Chloroquine diphosphate salt

SIGMA/C6628 - powder or crystals, 98.5-101.0% (EP)

Synonym: N4-(7-chloroquinolin-4-yl)-N1,N1-diethylpentane-1,4-diamine diphosphate; N⁴-(7-Chloro-4-quinolinyl)-N¹,N¹-dimethyl-1,4-pentanediamine diphosphate salt

CAS Number: 50-63-5
Empirical Formula (Hill Notation): C₁₈H₂₆ClN₃ · 2H₃PO₄
Molecular Weight: 515.86
EC Number: 200-055-2
MDL Number: MFCD00069852
Linear Formula: C₁₈H₂₆ClN₃ · 2H₃PO₄
Product Type: Chemical

Catalog Number	PKG Qty.	Price


45-C6628-25G	25 g	$76.50 1/EA	Add To Favorites
45-C6628-50G	50 g	$143.00 1/EA	Add To Favorites
45-C6628-100G	100 g	$256.00 1/EA	Add To Favorites
45-C6628-250G	250 g	$455.00 1/EA	Add To Favorites

Properties
Descriptions
Safety Info.
Basic Data

antibiotic activity spectrum	parasites
assay	98.5-101.0% (EP)
form	powder or crystals
InChI	1S/C18H26ClN3.2H3O4P/c1-4-22(5-2)12-6-7-14(3)21-17-10-11-20-18-13-15(19)8-9-16(17)18;21-5(2,3)4/h8-11,13-14H,4-7,12H2,1-3H3,(H,20,21);2(H3,1,2,3,4)
InChI key	QKICWELGRMTQCR-UHFFFAOYSA-N
mode of action	enzyme \| inhibits
mp	192-198 °C
Quality Level	200
SMILES string	OP(O)(O)=O.OP(O)(O)=O.CCN(CC)CCCC(C)Nc1ccnc2cc(Cl)ccc12

Application:	DNA intercalator. Also used to increase transfection efficiency. Chloroquine diphosphate salt has been used : • in in vitro antiplasmodial assays • in transfection and infection assays • in autophagy inhibition • in differentiation of induced pluripotent stem (iPS) cells into cardiomyocytes • in flow treatment of infected blood
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).
Features and Benefits:	This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm .
General description:	Chloroquine effectively eliminates the erythrocytic forms of malaria parasites at all developmental stages, although it does not impact the sporozoites. It also functions as an antibiotic. In addition, it can be utilized at a concentration of 200 mg/mL (PBS, pH 5.0) to dissociate antigen-antibody complexes without denaturing red blood cell antigens. Recent research indicates chloroquine′s potential as an antitumor medication for cancer treatment along with chemotherapy and radiation. Its antimalarial effects are achieved by inhibiting the polymerization of heme into hemozoin, which serves as a food source for the malarial parasite. Chloroquine forms a complex with the drug-hemozoin, capping the polymerizing chain and preventing further polymerization. As a result, free heme accumulates in the food vacuole, exerting toxic effects on the parasite. Additionally, chloroquine acts as an anti-autoimmune therapy by binding to transcriptional factors on T helper 17 cells and inhibiting their differentiation. Chloroquine diphosphate (CQ) is frequently employed as an inhibitor of the autophagic pathway. The combined use of chloroquine diphosphate and salidroside initiates apoptosis in human liver cells by modulating mitochondrial dysfunction and autophagy.
General description:	Chloroquine is a member of quinolone family and is a weak intercalating agent. Chloroquine is used for treating amebiasis, rheumatoid arthritis, discoid and systemic lupus erythematosus.
Other Notes:	2024 CiteAb Award Winner for Supplier Succeeding in Parkinson′s Research
Packaging:	25, 50, 100, 250 g in glass bottle

Symbol	GHS07
Signal word	Warning
Hazard statements	H302
Hazard Codes	Xn
Risk Statements	22
Safety Statements	22-24/25
RIDADR	NONH for all modes of transport
WGK Germany	WGK 3
Flash Point(F)	Not applicable
Flash Point(C)	Not applicable

Purity	98.5-101.0% (EP)
mp	192-198 °C
UNSPSC	12352107

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