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CAS NUMBER: 118-42-3
EC NUMBER: 204-249-8
MOLECULAR FORMULA: C18H26ClN3O
MOLECULAR WEIGHT: 335.9
IUPAC NAME: 2-[4-[(7-chloroquinolin-4-yl)amino]pentyl-ethylamino]ethanol
Hydroxychloroquine is an aminoquinoline that is chloroquine in which one of the N-ethyl groups is hydroxylated at position 2.
An antimalarial with properties similar to chloroquine that acts against erythrocytic forms of malarial parasites
Hydroxychloroquine is mainly used as the sulfate salt for the treatment of lupus erythematosus, rheumatoid arthritis, and light-sensitive skin eruptions.
Hydroxychloroquine has a role as an antimalarial, an antirheumatic drug, a dermatologic drug and an anticoronaviral agent.
Hydroxychloroquine is an aminoquinoline, an organochlorine compound, a primary alcohol, a secondary amino compound and a tertiary amino compound.
Hydroxychloroquine derives from a chloroquine.
Hydroxychloroquine is a conjugate base of a hydroxychloroquine(2+).
Hydroxychloroquine, sold under the brand name Plaquenil among others, is a medication used to prevent and treat malaria in areas where malaria remains sensitive to chloroquine.
Other uses include treatment of rheumatoid arthritis, lupus, and porphyria cutanea tarda.
Hydroxychloroquine is taken by mouth, often in the form of hydroxychloroquine sulfate.
Hydroxychloroquine is in the antimalarial and 4-aminoquinoline families of medication.
Hydroxychloroquine was approved for medical use in the United States in 1955.
Hydroxychloroquine is on the World Health Organization's List of Essential Medicines.
In 2019, Hydroxychloroquine was the 122nd most commonly prescribed medication in the United States, with more than 5 million prescriptions.
Hydroxychloroquine has been studied for an ability to prevent and treat coronavirus disease 2019 (COVID‑19).
But clinical trials found it ineffective for this purpose and a possible risk of dangerous side effects.
The speculative use of hydroxychloroquine for COVID‑19 threatens its availability for people with established indications
Hydroxychloroquine has been studied for the treatment and prevention of coronavirus disease 2019 (COVID-19).
Hydroxychloroquine is a prescription drug that’s been around since the 1940s. Doctors first used it to treat malaria.
What Conditions Does It Treat?
Hydroxychloroquine’s most often used to treat autoimmune disorders.
Hydroxychloroquine is a disease-modifying anti-rheumatic drug (DMARD).
Regulates the activity of the immune system, which can be overactive in some casesOver the long term hydroxychloroquine can reduce pain, swelling and joint stiffness.
If you have lupus, it may also improve the rash.
Hydroxychloroquine may be as long as 12 weeks before you notice the benefits.
Hydroxychloroquine is usually taken with other medications such as methotrexate.
Hydroxychloroquine is commonly used alongside other disease-modifying drugs including methotrexate – especially for rheumatoid arthritis.
There's no known interaction between alcohol and hydroxychloroquine
Hydroxychloroquine is a quinoline medicine used to treat or prevent malaria, a disease caused by parasites that enter the body through the bite of a mosquito.
Malaria is common in areas such as Africa, South America, and Southern Asia.
Hydroxychloroquine is not effective against all strains of malaria, or against malaria in areas where the infection has been resistant to a similar drug called chloroquine.
Hydroxychloroquine is also used to treat symptoms of rheumatoid arthritis and discoid or systemic lupus erythematosus.
Hydroxychloroquine (Plaquenil) is considered a disease-modifying anti-rheumatic drug (DMARD).
Hydroxychloroquine can decrease the pain and swelling of arthritis.
Hydroxychloroquine may prevent joint damage and reduce the risk of long-term disability.
Hydroxychloroquine is in a class of medications that was first used to prevent and treat malaria.
Today, Hydroxychloroquine is used to treat rheumatoid arthritis, some symptoms of lupus, childhood arthritis (or juvenile idiopathic arthritis) and other autoimmune diseases.
Hydroxychloroquine is not clear why hydroxychloroquine is effective at treating autoimmune diseases.
Hydroxychloroquine is believed that hydroxychloroquine interferes with the communication of cells in the immune system
Hydroxychloroquine is used to treat malaria, lupus erythematosus, and rheumatoid arthritis.
Hydroxychloroquine may be used as part of a combination therapy.
That means you may need to take it with other drugs.
Hydroxychloroquine is used to treat lupus erythematosus and rheumatoid arthritis.
Hydroxychloroquine is also used to prevent and treat malaria.
Hydroxychloroquine is an antimalarial drug. It treats malaria by killing the parasites that cause the disease.
Hydroxychloroquine may also be used to treat coronavirus (COVID-19) in certain hospitalized patients.
Hydroxychloroquine belongs to a group of medicines known as antimalarials.
Hydroxychloroquine works by preventing or treating malaria, a red blood cell infection transmitted by the bite of a mosquito.
Hydroxychloroquine is used to treat discoid lupus erythematosus (DLE) or systemic lupus erythematosus (SLE or lupus).
Hydroxychloroquine is also used to treat acute and chronic rheumatoid arthritis.
Hydroxychloroquine is a derivative of chloroquine that has both antimalarial and antiinflammatory activities and is now most often used as an antirheumatologic agent in systemic lupus erythematosis and rheumatoid arthritis.
Hydroxychloroquine therapy has not been associated with liver function abnormalities
Hydroxychloroquine is a racemic mixture consisting of an R and S enantiomer.
Hydroxychloroquine is an aminoquinoline like [chloroquine].
Hydroxychloroquine is a commonly prescribed medication in the treatment of uncomplicated malaria, rheumatoid arthritis, chronic discoid lupus erythematosus, and systemic lupus erythematosus.
Hydroxychloroquine is also used for the prophylaxis of malaria in regions where chloroquine resistance is unlikely.
Hydroxychloroquine was developed during World War II as a derivative of [quinacrine] with less severe side effects.
Chloroquine and hydroxychloroquine are both being investigated for the treatment of SARS-CoV-2.
Pharmacology and Biochemistry:
Hydroxychloroquine affects the function of lysozomes in humans as well as plasmodia.
Altering the pH of the lysozomes reduces low affinity self antigen presentation in autoimmue diseases and interferes with the ability of plasmodia to proteolyse hemoglobin for their energy requirements.
Hydroxychloroquine has a long duration of action as it may be taken on a weekly basis for some indications.
Hydroxychloroquine may lead to severe hypoglycemia and so diabetic patients are advised to monitor their blood glucose levels.
Hydroxychloroquine is not effective against malaria in areas where chloroquine resistance has been reported.
Metabolism/Metabolites:
Hydroxychloroquine is N-dealkylated by CYP3A4 to the active metabolite desethylhydroxychloroquine, as well as the inactive metabolites desethylchloroquine and bidesethylchloroquine.
Desethylhydroxychloroquine is the major metabolite.
Biological Half-Life:
Oral hydroxychloroquine has an absorption half life of 3-4 hours.
A 200mg oral dose of hydroxychloroquine has a half life of 537 hours or 22.4 days in blood, and 2963 hours or 123.5 days in plasma.
A 155mg intravenous dose has a half life of 40 days.
Mechanism of Action:
The exact mechanisms of hydroxychloroquine are unknown.
Hydroxychloroquine has been shown that hydroxychloroquine accumulates in the lysosomes of the malaria parasite, raising the pH of the vacuole.
This activity interferes with the parasite's ability to proteolyse hemoglobin, preventing the normal growth and replication of the parasite.
Hydroxychloroquine can also interfere with the action of parasitic heme polymerase, allowing for the accumulation of the toxic product beta-hematin.
Hydroxychloroquine accumulation in human organelles also raise their pH, which inhibits antigen processing, prevents the alpha and beta chains of the major histocompatibility complex (MHC) class II from dimerizing, inhibits antigen presentation of the cell, and reduces the inflammatory response.
Elevated pH in the vesicles may alter the recycling of MHC complexes so that only the high affinity complexes are presented on the cell surface.
Self peptides bind to MHC complexes with low affinity and so they will be less likely to be presented to autoimmune T cells.
Hydroxychloroquine also reduces the release of cytokines like interleukin-1 and tumor necrosis factor, possibly through inhibition of Toll-like receptors.
The raised pH in endosomes, prevent virus particles (such as SARS-CoV and SARS-CoV-2) from utilizing their activity for fusion and entry into the cell.
Hydroxychloroquine inhibits terminal glycosylation of ACE2, the receptor that SARS-CoV and SARS-CoV-2 target for cell entry.
ACE2 that is not in the glycosylated state may less efficiently interact with the SARS-CoV-2 spike protein, further inhibiting viral entry.
Hydroxychloroquine is also used for the prophylaxis of malaria in regions where chloroquine resistance is unlikely
Hydroxychloroquine is a drug that was used originally to treat malaria, especially in patients who could not tolerate the similar compound chloroquine.
Hydroxychloroquine also has been used to combat autoimmune diseases such as lupus erythematosus.
Hydroxychloroquine is an antimalarial that also displays anti-inflammatory activity.
Hydroxychloroquine has been used in the treatment and suppression of malaria, as well for the treatment of rheumatoid arthritis and systemic lupus erythematosus.
Hydroxychloroquine is a synthetically manufactured drug, developed based on the chemical structure of quinine.
Quinine is not a component of our drug Plaquenil, the active ingredient is hydroxychloroquine
Hydroxychloroquine is an aminoquinoline with:
-antimalarial
-anti-inflammatory
-antiviral activities
Hydroxychloroquine is active against the chloroquine-sensitive NF54 and D6 strains of P. falciparum (IC50s = 16.3 and 15 nM, respectively)
Hydroxychloroquine inhibits production of IL-22, IL-17A, and IL-6 induced by phorbol 12-myristate 13-acetate (TPA; Item No. 10008014) and ionomycin (Item No. 10004974) in peripheral blood mononuclear cells (PBMCs) isolated from healthy individuals or patients with systemic lupus erythematosus (SLE) or rheumatoid arthritis (RA).
Hydroxychloroquine inhibits accumulation of sequestosome-1 (SQSTM1) puncta, a marker of autophagy, in mouse embryonic fibroblasts (MEFs) in a concentration-dependent manner.
Hydroxychloroquine is a colorless crystalline solid
Hydroxychloroquine vused in the treatment of:
-malaria
-lupus erythematosus
Hydroxychloroquine is an immunomodulatory drug that has been used for 60 years to treat malaria and autoimmune diseases such as systemic lupus erythematosus and inflammatory arthritis
Potential new uses and benefits continue to emerge-rheumatoid arthritis
Hydroxychloroquine acts by suppressing Toll-like receptors to trigger important immunomodulatory effects.
Hydroxychloroquine is a well-established and effective therapy for systemic and cutaneous lupus and other autoimmune diseases.
Hydroxychloroquine prevents thrombosis in other diseases as well.
For example, it has been shown to reduce the incidence of thrombotic events in patients with primary antiphospholipid syndrome.
hydroxychloroquine has also shown benefit in rheumatoid arthritis, where it can be used by itself in mild disease or as part of combination therapy with active arthritis.
Compared with biologic therapy in patients with early aggressive rheumatoid arthritis, triple therapy with methotrexate, sulfasalazine, and hydroxychloroquine was nearly as effective in terms of quality of life
Metabolic Benefits:
Unexpectedly, hydroxychloroquine is associated with multiple metabolic benefits including improved lipid profiles and lower blood glucose levels.
These findings, in addition to a reduced incidence of thrombosis, were initially reported in the Baltimore Lupus Cohort in 1996.
Specifically, longitudinal evaluation of a cohort of lupus patients showed that hydroxychloroquine use was associated with a 7.6% reduction in total cholesterol and a 13.7% reduction in low-density lipoprotein cholesterol (LDL-C) over 3 months of therapy.
Similar findings, including a reduction in LDL-C and an increase in high-density lipo-protein cholesterol, were strongly associated with the addition of hydroxychloroquine to methotrexate or to methotrexate and etanercept in a large cohort of rheumatoid arthritis patients followed over 2 years of therapy.
In nondiabetic women with systemic lupus erythematosus or rheumatoid arthritis, average blood glucose was significantly lower in those taking hydroxychloroquine than in nonusers.
The incidence of insulin resistance was also lower, but the difference was not statistically significant.
Some have suggested that hydroxychloroquine may prevent diabetes mellitus.
In a retrospective case series, compared with rheumatoid arthritis patients not taking the drug, patients treated with hydroxychloroquine for more than 4 years had a 25% lower risk of developing diabetes mellitus.
In view of these metabolic benefits, especially regarding lipid regulation, and the above described antithrombotic properties of hydroxychloroquine, some researchers have recently hypothesized that hydroxychloroquine may be of benefit in patients with coronary artery disease.
They suggested that the inflammatory contribution to the mechanism of coronary artery disease could be lessened by hydroxychloroquine even in patients without lupus erythematosus or rheumatoid arthritis.
An antimalarial with properties similar to chloroquine that acts against eryt hrocytic forms of malarial parasites
Hydroxychloroquine is mainly used as the sulfate salt for the treatment of lupus erythematosus, rheumatoid arthritis, and light-sensitive skin eruptions.
Hydroxychloroquine is a 4-aminoquinolone that is used to prevent and treat malaria, caused by parasitic protozoan from the Plasmodium genus.
Hydroxychloroquine is also used to treat non-infectious diseases such as rheumatoid arthritis and lupus thanks to its immunomodulatory properties.
Recent studies revealed that hydroxychloroquine has beneficial effects on COVID-19 patients, as the current evidence shows that hydroxychloroquine inhibits SARS CoV-2 entry in host cells by interfering with endocytosis and affecting the glycoprofile on the spike glycoprotein.
Hydroxychloroquine (Plaquenil), like chloroquine, is a 4-aminoquinoline derivative used for the suppressive and acute treatment of malaria.
Hydroxychloroquine also has been used for rheumatoid arthritis and discoid and systemic lupus erythematosus.
Hydroxychloroquine has not been proved to be more effective than chloroquine.
Adverse reactions associated with its use are similar to those described for chloroquine.
Hydroxychloroquine, like chloroquine, is also used for treating acute forms of malaria caused by P. vivax, P. malariae, P. ovale, and also sensitive forms of P. falciparum.
Hydroxychloroquine is also effective and safe like chloroquine, although it does not have obvious advantages.
The only advantage is that it is somewhat better tolerated.
Hydroxychloroquines use is somewhat more limited than chloroquine.
Clinical Use:
Hydroxychloroquine is approved for the treatment of both systemic and cutaneous lupus erythematosus.
Both chloroquine and quinacrine (Atabrine) are also effective in this skin disease.
Low-dose chloroquine is used for the therapy of porphyria cutanea tarda in patients in whom phlebotomy has failed or is contraindicated.
Other skin diseases in which the drugs are useful (after sunscreens and avoidance of sun exposure) include polymorphous light eruption and solar urticaria.
Chemical Synthesis:
Hydroxychloroquine, 7-chloro-4-[4-[ethyl(2-hydroxyethyl)amino]- 1-methylbutylamino]quinoline (37.1.1.19), is made by a scheme similar to that of making chloroquine.
Reacting 1-chloro-4-pentanone with 2-ethylaminoethanol gives the corresponding aminoketone (37.1.1.17), which undergoes reductive amination in conditions analogous to those described above, making 4-[ethyl(2-hydroxyethyl)amino]-1-methylbutylamine (37.1.1.18).
Reacting this with 4,7-dichlroquinoline (37.1.1.1) makes the desired hydroxychloroquine.
PHYSICAL PROPERTIES OF HYDROXYCHLOROQUINE:
-Molecular Weight: 335.9
-XLogP3: 3.6
-Exact Mass: 335.1764402
-Monoisotopic Mass: 335.1764402
-Topological Polar Surface Area: 48.4 Ų
-Heavy Atom Count: 23
-Formal Charge: 0
-Complexity: 331
-Physical Description: Solid
-Melting Point: 90°C
-Solubility: 2.61e-02 g/L
-pKa: 9.67
-Boiling point: 516.7±50.0 °C
-Density: 1.1438
Description:
Hydroxychloroquine is a synthetic antimalarial agent which can also inhibit Toll-like receptor 7/9 (TLR7/9) signaling.
Hydroxychloroquine is efficiently inhibits SARS-CoV-2 infection in vitro.
Hydroxychloroquine, an analogue of chloroquine, was developed in 1946.
Hydroxychloroquine and chloroquine are FDA-approved to treat or prevent malaria.
Hydroxychloroquine is also FDA-approved to treat autoimmune conditions such as chronic discoid lupus erythematosus, systemic lupus erythematosus in adults, and rheumatoid arthritis.
Hydroxychloroquine is often taken in combination with other drugs such as methotrexate.
CHEMICAL PROPERTIES OF HYDROXYCHLOROQUINE:
-Collision Cross Section: 180.2 Ų
-LogP: 1.548
-Retention Index (Kovats): 2740
-Hydrogen Bond Donor Count: 2
-Hydrogen Bond Acceptor Count: 4
-Rotatable Bond Count: 9
-Isotope Atom Count: 0
-Defined Atom Stereocenter Count: 0
-Undefined Atom Stereocenter Count: 1
-Defined Bond Stereocenter Count: 0
-Undefined Bond Stereocenter Count: 0
-Covalently-Bonded Unit Count: 1
-Compound Is Canonicalized: Yes
STORAGE OF HYDROXYCHLOROQUINE:
Hydroxychloroquine must be stored in a dark place.
Hydroxychloroquine should be stored dry.
Hydroxychloroquine should be stored at Room Temperature.
Hydroxychloroquine should be stored at constant atmospheric pressure.
Hydroxychloroquine should be kept away from places where it can get moisture.
Hydroxychloroquine should preferably be stored in glass bottles.
Hydroxychloroquine should be stored in a clean, well-ventilated place.
Hydroxychloroquine Sulfonate should be stored in tightly closed containers.
Hydroxychloroquine should be stored separately from other reagents.
Hydroxychloroquine should be stored in a moisture-free environment.
SYNONYMS:
hydroxychloroquine
Plaquenil
Oxichloroquine
Hidroxicloroquina
Hydroxychloroquinum
oxichlorochine
2-((4-((7-Chloro-4-quinolyl)amino)pentyl)ethylamino)ethanol
2-((4-((7-Chloroquinolin-4-yl)amino)pentyl)(ethyl)amino)ethanol
7-Chloro-4-(4-(ethyl(2-hydroxyethyl)amino)-1-methylbutylamino)quinoline
Polirreumin
Oxychlorochin
2-(N-(4-(7-Chlor-4-chinolylamino)-4-methylbutyl)ethylamino)ethanol
7-Chloro-4-(4-(N-ethyl-N-beta-hydroxyethylamino)-1-methylbutylamino)quinoline
Oxichlorochinum
2-[4-[(7-chloroquinolin-4-yl)amino]pentyl-ethylamino]ethanol
2-[{4-[(7-chloroquinolin-4-yl)amino]pentyl}(ethyl)amino]ethanol
7-Chloro-4-(5-(N-ethyl-N-2-hydroxyethylamino)-2-pentyl)aminoquinoline
Ethanol, 2-((4-((7-chloro-4-quinolinyl)amino)pentyl)ethylamino)-
2-[[4-[(7-chloroquinolin-4-yl)amino]pentyl](ethyl)amino]ethanol
Ethanol, 2-[[4-[(7-chloro-4-quinolinyl)amino]pentyl]ethylamino]-
Idrossiclorochina
2-({4-[(7-chloroquinolin-4-yl)amino]pentyl}(ethyl)amino)ethan-1-ol
2-{N-[4-(7-Chloro-4-quinolylamino)pentyl]-N-ethylamino}ethanol
Ethanol, 2-((4-((7-chloro-4-quinolyl)amino)pentyl)ethylamino)-
7-chloro-4-[4-(N-ethyl-N-beta-hydroxyethylamino)-1-methylbutylamino]quinoline
7-chloro-4-[5-(N-ethyl-N-2-hydroxyethylamino)-2-pentyl]aminoquinoline
Polirreumin (TN)
Dolquine
Ethanol, 2-[[4-[(7-chloro-4-quinolyl)amino]pentyl]ethylamino]-
R-Hydroxychloroquine
Ercoquin (Salt/Mix)
Ethanol, 2-[[4-[(7-chloro-4-quinolinyl)amino]pentyl]ethylamino]-, sulfate (1:1)
2-[4-[(7-chloro-4-quinolyl)amino]pentyl-ethyl-amino]ethanol
7-Chloro-4-(4-(N-ethyl-N-.beta.-hydroxyethylamino)-1-methylbutylamino)quinoline
Oxichloroquine;Oxychlorochin;2-[[4-[(7-Chloroquinolin-4-yl)amino]pentyl](ethyl)amino]et
Hydroxychlorochin
Hydroxychloroquine
Hydroxychloroquine Sulfate
Hydroxychloroquine Sulfate (1:1) Salt
Oxychlorochin
Oxychloroquine
Plaquenil
