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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 of HYDROXYCHLOROQUINE SULFATE

SMILES

OS(O)(=O)=O.CCN(CCO)CCCC(C)NC1=CC=NC2=C1C=CC(Cl)=C2

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 C18H26ClN3O
Molecular Weight 335.872
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

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

Description
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

Curator's Comment: Synthesized by Surrey and Hammer in 1946, hydroxychloroquine (Plaquenil) was released in 1955 after it was found to be effective in SLE and RA

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
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
Primary
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
Primary
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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
129.6 ng/mL
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
HYDROXYCHLOROQUINE SULFATE blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
1.22 μM
400 mg single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
HYDROXYCHLOROQUINE SULFATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
50.3 ng/mL
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
HYDROXYCHLOROQUINE SULFATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
102.3 μM × h
400 mg single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
HYDROXYCHLOROQUINE SULFATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
537 h
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
HYDROXYCHLOROQUINE SULFATE blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
172.3 h
400 mg single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
HYDROXYCHLOROQUINE SULFATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
2963 h
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
HYDROXYCHLOROQUINE SULFATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
48%
unknown, unknown
HYDROXYCHLOROQUINE SULFATE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse 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:
healthy, 16 years
n = 1
Health Status: healthy
Age Group: 16 years
Sex: M
Population Size: 1
Sources:
Other AEs: Cardio-respiratory arrest...
Other AEs:
Cardio-respiratory arrest (grade 5)
Sources:
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
Co-administed with::
levothyroxine
aspirin
ibuprofen
Sources:
healthy, 16 years
n = 1
Health Status: healthy
Age Group: 16 years
Sex: F
Population Size: 1
Sources:
Other AEs: Tachycardia, Hypotension...
Other AEs:
Tachycardia
Hypotension
Depression
Hypokalemia
Sources:
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:
healthy, 18 years
n = 1
Health Status: healthy
Age Group: 18 years
Sex: F
Population Size: 1
Sources:
Other AEs: Hypotension, Hypokalemia...
Other AEs:
Hypotension
Hypokalemia
Sources:
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:
healthy, 2.5 years
n = 1
Health Status: healthy
Age Group: 2.5 years
Sex: M
Population Size: 1
Sources:
Other AEs: Cardio-respiratory arrest...
Other AEs:
Cardio-respiratory arrest (grade 5)
Sources:
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:
healthy, 29 years
n = 1
Health Status: healthy
Age Group: 29 years
Sex: M
Population Size: 1
Sources:
Other AEs: Vomiting, Ventricular tachycardia...
Other AEs:
Vomiting
Ventricular tachycardia
Sources:
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
Co-administed with::
temozolomide(150 mg/m2; daily for 7/14 d)
Sources:
unhealthy, median age 64 years
n = 8
Health Status: unhealthy
Condition: advanced solid malignancies
Age Group: median age 64 years
Sex: M+F
Population Size: 8
Sources:
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:
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
Co-administed with::
temozolomide(150 mg/m2; daily for 7/14 d)
Sources:
unhealthy, median age 64 years
n = 15
Health Status: unhealthy
Condition: advanced solid malignancies
Age Group: median age 64 years
Sex: M+F
Population Size: 15
Sources:
DLT: Heart block...
Dose limiting toxicities:
Heart block (grade 3, 6.7%)
Sources:
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
Co-administed with::
temozolomide(150 mg/m2; daily for 7/14 d)
Sources:
unhealthy, median age 64 years
n = 7
Health Status: unhealthy
Condition: advanced solid malignancies
Age Group: median age 64 years
Sex: M+F
Population Size: 7
Sources:
DLT: Rash...
Dose limiting toxicities:
Rash (grade 3, 14.3%)
Sources:
200 mg 2 times / day steady, oral
Dose: 200 mg, 2 times / day
Route: oral
Route: steady
Dose: 200 mg, 2 times / day
Sources:
unhealthy
n = 7
Health Status: unhealthy
Condition: cardiovascular disease
Population Size: 7
Sources:
Other AEs: Increased blood pressure...
Other AEs:
Increased blood pressure (below serious, 1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
Cardio-respiratory arrest grade 5
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:
healthy, 16 years
n = 1
Health Status: healthy
Age Group: 16 years
Sex: M
Population Size: 1
Sources:
Depression
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
Co-administed with::
levothyroxine
aspirin
ibuprofen
Sources:
healthy, 16 years
n = 1
Health Status: healthy
Age Group: 16 years
Sex: F
Population Size: 1
Sources:
Hypokalemia
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
Co-administed with::
levothyroxine
aspirin
ibuprofen
Sources:
healthy, 16 years
n = 1
Health Status: healthy
Age Group: 16 years
Sex: F
Population Size: 1
Sources:
Hypotension
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
Co-administed with::
levothyroxine
aspirin
ibuprofen
Sources:
healthy, 16 years
n = 1
Health Status: healthy
Age Group: 16 years
Sex: F
Population Size: 1
Sources:
Tachycardia
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
Co-administed with::
levothyroxine
aspirin
ibuprofen
Sources:
healthy, 16 years
n = 1
Health Status: healthy
Age Group: 16 years
Sex: F
Population Size: 1
Sources:
Hypokalemia
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:
healthy, 18 years
n = 1
Health Status: healthy
Age Group: 18 years
Sex: F
Population Size: 1
Sources:
Hypotension
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:
healthy, 18 years
n = 1
Health Status: healthy
Age Group: 18 years
Sex: F
Population Size: 1
Sources:
Cardio-respiratory arrest grade 5
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:
healthy, 2.5 years
n = 1
Health Status: healthy
Age Group: 2.5 years
Sex: M
Population Size: 1
Sources:
Ventricular tachycardia
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:
healthy, 29 years
n = 1
Health Status: healthy
Age Group: 29 years
Sex: M
Population Size: 1
Sources:
Vomiting
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:
healthy, 29 years
n = 1
Health Status: healthy
Age Group: 29 years
Sex: M
Population Size: 1
Sources:
Anemia grade 1-2, 13%
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
Co-administed with::
temozolomide(150 mg/m2; daily for 7/14 d)
Sources:
unhealthy, median age 64 years
n = 8
Health Status: unhealthy
Condition: advanced solid malignancies
Age Group: median age 64 years
Sex: M+F
Population Size: 8
Sources:
Bradycardia grade 1-2, 13%
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
Co-administed with::
temozolomide(150 mg/m2; daily for 7/14 d)
Sources:
unhealthy, median age 64 years
n = 8
Health Status: unhealthy
Condition: advanced solid malignancies
Age Group: median age 64 years
Sex: M+F
Population Size: 8
Sources:
Hypotension grade 1-2, 13%
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
Co-administed with::
temozolomide(150 mg/m2; daily for 7/14 d)
Sources:
unhealthy, median age 64 years
n = 8
Health Status: unhealthy
Condition: advanced solid malignancies
Age Group: median age 64 years
Sex: M+F
Population Size: 8
Sources:
Rash grade 1-2, 13%
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
Co-administed with::
temozolomide(150 mg/m2; daily for 7/14 d)
Sources:
unhealthy, median age 64 years
n = 8
Health Status: unhealthy
Condition: advanced solid malignancies
Age Group: median age 64 years
Sex: M+F
Population Size: 8
Sources:
Thrombocytopenia grade 1-2, 13%
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
Co-administed with::
temozolomide(150 mg/m2; daily for 7/14 d)
Sources:
unhealthy, median age 64 years
n = 8
Health Status: unhealthy
Condition: advanced solid malignancies
Age Group: median age 64 years
Sex: M+F
Population Size: 8
Sources:
Constipation grade 1-2, 25%
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
Co-administed with::
temozolomide(150 mg/m2; daily for 7/14 d)
Sources:
unhealthy, median age 64 years
n = 8
Health Status: unhealthy
Condition: advanced solid malignancies
Age Group: median age 64 years
Sex: M+F
Population Size: 8
Sources:
Diarrhea grade 1-2, 25%
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
Co-administed with::
temozolomide(150 mg/m2; daily for 7/14 d)
Sources:
unhealthy, median age 64 years
n = 8
Health Status: unhealthy
Condition: advanced solid malignancies
Age Group: median age 64 years
Sex: M+F
Population Size: 8
Sources:
Vomiting grade 1-2, 25%
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
Co-administed with::
temozolomide(150 mg/m2; daily for 7/14 d)
Sources:
unhealthy, median age 64 years
n = 8
Health Status: unhealthy
Condition: advanced solid malignancies
Age Group: median age 64 years
Sex: M+F
Population Size: 8
Sources:
Anorexia grade 1-2, 38%
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
Co-administed with::
temozolomide(150 mg/m2; daily for 7/14 d)
Sources:
unhealthy, median age 64 years
n = 8
Health Status: unhealthy
Condition: advanced solid malignancies
Age Group: median age 64 years
Sex: M+F
Population Size: 8
Sources:
Nausea grade 1-2, 50%
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
Co-administed with::
temozolomide(150 mg/m2; daily for 7/14 d)
Sources:
unhealthy, median age 64 years
n = 8
Health Status: unhealthy
Condition: advanced solid malignancies
Age Group: median age 64 years
Sex: M+F
Population Size: 8
Sources:
Fatigue grade 1-2, 88%
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
Co-administed with::
temozolomide(150 mg/m2; daily for 7/14 d)
Sources:
unhealthy, median age 64 years
n = 8
Health Status: unhealthy
Condition: advanced solid malignancies
Age Group: median age 64 years
Sex: M+F
Population Size: 8
Sources:
Nausea grade 3, 13%
DLT
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
Co-administed with::
temozolomide(150 mg/m2; daily for 7/14 d)
Sources:
unhealthy, median age 64 years
n = 8
Health Status: unhealthy
Condition: advanced solid malignancies
Age Group: median age 64 years
Sex: M+F
Population Size: 8
Sources:
Vomiting grade 3, 13%
DLT
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
Co-administed with::
temozolomide(150 mg/m2; daily for 7/14 d)
Sources:
unhealthy, median age 64 years
n = 8
Health Status: unhealthy
Condition: advanced solid malignancies
Age Group: median age 64 years
Sex: M+F
Population Size: 8
Sources:
Lymphopenia grade 3-4, 13%
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
Co-administed with::
temozolomide(150 mg/m2; daily for 7/14 d)
Sources:
unhealthy, median age 64 years
n = 8
Health Status: unhealthy
Condition: advanced solid malignancies
Age Group: median age 64 years
Sex: M+F
Population Size: 8
Sources:
Heart block grade 3, 6.7%
DLT
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
Co-administed with::
temozolomide(150 mg/m2; daily for 7/14 d)
Sources:
unhealthy, median age 64 years
n = 15
Health Status: unhealthy
Condition: advanced solid malignancies
Age Group: median age 64 years
Sex: M+F
Population Size: 15
Sources:
Rash grade 3, 14.3%
DLT
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
Co-administed with::
temozolomide(150 mg/m2; daily for 7/14 d)
Sources:
unhealthy, median age 64 years
n = 7
Health Status: unhealthy
Condition: advanced solid malignancies
Age Group: median age 64 years
Sex: M+F
Population Size: 7
Sources:
Increased blood pressure below serious, 1 patient
200 mg 2 times / day steady, oral
Dose: 200 mg, 2 times / day
Route: oral
Route: steady
Dose: 200 mg, 2 times / day
Sources:
unhealthy
n = 7
Health Status: unhealthy
Condition: cardiovascular disease
Population Size: 7
Sources:
Overview

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
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
Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Ocular manifestations of juvenile rheumatoid arthritis.
1975 Jun
Hydroxychloroquine ototoxicity in a patient with rheumatoid arthritis.
2000
Hydroxychloroquine-induced seizure in a patient with systemic lupus erythematosus.
2000 Dec
Hydroxychloroquine neuromyotoxicity.
2000 Dec
Combination therapy with disease modifying anti-rheumatic drugs in rheumatoid arthritis.
2001
Antimalarials--the 'real' advance in lupus.
2001
Antimalarial therapy: a panacea for mild lupus?
2001
Drugs for discoid lupus erythematosus.
2001
Sensorineural hearing loss in conjunction with aortic insufficiency in systemic lupus erythematosus.
2001
Patterns of disease-modifying antirheumatic drug use, medical resource consumption, and cost among rheumatoid arthritis patients.
2001 Apr
Middermal elastolysis in two patients with lupus erythematosus.
2001 Apr
Bromocriptine in rheumatic and autoimmune diseases.
2001 Aug
Angiooedema due to acquired deficiency of C1-esterase inhibitor associated with leucocytoclastic vasculitis.
2001 Aug-Sep
Progress in the treatment of rheumatoid arthritis.
2001 Dec 12
A linear erythema on the nose of a Korean girl.
2001 Feb
Corneal melt as the initial presentation of primary Sjögren's syndrome.
2001 Feb
Hydroxychloroquine retinopathy.
2001 Feb
[Cutaneous lupus erythematosus following argon laser treatment].
2001 Jan
Fatal toxic epidermal necrolysis associated with hydroxychloroquine.
2001 Jul
Hydroxychloroquine enhances the endocrine secretion of adenovirus-directed growth hormone from rat submandibular glands in vivo.
2001 Jul 1
Rheumatologists' attitudes toward routine screening for hydroxychloroquine retinopathy.
2001 Jun
Analysis of the ABCR (ABCA4) gene in 4-aminoquinoline retinopathy: is retinal toxicity by chloroquine and hydroxychloroquine related to Stargardt disease?
2001 Jun
Pregnancy in past or present lupus nephritis: a study of 32 pregnancies from a single centre.
2001 Jun
Western and Chinese antirheumatic drug-induced T cell apoptotic DNA damage uses different caspase cascades and is independent of Fas/Fas ligand interaction.
2001 Jun 1
[Photodermatosis induced by hydroxychloroquine: 4 cases].
2001 Jun-Jul
Management of a patient with sarcoid calcaneitis and dactylitis.
2001 Mar
Effect of different drugs on the level of DNA-hydrolyzing polyclonal IgG antibodies in sera of patients with Hashimoto's thyroiditis and nontoxic nodal goiter.
2001 Mar-Apr
Lupus profundus, indeterminate lymphocytic lobular panniculitis and subcutaneous T-cell lymphoma: a spectrum of subcuticular T-cell lymphoid dyscrasia.
2001 May
Combination therapy in rheumatoid arthritis.
2001 May
Bone loss prevention by an antimalarial drug.
2001 May-Jun
[Psychiatric manifestations of lupus erythematosus systemic and Sjogren's syndrome].
2001 Nov-Dec
Treatment of early seropositive rheumatoid arthritis: a two-year, double-blind comparison of minocycline and hydroxychloroquine.
2001 Oct
Verrucous form of chilblain lupus erythematosus.
2001 Sep
Treatment of hydroxychloroquine overdose.
2001 Sep
Mycophenolate mofetil treatment of severe renal disease in pediatric onset systemic lupus erythematosus.
2001 Sep
Delay to institution of therapy and induction of remission using single-drug or combination-disease-modifying antirheumatic drug therapy in early rheumatoid arthritis.
2002 Apr
How frequently and how soon should we screen our patients for the presence of antimalarial retinopathy?
2002 Feb
Second-line drugs used in recent-onset rheumatoid arthritis in Brittany (France).
2002 Jan
Chloroquine decreases cell-surface expression of tumour necrosis factor receptors in human histiocytic U-937 cells.
2002 Jan
Leflunomide induced fevers, thrombocytosis, and leukocytosis in a patient with relapsing polychondritis.
2002 Jan
Nonendemic pemphigus foliaceus in children.
2002 Mar
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Sample Use Guides

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
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 Fri Dec 15 15:13:55 GMT 2023
Edited
by admin
on Fri Dec 15 15:13:55 GMT 2023
Record UNII
8Q2869CNVH
Record Status Validated (UNII)
Record Version
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Name Type Language
HYDROXYCHLOROQUINE SULFATE
MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
Common 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
ERCOQUIN
Brand 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
Created by admin on Fri Dec 15 15:13:55 GMT 2023 , Edited by admin on Fri Dec 15 15:13:55 GMT 2023
NCI_THESAURUS C271
Created by admin on Fri Dec 15 15:13:55 GMT 2023 , Edited by admin on Fri Dec 15 15:13:55 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID1047811
Created by admin on Fri Dec 15 15:13:55 GMT 2023 , Edited by admin on Fri Dec 15 15:13:55 GMT 2023
PRIMARY
SMS_ID
100000090560
Created by admin on Fri Dec 15 15:13:55 GMT 2023 , Edited by admin on Fri Dec 15 15:13:55 GMT 2023
PRIMARY
FDA UNII
8Q2869CNVH
Created by admin on Fri Dec 15 15:13:55 GMT 2023 , Edited by admin on Fri Dec 15 15:13:55 GMT 2023
PRIMARY
RS_ITEM_NUM
1327000
Created by admin on Fri Dec 15 15:13:55 GMT 2023 , Edited by admin on Fri Dec 15 15:13:55 GMT 2023
PRIMARY
DRUG BANK
DBSALT000096
Created by admin on Fri Dec 15 15:13:55 GMT 2023 , Edited by admin on Fri Dec 15 15:13:55 GMT 2023
PRIMARY
RXCUI
153972
Created by admin on Fri Dec 15 15:13:55 GMT 2023 , Edited by admin on Fri Dec 15 15:13:55 GMT 2023
PRIMARY RxNorm
CAS
747-36-4
Created by admin on Fri Dec 15 15:13:55 GMT 2023 , Edited by admin on Fri Dec 15 15:13:55 GMT 2023
PRIMARY
EVMPD
SUB02587MIG
Created by admin on Fri Dec 15 15:13:55 GMT 2023 , Edited by admin on Fri Dec 15 15:13:55 GMT 2023
PRIMARY
PUBCHEM
12947
Created by admin on Fri Dec 15 15:13:55 GMT 2023 , Edited by admin on Fri Dec 15 15:13:55 GMT 2023
PRIMARY
CAS
14480-75-2
Created by admin on Fri Dec 15 15:13:55 GMT 2023 , Edited by admin on Fri Dec 15 15:13:55 GMT 2023
NON-SPECIFIC STOICHIOMETRY
ChEMBL
CHEMBL1535
Created by admin on Fri Dec 15 15:13:55 GMT 2023 , Edited by admin on Fri Dec 15 15:13:55 GMT 2023
PRIMARY
ECHA (EC/EINECS)
212-019-3
Created by admin on Fri Dec 15 15:13:55 GMT 2023 , Edited by admin on Fri Dec 15 15:13:55 GMT 2023
PRIMARY
MERCK INDEX
m6127
Created by admin on Fri Dec 15 15:13:55 GMT 2023 , Edited by admin on Fri Dec 15 15:13:55 GMT 2023
PRIMARY Merck Index
NCI_THESAURUS
C29101
Created by admin on Fri Dec 15 15:13:55 GMT 2023 , Edited by admin on Fri Dec 15 15:13:55 GMT 2023
PRIMARY
NSC
4375
Created by admin on Fri Dec 15 15:13:55 GMT 2023 , Edited by admin on Fri Dec 15 15:13:55 GMT 2023
PRIMARY
DAILYMED
8Q2869CNVH
Created by admin on Fri Dec 15 15:13:55 GMT 2023 , Edited by admin on Fri Dec 15 15:13:55 GMT 2023
PRIMARY
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