Chlorquinbis(phosphat)

Bezeichnung:Chlorquinbis(phosphat)

CAS-Nr50-63-5

Englisch Name:Chloroquine diphosphate

CBNumberCB5467578

SummenformelC18H32ClN3O8P2

Molgewicht515.86

MOL-Datei50-63-5.mol

Synonyma

Chloroquinbis(phosphat)

Chlorquinbis(phosphat)

Chlorquinbis(phosphat) physikalisch-chemischer Eigenschaften

Schmelzpunkt	200 °C (dec.) (lit.)
storage temp.	protect from light
Löslichkeit	H₂O: 50 mg/mL, clear
Aggregatzustand	solid
pka	pKa 8.10(H2O t = 20 c = 0.0025) (Uncertain)
Farbe	White
PH	pH(100g/l, 25℃) : 3.8～4.3
Wasserlöslichkeit	Soluble in water
Merck	14,2163
BRN	4223142
BCS Class	1
Stabilität	Stable for 2 years from date of purchase as supplied. Solutions in distilled water may be stored at -20° for up to 3 months.
InChIKey	QKICWELGRMTQCR-UHFFFAOYSA-N
CAS Datenbank	50-63-5(CAS DataBase Reference)
EPA chemische Informationen	Chloroquine diphosphate (50-63-5)

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	22-40-20/21/22
S-Sätze:	22-24/25-36
RIDADR	1544
WGK Germany	3
RTECS-Nr.	VB2450000
F	10
HazardClass	6.1(b)
PackingGroup	III
HS Code	2933492250
Toxizität	LD50 oral in rat: 623mg/kg

Gefahreninformationscode (GHS)

Chloroquine diphosphate Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
R40:Verdacht auf krebserzeugende Wirkung.
R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.
S-Sätze Betriebsanweisung:
S22:Staub nicht einatmen.
S24/25:Berührung mit den Augen und der Haut vermeiden.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Beschreibung
Chloroquine is an aminoquinoline that is an inhibitor of autophagy and has antimalarial, anti-inflammatory, anticancer, and antiviral activities. Chloroquine inhibits autophagosome-lysosome fusion in HeLa cells when used at a concentration of 100 μM. It is active against the chloroquine-sensitive GC03 strain of P. falciparum (IC₅₀ = 29.2 nM) but has decreased activity against mutant pfcrt P. falciparum (IC₅₀s = 100-150 nM). Chloroquine prevents infection by severe acute respiratory coronavirus 2 (SARS-CoV-2) in Vero cells (EC₅₀ = 1.13 μM) but does not inhibit SARS-CoV replication in the lungs in a mouse model of SARS-CoV infection. It inhibits the growth of human SSC25 and CAL 27 oral squamous cell carcinoma cells (IC₅₀s = 29.9 and 17.3 μM, respectively), as well as A498, SN12C, RXF 393, and 769-P renal cancer cells (IC₅₀s = 16, 62, 81, and 25 μM, respectively). It reduces tumor growth in a CAL 27 mouse xenograft model and a 4T1 mouse allograft model when administered at a dose of 50 mg/kg. Formulations containing chloroquine have been used in the prevention of malaria, as well as the treatment of rheumatoid arthritis and systemic lupus erythematosus (SLE), and have been associated with cardiotoxicity and myopathy.
Chemische Eigenschaften
White Solid
Originator
Nivaquine,Specia,France,1949
Verwenden
An antimalarial compound
Verwenden
antimalarial, antiamebic, antirheumatic, intercalating agent
Verwenden
Standard anti-malarial drug. Substrate for MRP in multidrug resistant cell line and inhibits photoaffinity labelling of MRP by quinoline-based photoactive drug IAAQ
Verwenden
Chloroquine diphosphate salt is used to study the role of endosomal acidification in cellular processes, such as the signaling of intracellular TLRs. It can be used as DNA intercalator & to dissociate antigen antibody complexes without denaturing red blood cell antigens. Chloroquine showed very high antiviral activity against NiV but very little activity against the other viruses at concentrations lower than 20 μM.
Manufacturing Process
105 g of 4,7-dichloroquinoline (MP 93 to 94°C) are heated with 200 g of 1- diethylamino-4-aminopentane for 7 hours in an oil bath to 180°C while stirring, until a test portion dissolved in diluted nitric acid does not show a precipitation with sodium acetate solution. The mixture is dissolved in diluted acetic acid and made alkaline by adding sodium lye.
The base is extracted with ether, dried with potassium carbonate, the ether removed by distillation and the residue fractionated. The 4-(5'- diethylaminopentyl-2'-amino)-7-chloroquinoline (BP 212 to 214C/0.2 mm) is obtained. On cooling the compound solidifies crystalline. It melts, recrystallized from benzene, at 88°C. The base combines with phosphoric acid to yield a diphosphate salt.
Therapeutic Function
Antimalarial
Allgemeine Beschreibung
Chloroquine phosphate is a phosphate salt of chloroquine. It belongs to the class of aminoquinoline drugs utilized as antimalarials and amebicides.
Biochem/physiol Actions
Standard anti-malarial drug. Substrate for MRP in multidrug resistant cell line and inhibits photoaffinity labeling of MRP by quinoline-based photoactive drug IAAQ (N-[4-[1-hydroxy-2-(dibutylamino)ethyl]quinolin-8-yl]-4-azidosalicylamide).
Lager
Desiccate at RT
Einzelnachweise
1) Frieboes et al. (2014), Chloroquine-mediated cell death in metastatic pancreatic adenocarcinoma through inhibition of autophagy; JOP, 15 189 2) Jiang et al. (2010), Antitumor and antimetastatic activities of chloroquine diphosphate in a murine model of breast cancer; Biomed. Pharmacother., 64 609 3) Choi et al. (2014), Chloroquine eliminates cancer stem cells through deregulation of Jak2 and DNMT1; Stem Cells, 32 2309 4) Mulcahy Levy et al. (2014), Autophagy inhibition improves chemosensitivity in BRAFV600E brain tumors; Cancer Discov., 4 773

Chloroquine diphosphate Upstream-Materialien And Downstream Produkte

Chlorquinbis(phosphat) Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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