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Hydroxychloroquine sulfate

Hydroxychloroquine sulfate
Hydroxychloroquine sulfate structure
CAS No.
747-36-4
Chemical Name:
Hydroxychloroquine sulfate
Synonyms
Quensyl;Ercoquin;Plaquinol;HCQ sulfate;plaquenilsulfate;Hydroxychloroquin;Acidum iopanoicum;Hydroxychlorquine sulfate;Hydroxycloroquine sulfate;HYDROXYCHLOROQUINESULPATE
CBNumber:
CB4423632
Molecular Formula:
C18H28ClN3O5S
Formula Weight:
433.95
MOL File:
747-36-4.mol

Hydroxychloroquine sulfate Properties

Melting point:
240 °C
storage temp. 
protect from light
solubility 
H2O: >20mg/mL
form 
Crystalline Powder
color 
white to off-white
Water Solubility 
FREELY SOLUBLE
Merck 
14,4818
InChIKey
JCBIVZZPXRZKTI-UHFFFAOYSA-N
EWG's Food Scores
1
FDA UNII
8Q2869CNVH
NCI Drug Dictionary
hydroxychloroquine sulfate
EPA Substance Registry System
Ethanol, 2-[[4-[(7-chloro-4-quinolinyl)amino]pentyl]ethylamino]-, sulfate (1:1) (747-36-4)
SAFETY
  • Risk and Safety Statements
Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H302-H315-H319
Precautionary statements  P301+P312+P330-P305+P351+P338
Hazard Codes  Xn,Xi
Risk Statements  42/43-36/37/38-36-22
Safety Statements  37/39-26
WGK Germany  3
RTECS  KK3342500
HS Code  29334990

Hydroxychloroquine sulfate price More Price(11)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 90527 Hydroxycloroquine sulfate analytical standard 747-36-4 50mg $49 2021-03-22 Buy
Sigma-Aldrich 1327000 Hydroxychloroquine sulfate United States Pharmacopeia (USP) Reference Standard 747-36-4 200mg $366 2021-03-22 Buy
TCI Chemical H1306 Hydroxychloroquine Sulfate >98.0%(HPLC)(N) 747-36-4 5g $65 2021-03-22 Buy
TCI Chemical H1306 Hydroxychloroquine Sulfate >98.0%(HPLC)(N) 747-36-4 25g $215 2021-03-22 Buy
Cayman Chemical 17911 Hydroxychloroquine (sulfate) ≥95% 747-36-4 25mg $25 2021-03-22 Buy

Hydroxychloroquine sulfate Chemical Properties,Uses,Production

Description

Hydroxychloroquine sulfate (also known as hydroxychloroquine) is an antimalarial medicine approved in the United States for either prevention or treatment of certain types of malaria, lupus erythematosus, and rheumatoid arthritis. It is sold under the brand name Plaquenil and it is also sold as a generic medicine. It is available in tablets of 155mg base (200mg salt).
hydroxychloroquine sulfate tablets 200 mg
Hydroxychloroquine sulfate has not been approved for the treatment of COVID-19. It has been used experimentally to treat certain people with COVID-19, including hospitalized patients. Hydroxychloroquine sulfate is being used to try and stop the COVID-19 virus from spreading inside your body. This may help you to get better.
Hydroxychloroquine sulfate is experimental because we do not know if it works for COVID-19. It is not approved by FDA for the treatment of COVID-19, but emergency use has been authorized for adults and adolescents who weigh 50 kg (110 pounds) or more and are hospitalized with COVID-19 if a clinical trial is not available or you are not able to participate in a clinical trial. There is limited information known about the safety and effectiveness (whether this will make you better) of using hydroxychloroquine sulfate for hospitalized patients with COVID-19.

Chemical Properties

White Cyrstalline Solid

Originator

Plaquenil,Winthrop,US,1956

Uses

antimalarial, lupus suppressant

Uses

An antimalarial; antirheumatic; lupus erythematosus suppressant

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

Pharmacology

Antimalarial action: Hydroxychloroquine binds to DNA, interfering with protein synthesis. It also inhibits DNA and RNA polymerases. It’s active against asexual erythrocytic forms of Plasmodium malariae, P. ovale, P. vivax, and many strains of P. falciparum.
Amebicidal action: Mechanism of action is unknown.
Anti-inflammatory action: Mechanism of action is unknown. Drug may antagonize histamine and serotonin and inhibit prostaglandin effects by inhibiting conversion of arachidonic acid to prostaglandin F2; it may also inhibit chemotaxis of polymorphonuclear leukocytes, macrophages, and eosinophils.

Pharmacokinetics

Absorption: Absorbed readily and almost completely.
Distribution: Bound to plasma proteins. It’s concentrated in the liver, spleen, kidneys, heart, and brain and is strongly bound in melanin-containing cells.
Metabolism: Metabolized by the liver to desethylchloroquine and desethyl hydroxychloroquine.
Excretion: Most of an administered dose is excreted unchanged in urine. Drug and its metabolites are excreted slowly in urine; unabsorbed drug is excreted in feces. Small amounts of drug may be present in urine for months after it’s discontinued. Drug appears in breast milk.

Clinical Use

Hydroxychloroquine sulfate is highly water soluble and exists in two different forms of different melting points. It is readily absorbed on oral administration, reaching peak plasma levels within 1 to 3 hours. It concentrates in organs such as the liver, spleen, kidneys, heart, lung, and brain, thereby prolonging elimination. Hydroxychloroquine is metabolized by N-dealkylation of the tertiary amines, followed by oxidative deamination of the resulting primary amine to the carboxylic acid derivative. In addition to possessing corneal and renal toxicity, hydroxychloroquine also may cause CNS, neuromuscular, GI, and hematological side effects. Hydroxychloroquine sulfate is indicated for the treatment of rheumatoid arthritis, lupus erythematosus, and malaria.

Side effects

In addition to possessing corneal and renal toxicity, hydroxychloroquine also may cause CNS, neuromuscular, GI, and hematological side effects. Hydroxychloroquine sulfate is indicated for the treatment of rheumatoid arthritis, lupus erythematosus, and malaria

Overdosage

Symptoms of drug overdose may appear within 30 minutes after ingestion and may include headache, drowsiness, visual changes, CV collapse, and seizures followed by respiratory and cardiac arrest.
Treatment is symptomatic. Empty stomach by emesis or lavage. After lavage, activated charcoal in an amount at least five times the estimated amount of drug ingested may be helpful if given within 30 minutes of ingestion.
Ultra-short-acting barbiturates may help control seizures. Intubation may become necessary. Peritoneal dialysis and exchange transfusions may also be useful. Forced fluids and acidification of the urine are helpful after the acute phase.

Drug interactions

Anti-arrhythmics: increased risk of ventricular arrhythmias when hydroxychloroquine administered with amiodarone – avoid concomitant use
Digoxin: Hydroxychloroquine sulfate has been reported to increase plasma digoxin levels: serum digoxin levels should be closely monitored in patients receiving concomitant therapy.
Antibacterials: increased risk of ventricular arrhythmias when hydroxychloroquine administered with moxifloxacin – avoid concomitant use.
Ciclosporin: hydroxychloroquine increases plasma concentration of ciclosporin (increased risk of toxicity) .
Antacids: as with chloroquine, antacids may reduce absorption of hydroxychloroquine so it is advised that a 4 hour interval be observed between hydroxychloroquine and antacid dosaging.
Antidiabetic medicines: As hydroxychloroquine may enhance the effects of hypoglycaemic treatment, a decrease in doses of insulin or antidiabetic drugs may be required.
Tamoxifen: may enhance the adverse/toxic effect of Hydroxychloroquine. Specifically, concomitant use of tamoxifen and hydroxychloroquine may increase the risk of retinal toxicity.

Hydroxychloroquine sulfate Preparation Products And Raw materials

Raw materials

Preparation Products


Hydroxychloroquine sulfate Suppliers

Global( 344)Suppliers
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View Lastest Price from Hydroxychloroquine sulfate manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2021-10-27 Hydroxychloroquine sulfate
747-36-4
US $50.00 / KG 1KG 99% 1 ton Hanhong Medicine Technology (Hubei) Co., Ltd.
2021-10-27 Hydroxychloroquinesulfate
US $0.00 / KG 100g 98%+ 100kg WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
2021-10-27 Hydroxychloroquine sulfate
747-36-4
US $0.00 / KG 100g 98%+ 100kg WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD

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