HYDROXYCHLOROQUINE SULFATE

Details

Stereochemistry	RACEMIC
Molecular Formula	C18H26ClN3O.H2O4S
Molecular Weight	433.95
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OS(O)(=O)=O.CCN(CCO)CCCC(C)NC1=C2C=CC(Cl)=CC2=NC=C1

InChI

InChIKey=JCBIVZZPXRZKTI-UHFFFAOYSA-N

InChI=1S/C18H26ClN3O.H2O4S/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;1-5(2,3)4/h6-9,13-14,23H,3-5,10-12H2,1-2H3,(H,20,21);(H2,1,2,3,4)

HIDE SMILES / InChI

Molecular Formula	H2O4S
Molecular Weight	98.078
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C18H26ClN3O
Molecular Weight	335.872
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: http://www.drugbank.ca/drugs/DB01611
Curator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2007/009768s041lbl.pdf

Hydroxychloroquine possesses antimalarial properties and also exerts a beneficial effect in lupus erythematosus (chronic discoid or systemic) and acute or chronic rheumatoid arthritis. Although the exact mechanism of action is unknown, it may be based on ability of hydroxychloroquine to bind to and alter DNA. Hydroxychloroquine has also has been found to be taken up into the acidic food vacuoles of the parasite in the erythrocyte. This increases the pH of the acid vesicles, interfering with vesicle functions and possibly inhibiting phospholipid metabolism. In suppressive treatment, hydroxychloroquine inhibits the erythrocytic stage of development of plasmodia. In acute attacks of malaria, it interrupts erythrocytic schizogony of the parasite. Its ability to concentrate in parasitized erythrocytes may account for their selective toxicity against the erythrocytic stages of plasmodial infection. As an antirheumatic, hydroxychloroquine is thought to act as a mild immunosuppressant, inhibiting the production of rheumatoid factor and acute phase reactants. It also accumulates in white blood cells, stabilizing lysosomal membranes and inhibiting the activity of many enzymes, including collagenase and the proteases that cause cartilage breakdown. Hydroxychloroquine is used for the suppressive treatment and treatment of acute attacks of malaria due to Plasmodium vivax, P. malariae, P. ovale, and susceptible strains of P. falciparum. It is also indicated for the treatment of discoid and systemic lupus erythematosus, and rheumatoid arthritis.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Toll-like receptor 7 13 Target ID: CHEMBL5936 Sources: http://www.drugbank.ca/drugs/DB01611	Antagonist 2849		2.78 µM [IC50]
Toll-like receptor 9 4 Target ID: CHEMBL5804 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24342772	Antagonist 2849		0.08 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Malaria 96 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2007/009768s041lbl.pdf	Curative	Approved 8583	PLAQUENIL Approved Use PLAQUENIL is indicated for the suppressive treatment and treatment of acute attacks of malaria due to Plasmodium vivax, P. malariae, P. ovale, and susceptible strains of P. falciparum. It is also indicated for the treatment of discoid and systemic lupus erythematosus, and rheumatoid arthritis. Launch Date 1955
Systemic lupus erythematosus 15 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2007/009768s041lbl.pdf	Primary	Approved 8583	PLAQUENIL Approved Use PLAQUENIL is indicated for the suppressive treatment and treatment of acute attacks of malaria due to Plasmodium vivax, P. malariae, P. ovale, and susceptible strains of P. falciparum. It is also indicated for the treatment of discoid and systemic lupus erythematosus, and rheumatoid arthritis. Launch Date 1955
Rheumatoid arthritis 320 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2007/009768s041lbl.pdf	Primary	Approved 8583	PLAQUENIL Approved Use PLAQUENIL is indicated for the suppressive treatment and treatment of acute attacks of malaria due to Plasmodium vivax, P. malariae, P. ovale, and susceptible strains of P. falciparum. It is also indicated for the treatment of discoid and systemic lupus erythematosus, and rheumatoid arthritis. Launch Date 1955

C_max

Value	Dose	Co-administered	Analyte	Population
50.3 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/009768Orig1s051lbl.pdf	155 mg single, oral dose: 155 mg route of administration: Oral experiment type: SINGLE co-administered:		HYDROXYCHLOROQUINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
129.6 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/009768Orig1s051lbl.pdf	155 mg single, oral dose: 155 mg route of administration: Oral experiment type: SINGLE co-administered:		HYDROXYCHLOROQUINE blood	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
2500 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24991839/	465 mg 2 times / day multiple, oral dose: 465 mg route of administration: Oral experiment type: MULTIPLE co-administered: TEMOZOLOMIDE	TEMOZOLOMIDE	HYDROXYCHLOROQUINE blood	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1.22 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19188392	310 mg single, oral dose: 310 mg route of administration: Oral experiment type: SINGLE co-administered:		HYDROXYCHLOROQUINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
102.3 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19188392	310 mg single, oral dose: 310 mg route of administration: Oral experiment type: SINGLE co-administered:		HYDROXYCHLOROQUINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
2963 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/009768Orig1s051lbl.pdf	155 mg single, oral dose: 155 mg route of administration: Oral experiment type: SINGLE co-administered:	HYDROXYCHLOROQUINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
537 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/009768Orig1s051lbl.pdf	155 mg single, oral dose: 155 mg route of administration: Oral experiment type: SINGLE co-administered:	HYDROXYCHLOROQUINE blood	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
172.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19188392	310 mg single, oral dose: 310 mg route of administration: Oral experiment type: SINGLE co-administered:	HYDROXYCHLOROQUINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
48% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8359187	unknown, unknown		HYDROXYCHLOROQUINE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
12 g 1 times / day single, oral Studied dose Dose: 12 g, 1 times / day Route: oral Route: single Dose: 12 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/11555803/	healthy, 16 years Health Status: healthy Age Group: 16 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/11555803/	Other AEs: Cardio-respiratory arrest... Other AEs: Cardio-respiratory arrest (grade 5) Sources: https://pubmed.ncbi.nlm.nih.gov/11555803/
200 mg 1 times / day single, oral Studied dose Dose: 200 mg, 1 times / day Route: oral Route: single Dose: 200 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/11555803/	healthy, 16 years Health Status: healthy Age Group: 16 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/11555803/	Other AEs: Tachycardia, Hypotension... Other AEs: Tachycardia Hypotension Depression Hypokalemia Sources: https://pubmed.ncbi.nlm.nih.gov/11555803/
20 g 1 times / day single, oral Studied dose Dose: 20 g, 1 times / day Route: oral Route: single Dose: 20 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/11555803/	healthy, 18 years Health Status: healthy Age Group: 18 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/11555803/	Other AEs: Hypotension, Hypokalemia... Other AEs: Hypotension Hypokalemia Sources: https://pubmed.ncbi.nlm.nih.gov/11555803/
12 g 1 times / day single, oral Studied dose Dose: 12 g, 1 times / day Route: oral Route: single Dose: 12 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/11555803/	healthy, 2.5 years Health Status: healthy Age Group: 2.5 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/11555803/	Other AEs: Cardio-respiratory arrest... Other AEs: Cardio-respiratory arrest (grade 5) Sources: https://pubmed.ncbi.nlm.nih.gov/11555803/
4 g 1 times / day single, oral Studied dose Dose: 4 g, 1 times / day Route: oral Route: single Dose: 4 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/11555803/	healthy, 29 years Health Status: healthy Age Group: 29 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/11555803/	Other AEs: Vomiting, Ventricular tachycardia... Other AEs: Vomiting Ventricular tachycardia Sources: https://pubmed.ncbi.nlm.nih.gov/11555803/
600 mg 2 times / day multiple, oral Highest studied dose Dose: 600 mg, 2 times / day Route: oral Route: multiple Dose: 600 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/24991839/	unhealthy, median age 64 years Health Status: unhealthy Age Group: median age 64 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/24991839/	DLT: Nausea, Vomiting... Other AEs: Lymphopenia, Anemia... Dose limiting toxicities: Nausea (grade 3, 13%) Vomiting (grade 3, 13%) Other AEs: Lymphopenia (grade 3-4, 13%) Anemia (grade 1-2, 13%) Thrombocytopenia (grade 1-2, 13%) Anorexia (grade 1-2, 38%) Bradycardia (grade 1-2, 13%) Constipation (grade 1-2, 25%) Diarrhea (grade 1-2, 25%) Fatigue (grade 1-2, 88%) Hypotension (grade 1-2, 13%) Nausea (grade 1-2, 50%) Rash (grade 1-2, 13%) Vomiting (grade 1-2, 25%) Sources: https://pubmed.ncbi.nlm.nih.gov/24991839/
200 mg 2 times / day multiple, oral Studied dose Dose: 200 mg, 2 times / day Route: oral Route: multiple Dose: 200 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/24991839/	unhealthy, median age 64 years Health Status: unhealthy Age Group: median age 64 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/24991839/	DLT: Heart block... Dose limiting toxicities: Heart block (grade 3, 6.7%) Sources: https://pubmed.ncbi.nlm.nih.gov/24991839/
500 mg 2 times / day multiple, oral Studied dose Dose: 500 mg, 2 times / day Route: oral Route: multiple Dose: 500 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/24991839/	unhealthy, median age 64 years Health Status: unhealthy Age Group: median age 64 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/24991839/	DLT: Rash... Dose limiting toxicities: Rash (grade 3, 14.3%) Sources: https://pubmed.ncbi.nlm.nih.gov/24991839/
200 mg 2 times / day steady, oral Dose: 200 mg, 2 times / day Route: oral Route: steady Dose: 200 mg, 2 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT01537315	unhealthy Health Status: unhealthy Sources: https://clinicaltrials.gov/ct2/show/NCT01537315	Other AEs: Increased blood pressure... Other AEs: Increased blood pressure (below serious, 1 patient) Sources: https://clinicaltrials.gov/ct2/show/NCT01537315

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946		substrate 1388 inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP2C8 810 CYP3A5 446

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2D6 2546	inhibitor 4027 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2015042/	yes		yes (co-administration study) Comment: Concomitant administration of HCQ increased the bioavailability of metoprolol, as indicated by significant increases in the area under the plasma concentration-time curve (65 ± 4.6%) and maximal plasma concentrations (72 ± 6.9%) of metoprolol Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2015042/

Drug as victim

Target	Modality	Activity
CYP2C8 810	substrate 4014 Sources: https://onlinelibrary.wiley.com/doi/full/10.1002/art.39402; https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7600351/	likely
CYP2D6 1388	substrate 4014 Sources: https://onlinelibrary.wiley.com/doi/full/10.1002/art.39402; https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7600351/	likely
CYP3A4 1946	substrate 4014 Sources: https://onlinelibrary.wiley.com/doi/full/10.1002/art.39402; https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7600351/	likely
CYP3A5 446	substrate 4014 Sources: https://onlinelibrary.wiley.com/doi/full/10.1002/art.39402; https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7600351/	likely

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubmed.ncbi.nlm.nih.gov/33674391/

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:5801	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:5801
ChemicalBook	CB6866802	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB6866802
eMolecules	901965	https://www.emolecules.com/cgi-bin/more?vid=901965
MolPort	MolPort-003-847-792	https://www.molport.com/shop/molecule-link/MolPort-003-847-792

PubMed

Title	Date	PubMed
IgM antibodies against cytomegalovirus in SLE nephritis: viral infection or aspecific autoantibody?	2002-04-09	11936434
Evidence of transplacental passage of hydroxychloroquine in humans.	2002-04	11953993
Delay to institution of therapy and induction of remission using single-drug or combination-disease-modifying antirheumatic drug therapy in early rheumatoid arthritis.	2002-04	11953964
Canadian Consensus Conference on hydroxychloroquine.	2002-04	11950041
Randomized double blind trial of an extract from the pentacyclic alkaloid-chemotype of uncaria tomentosa for the treatment of rheumatoid arthritis.	2002-04	11950006
Pharmacoeconomics of long-term treatment of rheumatoid arthritis.	2002-04	11934345
Hydroxychloroquine reverses platelet activation induced by human IgG antiphospholipid antibodies.	2002-03	11916085
Nonendemic pemphigus foliaceus in children.	2002-03	11862179
The effectiveness of hydroxychloroquine in patients with type 2 diabetes mellitus who are refractory to sulfonylureas--a randomized trial.	2002-03	11850097
[Psychiatric manifestations of lupus erythematosus systemic and Sjogren's syndrome].	2002-02-28	11865567
Antimalarial agents in pregnancy.	2002-02-09	11853823
[Primary Gougerot-Sjögren syndrome in a 13-year-old girl].	2002-02	11915495
How frequently and how soon should we screen our patients for the presence of antimalarial retinopathy?	2002-02	11840465
Prescribing trends in disease modifying antirheumatic drugs for rheumatoid arthritis: a survey of practicing Canadian rheumatologists.	2002-02	11838842
Hydroxychloroquine ototoxicity in a child with idiopathic pulmonary haemosiderosis.	2002-01-11	11738695
Second-line drugs used in recent-onset rheumatoid arthritis in Brittany (France).	2002-01	11858354
Chloroquine decreases cell-surface expression of tumour necrosis factor receptors in human histiocytic U-937 cells.	2002-01	11849318
Treatment of severe immune thrombocytopenia associated with systemic lupus erythematosus: 59 cases.	2002-01	11824975
Leflunomide induced fevers, thrombocytosis, and leukocytosis in a patient with relapsing polychondritis.	2002-01	11824960
Safety and efficacy of disease-modifying anti-rheumatic agents: focus on the benefits and risks of etanercept.	2002	11945114
Sustained normalization of cerebral blood-flow after iloprost therapy in a patient with neuropsychiatric systemic lupus erythematosus.	2002	11898921
Progress in the treatment of rheumatoid arthritis.	2001-12-12	11735734
[Combined basic therapeutic drugs. From individual hope to targeted use].	2001-12	11826745
Hydroxychloroquine retinopathy.	2001-12	11733247
Angiooedema due to acquired deficiency of C1-esterase inhibitor associated with leucocytoclastic vasculitis.	2001-11-27	11720182
Dermatomyositis.	2001-11-01	11730311
Vitamin D levels in women with systemic lupus erythematosus and fibromyalgia.	2001-11	11708429
Dermatomyositis and Graves' disease.	2001-10-03	11579725
Modulation of hormones in the treatment of lupus.	2001-10	11680780
Treatment of early seropositive rheumatoid arthritis: a two-year, double-blind comparison of minocycline and hydroxychloroquine.	2001-10	11665963
Leflunomide for the treatment of systemic lupus erythematosus: comment on the article by McMurray.	2001-10	11642648
Ocular toxicity and antenatal exposure to chloroquine or hydroxychloroquine for rheumatic diseases.	2001-09-08	11564493
Verrucous form of chilblain lupus erythematosus.	2001-09	11763388
Treatment of hydroxychloroquine overdose.	2001-09	11555803
Mycophenolate mofetil treatment of severe renal disease in pediatric onset systemic lupus erythematosus.	2001-09	11550982
Effect of hydroxychloroquine on progression of dementia in early Alzheimer's disease: an 18-month randomised, double-blind, placebo-controlled study.	2001-08-11	11513909
Systemic lupus erythematosus: current management.	2001-08-06	11548075
Early hydroxychloroquine macular toxicity.	2001-08	11508449
Bromocriptine in rheumatic and autoimmune diseases.	2001-08	11503136
Fatal toxic epidermal necrolysis associated with hydroxychloroquine.	2001-07	11488840
[Lymphedema of the upper limb, a complication of rheumatoid polyarthritis].	2001-06-30	11484403
Progression of hydroxychloroquine retinopathy after discontinuation of therapy: case report.	2001-05	11480331
Treatment of rheumatoid arthritis: unknown long-term effects.	2001-04	11718162
Leflunomide and rheumatoid arthritis: new preparation. Neither the safest nor the most effective slow-acting antirheumatic drug.	2001-04	11718154
Hydroxychloroquine sulphate inhibits in vitro apoptosis of circulating lymphocytes in patients with systemic lupus erythematosus.	2001-03	11495297
Antimalarial drugs in systemic lupus erythematosus: use in pregnancy.	2001	11735661
[Amphiphilic cationic drug myopathy, drug-induced lysosomal storage lipidosis].	2001	11596386
Management of hepatitis C virus-related arthritis.	2001	11580301
Combination therapy with disease modifying anti-rheumatic drugs in rheumatoid arthritis.	2001	11543695
Hydroxychloroquine-induced vertigo.	1975-09-01	1173923

Patents

Sample Use Guides

In Vivo Use Guide

Malaria: Suppression— In adults, 400 mg (=310 mg base) on exactly the same day of each week. In infants and children, the weekly suppressive dosage is 5 mg, calculated as base, per kg of body weight, but should not exceed the adult dose regardless of weight.

Route of Administration: Oral

In Vitro Use Guide

After 48 hours of stimulation with PMA and ionomycin, Hydroxychloroquine (25-100 uM) inhibited the production of IL-6, IL-17 and IL-22 in the PBMCs of healthy volunteers

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:51:04 GMT 2025` Edited by `admin` on `Mon Mar 31 17:51:04 GMT 2025`
Record UNII	8Q2869CNVH
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

HYDROXYCHLOROQUINE SULFATE

Common Name

English

ERCOQUIN

Preferred Name

English

HYDROXYCHLOROQUINE SULPHATE

Common Name

English

PLAQUENIL SULFATE

Brand Name

English

HYDROXYCHLOROQUINE SULFATE [JAN]

Common Name

English

HYDROXYCHLOROQUINE SULFATE [EP MONOGRAPH]

Common Name

English

NSC-4375

Code

English

(±)-2-((4-((7-CHLORO-4-QUINOLYL)AMINO)PENTYL)ETHYLAMINO)ETHANOL SULFATE (1:1) (SALT)

Common Name

English

HYDROXYCHLOROQUINE SULFATE [USP MONOGRAPH]

Common Name

English

HYDROXYCHLOROQUINE SULFATE [MART.]

Common Name

English

Hydroxychloroquine sulfate [WHO-DD]

Common Name

English

ETHANOL, 2-((4-((7-CHLORO-4-QUINOLINYL)AMINO)PENTYL)ETHYL)AMINO-, (±)-, SULFATE (1:1) SALT

Common Name

English

HYDROXYCHLOROQUINE SULFATE [MI]

Common Name

English

HYDROXYCHLOROQUINE SULFATE [VANDF]

Common Name

English

HYDROXYCHLOROQUINE SULFATE [USP-RS]

Common Name

English

HYDROXYCHLOROQUINE SULFATE [ORANGE BOOK]

Common Name

English

OXIKLORIN

Brand Name

English

ETHANOL, 2-((4-((7-CHLORO-4-QUINOLINYL)AMINO)PENTYL)ETHYL)AMINO-, (±)-, SULPHATE (1:1) SALT

Common Name

English

(±)-2-((4-((7-CHLORO-4-QUINOLYL)AMINO)PENTYL)ETHYLAMINO)ETHANOL SULPHATE (1:1) (SALT)

Common Name

English

QUENSYL

Brand Name

English

PLAQUENIL

Brand Name

English

Classification Tree Code System Code

EU-Orphan Drug

EU/3/17/1963