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Hydroxychloroquine sulfate

Product Name
Hydroxychloroquine sulfate
CAS No.
747-36-4
Chemical Name
Hydroxychloroquine sulfate
Synonyms
HYDROXYCHLOROQUINE SULPHATE;Hydroxycloroquine sulfate;7-Chloro-4-[4-(N-ethyl-N-b-hydroxyethylamino)-1-methylbutylamino]quinoline sulfate;Quensyl;Ercoquin;Plaquinol;HCQ sulfate;plaquenilsulfate;Hydroxychloroquin;Acidum iopanoicum
CBNumber
CB4423632
Molecular Formula
C18H28ClN3O5S
Formula Weight
433.95
MOL File
747-36-4.mol
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Hydroxychloroquine sulfate Property

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
Stability:
Stable for 2 years from date of purchase as supplied. Solutions in water may be stored at -20°C for up to 3 months.
InChIKey
JCBIVZZPXRZKTI-UHFFFAOYSA-N
EPA Substance Registry System
Ethanol, 2-[[4-[(7-chloro-4-quinolinyl)amino]pentyl]ethylamino]-, sulfate (1:1) (747-36-4)
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Safety

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
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
H-157
Product name
Hydroxychloroquine sulfate solution
Purity
1?mg/mL (Methanol:Water (80:20) (v/v), (as free base)), certified reference material, ampule of 1?mL, Cerilliant?
Packaging
1ML
Price
$131
Updated
2024/03/01
Sigma-Aldrich
Product number
90527
Product name
Hydroxycloroquine sulfate
Purity
analytical standard
Packaging
50mg
Price
$61.4
Updated
2024/03/01
Sigma-Aldrich
Product number
1327000
Product name
Hydroxychloroquine sulfate
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
200mg
Price
$436
Updated
2024/03/01
Sigma-Aldrich
Product number
5.09272
Product name
Hydroxychloroquine Sulfate
Packaging
25MG
Price
$273
Updated
2023/06/20
TCI Chemical
Product number
H1306
Product name
Hydroxychloroquine Sulfate
Purity
>98.0%(HPLC)(N)
Packaging
5g
Price
$66
Updated
2024/03/01
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Hydroxychloroquine sulfate Chemical Properties,Usage,Production

Description

Hydroxychloroquine is an aminoquinoline with antimalarial, anti-inflammatory, and antiviral activities. It is active against the chloroquine-sensitive NF54 and D6 strains of P. falciparum (IC50s = 16.3 and 15 nM, respectively) but has decreased activity against chloroquine-resistant P. falciparum strains (IC50s = 422.7-1,735.3 nM). Hydroxychloroquine inhibits production of IL-22, IL-17A, and IL-6 induced by phorbol 12-myristate 13-acetate (TPA; ) and ionomycin in peripheral blood mononuclear cells (PBMCs) isolated from healthy individuals or patients with systemic lupus erythematosus (SLE) or rheumatoid arthritis (RA). It inhibits accumulation of sequestosome-1 (SQSTM1) puncta, a marker of autophagy, in mouse embryonic fibroblasts (MEFs) in a concentration-dependent manner. Hydroxychloroquine reduces viral titers of severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) in the culture supernatant of infected Vero E6 cells but does not reduce SARS-CoV-2 viral titers in an in vitro human airway epithelium model or the respiratory tract of infected cynomolgus macaques. Formulations containing hydroxychloroquine have been used in the prevention or treatment of malaria, as well as in the treatment of RA and SLE.

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 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

Hydroxychloroquine Sulfate can be used as a pharmaceutical secondary standard for the determination of the analyte in pharmaceutical formulations, and biological samples by various analytical techniques.
These Secondary Standards are qualified as Certified Reference Materials. These are suitable for use in several analytical applications including but not limited to pharma release testing, pharma method development for qualitative and quantitative analyses, food and beverage quality control testing, and other calibration requirements.

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

General Description

Hydroxychloroquine Sulfate (Hydroxychloroquine Sulphate) is a salt of hydroxychloroquine (HCQ, Plaquenil), a 4-aminoquinoline based antiviral drug.
Pharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.

Biochem/physiol Actions

Hydroxychloroquine sulfate is an anti-inflammatory (via TNF), disease-modifying antirheumatic drug (DMARD), and a heme polymerase inhibitor. It is used in treating malaria.

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.

Metabolism

Hydroxychloroquine is metabolised to chloroquine, which in turn is extensively metabolised in the liver, mainly to monodesethylchloroquine with smaller amounts of bisdesethylchloroquine (didesethylchloroquinine) and other metabolites being formed. Monodesethylchloroquine has been reported to have some activity against Plasmodium falciparum. Chloroquine and its metabolites are excreted in the urine, with about half of a dose appearing as unchanged drug and about 10% as the monodesethyl metabolite.

storage

Store at +4°C

Hydroxychloroquine sulfate Preparation Products And Raw materials

Raw materials

Preparation Products

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Hydroxychloroquine sulfate Suppliers

Shanghai Luofa Biochemical Technology Co., Ltd.
Tel
021-51111890 15317326293
Email
sales@molnova.com
Country
China
ProdList
4195
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58
Shanghai jing Hao pharmaceutical technology co., LTD
Tel
021-68900963 15618693615
Fax
021-68900963
Email
sales@jinghaopharma.com
Country
China
ProdList
310
Advantage
58
Guangzhou Dihao Medical Technology Co., Ltd
Tel
18602015453
Email
2667751176@qq.com
Country
China
ProdList
485
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58
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
94657
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Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
021-61259108 18621169109
Fax
86-21-61259102
Email
market03@meryer.com
Country
China
ProdList
40228
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TCI (Shanghai) Development Co., Ltd.
Tel
021-67121386
Fax
021-67121385
Email
Sales-CN@TCIchemicals.com
Country
China
ProdList
24529
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81
Ark Pharm, Inc.
Tel
847-367-3680
Fax
847-367-3681
Email
sales@arkpharminc.com
Country
United States
ProdList
1670
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Energy Chemical
Tel
021-021-58432009 400-005-6266
Fax
021-58436166
Email
sales8178@energy-chemical.com
Country
China
ProdList
44689
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Capot Chemical Co., Ltd
Tel
+86 (0) 571 85 58 67 18
Fax
0086-571-85864795
Email
sales@capotchem.com
Country
China
ProdList
18207
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66
Pure Chemistry Scientific Inc.
Tel
001-857-928-2050 or 1-888-588-9418
Fax
001-617-206-9595
Email
sales@chemreagents.com
Country
United States
ProdList
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View Lastest Price from Hydroxychloroquine sulfate manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
Hydroxychloroquine sulfate 747-36-4
Price
US $0.00-0.00/Kg/Drum
Min. Order
1KG
Purity
98%-102%;USP
Supply Ability
500KG
Release date
2021-06-18
Watson Biotechnology Co.,Ltd
Product
Hydroxychloroquinesulfate 747-36-4
Price
US $45.00-26.00/kg
Min. Order
25kg
Purity
0.99
Supply Ability
20MT
Release date
2024-07-24
BEIJING SJAR TECHNOLOGY DEVELOPMENT CO., LTD.
Product
Hydroxychloroquine Sulfate 747-36-4
Price
US $0.00/g
Min. Order
1g
Purity
More Than 99%
Supply Ability
50kg/Month
Release date
2024-10-11

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