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Hydroxychloroquine

description Application in Particular Diseases
Hydroxychloroquine
Hydroxychloroquine structure
CAS No.
118-42-3
Chemical Name:
Hydroxychloroquine
Synonyms
C07043;win1258;plaquenil;Oxychloroquine;Hydroychloroquine;hydroxychloroquine;2-((4-((7-chloro-4-quinolyl)amino)pentyl)ethylamino)ethanol;2-((4-((7-chloro-4-quinolyl)amino)pentyl)ethylamino)-ethano;2-[[4-[(7-Chloroquinolin-4-yl)amino]pentyl](ethyl)amino]ethanol;Ethanol, 2-[[4-[(7-chloro-4-quinolinyl)amino]pentyl]ethylamino]-
CBNumber:
CB6866802
Molecular Formula:
C18H26ClN3O
Formula Weight:
335.87
MOL File:
118-42-3.mol

Hydroxychloroquine Properties

Melting point:
89-91°
Boiling point:
516.7±50.0 °C(Predicted)
Density 
1.1438 (rough estimate)
refractive index 
1.5790 (estimate)
storage temp. 
Keep in dark place,Sealed in dry,Room Temperature
pka
14.76±0.10(Predicted)
FDA UNII
4QWG6N8QKH
NCI Dictionary of Cancer Terms
hydroxychloroquine
NCI Drug Dictionary
hydroxychloroquine
ATC code
P01BA02
NIST Chemistry Reference
Hydroxychloroquine(118-42-3)
EPA Substance Registry System
Ethanol, 2-[[4-[(7-chloro-4-quinolinyl)amino]pentyl]ethylamino]- (118-42-3)

Hydroxychloroquine Chemical Properties,Uses,Production

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.

Application in Particular Diseases

In Rheumatic Arthritis:
Hydroxychloroquine lacks the myelosuppressive, hepatic, and renal toxicities seen with some other DMARDs, which simplifies monitoring. Its onset may be delayed for up to 6 weeks, but the drug should not be considered a therapeutic failure until after 6 months of therapy with no response.
Short-term toxicities include GI (nausea, vomiting, diarrhea), ocular (accommodation defects, benign corneal deposits, blurred vision, scotomas, night blindness, preretinopathy), dermatologic (rash, alopecia, skin pigmentation), and neurologic (headache, vertigo, insomnia) effects. Periodic ophthalmologic examinations are necessary for early detection of reversible retinal toxicity.

Originator

Plaquenil,Winthrop,US,1956

Uses

Hydroxychloroquine is used to treat autoimmune diseases, such as systemic lupus erythematosus and rheumatoid arthritis, in addition to malaria.
Hydroxychloroquine is a disease-modifying anti-rheumatic drug (DMARD). It regulates the activity of the immune system, which may be overactive in some conditions. Hydroxychloroquine can modify the underlying disease process, rather than simply treating the symptoms.
Hydroxychloroquine is used to treat:
rheumatoid arthritis
discoid and systemic lupus erythematosus (SLE)
juvenile idiopathic arthritis (JIA).
Over the long term hydroxychloroquine can reduce pain, swelling and joint stiffness. If you have lupus, it may also improve the rash. It may be as long as 12 weeks before you notice the benefits.

Definition

ChEBI: 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, it is mainly used s the sulfate salt for the treatment of lupus erythematosus, rheumatoid arthritis, and light-sensitive skin eruptions.

Indications

Hydroxychloroquine (Plaquenil), like chloroquine, is a 4-aminoquinoline derivative used for the suppressive and acute treatment of malaria. It 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.The drug should not be used in patients with psoriasis or porphyria, since it may exacerbate these conditions.

Manufacturing Process

A mixture of 323 grams of 1-chloro-4-pentanone, 480 grams of N-ethyl-N-2- hydroxyethylamine and 400 grams of sodium chloride (to aid in subsequent filtration) in 1.3 liters of xylene was heated with stirring on a steam bath for two hours and then refluxed for three hours. After standing overnight, the mixture was filtered and the filter cake washed with xylene. The filtrate was fractionally distilled, yielding 207.3 grams of a fraction distilling at 89° to 90°C at 0.35 mm; nD25 = 1.4600. This fraction, 1-(N-ethyl-N-2- hydroxyethylamino)-4-pentanone, was used in the next step of the synthesis. A sample of the fraction was further purified by distillation through a column and gave an analytically pure sample of 1-(N-ethyl-N-2-hydroxyethylamino)- 4-pentanone, boiling at 85° to 87°C at 0.4 mm.
The 1-(N-ethyl-N-2-hydroxyethylamino)-4-pentanone from above (284.2 grams) was dissolved in 300 grams of 28% ammoniacal methanol and reduced catalytically with Raney nickel (at an initial pressure of 1,000 pounds) at room temperature. After 24 hours the catalyst was filtered off and the product distilled in vacuo through a column, yielding 254 grams of a fraction distilling at 88.5° to 96°C at 0.3 mm and comprising mainly 5-(N-ethyl-N-2- hydroxyethylamino)-2-pentylamine. An analytical sample of this fraction distilled at 93°C at 0.6 mm.
A mixture of 90 grams of 4,7-dichloroquinoline, 90 grams of phenol, 1 gram of potassium iodide and 132 grams of 5-(N-ethyl-N-2-hydroxyethylamino)-2- pentylamine from above was heated with stirring for 13 hours at 125° to 130°C. Methanol (1.9 liters) was added and the the mixture was filtered with charcoal. The filtrate was treated with 270 cc of a solution of 100 grams of phosphoric acid in 300 cc of methanol. The walls of the flask containing the filtrate were scratched with a glass rod and the mixture was allowed to stand for two days. The solid was filtered off, washed with methanol and dried, yielding 101 grams of crude 7-chloro-4-[5-(N-ethyl-N-2-hydroxyethylamino)- 2-pentyl]aminoquinoline diphosphate, MP 155° to 156°C.
Additional quinoline diphosphate was obtained as a gummy mass from the filtrate by concentrating the latter to about half its volume and adding acetone. The crude gummy diphosphate was dissolved in water, basified with ammonium hydroxide and the resulting liberated basic quinoline extracted with chloroform. After removal of the chloroform by distillation, the residue was dissolved in ether and crystallization was induced by scratching the walls of the flask with the glass rod. About 30 grams of the crude quinoline base, melting at 77° to 82°C, separated. Recrystallization of this material from ethylene dichloride or ethyl acetate yielded the purified 7-chloro-4-[5-(Nethyl-N-2-hydroxyethylamino)2-pentyl] aminoquinoline, MP 89° to 91°C. The base may then be dissolved in ethanol and precipitated as the sulfate by reaction with an equimolar quantity of sulfuric acid.

Therapeutic Function

Antimalarial

Mechanism of action

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. It is also effective and safe like chloroquine, although it does not have obvious advantages. The only advantage is that it is somewhat better tolerated. Its use is somewhat more limited than chloroquine. Synonyms of this drug are plaquenil, quensyl, toremonil, and others.

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.

Hydroxychloroquine Preparation Products And Raw materials

Raw materials

Preparation Products


Hydroxychloroquine Suppliers

Global( 105)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Hebei Minshang Biotechnology Co., Ltd
+86-13582176207 +86-13582176207
cathy@hbminshang.cn CHINA 304 58
Shanghai Dumi Biotechnology Co.,LTD
15373897440 +8617172178822
cassie@chinadumi.com CHINA 117 58
Shanghai Dumi Biotechnology Co.,ltd
17172178855 +8617172178855
aimee@chinadumi.com CHINA 241 58
SHANDONG ZHI SHANG CHEMICAL CO.LTD
+86 18953170293
+86 0531-67809011 sales@sdzschem.com CHINA 2941 58
Accela ChemBio Inc.
(+1)-858-699-3322
(+1)-858-876-1948 info@accelachem.com United States 19969 58
Hebei Guanlang Biotechnology Co., Ltd.
+8619930503282
sales3@crovellbio.com China 5882 58
Shanghai Jinghao Pharmaceutical Co.,Ltd
+86-21-68900963
+86-21-68900963 sales@jinghaopharma.com CHINA 153 58
Hebei shuoxi biotechnology co. LTD
+8613081092107
whatsapp:+8613081092107 julia@hbshuoxi.com CHINA 973 58
CONIER CHEM AND PHARMA LIMITED
86-18523575427
sales@conier.com CHINA 47498 58
career henan chemical co
13203830695 0086-371-86658258
0086-371-86658258 factory@coreychem.com CHINA 29864 58

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View Lastest Price from Hydroxychloroquine manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2021-11-25 Hydroxychloroquine
118-42-3
US $10.00 / Kg/Bag 1KG 99% 10 Tons Hebei Senko Biotechnology Co., Ltd.
2021-10-29 2-[[4-[(7-Chloroquinolin-4-yl)amino]pentyl](ethyl)amino]ethanol
118-42-3
US $10.00 / KG 100KG 99% 20t Shijiazhuang Erche Biotechnology Co., Ltd
2021-10-19 hydroxychloroquine
118-42-3
US $48.00-40.00 / KG 1KG 99% 20tons Guangzhou Sunton Biotechnology Co., Ltd.

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