1
Tablet	Oral	200 mg
Tablet, film coated	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 Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available
MS	Mass Spectrum (Electron Ionization)	splash10-0f6t-3972000000-7c193125680c0c9e276f	View in MoNA

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

Substituents

Chloroquinoline / 4-aminoquinoline / Haloquinoline / Aminopyridine / Secondary aliphatic/aromatic amine / Aryl chloride / Aryl halide / Pyridine / Benzenoid / Heteroaromatic compound

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 ]

Details

2. 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 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
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 ]

Details

3. 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 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
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

Details

1. 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 antidepressants.
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 ]

Drug created on August 29, 2007 14:00 / Updated on July 18, 2017 17:00

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Structure for DB01611 (Hydroxychloroquine)

Targets

References

References

References

Enzymes

References