Hydroxychloroquine
Identification
- Name
- Hydroxychloroquine
- Accession Number
- DB01611
- Type
- Small Molecule
- Groups
- Approved
- Description
Hydroxychloroquine is a racemic mixture consisting of an R and S enantiomer.2 Hydroxychloroquine is an aminoquinoline like chloroquine.13 It is a commonly prescribed medication in the treatment of uncomplicated malaria, rheumatoid arthritis, chronic discoid lupus erythematosus, and systemic lupus erythematosus.13 Hydroxychloroquine is also used for the prophylaxis of malaria in regions where chloroquine resistance is unlikely.13 It was developed during World War II as a derivative of quinacrine with less severe side effects.6 Chloroquine and hydroxychloroquine are both being investigated for the treatment of SARS-CoV-2.7
The FDA emergency use authorization for hydroxychloroquine and chloroquine in the treatment of COVID-19 was revoked on 15 June 2020.14
Hydroxychloroquine was granted FDA approval on 18 April 1955.13
A recent study reported a fatality in the group being treated with hydroxychloroquine for COVID-19.10
- 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 Unlock Additional DataPlaquenil Tablet 200 mg/1 Oral Aphena Pharma Solutions Tennessee, Inc. 2013-06-28 Not applicable US 
Plaquenil Tablet 200 mg/1 Oral Carilion Materials Management 2013-06-28 Not applicable US Plaquenil Tablet Oral Sanofi Aventis 1957-12-31 Not applicable Canada 
Plaquenil Tablet 200 mg/1 Oral RedPharm Drug, Inc. 2020-01-01 Not applicable US Plaquenil Tablet 200 mg/1 Oral Proficient Rx LP 2013-06-28 Not applicable US Plaquenil Tablet 200 mg/1 Oral Concordia Pharmaceuticals Inc. 2013-06-28 Not applicable US Plaquenil Tablet 200 mg/1 Oral AvKARE, Inc. 2016-07-14 2019-03-31 US Plaquenil Tablet, film coated 200 mg/1 Oral Sanofi Aventis 1955-04-18 2013-05-31 US Plaquenil Tablet 200 mg/1 Oral Covis Pharmaceuticals, Inc. 2013-06-28 2017-12-31 US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Unlock Additional DataApo-hydroxyquine Tablet Oral Apotex Corporation 2002-12-13 Not applicable Canada Hydroxychloroquine Sulfate Tablet, film coated 200 mg/1 Oral Hikma Pharmaceuticals USA Inc. 2007-08-15 2014-01-31 US Hydroxychloroquine Sulfate Tablet, film coated 200 mg/1 Oral A-S Medication Solutions 2016-03-30 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 Doh Central Pharmacy 2017-08-27 Not applicable US Hydroxychloroquine Sulfate Tablet, film coated 200 mg/1 Oral Amneal Pharmaceuticals NY LLC 2018-05-17 Not applicable US Hydroxychloroquine sulfate Tablet, film coated 200 mg/1 Oral Cadila Healthcare Limited 2008-01-03 Not applicable US Hydroxychloroquine Sulfate Tablet 200 mg/1 Oral Remedy Repack 2011-04-13 2011-04-14 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 Major Pharmaceuticals 1995-11-30 2019-11-30 US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- International/Other Brands
- Dolquine (Inmunosyn) / HCQS (Medigroup) / Polirreumin (TRB) / Quensyl (Sanofi)
- Categories
- Aminoquinolines
- Anti-Infective Agents
- Antimalarials
- Antiparasitic Agents
- Antiparasitic Products, Insecticides and Repellents
- Antiprotozoals
- Antirheumatic Agents
- Cytochrome P-450 CYP2C8 Substrates
- Cytochrome P-450 CYP2D6 Inhibitors
- Cytochrome P-450 CYP2D6 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2D6 Substrates
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Drugs causing inadvertant photosensitivity
- Enzyme Inhibitors
- Heterocyclic Compounds, Fused-Ring
- Immunosuppressive Agents
- P-glycoprotein inhibitors
- Photosensitizing Agents
- 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
Hydroxychloroquine is indicated for the prophylaxis of malaria where chloroquine resistance is not reported, treatment of uncomplicated malaria (caused by P. falciparum, P. malariae, P. ovale, or P. vivax), chronic discoid lupus erythematosus, systemic lupus erythematosus, acute rheumatoid arthritis, and chronic rheumatoid arthritis.13
- Associated Conditions
- Discoid Lupus Erythematosus (DLE)
- Plasmodium Infections
- Porphyria Cutanea Tarda
- Q Fever
- Rheumatoid Arthritis
- Sjögren's Syndrome
- Systemic Lupus Erythematosus (SLE)
- Uncomplicated Malaria caused by Plasmodium Vivax
- Uncomplicated Malaria caused by Plasmodium malariae
- Uncomplicated Malaria caused by Plasmodium ovale
- Uncomplicated Malaria caused by Plasmodium falciparum
- Pharmacodynamics
Hydroxychloroquine affects the function of lysozomes in humans as well as plasmodia.4 Altering the pH of the lysozomes reduces low affinity self antigen presentation in autoimmue diseases and interferes with the ability of plasmodia to proteolyse hemoglobin for their energy requirements.4 Hydroxychloroquine has a long duration of action as it may be taken on a weekly basis for some indications.13 Hydroxychloroquine may lead to severe hypoglycemia and so diabetic patients are advised to monitor their blood glucose levels.13 Hydroxychloroquine is not effective against malaria in areas where chloroquine resistance has been reported.13
- Mechanism of action
The exact mechanisms of hydroxychloroquine are unknown. It has been shown that hydroxychloroquine accumulates in the lysosomes of the malaria parasite, raising the pH of the vacuole.4 This activity interferes with the parasite's ability to proteolyse hemoglobin, preventing the normal growth and replication of the parasite.4 Hydroxychloroquine can also interfere with the action of parasitic heme polymerase, allowing for the accumulation of the toxic product beta-hematin.5
Hydroxychloroquine accumulation in human organelles also raise their pH, which inhibits antigen processing, prevents the alpha and beta chains of the major histocompatibility complex (MHC) class II from dimerizing, inhibits antigen presentation of the cell, and reduces the inflammatory response.4 Elevated pH in the vesicles may alter the recycling of MHC complexes so that only the high affinity complexes are presented on the cell surface.4 Self peptides bind to MHC complexes with low affinity and so they will be less likely to be presented to autoimmune T cells.4 Hydroxychloroquine also reduces the release of cytokines like interleukin-1 and tumor necrosis factor, possibly through inhibition of Toll-like receptors.4,11
The raised pH in endosomes, prevent virus particles (such as SARS-CoV and SARS-CoV-2) from utilizing their activity for fusion and entry into the cell.8
Hydroxychloroquine inhibits terminal glycosylation of ACE2, the receptor that SARS-CoV and SARS-CoV-2 target for cell entry.9,8 ACE2 that is not in the glycosylated state may less efficiently interact with the SARS-CoV-2 spike protein, further inhibiting viral entry.8
Target Actions Organism ADNA cross-linking/alkylationHumans AToll-like receptor 7 antagonistHumans AToll-like receptor 9 antagonistHumans UAngiotensin-converting enzyme 2 modulatorHumans - Absorption
Hydroxychloroquine is 67-74% bioavailable.2 Bioavailability of the R and S enantiomers were not significantly different.2 Following a 200mg oral dose, hydroxychloroquine reached a Cmax of 129.6ng/mL with a Tmax of 3.26h in the blood and a Cmax of 50.3ng/mL with a Tmax of 3.74h in the plasma.13 Following 155mg and 310mg intravenous doses, Cmax in the blood ranged from 1161-2436ng/mL with an average of 1918ng/mL.13
- Volume of distribution
Hydroxychloroquine has a volume of distribution of 5522L from blood and 44,257L from plasma.2
- Protein binding
The S enantiomer of hydroxychloroquine is 64% protein bound in plasma.2 It is 50% bound to serum albumin and 29% bound to alpha-1-acid glycoprotein.2 The R enantiomer is 37% protein bound in plasma.2 It is 29% bound to serum albumin and 41% bound to alpha-1-acid glycoprotein.2 In total, hydroxychloroquine is 50% protein bound in plasma.2
- Metabolism
Hydroxychloroquine is N-dealkylated by CYP3A4 to the active metabolite desethylhydroxychloroquine, as well as the inactive metabolites desethylchloroquine and bidesethylchloroquine.1,3 Desethylhydroxychloroquine is the major metabolite.13
- Route of elimination
40-50% of hydroxychloroquine is excreted renally, while only 16-21% of a dose is excreted in the urine as unchanged drug.2 5% of a dose is sloughed off in skin and 24-25% is eliminated through the feces.12
- Half life
Oral hydroxychloroquine has an absorption half life of 3-4 hours.2,13 A 200mg oral dose of hydroxychloroquine has a half life of 537 hours or 22.4 days in blood, and 2963 hours or 123.5 days in plasma.13 A 155mg intravenous dose has a half life of 40 days.13
- Clearance
The clearance of hydroxychloroquine is 96mL/min.2
- Toxicity
Patients experiencing an overdose may present with headache, drowsiness, visual disturbances, cardiovascular collapse, convulsions, hypokalemia, rhythm and conduction disorders including QT prolongation, torsades de pointes, ventricular tachycardia, and ventricular fibrillation.13 This may progress to sudden respiratory and cardiac arrest.13 Overdose should be treated with immediate gastric lavage and activated charcoal at a dose of at least 5 times the hydroxychloroquine dose within 30 minutes.2,13 Parenteral diazepam may be given to treat cardiotoxicity, transfusion may reduce serum concentrations of drug, patients should be monitored for at least 6 hours, fluids should be given, and ammonium chloride should be given to acidify urine and promote urinary excretion.13 Patients may also be given epinephrine.11
- Affected organisms
- Plasmodium
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.
Learn moreStructured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.
Learn moreStructured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.
Learn moreInteractions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Unlock Additional Data2-Methoxyethanol The risk or severity of adverse effects can be increased when Hydroxychloroquine is combined with 2-Methoxyethanol. 2,4-thiazolidinedione The therapeutic efficacy of 2,4-thiazolidinedione can be increased when used in combination with Hydroxychloroquine. 4-Methoxyamphetamine The metabolism of 4-Methoxyamphetamine can be decreased when combined with Hydroxychloroquine. 5-methoxy-N,N-dimethyltryptamine The metabolism of 5-methoxy-N,N-dimethyltryptamine can be decreased when combined with Hydroxychloroquine. 7-Nitroindazole The therapeutic efficacy of 7-Nitroindazole can be decreased when used in combination 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. 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. Acarbose The therapeutic efficacy of Acarbose can be increased when used in combination with Hydroxychloroquine. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
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- Food Interactions
- Take with food. Take with a meal or glass of milk.
References
- Synthesis Reference
U.S. Patent 2,546,658.
- General References
- Lim HS, Im JS, Cho JY, Bae KS, Klein TA, Yeom JS, Kim TS, Choi JS, Jang IJ, Park JW: Pharmacokinetics of hydroxychloroquine and its clinical implications in chemoprophylaxis against malaria caused by Plasmodium vivax. Antimicrob Agents Chemother. 2009 Apr;53(4):1468-75. doi: 10.1128/AAC.00339-08. Epub 2009 Feb 2. [PubMed:19188392]
- Furst DE: Pharmacokinetics of hydroxychloroquine and chloroquine during treatment of rheumatic diseases. Lupus. 1996 Jun;5 Suppl 1:S11-5. [PubMed:8803904]
- Collins KP, Jackson KM, Gustafson DL: Hydroxychloroquine: A Physiologically-Based Pharmacokinetic Model in the Context of Cancer-Related Autophagy Modulation. J Pharmacol Exp Ther. 2018 Jun;365(3):447-459. doi: 10.1124/jpet.117.245639. Epub 2018 Feb 8. [PubMed:29438998]
- Fox RI: Mechanism of action of hydroxychloroquine as an antirheumatic drug. Semin Arthritis Rheum. 1993 Oct;23(2 Suppl 1):82-91. [PubMed:8278823]
- Chou AC, Fitch CD: Heme polymerase: modulation by chloroquine treatment of a rodent malaria. Life Sci. 1992;51(26):2073-8. doi: 10.1016/0024-3205(92)90158-l. [PubMed:1474861]
- Shippey EA, Wagler VD, Collamer AN: Hydroxychloroquine: An old drug with new relevance. Cleve Clin J Med. 2018 Jun;85(6):459-467. doi: 10.3949/ccjm.85a.17034. [PubMed:29883308]
- Devaux CA, Rolain JM, Colson P, Raoult D: New insights on the antiviral effects of chloroquine against coronavirus: what to expect for COVID-19? Int J Antimicrob Agents. 2020 Mar 11:105938. doi: 10.1016/j.ijantimicag.2020.105938. [PubMed:32171740]
- Vincent MJ, Bergeron E, Benjannet S, Erickson BR, Rollin PE, Ksiazek TG, Seidah NG, Nichol ST: Chloroquine is a potent inhibitor of SARS coronavirus infection and spread. Virol J. 2005 Aug 22;2:69. doi: 10.1186/1743-422X-2-69. [PubMed:16115318]
- Wang M, Cao R, Zhang L, Yang X, Liu J, Xu M, Shi Z, Hu Z, Zhong W, Xiao G: Remdesivir and chloroquine effectively inhibit the recently emerged novel coronavirus (2019-nCoV) in vitro. Cell Res. 2020 Mar;30(3):269-271. doi: 10.1038/s41422-020-0282-0. Epub 2020 Feb 4. [PubMed:32020029]
- Gautret P, Lagier JC, Parola P, Hoang VT, Meddeb L, Mailhe M, Doudier B, Courjon J, Giordanengo V, Vieira VE, Dupont HT, Honore S, Colson P, Chabriere E, La Scola B, Rolain JM, Brouqui P, Raoult D: Hydroxychloroquine and azithromycin as a treatment of COVID-19: results of an open-label non-randomized clinical trial. Int J Antimicrob Agents. 2020 Mar 20:105949. doi: 10.1016/j.ijantimicag.2020.105949. [PubMed:32205204]
- Chary MA, Barbuto AF, Izadmehr S, Hayes BD, Burns MM: COVID-19: Therapeutics and Their Toxicities. J Med Toxicol. 2020 Apr 30. pii: 10.1007/s13181-020-00777-5. doi: 10.1007/s13181-020-00777-5. [PubMed:32356252]
- Browning, David J. (2014). Hydroxychloroquine and chloroquine retinopathy. Springer. [ISBN:9781493905973]
- FDA Approved Drug Products: Hydroxychloroquine Oral Tablets [Link]
- FDA: Emergency use Authorization for Hydroxychloroquine and Chloroquine Revoked [Link]
- External Links
- Human Metabolome Database
- HMDB0015549
- KEGG Drug
- D08050
- KEGG Compound
- C07043
- PubChem Compound
- 3652
- PubChem Substance
- 46508459
- ChemSpider
- 3526
- RxNav
- 5521
- 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 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. pKa 9.67 https://watermark.silverchair.com/dkg319.pdf?token=AQECAHi208BE49Ooan9kkhW_Ercy7Dm3ZL_9Cf3qfKAc485ysgAAAjkwggI1BgkqhkiG9w0BBwagggImMIICIgIBADCCAhsGCSqGSIb3DQEHATAeBglghkgBZQMEAS4wEQQMINydGQAq9Ykq8ITSAgEQgIIB7KN6oy2fz4KHncExNPnuAQKYKCeJ2g-83oHmwqGXYloWqkUp7V_gNgs5P23NTTIZEIF_Tkfp9eBMlYlDl9YykaAzqA5UdihXdzBCxmyGaNX6adn_ov0d4hq2omPSpPVCW2dnKAaalROUpR1cm7FYyTXdiDdOn2LWFKDKmA7uuEFJ1ma7-5iCQKV86x7H1W4HOu7WEBQ_dgJPGZVH64g4KrC5SEw-ekFVVL4w40J_LDqVn5mR8sS57huG_Y7d4CWhtyc6Ko27hCp_nBEeaAo95nB4odR0zFGSEASSQZXGMaO2D8zHqk1wCTDVrTLJuyzjEFMel6T-k3yZQwIVdoNxcEY1bh8VwnEz0ugIrqAkimv5xjB9m8en6H1VhrEIhOVmW2GNJGF3No03F01vn3ePhKCXzgu7v3591flqV46i7r2ZnUYNDmE39IbXww4fqX_551wAPap6lMJ0fMsD_z2l3OzHUVis9cMUJm-nC3LtunwGotVRT4Xf8s7Y-La-5NGHI9KoQPfonM-jJcQ5C9sJFkQHasuB2_a3Inu_DFo-KMOAevqW4txzmR-QnwwV13kIHkcEP03vP0ByDKcsQM2mf2py_K2JxTENhiK0B2xc30W2W4fC1HbkrT-Jd9YStj2-A83nNX0_GMFSn4DT3A - 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
References
- 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]
- 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]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Modulator
- General Function
- Zinc ion binding
- Specific Function
- Carboxypeptidase which converts angiotensin I to angiotensin 1-9, a peptide of unknown function, and angiotensin II to angiotensin 1-7, a vasodilator. Also able to hydrolyze apelin-13 and dynorphin...
- Gene Name
- ACE2
- Uniprot ID
- Q9BYF1
- Uniprot Name
- Angiotensin-converting enzyme 2
- Molecular Weight
- 92462.4 Da
References
- Vincent MJ, Bergeron E, Benjannet S, Erickson BR, Rollin PE, Ksiazek TG, Seidah NG, Nichol ST: Chloroquine is a potent inhibitor of SARS coronavirus infection and spread. Virol J. 2005 Aug 22;2:69. doi: 10.1186/1743-422X-2-69. [PubMed:16115318]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Lim HS, Im JS, Cho JY, Bae KS, Klein TA, Yeom JS, Kim TS, Choi JS, Jang IJ, Park JW: Pharmacokinetics of hydroxychloroquine and its clinical implications in chemoprophylaxis against malaria caused by Plasmodium vivax. Antimicrob Agents Chemother. 2009 Apr;53(4):1468-75. doi: 10.1128/AAC.00339-08. Epub 2009 Feb 2. [PubMed:19188392]
- Collins KP, Jackson KM, Gustafson DL: Hydroxychloroquine: A Physiologically-Based Pharmacokinetic Model in the Context of Cancer-Related Autophagy Modulation. J Pharmacol Exp Ther. 2018 Jun;365(3):447-459. doi: 10.1124/jpet.117.245639. Epub 2018 Feb 8. [PubMed:29438998]
- Chary MA, Barbuto AF, Izadmehr S, Hayes BD, Burns MM: COVID-19: Therapeutics and Their Toxicities. J Med Toxicol. 2020 Apr 30. pii: 10.1007/s13181-020-00777-5. doi: 10.1007/s13181-020-00777-5. [PubMed:32356252]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- 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
- 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]
- Chary MA, Barbuto AF, Izadmehr S, Hayes BD, Burns MM: COVID-19: Therapeutics and Their Toxicities. J Med Toxicol. 2020 Apr 30. pii: 10.1007/s13181-020-00777-5. doi: 10.1007/s13181-020-00777-5. [PubMed:32356252]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2C8
- Uniprot ID
- P10632
- Uniprot Name
- Cytochrome P450 2C8
- Molecular Weight
- 55824.275 Da
References
- Chary MA, Barbuto AF, Izadmehr S, Hayes BD, Burns MM: COVID-19: Therapeutics and Their Toxicities. J Med Toxicol. 2020 Apr 30. pii: 10.1007/s13181-020-00777-5. doi: 10.1007/s13181-020-00777-5. [PubMed:32356252]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Toxic substance binding
- Specific Function
- Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Serum albumin
- Molecular Weight
- 69365.94 Da
References
- Furst DE: Pharmacokinetics of hydroxychloroquine and chloroquine during treatment of rheumatic diseases. Lupus. 1996 Jun;5 Suppl 1:S11-5. [PubMed:8803904]
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Not Available
- Specific Function
- Functions as transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in...
Components:
References
- Furst DE: Pharmacokinetics of hydroxychloroquine and chloroquine during treatment of rheumatic diseases. Lupus. 1996 Jun;5 Suppl 1:S11-5. [PubMed:8803904]
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]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids (By similarity). Selectively inhibit...
- Gene Name
- SLCO1A2
- Uniprot ID
- P46721
- Uniprot Name
- Solute carrier organic anion transporter family member 1A2
- Molecular Weight
- 74144.105 Da
References
- Xu C, Zhu L, Chan T, Lu X, Shen W, Madigan MC, Gillies MC, Zhou F: Chloroquine and Hydroxychloroquine Are Novel Inhibitors of Human Organic Anion Transporting Polypeptide 1A2. J Pharm Sci. 2016 Feb;105(2):884-890. doi: 10.1002/jps.24663. Epub 2016 Jan 12. [PubMed:26429523]
Drug created on August 29, 2007 14:00 / Updated on July 11, 2020 00:05
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