Identification

Name
Hydroxychloroquine
Accession Number
DB01611
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The FDA emergency use authorization for hydroxychloroquine and chloroquine in the treatment of COVID-19 was revoked on 15 June 2020.14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

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 335.872
Monoisotopic: 335.176440176
Chemical Formula
C18H26ClN3O
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

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
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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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

TargetActionsOrganism
ADNA
cross-linking/alkylation
Humans
AToll-like receptor 7
antagonist
Humans
AToll-like receptor 9
antagonist
Humans
UAngiotensin-converting enzyme 2
modulator
Humans
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

Hover over products below to view reaction partners

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

Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More
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

Interactions

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.
DrugInteraction
AbametapirThe serum concentration of Hydroxychloroquine can be increased when it is combined with Abametapir.
AbataceptThe risk or severity of adverse effects can be increased when Abatacept is combined with Hydroxychloroquine.
AcarboseThe therapeutic efficacy of Acarbose can be increased when used in combination with Hydroxychloroquine.
AcebutololThe risk or severity of QTc prolongation can be decreased when Hydroxychloroquine is combined with Acebutolol.
AcetaminophenThe metabolism of Acetaminophen can be decreased when combined with Hydroxychloroquine.
AcetazolamideThe therapeutic efficacy of Hydroxychloroquine can be decreased when used in combination with Acetazolamide.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be increased when used in combination with Hydroxychloroquine.
AcetophenazineThe risk or severity of QTc prolongation can be increased when Hydroxychloroquine is combined with Acetophenazine.
AcetyldigitoxinThe serum concentration of Acetyldigitoxin can be increased when it is combined with Hydroxychloroquine.
AcrivastineThe risk or severity of QTc prolongation can be increased when Hydroxychloroquine is combined with Acrivastine.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    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.

Products

Product Ingredients
IngredientUNIICASInChI Key
Hydroxychloroquine sulfate8Q2869CNVH747-36-4JCBIVZZPXRZKTI-UHFFFAOYSA-N
Product Images
International/Other Brands
Dolquine (Inmunosyn) / HCQS (Medigroup) / Polirreumin (TRB) / Quensyl (Sanofi)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
PlaquenilTablet, film coated200 mg/1OralSanofi Aventis1955-04-182013-05-31US flag
PlaquenilTablet200 mgOralSanofi Aventis1957-12-31Not applicableCanada flag
PlaquenilTablet200 mg/1OralCarilion Materials Management2013-06-28Not applicableUS flag
PlaquenilTablet200 mg/1OralConcordia Pharmaceuticals Inc.2013-06-28Not applicableUS flag
PlaquenilTablet200 mg/1OralCovis Pharmaceuticals, Inc.2013-06-282017-12-31US flag
PlaquenilTablet200 mg/1OralRedPharm Drug, Inc.2020-01-01Not applicableUS flag
PlaquenilTablet200 mg/1OralAvKARE, Inc.2016-07-142019-03-31US flag
PlaquenilTablet200 mg/1OralAphena Pharma Solutions Tennessee, Inc.2013-06-28Not applicableUS flag
PlaquenilTablet200 mg/1OralProficient Rx LP2013-06-28Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Apo-hydroxyquineTabletOralApotex Corporation2002-12-13Not applicableCanada flag
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralA-S Medication Solutions2016-03-30Not applicableUS flag
Hydroxychloroquine SulfateTablet200 mg/1OralAvPAK2020-05-15Not applicableUS flag
Hydroxychloroquine SulfateTablet200 mg/1OralAvera McKennan Hospital2015-03-242017-05-24US flag69189 005820180907 15195 cadq7q
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralAphena Pharma Solutions Tennessee, Inc.2014-05-19Not applicableUS flag
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralSun Pharmaceutical Industries Limited2009-01-07Not applicableUS flag
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralWinthrop U.S.1995-11-012013-09-30US flag
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralDoh Central Pharmacy2017-08-27Not applicableUS flag
Hydroxychloroquine sulfateTablet, film coated200 mg/1OralZydus Pharmaceuticals (USA) Inc.2008-01-03Not applicableUS flag
Hydroxychloroquine sulfateTablet, film coated200 mg/1OralNorthstar Rx Llc.2019-10-01Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Categories

ATC Codes
P01BA02 — Hydroxychloroquine
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
1,2-aminoalcohol / 4-aminoquinoline / Alcohol / Alkanolamine / Amine / Aminopyridine / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle
show 18 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
tertiary amino compound, organochlorine compound, secondary amino compound, primary alcohol, aminoquinoline (CHEBI:5801)

Chemical Identifiers

UNII
4QWG6N8QKH
CAS number
118-42-3
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

References

Synthesis Reference

U.S. Patent 2,546,658.

General References
  1. 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]
  2. Furst DE: Pharmacokinetics of hydroxychloroquine and chloroquine during treatment of rheumatic diseases. Lupus. 1996 Jun;5 Suppl 1:S11-5. [PubMed:8803904]
  3. 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]
  4. Fox RI: Mechanism of action of hydroxychloroquine as an antirheumatic drug. Semin Arthritis Rheum. 1993 Oct;23(2 Suppl 1):82-91. [PubMed:8278823]
  5. 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]
  6. 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]
  7. 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]
  8. 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]
  9. 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]
  10. 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]
  11. 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]
  12. Browning, David J. (2014). Hydroxychloroquine and chloroquine retinopathy. Springer. [ISBN:9781493905973]
  13. FDA Approved Drug Products: Hydroxychloroquine Oral Tablets [Link]
  14. FDA: Emergency use Authorization for Hydroxychloroquine and Chloroquine Revoked [Link]
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
AHFS Codes
  • 08:30.08 — Antimalarials

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentInfections, Coronavirus / Novel Coronavirus Infectious Disease (COVID-19)1
4Active Not RecruitingTreatmentNovel Coronavirus Infectious Disease (COVID-19)1
4Active Not RecruitingTreatmentRheumatoid Arthritis1
4CompletedBasic SciencePre-Diabetic1
4CompletedBasic ScienceRheumatoid Arthritis1
4CompletedPreventionSystemic Lupus Erythematosus (SLE)1
4CompletedTreatmentAcute Coronary Syndromes (ACS) / Antirheumatic Agents / Cardiovascular Heart Disease / Hydroxychloroquine / Inflammatory Reaction / Myocardial Infarction1
4CompletedTreatmentAlopecia Areata (AA)1
4CompletedTreatmentAnkylosing Spondylitis (AS)1
4CompletedTreatmentBorrelia Infection / Lyme Disease1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Amerisource Health Services Corp.
  • Amneal Pharmaceuticals
  • Apotheca Inc.
  • A-S Medication Solutions LLC
  • Cadila Healthcare Ltd.
  • Cardinal Health
  • Caremark LLC
  • Comprehensive Consultant Services Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Ipca Laboratories Ltd.
  • Kaiser Foundation Hospital
  • Major Pharmaceuticals
  • Mallinckrodt Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mylan
  • Nucare Pharmaceuticals Inc.
  • Ohm Laboratories Inc.
  • Pharmedix
  • Physicians Total Care Inc.
  • Professional Co.
  • Qualitest
  • Ranbaxy Laboratories
  • Resource Optimization and Innovation LLC
  • Sandoz
  • Sanofi-Aventis Inc.
  • Southwood Pharmaceuticals
  • Teva Pharmaceutical Industries Ltd.
  • United Research Laboratories Inc.
  • Watson Pharmaceuticals
  • West-Ward Pharmaceuticals
  • Winthrop Us
  • Zydus Pharmaceuticals
Dosage Forms
FormRouteStrength
TabletOral
TabletOral200 mg
TabletOral400 mg
Tablet, coatedOral200 mg
Tablet, film coatedOral
TabletOral200 1/1
Tablet, film coatedEnteral200 mg/1
Tablet, film coatedOral200 mg/1
Tablet, coated200 MG
Tablet, film coated200 mg
PillOral200 mg
TabletOral200 mg/1
Tablet, film coatedOral200 MG
Tablet, coatedOral155 mg
Prices
Unit descriptionCostUnit
Hydroxychloroquine sulf powder4.8USD g
Plaquenil 200 mg tablet3.14USD tablet
Hydroxychloroquine Sulfate 200 mg tablet1.28USD tablet
Hydroxychloroquine 200 mg tablet1.17USD tablet
Plaquenil Sulfate 200 mg Tablet0.66USD tablet
Apo-Hydroxyquine 200 mg Tablet0.35USD tablet
Mylan-Hydroxychloroquine 200 mg Tablet0.35USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)89-91U.S. Patent 2,546,658.
pKa9.67https://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
PropertyValueSource
Water Solubility0.0261 mg/mLALOGPS
logP3.87ALOGPS
logP2.89ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)15.59ChemAxon
pKa (Strongest Basic)9.76ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area48.39 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity97.97 m3·mol-1ChemAxon
Polarizability38.3 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9892
Blood Brain Barrier+0.5602
Caco-2 permeable-0.5154
P-glycoprotein substrateSubstrate0.8348
P-glycoprotein inhibitor INon-inhibitor0.7297
P-glycoprotein inhibitor IIInhibitor0.5106
Renal organic cation transporterNon-inhibitor0.5742
CYP450 2C9 substrateNon-substrate0.8239
CYP450 2D6 substrateNon-substrate0.9117
CYP450 3A4 substrateNon-substrate0.5384
CYP450 1A2 substrateNon-inhibitor0.5864
CYP450 2C9 inhibitorNon-inhibitor0.8457
CYP450 2D6 inhibitorNon-inhibitor0.6111
CYP450 2C19 inhibitorNon-inhibitor0.8782
CYP450 3A4 inhibitorNon-inhibitor0.6287
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7058
Ames testAMES toxic0.6907
CarcinogenicityNon-carcinogens0.837
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.6348 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6798
hERG inhibition (predictor II)Inhibitor0.7173
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-0f6t-3972000000-7c193125680c0c9e276f
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Kind
Nucleotide
Organism
Humans
Pharmacological action
Yes
Actions
Cross-linking/alkylation
DNA is the molecule of heredity, as it is responsible for the genetic propagation of most inherited traits. It is a polynucleic acid that carries genetic information on cell growth, division, and function. DNA consists of two long strands of nucleotides twisted into a double helix and held together by hydrogen bonds. The sequence of nucleotides determines hereditary characteristics. Each strand serves as the template for subsequent DNA replication and as a template for mRNA production, leading to protein synthesis via ribosomes.
References
  1. 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
  1. Sun S, Rao NL, Venable J, Thurmond R, Karlsson L: TLR7/9 antagonists as therapeutics for immune-mediated inflammatory disorders. Inflamm Allergy Drug Targets. 2007 Dec;6(4):223-35. [PubMed:18220957]
  2. Trevani AS, Chorny A, Salamone G, Vermeulen M, Gamberale R, Schettini J, Raiden S, Geffner J: Bacterial DNA activates human neutrophils by a CpG-independent pathway. Eur J Immunol. 2003 Nov;33(11):3164-74. [PubMed:14579285]
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
  1. Sun S, Rao NL, Venable J, Thurmond R, Karlsson L: TLR7/9 antagonists as therapeutics for immune-mediated inflammatory disorders. Inflamm Allergy Drug Targets. 2007 Dec;6(4):223-35. [PubMed:18220957]
  2. Trevani AS, Chorny A, Salamone G, Vermeulen M, Gamberale R, Schettini J, Raiden S, Geffner J: Bacterial DNA activates human neutrophils by a CpG-independent pathway. Eur J Immunol. 2003 Nov;33(11):3164-74. [PubMed:14579285]
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
  1. 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
  1. 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]
  2. 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]
  3. 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
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. 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]
  2. 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
  1. 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
  1. 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
  1. 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
  1. Crowe A, Ilett KF, Karunajeewa HA, Batty KT, Davis TM: Role of P glycoprotein in absorption of novel antimalarial drugs. Antimicrob Agents Chemother. 2006 Oct;50(10):3504-6. doi: 10.1128/AAC.00708-06. Epub 2006 Aug 17. [PubMed:16917012]
  2. Plaquenil (hydroxychloroquine sulfate) - Drug Summary [Link]
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
  1. 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 October 23, 2020 21:53

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