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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
Hydroxychloroquine-induced vertigo.
1975 Sep 1
Antimalarial drugs in systemic lupus erythematosus: use in pregnancy.
2001
[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
Treatment of rheumatoid arthritis: unknown long-term effects.
2001 Apr
Leflunomide and rheumatoid arthritis: new preparation. Neither the safest nor the most effective slow-acting antirheumatic drug.
2001 Apr
Early hydroxychloroquine macular toxicity.
2001 Aug
Bromocriptine in rheumatic and autoimmune diseases.
2001 Aug
Effect of hydroxychloroquine on progression of dementia in early Alzheimer's disease: an 18-month randomised, double-blind, placebo-controlled study.
2001 Aug 11
Systemic lupus erythematosus: current management.
2001 Aug 6
Angiooedema due to acquired deficiency of C1-esterase inhibitor associated with leucocytoclastic vasculitis.
2001 Aug-Sep
[Combined basic therapeutic drugs. From individual hope to targeted use].
2001 Dec
Hydroxychloroquine retinopathy.
2001 Dec
Progress in the treatment of rheumatoid arthritis.
2001 Dec 12
Fatal toxic epidermal necrolysis associated with hydroxychloroquine.
2001 Jul
[Lymphedema of the upper limb, a complication of rheumatoid polyarthritis].
2001 Jun 30
Hydroxychloroquine sulphate inhibits in vitro apoptosis of circulating lymphocytes in patients with systemic lupus erythematosus.
2001 Mar
Progression of hydroxychloroquine retinopathy after discontinuation of therapy: case report.
2001 May
Vitamin D levels in women with systemic lupus erythematosus and fibromyalgia.
2001 Nov
Dermatomyositis.
2001 Nov 1
[Psychiatric manifestations of lupus erythematosus systemic and Sjogren's syndrome].
2001 Nov-Dec
Modulation of hormones in the treatment of lupus.
2001 Oct
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
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
Ocular toxicity and antenatal exposure to chloroquine or hydroxychloroquine for rheumatic diseases.
2001 Sep 8
Dermatomyositis and Graves' disease.
2001 Sep-Oct
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
How frequently and how soon should we screen our patients for the presence of antimalarial retinopathy?
2002 Feb
Prescribing trends in disease modifying antirheumatic drugs for rheumatoid arthritis: a survey of practicing Canadian rheumatologists.
2002 Feb
Antimalarial agents in pregnancy.
2002 Feb 9
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
Treatment of severe immune thrombocytopenia associated with systemic lupus erythematosus: 59 cases.
2002 Jan
Leflunomide induced fevers, thrombocytosis, and leukocytosis in a patient with relapsing polychondritis.
2002 Jan
Hydroxychloroquine ototoxicity in a child with idiopathic pulmonary haemosiderosis.
2002 Jan 11
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
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

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