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Details

Stereochemistry RACEMIC
Molecular Formula C18H26ClN3O
Molecular Weight 335.872
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HYDROXYCHLOROQUINE

SMILES

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

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

Description

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

PubMed

PubMed

TitleDatePubMed
Drugs for discoid lupus erythematosus.
2001
Sensorineural hearing loss in conjunction with aortic insufficiency in systemic lupus erythematosus.
2001
Middermal elastolysis in two patients with lupus erythematosus.
2001 Apr
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
Bone loss prevention by an antimalarial drug.
2001 May-Jun
Safety and efficacy of disease-modifying anti-rheumatic agents: focus on the benefits and risks of etanercept.
2002
Sustained normalization of cerebral blood-flow after iloprost therapy in a patient with neuropsychiatric systemic lupus erythematosus.
2002
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
Randomized double blind trial of an extract from the pentacyclic alkaloid-chemotype of uncaria tomentosa for the treatment of rheumatoid arthritis.
2002 Apr
Pharmacoeconomics of long-term treatment of rheumatoid arthritis.
2002 Apr
[Primary Gougerot-Sjögren syndrome in a 13-year-old girl].
2002 Feb
IgM antibodies against cytomegalovirus in SLE nephritis: viral infection or aspecific autoantibody?
2002 Jan-Feb
Hydroxychloroquine reverses platelet activation induced by human IgG antiphospholipid antibodies.
2002 Mar
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
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 Mon Oct 21 20:54:06 UTC 2019 , Edited by admin on Mon Oct 21 20:54:06 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 2.4
Created by admin on Mon Oct 21 20:54:06 UTC 2019 , Edited by admin on Mon Oct 21 20:54:06 UTC 2019
NCI_THESAURUS C271
Created by admin on Mon Oct 21 20:54:06 UTC 2019 , Edited by admin on Mon Oct 21 20:54:06 UTC 2019
WHO-ATC P01BA02
Created by admin on Mon Oct 21 20:54:06 UTC 2019 , Edited by admin on Mon Oct 21 20:54:06 UTC 2019
LIVERTOX 489
Created by admin on Mon Oct 21 20:54:06 UTC 2019 , Edited by admin on Mon Oct 21 20:54:06 UTC 2019
NDF-RT N0000175482
Created by admin on Mon Oct 21 20:54:06 UTC 2019 , Edited by admin on Mon Oct 21 20:54:06 UTC 2019
NDF-RT N0000175713
Created by admin on Mon Oct 21 20:54:06 UTC 2019 , Edited by admin on Mon Oct 21 20:54:06 UTC 2019
Code System Code Type Description
MERCK INDEX
M6127
Created by admin on Mon Oct 21 20:54:06 UTC 2019 , Edited by admin on Mon Oct 21 20:54:06 UTC 2019
PRIMARY Merck Index
WIKIPEDIA
HYDROXYCHLOROQUINE
Created by admin on Mon Oct 21 20:54:06 UTC 2019 , Edited by admin on Mon Oct 21 20:54:06 UTC 2019
PRIMARY
EVMPD
SUB08077MIG
Created by admin on Mon Oct 21 20:54:06 UTC 2019 , Edited by admin on Mon Oct 21 20:54:06 UTC 2019
PRIMARY
IUPHAR
7198
Created by admin on Mon Oct 21 20:54:06 UTC 2019 , Edited by admin on Mon Oct 21 20:54:06 UTC 2019
PRIMARY
RXCUI
5521
Created by admin on Mon Oct 21 20:54:06 UTC 2019 , Edited by admin on Mon Oct 21 20:54:06 UTC 2019
PRIMARY RxNorm
EPA CompTox
118-42-3
Created by admin on Mon Oct 21 20:54:06 UTC 2019 , Edited by admin on Mon Oct 21 20:54:06 UTC 2019
PRIMARY
MESH
D006886
Created by admin on Mon Oct 21 20:54:06 UTC 2019 , Edited by admin on Mon Oct 21 20:54:06 UTC 2019
PRIMARY
DRUG BANK
DB01611
Created by admin on Mon Oct 21 20:54:06 UTC 2019 , Edited by admin on Mon Oct 21 20:54:06 UTC 2019
PRIMARY
NCI_THESAURUS
C557
Created by admin on Mon Oct 21 20:54:06 UTC 2019 , Edited by admin on Mon Oct 21 20:54:06 UTC 2019
PRIMARY
PUBCHEM
3652
Created by admin on Mon Oct 21 20:54:06 UTC 2019 , Edited by admin on Mon Oct 21 20:54:06 UTC 2019
PRIMARY
ChEMBL
CHEMBL1535
Created by admin on Mon Oct 21 20:54:06 UTC 2019 , Edited by admin on Mon Oct 21 20:54:06 UTC 2019
PRIMARY
LactMed
118-42-3
Created by admin on Mon Oct 21 20:54:06 UTC 2019 , Edited by admin on Mon Oct 21 20:54:06 UTC 2019
PRIMARY
ECHA (EC/EINECS)
204-249-8
Created by admin on Mon Oct 21 20:54:06 UTC 2019 , Edited by admin on Mon Oct 21 20:54:06 UTC 2019
PRIMARY
CAS
118-42-3
Created by admin on Mon Oct 21 20:54:06 UTC 2019 , Edited by admin on Mon Oct 21 20:54:06 UTC 2019
PRIMARY
INN
796
Created by admin on Mon Oct 21 20:54:06 UTC 2019 , Edited by admin on Mon Oct 21 20:54:06 UTC 2019
PRIMARY