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The FDA emergency use authorization for hydroxychloroquine and chloroquine in the treatment of COVID-19 was revoked on 15 June 2020.¹⁴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

3D

Download

MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Hydroxychloroquine (DB01611)

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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

• 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

Contraindications & Blackbox Warnings

Learn about our commercial Contraindications & Blackbox Warnings data.

Learn More

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/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 C_max of 129.6ng/mL with a T_max of 3.26h in the blood and a C_max of 50.3ng/mL with a T_max of 3.74h in the plasma.¹³ Following 155mg and 310mg intravenous doses, C_max 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

• Hydroxychloroquine
  • Desethylchloroquine
  • Desethylhydroxychloroquine
  • Bidesethylchloroquine

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.

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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.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
Unlock Additional Data
Abametapir	The serum concentration of Hydroxychloroquine can be increased when it is combined with Abametapir.
Abatacept	The risk or severity of adverse effects can be increased when Abatacept is combined with Hydroxychloroquine.
Acarbose	The therapeutic efficacy of Acarbose can be increased when used in combination with Hydroxychloroquine.
Acebutolol	The risk or severity of QTc prolongation can be decreased when Hydroxychloroquine is combined with Acebutolol.
Acetaminophen	The metabolism of Acetaminophen can be decreased when combined with Hydroxychloroquine.
Acetazolamide	The therapeutic efficacy of Hydroxychloroquine can be decreased when used in combination with Acetazolamide.
Acetohexamide	The therapeutic efficacy of Acetohexamide can be increased when used in combination with Hydroxychloroquine.
Acetophenazine	The risk or severity of QTc prolongation can be increased when Hydroxychloroquine is combined with Acetophenazine.
Acetyldigitoxin	The serum concentration of Acetyldigitoxin can be increased when it is combined with Hydroxychloroquine.
Acrivastine	The 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

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

Product Images

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International/Other Brands

Dolquine (Inmunosyn) / HCQS (Medigroup) / Polirreumin (TRB) / Quensyl (Sanofi)

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Unlock Additional Data
Plaquenil	Tablet	200 mg/1	Oral	RedPharm Drug, Inc.	2020-01-01	Not applicable
Plaquenil	Tablet	200 mg/1	Oral	AvKARE, Inc.	2016-07-14	2019-03-31
Plaquenil	Tablet	200 mg/1	Oral	Covis Pharmaceuticals, Inc.	2013-06-28	2017-12-31
Plaquenil	Tablet	200 mg/1	Oral	Proficient Rx LP	2013-06-28	Not applicable
Plaquenil	Tablet	200 mg/1	Oral	Aphena Pharma Solutions Tennessee, Inc.	2013-06-28	Not applicable
Plaquenil	Tablet	200 mg/1	Oral	Concordia Pharmaceuticals Inc.	2013-06-28	Not applicable
Plaquenil	Tablet	200 mg	Oral	Sanofi Aventis	1957-12-31	Not applicable
Plaquenil	Tablet, film coated	200 mg/1	Oral	Sanofi Aventis	1955-04-18	2013-05-31
Plaquenil	Tablet	200 mg/1	Oral	Carilion Materials Management	2013-06-28	Not applicable

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

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Unlock Additional Data
Apo-hydroxyquine	Tablet		Oral	Apotex Corporation	2002-12-13	Not applicable
Hydroxychloroquine Sulfate	Tablet	200 mg/1	Oral	PD-Rx Pharmaceuticals, Inc.	2018-06-18	Not applicable
Hydroxychloroquine Sulfate	Tablet, film coated	200 mg/1	Oral	A-S Medication Solutions	2014-05-19	2017-05-31
Hydroxychloroquine Sulfate	Tablet	200 mg/1	Oral	Accord Healthcare, Inc.	2020-05-12	Not applicable
Hydroxychloroquine Sulfate	Tablet	200 mg/1	Oral	Avera McKennan Hospital	2015-03-24	2017-05-24
Hydroxychloroquine Sulfate	Tablet, film coated	200 mg/1	Oral	Ohm Laboratories, Inc.	2009-01-07	Not applicable
Hydroxychloroquine Sulfate	Tablet, film coated	200 mg/1	Oral	Hikma Pharmaceuticals USA Inc.	2007-08-15	2014-01-31
Hydroxychloroquine Sulfate	Tablet, film coated	200 mg/1	Oral	Teva	1995-09-01	2013-09-30
Hydroxychloroquine Sulfate	Tablet, film coated	200 mg/1	Oral	Blenheim Pharmacal, Inc.	2013-12-20	Not applicable
Hydroxychloroquine Sulfate	Tablet	200 1/1	Oral	Havix Group Inc d-b-a Aavis Pharmaceuticals	2020-07-20	Not applicable

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

• P01BA — Aminoquinolines
• P01B — ANTIMALARIALS
• P01 — ANTIPROTOZOALS
• P — ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS

Drug 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

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 / Organopnictogen compounds / Organochlorides / Hydrocarbon derivatives

show 3 more

Substituents

1,2-aminoalcohol / 4-aminoquinoline / Alcohol / Alkanolamine / Amine / Aminopyridine / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle / Benzenoid / Chloroquinoline / Haloquinoline / Heteroaromatic compound / Hydrocarbon derivative / Organic nitrogen compound / Organic oxygen compound / Organochloride / Organohalogen compound / Organonitrogen compound / Organooxygen compound / Organopnictogen compound / Primary alcohol / Pyridine / Secondary aliphatic/aromatic amine / Secondary amine / Tertiary aliphatic amine / Tertiary amine

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]

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

AHFS Codes

• 08:30.08 — Antimalarials

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
4	Active Not Recruiting	Treatment	Infections, Coronavirus / Novel Coronavirus Infectious Disease (COVID-19)	1
4	Active Not Recruiting	Treatment	Novel Coronavirus Infectious Disease (COVID-19)	1
4	Active Not Recruiting	Treatment	Rheumatoid Arthritis	1
4	Completed	Basic Science	Pre-Diabetic	1
4	Completed	Basic Science	Rheumatoid Arthritis	1
4	Completed	Prevention	Systemic Lupus Erythematosus (SLE)	1
4	Completed	Treatment	Acute Coronary Syndromes (ACS) / Antirheumatic Agents / Cardiovascular Heart Disease / Hydroxychloroquine / Inflammatory Reaction / Myocardial Infarction	1
4	Completed	Treatment	Alopecia Areata (AA)	1
4	Completed	Treatment	Ankylosing Spondylitis (AS)	1
4	Completed	Treatment	Borrelia Infection / Lyme Disease	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

• Amerisource Health Services Corp.
• Amneal Pharmaceuticals
• Apotheca Inc.
• A-S Medication Solutions LLC
• Cadila Healthcare Ltd.
• Cardinal Health
• Caremark LLC
• Comprehensive Consultant Services Inc.
• Dispensing Solutions
• Diversified Healthcare Services Inc.
• Ipca Laboratories Ltd.
• Kaiser Foundation Hospital
• Major Pharmaceuticals
• Mallinckrodt Inc.
• Murfreesboro Pharmaceutical Nursing Supply
• Mylan
• Nucare Pharmaceuticals Inc.
• Ohm Laboratories Inc.
• Pharmedix
• Physicians Total Care Inc.
• Professional Co.
• Qualitest
• Ranbaxy Laboratories
• Resource Optimization and Innovation LLC
• Sandoz
• Sanofi-Aventis Inc.
• Southwood Pharmaceuticals
• Teva Pharmaceutical Industries Ltd.
• United Research Laboratories Inc.
• Watson Pharmaceuticals
• West-Ward Pharmaceuticals
• Winthrop Us
• Zydus Pharmaceuticals

Dosage Forms

Form	Route	Strength
Tablet	Oral
Tablet, film coated	Oral
Tablet	Oral	200 1/1
Tablet, film coated	Enteral	200 mg/1
Tablet, film coated	Oral	200 mg/1
Tablet	Oral	200 mg
Tablet	Oral	200 mg/1
Tablet, film coated	Oral	200 MG

Prices

Unit description	Cost	Unit
Hydroxychloroquine sulf powder	4.8USD	g
Plaquenil 200 mg tablet	3.14USD	tablet
Hydroxychloroquine Sulfate 200 mg tablet	1.28USD	tablet
Hydroxychloroquine 200 mg tablet	1.17USD	tablet
Plaquenil Sulfate 200 mg Tablet	0.66USD	tablet
Apo-Hydroxyquine 200 mg Tablet	0.35USD	tablet
Mylan-Hydroxychloroquine 200 mg Tablet	0.35USD	tablet

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	89-91	U.S. Patent 2,546,658.
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

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

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

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Drug created on August 29, 2007 14:00 / Updated on August 14, 2020 04:24