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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyHydroxychloroquine
Identification
- Name
- Hydroxychloroquine
- Accession Number
- DB01611
- Type
- Small Molecule
- Groups
- Approved
- Description
A chemotherapeutic agent that acts against erythrocytic forms of malarial parasites.
- Structure
Structure for Hydroxychloroquine (DB01611)
- Synonyms
- (±)-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-β-hydroxyethylamino)-1-methylbutylamino)quinoline
- 7-chloro-4-[4-(N-ethyl-N-β-hydroxyethylamino)-1-methylbutylamino]quinoline
- 7-chloro-4-[5-(N-ethyl-N-2-hydroxyethylamino)-2-pentyl]aminoquinoline
- Hidroxicloroquina
- Hydroxychloroquine
- Hydroxychloroquinum
- Oxichlorochine
- Oxichloroquine
- 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 US 
Plaquenil Tablet 200 mg/1 Oral Concordia Pharmaceuticals Inc. 2013-06-28 Not applicable US Plaquenil Tablet 200 mg/1 Oral Aphena Pharma Solutions Tennessee, Inc. 2013-06-28 Not applicable US Plaquenil Tablet 200 mg/1 Oral Av Kare, Inc. 2016-07-14 Not applicable US Plaquenil Tablet 200 mg/1 Oral Carilion Materials Management 2013-06-28 Not applicable US Plaquenil Tablet, film coated 200 mg/1 Oral Sanofi Aventis 1955-04-18 2013-05-31 US Plaquenil Tablet 200 mg Oral Sanofi Aventis 1957-12-31 Not applicable Canada 
- 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 Major 1995-11-30 Not applicable US Hydroxychloroquine sulfate Tablet, film coated 200 mg/1 Oral bryant ranch prepack 2008-01-03 Not applicable US Hydroxychloroquine Sulfate Tablet, film coated 200 mg/1 Oral A-S Medication Solutions 2009-01-07 Not applicable US Hydroxychloroquine Sulfate Tablet, film coated 200 mg/1 Oral West Ward Pharmaceutical 2007-08-15 Not applicable US Hydroxychloroquine Sulfate Tablet 200 mg/1 Oral Dr. Reddy's Laboratories Inc. 2018-05-01 Not applicable US Hydroxychloroquine Sulfate Tablet 200 mg/1 Oral Av Kare, Inc. 2012-02-29 2015-11-04 US Hydroxychloroquine Sulfate Tablet, film coated 200 mg/1 Oral Sun Pharmaceutical Industries Limited 2009-01-07 Not applicable US Hydroxychloroquine sulfate Tablet, film coated 200 mg/1 Oral McKesson Corporation 2008-01-03 Not applicable US Hydroxychloroquine Sulfate Tablet, film coated 200 mg/1 Oral Ohm Laboratories, Inc. 2009-01-07 Not applicable US - International/Other Brands
- Axokine (AstraZeneca) / Dolquine (Inmunosyn) / HCQS (Medigroup) / Polirreumin (TRB) / Quensyl (Sanofi)
- Categories
- Aminoquinolines
- Anti-Infective Agents
- Antimalarials
- Antiparasitic Agents
- Antiparasitic Products, Insecticides and Repellents
- Antiprotozoals
- Chloroquine
- Cytochrome P-450 CYP2D6 Inhibitors
- Cytochrome P-450 Enzyme Inhibitors
- Enzyme Inhibitors
- Immunosuppressive Agents
- P-glycoprotein/ABCB1 Inhibitors
- Potential QTc-Prolonging Agents
- QTc Prolonging Agents
- Quinolines
- 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/alkylationHumans AToll-like receptor 7 antagonistHumans AToll-like receptor 9 antagonistHumans - 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
- 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
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/1 Tablet Oral 200 mg - 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
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
Yes
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]
- Kind
- Protein
- Organism
- Humans
- 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]
- Kind
- Protein
- Organism
- Humans
- 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
- Kind
- Protein
- Organism
- Humans
- 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
- Kind
- Protein
- Organism
- Humans
- 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 February 18, 2019 20:23