Hydroxychloroquine

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Identification

Summary

Hydroxychloroquine is an antimalarial medication used to treat uncomplicated cases of malaria and for chemoprophylaxis in specific regions. Also a disease modifying anti-rheumatic drug (DMARD) indicated for treatment of rheumatoid arthritis and lupus erythematosus.

Brand Names

Plaquenil, Sovuna

Generic Name

Hydroxychloroquine

DrugBank Accession Number

DB01611

Background

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The FDA emergency use authorization for hydroxychloroquine and chloroquine in the treatment of COVID-19 was revoked on 15 June 2020.¹⁴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

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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

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Management of	Acute rheumatoid arthritis		••••••••••••	•••••		••••••
Prevention of	Malaria		••••••••••••	•••••• •••••••••		••••••
Treatment of	Porphyria cutanea tarda		••• •••••
Used in combination to treat	Q fever	Regimen in combination with: Doxycycline (DB00254)	••• •••••
Management of	Sjogren syndrome		••• •••••

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Pharmacodynamics

Hydroxychloroquine affects the function of lysosomes in humans as well as plasmodia.⁴ Altering the pH of the lysosomes reduces low-affinity self-antigen presentation in autoimmune diseases and interferes with the ability of plasmodia to proteolyze 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 active against the erythrocytic forms of chloroquine-sensitive strains of P. falciparum, P. malariae, P. vivax, and P. ovale. Hydroxychloroquine is not active against the gametocytes and exoerythrocytic forms including the hypnozoite liver stage forms of P. vivax and P. ovale.¹⁵ 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, an enzyme that uses ferriprotoporphyrin IX (FP) released from hemoglobin as a substrate to form beta-hematin. By reducing the activity of heme polymerase without inhibiting the release of FP, hydroxychloroquine leads to the accumulation of FP in a toxic form.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
AToll-like receptor 7	antagonist	Humans
AToll-like receptor 9	antagonist	Humans
ADNA	cross-linking/alkylation	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 single 200 mg oral dose of hydroxychloroquine to healthy male volunteers, whole blood hydroxychloroquine C_max was 129.6 ng/mL (plasma C_max was 50.3 ng/mL) with T_max of 3.3 hours (plasma T_max 3.7 hours). Following a single oral hydroxychloroquine dose of 200 mg, the mean fraction of the dose absorbed was 0.74 (compared to the administration of 155 mg of hydroxychloroquine intravenous infusion). Peak blood concentrations of metabolites were observed at the same time as peak levels of hydroxychloroquine.¹⁵

After administration of single 155 mg and 310 mg intravenous doses, peak blood concentrations ranged from 1161 ng/mL to 2436 ng/mL (mean 1918 ng/mL) following the 155 mg infusion and 6 months following the 310 mg infusion. Pharmacokinetic parameters were not significantly different over the therapeutic dose range of 155 mg and 310 mg indicating linear kinetics.¹⁵

In patients with rheumatoid arthritis, there was large variability as to the fraction of the dose absorbed (i.e. 30 to 100%), and mean hydroxychloroquine levels were significantly higher in patients with less disease activity.¹⁵

Volume of distribution

Hydroxychloroquine is extensively distributed to tissues; it has a volume of distribution of 5522L from blood and 44,257L from plasma.^15,2

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

A half-life of 123.5 days in plasma was observed following a single 200 mg oral PLAQUENIL dose to healthy male volunteers. Urine hydroxychloroquine levels were still detectable after 3 months with approximately 10% of the dose excreted as the parent drug. Results following a single dose of a 200 mg tablet versus i.v. infusion (155 mg), demonstrated a half-life of about 40 days and a large volume of distribution. Following chronic oral administration of hydroxychloroquine, the absorption half-life was approximately 3 to 4 hours and the terminal half-life ranged from 40 to 50 days.¹⁵

Clearance

The clearance of hydroxychloroquine is 96mL/min.² Renal clearance of unchanged drug was approximately 16% to 30%.¹⁵

Adverse Effects

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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

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
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Abametapir	The serum concentration of Hydroxychloroquine can be increased when it is combined with Abametapir.
Abatacept	The metabolism of Hydroxychloroquine can be increased when combined with Abatacept.
Abiraterone	The metabolism of Hydroxychloroquine can be decreased when combined with Abiraterone.
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.

Food Interactions

• Take with food. Take with a meal or glass of milk.

Products

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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
Hydroxychloroquine	Tablet	200 mg	Oral	Sanis Health Inc	2022-04-18	Not applicable
Hydroxychloroquine Sulfate	Tablet, film coated	300 mg/1	Oral	ANI Pharmaceuticals, Inc.	2022-01-14	Not applicable
Hydroxychloroquine Sulfate	Tablet, film coated	200 mg/1	Oral	ANI Pharmaceuticals, Inc.	2022-01-14	Not applicable
Nra-hydroxychloroquine	Tablet	200 mg	Oral	Nora Pharma Inc	2021-09-14	Not applicable
Plaquenil	Tablet	200 mg/1	Oral	RedPharm Drug, Inc.	2020-01-01	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Ach-hydroxychloroquine Sulfate	Tablet	200 mg	Oral	Accord Healthcare, S.L.U.	Not applicable	Not applicable
Ag-hydroxychloroquine	Tablet	200 mg	Oral	Angita Pharma Inc.	Not applicable	Not applicable
Apo-hydroxyquine	Tablet	200 mg	Oral	Apotex Corporation	2002-12-13	Not applicable
Hydroxychloroquine	Tablet	200 mg/1	Oral	Chartwell Rx, Llc	2018-07-06	Not applicable
Hydroxychloroquine Sulfate	Tablet	300 mg/1	Oral	bryant ranch prepack	2022-10-24	Not applicable

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
• Neurotoxic 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)

Affected organisms

• Plasmodium

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. [Article]
2. Furst DE: Pharmacokinetics of hydroxychloroquine and chloroquine during treatment of rheumatic diseases. Lupus. 1996 Jun;5 Suppl 1:S11-5. [Article]
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. [Article]
4. Fox RI: Mechanism of action of hydroxychloroquine as an antirheumatic drug. Semin Arthritis Rheum. 1993 Oct;23(2 Suppl 1):82-91. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
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]
15. FDA Approved Drug Products: PLAQUENIL (hydroxychloroquine sulfate) tablets, for oral use (July 2023) [Link]

External Links

Human Metabolome Database

HMDB0015549

KEGG Drug

D08050

KEGG Compound

C07043

PubChem Compound

3652

PubChem Substance

46508459

ChemSpider

3526

BindingDB

50467780

RxNav

5521

ChEBI

5801

ChEMBL

CHEMBL1535

Therapeutic Targets Database

DAP000878

PharmGKB

PA164777036

RxList

RxList Drug Page

Drugs.com

Drugs.com Drug Page

Wikipedia

Hydroxychloroquine

Clinical Trials

Clinical Trials

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Phase	Status	Purpose	Conditions	Count	Start Date	Why Stopped	100+ additional columns
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Not Available	Completed	Not Available	Cicatricial Alopecia / Frontal Fibrosing Alopecia / Hair Diseases / Hair Loss / Lichen Planopilaris / Scarring Alopecia	1	somestatus	stop reason	just information to hide
Not Available	Completed	Not Available	Coronavirus Disease 2019 (COVID‑19)	1	somestatus	stop reason	just information to hide
Not Available	Completed	Not Available	Coronavirus Disease 2019 (COVID‑19) / Diarrhea	1	somestatus	stop reason	just information to hide
Not Available	Completed	Not Available	Coronavirus Disease 2019 (COVID‑19) / Hydroxychloroquine / Ivermectin	1	somestatus	stop reason	just information to hide
Not Available	Completed	Not Available	Coronavirus Disease 2019 (COVID‑19) / Rheumatoid Arthritis	1	somestatus	stop reason	just information to hide

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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	400 mg
Tablet	Oral	200.000 mg
Tablet, coated	Oral	400 mg
Tablet, sugar coated	Oral	100 mg
Tablet, sugar coated	Oral	200 mg
Tablet, film coated	Oral
Tablet	Oral	100 mg/1
Tablet	Oral	300 mg/1
Tablet	Oral	400 mg/1
Tablet, film coated	Enteral	200 mg/1
Tablet, film coated	Oral	200 mg/1
Tablet, film coated	Oral	300 mg/1
Tablet, film coated		200 MG
Pill	Oral	200 mg
Tablet	Oral	200 mg
Tablet	Oral	200 mg/1
Tablet, film coated	Oral	200 mg
Tablet, coated	Oral	155 mg
Tablet, 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	splash10-05fr-9262000000-58dde1657b5d6098be9b
Mass Spectrum (Electron Ionization)	MS	splash10-0f6t-3972000000-7c193125680c0c9e276f
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-00kr-0009000000-b6c98fa1072e205b08b1
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-001i-9028000000-36d7be64b65a16fef029
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-001i-7049000000-b07fb24916ee05fea74a
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-014v-0279000000-aeaddc62b82ea5d7871d
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-05rd-9760000000-4b741469863f0c27e19c
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0059-3920000000-fab6fdb0bc75c0b564ed
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å2)	Source type	Source
[M-H]-	186.2340756	predicted	DarkChem Lite v0.1.0
[M-H]-	178.0916	predicted	DeepCCS 1.0 (2019)
[M+H]+	186.3571756	predicted	DarkChem Lite v0.1.0
[M+H]+	180.4496	predicted	DeepCCS 1.0 (2019)
[M+Na]+	185.8199756	predicted	DarkChem Lite v0.1.0
[M+Na]+	186.54695	predicted	DeepCCS 1.0 (2019)

Targets

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Details1. Toll-like receptor 7

Kind

Protein

Organism

Humans

Pharmacological action

Yes

Actions

Antagonist

General Function

Endosomal receptor that plays a key role in innate and adaptive immunity (PubMed:14976261, PubMed:32433612). Controls host immune response against pathogens through recognition of uridine-containing single strand RNAs (ssRNAs) of viral origin or guanosine analogs (PubMed:12738885, PubMed:27742543, PubMed:31608988, PubMed:32706371, PubMed:35477763). Upon binding to agonists, undergoes dimerization that brings TIR domains from the two molecules into direct contact, leading to the recruitment of TIR-containing downstream adapter MYD88 through homotypic interaction (PubMed:27742543). In turn, the Myddosome signaling complex is formed involving IRAK4, IRAK1, TRAF6, TRAF3 leading to activation of downstream transcription factors NF-kappa-B and IRF7 to induce pro-inflammatory cytokines and interferons, respectively (PubMed:27742543, PubMed:32706371)

Specific Function

double-stranded RNA binding

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. [Article]
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. [Article]
3. Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]

Details2. Toll-like receptor 9

Kind

Protein

Organism

Humans

Pharmacological action

Yes

Actions

Antagonist

General 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 is a nucleotide-sensing TLR which is activated by unmethylated cytidine-phosphate-guanosine (CpG) dinucleotides (PubMed:14716310). Acts via MYD88 and TRAF6, leading to NF-kappa-B activation, cytokine secretion and the inflammatory response (PubMed:11564765, PubMed:17932028). Controls lymphocyte response to Helicobacter infection (By similarity). Upon CpG stimulation, induces B-cell proliferation, activation, survival and antibody production (PubMed:23857366)

Specific Function

interleukin-1 receptor binding

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. [Article]
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. [Article]

Details3. DNA

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. [Article]

Details4. Angiotensin-converting enzyme 2

Kind

Protein

Organism

Humans

Pharmacological action

Unknown

Actions

Modulator

General Function

Essential counter-regulatory carboxypeptidase of the renin-angiotensin hormone system that is a critical regulator of blood volume, systemic vascular resistance, and thus cardiovascular homeostasis (PubMed:27217402). Converts angiotensin I to angiotensin 1-9, a nine-amino acid peptide with anti-hypertrophic effects in cardiomyocytes, and angiotensin II to angiotensin 1-7, which then acts as a beneficial vasodilator and anti-proliferation agent, counterbalancing the actions of the vasoconstrictor angiotensin II (PubMed:10924499, PubMed:10969042, PubMed:11815627, PubMed:14504186, PubMed:19021774). Also removes the C-terminal residue from three other vasoactive peptides, neurotensin, kinetensin, and des-Arg bradykinin, but is not active on bradykinin (PubMed:10969042, PubMed:11815627). Also cleaves other biological peptides, such as apelins (apelin-13, [Pyr1]apelin-13, apelin-17, apelin-36), casomorphins (beta-casomorphin-7, neocasomorphin) and dynorphin A with high efficiency (PubMed:11815627, PubMed:27217402, PubMed:28293165). In addition, ACE2 C-terminus is homologous to collectrin and is responsible for the trafficking of the neutral amino acid transporter SL6A19 to the plasma membrane of gut epithelial cells via direct interaction, regulating its expression on the cell surface and its catalytic activity (PubMed:18424768, PubMed:19185582)

Specific Function

carboxypeptidase activity

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. [Article]

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Drug created at August 29, 2007 20:00 / Updated at October 21, 2024 08:50