Identification

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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.8 It is a commonly prescribed medication in the treatment of uncomplicated malaria, rheumatoid arthritis, chronic discoid lupus erythematosus, and systemic lupus erythematosus.8 Hydroxychloroquine is also used for the prophylaxis of malaria in regions where chloroquine resistance is unlikely.8 Hydroxychloroquine was developed during World War II as a derivative of quinacrine with less severe side effects.6

Hydroxychloroquine was granted FDA approval on 18 April 1955.8

Structure
Thumb
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
IngredientUNIICASInChI Key
Hydroxychloroquine sulfate8Q2869CNVH747-36-4JCBIVZZPXRZKTI-UHFFFAOYSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
PlaquenilTablet, film coated200 mg/1OralSanofi Aventis1955-04-182013-05-31Us
PlaquenilTablet200 mg/1OralCovis Pharmaceuticals, Inc.2013-06-282017-12-31Us
PlaquenilTablet200 mgOralSanofi Aventis1957-12-31Not applicableCanada
PlaquenilTablet200 mg/1OralAphena Pharma Solutions Tennessee, Inc.2013-06-28Not applicableUs
PlaquenilTablet200 mg/1OralAvKARE, Inc.2016-07-142019-03-31Us
PlaquenilTablet200 mg/1OralCarilion Materials Management2013-06-28Not applicableUs
PlaquenilTablet200 mg/1OralConcordia Pharmaceuticals Inc.2013-06-28Not applicableUs
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 End
Apo-hydroxyquineTabletOralApotex Corporation2002-12-13Not applicableCanada
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralA-S Medication Solutions2009-01-07Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralMajor Pharmaceuticals1995-11-30Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralA-S Medication Solutions2009-01-07Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1EnteralMylan Institutional Inc.2016-03-28Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralBlenheim Pharmacal, Inc.2013-12-20Not applicableUs
Hydroxychloroquine sulfateTablet, film coated200 mg/1OralCardinal Health2008-08-05Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralOhm Laboratories, Inc.2009-01-07Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralNcs Health Care Of Ky, Inc Dba Vangard Labs2018-07-10Not applicableUs
Hydroxychloroquine SulfateTablet, film coated200 mg/1OralAmneal Pharmaceuticals NY LLC2018-05-17Not applicableUs
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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International/Other Brands
Axokine (AstraZeneca) / Dolquine (Inmunosyn) / HCQS (Medigroup) / Polirreumin (TRB) / Quensyl (Sanofi)
Categories
UNII
4QWG6N8QKH
CAS number
118-42-3
Weight
Average: 335.872
Monoisotopic: 335.176440176
Chemical Formula
C18H26ClN3O
InChI Key
XXSMGPRMXLTPCZ-UHFFFAOYSA-N
InChI
InChI=1S/C18H26ClN3O/c1-3-22(11-12-23)10-4-5-14(2)21-17-8-9-20-18-13-15(19)6-7-16(17)18/h6-9,13-14,23H,3-5,10-12H2,1-2H3,(H,20,21)
IUPAC Name
2-({4-[(7-chloroquinolin-4-yl)amino]pentyl}(ethyl)amino)ethan-1-ol
SMILES
CCN(CCO)CCCC(C)NC1=C2C=CC(Cl)=CC2=NC=C1

Pharmacology

Indication

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.8

Associated Conditions
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.8 Hydroxychloroquine may lead to severe hypoglycemia and so diabetic patients are advised to monitor their blood glucose levels.8 Hydroxychloroquine is not effective against malaria in areas where chloroquine resistance has been reported.8

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 lysosomes also raises the pH of the vacuole, 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 may also reduce the release of cytokines like interleukin-1 and tumor necrosis factor.4

TargetActionsOrganism
ADNA
cross-linking/alkylation
Humans
AToll-like receptor 7
antagonist
Humans
AToll-like receptor 9
antagonist
Humans
Additional Data Available
Adverse Effects

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Contraindications

Structured 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.

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Blackbox Warnings

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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.8 Following 155mg and 310mg intravenous doses, Cmax in the blood ranged from 1161-2436ng/mL with an average of 1918ng/mL.8

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.8

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.7

Half life

Oral hydroxychloroquine has an absorption half life of 3-4 hours.2,8 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.8 A 155mg intravenous dose has a half life of 40 days.8

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.8 This may progress to sudden respiratory and cardiac arrest.8 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.2,8 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.8

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
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Hydroxychloroquine.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Hydroxychloroquine.
2-MethoxyethanolThe risk or severity of adverse effects can be increased when Hydroxychloroquine is combined with 2-Methoxyethanol.
2,4-thiazolidinedioneThe therapeutic efficacy of 2,4-thiazolidinedione can be increased when used in combination with Hydroxychloroquine.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Hydroxychloroquine.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Hydroxychloroquine.
4-MethoxyamphetamineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Hydroxychloroquine.
5-androstenedioneThe metabolism of Hydroxychloroquine can be decreased when combined with 5-androstenedione.
5-methoxy-N,N-dimethyltryptamineThe metabolism of 5-methoxy-N,N-dimethyltryptamine can be decreased when combined with Hydroxychloroquine.
6-Deoxyerythronolide BThe metabolism of Hydroxychloroquine can be decreased when combined with 6-Deoxyerythronolide B.
Additional Data Available
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  • Severity
    Severity

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  • Evidence Level
    Evidence Level

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  • Action
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Food Interactions
Not Available

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. Browning, David J. (2014). Hydroxychloroquine and chloroquine retinopathy. Springer. [ISBN:9781493905973]
  8. FDA Approved Drug Products: Hydroxychloroquine Oral Tablets [Link]
External Links
Human Metabolome Database
HMDB0015549
KEGG Drug
D08050
KEGG Compound
C07043
PubChem Compound
3652
PubChem Substance
46508459
ChemSpider
3526
ChEBI
5801
ChEMBL
CHEMBL1535
Therapeutic Targets Database
DAP000878
PharmGKB
PA164777036
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Hydroxychloroquine
ATC Codes
P01BA02 — Hydroxychloroquine
AHFS Codes
  • 08:30.08 — Antimalarials

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedSupportive CareLiver Cirrhosis / Muscle Cramps1
0CompletedTreatmentMelanoma (Skin)1
0CompletedTreatmentPlasma Cell Myeloma1
0TerminatedTreatmentProstate Cancer1
1Active Not RecruitingTreatmentAdult Solid Neoplasm1
1Active Not RecruitingTreatmentAdult Solid Neoplasm / Advanced Malignant Solid Neoplasm / Hormone-Resistant Prostate Cancer / Hormone-Resistant Prostate Carcinoma / Recurrent Melanoma / Recurrent Prostate Carcinoma / Renal Cell Carcinoma Recurrent / Stage III Cutaneous Melanoma AJCC v7 / Stage III Prostate Cancer AJCC v7 / Stage III Renal Cell Cancer AJCC v7 / Stage IIIA Cutaneous Melanoma AJCC v7 / Stage IIIA Skin Melanoma / Stage IIIB Cutaneous Melanoma AJCC v7 / Stage IIIB Skin Melanoma / Stage IIIC Cutaneous Melanoma AJCC v7 / Stage IIIC Skin Melanoma / Stage IV Cutaneous Melanoma AJCC v6 and v7 / Stage IV Prostate Cancer / Stage IV Prostate Cancer AJCC v7 / Stage IV Renal Cell Cancer / Stage IV Renal Cell Cancer AJCC V7 / Stage IV Skin Melanoma1
1Active Not RecruitingTreatmentAdvanced Cancers1
1Active Not RecruitingTreatmentMalignant Solid Tumours1
1CompletedTreatmentCystic Fibrosis (CF)1
1CompletedTreatmentImmunosuppression / Rheumatism1
1CompletedTreatmentLymphangioleiomyomatosis1
1CompletedTreatmentMelanoma1
1CompletedTreatmentRecurrent Plasma Cell Myeloma / Refractory Plasma Cell Myeloma1
1CompletedTreatmentRefractory or Relapsed Solid Tumors1
1CompletedTreatmentTumors, Solid1
1CompletedTreatmentUnspecified Adult Solid Tumor, Protocol Specific2
1RecruitingTreatmentMetastatic Pancreatic Carcinoma / Stage II Pancreatic Cancer / Stage IIA Pancreatic Cancer / Stage IIB Pancreatic Cancer / Stage III Pancreatic Cancer / Stage IV Pancreatic Cancer / Unresectable Pancreatic Carcinoma1
1RecruitingTreatmentTumors, Solid1
1TerminatedTreatmentAcute Myelogenous Leukaemia (AML)1
1TerminatedTreatmentBone Metastases / Unspecified Adult Solid Tumor, Protocol Specific1
1TerminatedTreatmentEstrogen Receptor Positive Breast Cancer1
1TerminatedTreatmentLung Cancer Non-Small Cell Cancer (NSCLC)1
1TerminatedTreatmentRenal Cell Adenocarcinoma1
1Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections1
1, 2Active Not RecruitingTreatmentAdvanced Adenocarcinoma / Metastatic Adenocarcinoma1
1, 2Active Not RecruitingTreatmentMetastatic Renal Cell Carcinoma1
1, 2CompletedDiagnosticSystemic Lupus Erythematosus (SLE)1
1, 2CompletedTreatmentAcute HIV Infection1
1, 2CompletedTreatmentAdenocarcinomas / Malignant Neoplasm of Colon / Metastasis / Rectal Carcinoma1
1, 2CompletedTreatmentBrain and Central Nervous System Tumors1
1, 2CompletedTreatmentHistological 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 Months1
1, 2CompletedTreatmentMalignant Neoplasm of Pancreas1
1, 2CompletedTreatmentMultiple Myeloma and Plasma Cell Neoplasm1
1, 2Not Yet RecruitingTreatmentMyelodysplastic Syndromes / Progressive Disease1
1, 2Not Yet RecruitingTreatmentType 2 Diabetes Mellitus1
1, 2RecruitingTreatmentAcne Inversa / Follicular Occlusion Tetrad / Follicular Occlusion Triad / Furuncle / Hidradenitis / Hidradenitis Suppurativa (HS)1
1, 2RecruitingTreatmentAdvanced BRAF Mutant Melanoma1
1, 2RecruitingTreatmentAnatomic Stage I Breast Cancer AJCC v8 / Anatomic Stage IA Breast Cancer AJCC v8 / Anatomic Stage IB Breast Cancer AJCC v8 / Anatomic Stage II Breast Cancer AJCC v8 / Anatomic Stage IIA Breast Cancer AJCC v8 / Anatomic Stage IIB Breast Cancer AJCC v8 / Anatomic Stage III Breast Cancer AJCC v8 / Anatomic Stage IIIA Breast Cancer AJCC v8 / Anatomic Stage IIIB Breast Cancer AJCC v8 / Anatomic Stage IIIC Breast Cancer AJCC v8 / Anatomic Stage IV Breast Cancer AJCC v8 / Estrogen Receptor Positive / HER2/Neu Negative / MKI67 Positive / One to five years postmenopausal / Prognostic Stage I Breast Cancer AJCC v8 / Prognostic Stage IA Breast Cancer AJCC v8 / Prognostic Stage IB Breast Cancer AJCC v8 / Prognostic Stage IIA Breast Cancer AJCC v8 / Prognostic Stage IIB Breast Cancer AJCC v8 / Prognostic Stage III Breast Cancer AJCC v8 / Prognostic Stage IIIA Breast Cancer AJCC v8 / Prognostic Stage IIIB Breast Cancer AJCC v8 / Prognostic Stage IIIC Breast Cancer AJCC v8 / Prognostic Stage IV Breast Cancer AJCC v81
1, 2RecruitingTreatmentColorectal Cancers1
1, 2RecruitingTreatmentDisseminated Sclerosis1
1, 2RecruitingTreatmentMelanoma1
1, 2RecruitingTreatmentPlatinum-resistant Epithelial Ovarian Cancer1
1, 2RecruitingTreatmentProstate Cancer1
1, 2RecruitingTreatmentRecurrent Osteosarcoma / Refractory Osteosarcoma1
1, 2SuspendedTreatmentCancer, Breast1
1, 2TerminatedTreatmentCancer, Breast1
1, 2TerminatedTreatmentHepatitis C Viral Infection1
1, 2TerminatedTreatmentLung Cancers1
1, 2Unknown StatusTreatmentChronic Hepatitis C Virus (HCV) Infection1
1, 2Unknown StatusTreatmentLung Cancer Non-Small Cell Cancer (NSCLC)1
2Active Not RecruitingTreatmentColorectal Cancers1
2Active Not RecruitingTreatmentLung Cancer Non-Small Cell Cancer (NSCLC)1
2Active Not RecruitingTreatmentMalignant Neoplasm of Pancreas2
2Active Not RecruitingTreatmentProstate Cancer1
2CompletedTreatmentAdvanced Non-Small Cell Lung Cancer / Lung Cancer Non-Small Cell Cancer (NSCLC) / Non-Small Cell Lung Cancer Recurrent1
2CompletedTreatmentColorectal Cancers1
2CompletedTreatmentGlioblastomas1
2CompletedTreatmentHydroxychloroquine / IgA Patients1
2CompletedTreatmentKnee Osteoarthritis (Knee OA)1
2CompletedTreatmentLichen Planus, Oral1
2CompletedTreatmentMalignant Neoplasm of Pancreas1
2CompletedTreatmentProstate Cancer1
2Not Yet RecruitingTreatmentRecurrent Prostate Cancer1
2RecruitingPreventionAutoantibody-Associated Heart Block / Congenital Heart Block / Neonatal Lupus1
2RecruitingPreventionHealthy Participants / Healthy Volunteers / Rheumatoid Arthritis (RA) Prevention / Rheumatoid Arthritis Prevention1
2RecruitingPreventionSystemic Lupus Erythematosus (SLE) / Systemic Lupus Erythematosus Encephalitis1
2RecruitingPreventionType1 Diabetes Mellitus1
2RecruitingTreatmentAntiphospholipid Syndrome (APS)1
2RecruitingTreatmentAortic Stiffness / Atherosclerosis / Cardiovascular Disease (CVD) / Chronic Kidney Disease (CKD) / Inflammatory Reaction1
2RecruitingTreatmentBreast Cancer Stage IIB1
2RecruitingTreatmentCerebrohepatorenal syndrome / Peroxisome Biogenesis Disorder (PBD)1
2RecruitingTreatmentCrohn's Disease (CD)1
2RecruitingTreatmentDiabetes Mellitus Type 2 With Hyperglycemia1
2RecruitingTreatmentHepatocellular Cancer1
2RecruitingTreatmentInsulin Dependent Diabetes / Pancreatitis, Chronic1
2RecruitingTreatmentLung Cancer Small Cell Lung Cancer (SCLC)1
2RecruitingTreatmentMultiple Sclerosis, Primary Progressive1
2RecruitingTreatmentPorphyria Cutanea Tarda1
2SuspendedTreatmentChildren´s Interstitial Lung Disease / Diffuse Parenchymal Lung Diseases / Interstitial Lung Disease (ILD)1
2SuspendedTreatmentPancreatic Cancer Resectable / Pancreatic Cancer, Resectable Adenocarcinoma of the Pancreas1
2TerminatedTreatmentArteriosclerosis / Cardiovascular Disease (CVD) / Chronic Renal Failure (CRF)1
2TerminatedTreatmentB-Cell Chronic Lymphocytic Leukemia1
2TerminatedTreatmentProstate Cancer1
2TerminatedTreatmentSarcomas1
2TerminatedTreatmentSystemic Lupus Erythematosus (SLE)1
2Unknown StatusPreventionFlu caused by Influenza1
2Unknown StatusTreatmentCancer, Breast1
2Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections1
2Unknown StatusTreatmentLeukemias1
2WithdrawnTreatmentAbortions spontaneous / Recurrent Pregnancy Losses1
3CompletedSupportive CareGraft Versus Host Disease (GVHD)1
3CompletedTreatmentAutoimmune Diseases / Eye Dryness / Sjögren's Syndrome1
3CompletedTreatmentCutaneous Lupus Erythematosus-Systemic Lupus Erythematosus1
3CompletedTreatmentInsulin Resistance / Rheumatoid Arthritis1
3CompletedTreatmentOsteoarthritis (OA)1
3CompletedTreatmentPrimary Sjögren's Syndrome1
3CompletedTreatmentRheumatoid Arthritis6
3CompletedTreatmentSarcoidosis, Pulmonary1
3CompletedTreatmentSeronegative Spondyloarthropathies1
3RecruitingTreatmentFirst Trimester Abortion / Recurrent Miscarriages1
3RecruitingTreatmentRecurrent Pregnancy Losses1
3RecruitingTreatmentThrombocytopenias1
3TerminatedPreventionAntiphospholipid Syndrome1
4CompletedBasic SciencePre-Diabetic1
4CompletedPreventionSystemic Lupus Erythematosus (SLE)1
4CompletedTreatmentAlopecia Areata (AA)1
4CompletedTreatmentAnkylosing Spondylitis (AS)1
4CompletedTreatmentBorrelia Infection / Lyme Disease1
4CompletedTreatmentImmune Thrombocytopenia1
4CompletedTreatmentPrimary IgA Nephropathy1
4CompletedTreatmentRheumatoid Arthritis6
4Not Yet RecruitingPreventionBMI >30 kg/m22
4Not Yet RecruitingTreatmentAnkylosing Spondylitis (AS) / Spondyloarthritis1
4Not Yet RecruitingTreatmentInsufficient Response to Methotrexate / Rheumatoid Arthritis1
4Not Yet RecruitingTreatmentRheumatoid Arthritis1
4RecruitingPreventionNonvalvular Atrial Fibrillation1
4RecruitingTreatmentAcute Coronary Syndromes (ACS) / Antirheumatic Agents / Cardiovascular Disease (CVD) / Hydroxychloroquine / Inflammatory Reaction / Myocardial Infarction / Unstable Angina Pectoris1
4RecruitingTreatmentCoronary Artery Disease1
4RecruitingTreatmentCutaneous Lupus / Juvenile SLE / Systemic Lupus Erythematosus (SLE)1
4RecruitingTreatmentIndividuals Undergoing Cardiac and General Surgery1
4RecruitingTreatmentPrimary IgA Nephropathy1
4RecruitingTreatmentRheumatoid Arthritis3
Not AvailableCompletedNot AvailablePatients With Systemic Lupus, or Skin Lupus / Systemic Lupus, Skin Lupus1
Not AvailableCompletedNot AvailableSjögren's Syndrome / Xerostomia1
Not AvailableCompletedBasic ScienceHuman Immunodeficiency Virus (HIV)1
Not AvailableCompletedTreatmentHashimoto's Thyroiditis1
Not AvailableCompletedTreatmentRheumatoid Arthritis2
Not AvailableNot Yet RecruitingNot AvailableAutoimmune Diseases1
Not AvailableNot Yet RecruitingNot AvailableLIPIN1 Deficiency1
Not AvailableNot Yet RecruitingTreatmentMetastatic NRAS Melanoma1
Not AvailableRecruitingNot AvailableChildren / Immunosuppressive Treatment / Nephritis, Lupus / Steroid1
Not AvailableRecruitingNot AvailableChloroquine Retinopathy / Proliferative Nephritis1
Not AvailableRecruitingBasic ScienceInsulin Resistance1
Not AvailableRecruitingOtherType 2 Diabetes Mellitus1
Not AvailableRecruitingPreventionBehcet's Syndrome, Vascular Type / Study Focuses on the Long-term Effect of Hydroxychloroquine on the Prevention of Thrombotic Events of the Disease1
Not AvailableRecruitingTreatmentRecurrent Pregnancy Losses / Undifferentiated Connective Tissue Disease1
Not AvailableRecruitingTreatmentSurfactant Dysfunction1
Not AvailableRecruitingTreatmentSystemic Lupus Erythematosus (SLE)1
Not AvailableUnknown StatusTreatmentHashimoto's Thyroiditis1
Not AvailableWithdrawnTreatmentChronic Urticaria1

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
Tablet, film coatedEnteral200 mg/1
Tablet, film coatedOral200 mg/1
TabletOral200 mg
TabletOral200 mg/1
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

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

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]

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]
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
  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]

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 22, 2019 00:09