U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C18H26ClN3O
Molecular Weight 335.8722
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HYDROXYCHLOROQUINE

SMILES

CCN(CCCC(C)Nc1ccnc2cc(ccc12)Cl)CCO

InChI

InChIKey=XXSMGPRMXLTPCZ-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C18H26ClN3O
Molecular Weight 335.8722
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

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

-4.64227205E11
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

-4.64227205E11
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

-4.64227205E11
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
Hydroxychloroquine-induced vertigo.
1975 Sep 1
[Amphiphilic cationic drug myopathy, drug-induced lysosomal storage lipidosis].
2001
Management of hepatitis C virus-related arthritis.
2001
Combination therapy with disease modifying anti-rheumatic drugs in rheumatoid arthritis.
2001
Hydroxychloroquine (HCQ) in lupus pregnancy: double-blind and placebo-controlled study.
2001
Antimalarials--the 'real' advance in lupus.
2001
Treatment of systemic lupus erythematosus with bromocriptine.
2001
Complete heart block in an adult with systemic lupus erythematosus and recent onset of hydroxychloroquine therapy.
2001
Therapeutic response and long-term follow-up in a systemic lupus erythematosus patient presenting with Kikuchi's disease.
2001
Vascular stiffness in women with systemic lupus erythematosus.
2001 Apr
Middermal elastolysis in two patients with lupus erythematosus.
2001 Apr
Rational use of new and existing disease-modifying agents in rheumatoid arthritis.
2001 Apr 17
Pilot tolerability studies of hydroxychloroquine and colchicine in Alzheimer disease.
2001 Apr-Jun
Early hydroxychloroquine macular toxicity.
2001 Aug
Systemic lupus erythematosus: current management.
2001 Aug 6
Angiooedema due to acquired deficiency of C1-esterase inhibitor associated with leucocytoclastic vasculitis.
2001 Aug-Sep
A linear erythema on the nose of a Korean girl.
2001 Feb
Lymphocytic infiltration of the skin is a photosensitive variant of lupus erythematosus: evidence by phototesting.
2001 Feb
[Psychological and behavioral disorders with good outcome in neurosarcoidosis].
2001 Feb
Newer and alternative non-steroidal treatments for asthmatic inflammation.
2001 Jan-Feb
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
Treating early rheumatoid arthritis in the younger patient.
2001 Jun
Conventional DMARD options for patients with a suboptimal response to methotrexate.
2001 Jun
Disease modifying antirheumatic drugs: longterm safety issues.
2001 Jun
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
The additive in vitro anti-HIV-1 effect of chloroquine, when combined with zidovudine and hydroxyurea.
2001 Jun 15
[Photodermatosis induced by hydroxychloroquine: 4 cases].
2001 Jun-Jul
[Subacute cutaneous lupus gyratus repens].
2001 Mar
Reversible blindness resulting from optic chiasmitis secondary to systemic lupus erythematosus.
2001 Mar
Current concepts regarding pharmacologic treatment of rheumatoid and osteoarthritis.
2001 May
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
Treatment with cyclosporin switching to hydroxychloroquine in patients with rheumatoid arthritis.
2001 May
Bone loss prevention by an antimalarial drug.
2001 May-Jun
Treatment of early seropositive rheumatoid arthritis: a two-year, double-blind comparison of minocycline and hydroxychloroquine.
2001 Oct
Leflunomide for the treatment of systemic lupus erythematosus: comment on the article by McMurray.
2001 Oct
Treatment of hydroxychloroquine overdose.
2001 Sep
Mycophenolate mofetil treatment of severe renal disease in pediatric onset systemic lupus erythematosus.
2001 Sep
Ocular toxicity and antenatal exposure to chloroquine or hydroxychloroquine for rheumatic diseases.
2001 Sep 8
Dermatomyositis and Graves' disease.
2001 Sep-Oct
Evidence of transplacental passage of hydroxychloroquine in humans.
2002 Apr
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
Canadian Consensus Conference on hydroxychloroquine.
2002 Apr
Pharmacoeconomics of long-term treatment of rheumatoid arthritis.
2002 Apr
Prescribing trends in disease modifying antirheumatic drugs for rheumatoid arthritis: a survey of practicing Canadian rheumatologists.
2002 Feb
Hydroxychloroquine reverses platelet activation induced by human IgG antiphospholipid antibodies.
2002 Mar
Nonendemic pemphigus foliaceus in children.
2002 Mar
The effectiveness of hydroxychloroquine in patients with type 2 diabetes mellitus who are refractory to sulfonylureas--a randomized trial.
2002 Mar
Patents

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 Jun 25 23:49:01 UTC 2021
Edited
by admin
on Fri Jun 25 23:49:01 UTC 2021
Record UNII
4QWG6N8QKH
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
HYDROXYCHLOROQUINE
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
HYDROXYCHLOROQUINE [INN]
Common Name English
HYDROXYCHLOROQUINE [WHO-DD]
Common Name English
HYDROXYCHLOROQUINE [MI]
Common Name English
(+/-)-2-((4-((7-CHLORO-4-QUINOLYL)AMINO)PENTYL)ETHYLAMINO)ETHANOL
Systematic Name English
HYDROXYCHLOROQUINE [VANDF]
Common Name English
POLIRREUMIN
Brand Name English
ETHANOL, 2-((4-((7-CHLORO-4-QUINOLINYL)AMINO)PENTYL)ETHYL)AMINO-, (+/-)-
Systematic Name English
Classification Tree Code System Code
EU-Orphan Drug EU/3/16/1820
Created by admin on Fri Jun 25 23:49:01 UTC 2021 , Edited by admin on Fri Jun 25 23:49:01 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 2.4
Created by admin on Fri Jun 25 23:49:01 UTC 2021 , Edited by admin on Fri Jun 25 23:49:01 UTC 2021
NCI_THESAURUS C271
Created by admin on Fri Jun 25 23:49:01 UTC 2021 , Edited by admin on Fri Jun 25 23:49:01 UTC 2021
WHO-ATC P01BA02
Created by admin on Fri Jun 25 23:49:01 UTC 2021 , Edited by admin on Fri Jun 25 23:49:01 UTC 2021
LIVERTOX 489
Created by admin on Fri Jun 25 23:49:01 UTC 2021 , Edited by admin on Fri Jun 25 23:49:01 UTC 2021
NDF-RT N0000175482
Created by admin on Fri Jun 25 23:49:01 UTC 2021 , Edited by admin on Fri Jun 25 23:49:01 UTC 2021
NDF-RT N0000175713
Created by admin on Fri Jun 25 23:49:01 UTC 2021 , Edited by admin on Fri Jun 25 23:49:01 UTC 2021
Code System Code Type Description
DRUG CENTRAL
1395
Created by admin on Fri Jun 25 23:49:01 UTC 2021 , Edited by admin on Fri Jun 25 23:49:01 UTC 2021
PRIMARY
MERCK INDEX
M6127
Created by admin on Fri Jun 25 23:49:01 UTC 2021 , Edited by admin on Fri Jun 25 23:49:01 UTC 2021
PRIMARY Merck Index
WIKIPEDIA
HYDROXYCHLOROQUINE
Created by admin on Fri Jun 25 23:49:01 UTC 2021 , Edited by admin on Fri Jun 25 23:49:01 UTC 2021
PRIMARY
EVMPD
SUB08077MIG
Created by admin on Fri Jun 25 23:49:01 UTC 2021 , Edited by admin on Fri Jun 25 23:49:01 UTC 2021
PRIMARY
IUPHAR
7198
Created by admin on Fri Jun 25 23:49:01 UTC 2021 , Edited by admin on Fri Jun 25 23:49:01 UTC 2021
PRIMARY
RXCUI
5521
Created by admin on Fri Jun 25 23:49:01 UTC 2021 , Edited by admin on Fri Jun 25 23:49:01 UTC 2021
PRIMARY RxNorm
FDA UNII
4QWG6N8QKH
Created by admin on Fri Jun 25 23:49:01 UTC 2021 , Edited by admin on Fri Jun 25 23:49:01 UTC 2021
PRIMARY
EPA CompTox
118-42-3
Created by admin on Fri Jun 25 23:49:01 UTC 2021 , Edited by admin on Fri Jun 25 23:49:01 UTC 2021
PRIMARY
MESH
D006886
Created by admin on Fri Jun 25 23:49:01 UTC 2021 , Edited by admin on Fri Jun 25 23:49:01 UTC 2021
PRIMARY
DRUG BANK
DB01611
Created by admin on Fri Jun 25 23:49:01 UTC 2021 , Edited by admin on Fri Jun 25 23:49:01 UTC 2021
PRIMARY
NCI_THESAURUS
C557
Created by admin on Fri Jun 25 23:49:01 UTC 2021 , Edited by admin on Fri Jun 25 23:49:01 UTC 2021
PRIMARY
PUBCHEM
3652
Created by admin on Fri Jun 25 23:49:01 UTC 2021 , Edited by admin on Fri Jun 25 23:49:01 UTC 2021
PRIMARY
ChEMBL
CHEMBL1535
Created by admin on Fri Jun 25 23:49:01 UTC 2021 , Edited by admin on Fri Jun 25 23:49:01 UTC 2021
PRIMARY
ECHA (EC/EINECS)
204-249-8
Created by admin on Fri Jun 25 23:49:01 UTC 2021 , Edited by admin on Fri Jun 25 23:49:01 UTC 2021
PRIMARY
CAS
118-42-3
Created by admin on Fri Jun 25 23:49:01 UTC 2021 , Edited by admin on Fri Jun 25 23:49:01 UTC 2021
PRIMARY
LACTMED
Hydroxychloroquine
Created by admin on Fri Jun 25 23:49:01 UTC 2021 , Edited by admin on Fri Jun 25 23:49:01 UTC 2021
PRIMARY
INN
796
Created by admin on Fri Jun 25 23:49:01 UTC 2021 , Edited by admin on Fri Jun 25 23:49:01 UTC 2021
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
TARGET ORGANISM->INHIBITOR
after 24 hours incubation; works in cell culture may not work in-vivo
EC50
TARGET ORGANISM->INHIBITOR
EC50
TARGET -> INHIBITOR
Related Record Type Details
METABOLITE ACTIVE -> PARENT
METABOLITE ACTIVE -> PARENT
METABOLITE ACTIVE -> PARENT
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC SINGLE DOSE

ORAL ADMINISTRATION

Tmax PHARMACOKINETIC ORAL ADMINISTRATION

SINGLE DOSE