Chloroquine diphosphate

An antimalarial drug used for the treatment and prevention of malaria caused by chloroquine-sensitive Plasmodium species. Chloroquine accumulates in the acidic digestive vacuoles of malaria parasites and interferes with heme detoxification, leading to the accumulation of toxic heme species. It also increases lysosomal pH and modulates endosomal and lysosomal processes, contributing to its anti-inflammatory and immunomodulatory effects. Clinical use is limited by widespread resistance in Plasmodium falciparum and potential adverse effects, including retinopathy and cardiac toxicity

CAS Number: 50-63-5

Molecular Mass: 515.9 g/mol

Formula: C₁₈H₃₂ClN₃O₈P₂

Smiles: CCN(CC)CCCC(C)Nc1ccnc2cc(Cl)ccc12.O=P(O)(O)O.O=P(O)(O)O

Synonymes:

Chloroquine diphosphate, Chloroquine phosphate, Aralen phosphate, Resochin, Arechin, Avloclor, Delagil, Chingamin phosphate, Malaquin, Chloroquini phosphas, NSC-14050, 6E17K3343P, SN-7618, WR-1522, 7-Chloro-4-((4-(diethylamino)-1-methylbutyl)amino)quinoline phosphate (1:2), 1,4-Pentanediamine, N4-(7-chloro-4-quinolinyl)-N1,N1-diethyl-, phosphate (1:2), N(4)-(7-Chloro-4-quinolinyl)-N(1),N(1)-diethyl-1,4-pentanediamine, phosphate (1:2), khingamin phosphate, NSC14050, Malarivon, Chloroquinum Phos., RefChem:5672, Chloroquine diphosphate salt, Aralen diphosphate, Chloroquine bis(phosphate), Chloroquine (phosphate), Miniquine, Tanakan, Tanakene, Gontochin phosphate, Chloroquin diphosphate, NSC 14050, Ipsen 225, N4-(7-chloroquinolin-4-yl)-N1,N1-diethylpentane-1,4-diamine bis(phosphate), MFCD00069852, DTXSID7044681, 3377 RP, Chloroquine (phosphate) (Standard), SN 7,618, Alermine, H-Stadur, 1,4-Pentanediamine, N(sup 4)-(7-chloro-4-quinolinyl)-N(sup 1),N(sup 1)-diethyl-, phosphate (1:2), Chlorochin diphosphate, DTXCID5024681, Tanakan (antimalarial), dl-Chloroquine diphosphate, C18H32ClN3O8P2, Chloroquinediphosphate, CCRIS 1554, 4-N-(7-chloroquinolin-4-yl)-1-N,1-N-diethylpentane-1,4-diamine, phosphoric acid, SR-01000075548, EINECS 200-055-2, WR 1522, Chloroquine dihydrogen phosphate (1:2), Unikinon, AI3-14952, UNII-6E17K3343P, Chloroquine phosphate [USP:BAN], Chloroquindiphosphat, Prestwick_867, 50-63-5 (DIPHOSPHATE), Aralen (TN), Chloroquine phospha te, CAS-50-63-5, NCGC00015256-01, 7-Chlor-4-(4-(diaethylamino)-1-methylbutylamino)-chinolindiphosphat [German], Chloroquine phosphate (USP), SCHEMBL40827, CHEMBL58510, SPECTRUM1500179, orb1310848, SCHEMBL29383276, HMS501E06, QKICWELGRMTQCR-UHFFFAOYSA-N, HMS1569N17, HMS1920O05, HMS2091C16, HMS2096N17, HMS3260L14, HMS3713N17, MSK10133, CHLOROQUINE DIPHOSPHATE [MI], Tox21_110115, Tox21_202838, Tox21_500296, 7-Chlor-4-(4-(diaethylamino)-1-methylbutylamino)-chinolindiphosphat, CCG-39643, CHLOROQUINE PHOSPHATE [VANDF], EBC-07364, HB5073, HY-17589R, s4157, CHLOROQUINE PHOSPHATE [MART.], AKOS004910410, CHLOROQUINE PHOSPHATE [USP-RS], CHLOROQUINE PHOSPHATE [WHO-DD], CHLOROQUINE PHOSPHATE [WHO-IP], N4-(7-chloro-4-quinolyl)-N1,N1-diethyl-pentane-1,4-diamine, phosphoric acid, Quinoline, 7-chloro-4-(4-diethylamino-1-methyl-butylamino)-, diphosphate, Tox21_110115_1, CS-3811, DT-0015, FC20382, LP00296, 1,4-Pentanediamine, N4-(7-chloro-4-quinolinyl)-N',N'-diethyl-, (+-)-, phosphate (1:2), Quinoline, 7-chloro-4-((4-(diethylamino)-1-methylbutyl)amino)-, phosphate (1:2), NCGC00015256-12, NCGC00093746-01, NCGC00093746-02, NCGC00093746-03, NCGC00260384-01, NCGC00260981-01, AC-12463, CHLOROQUINE PHOSPHATE [GREEN BOOK], HY-17589, SY021941, CHLOROQUINE PHOSPHATE [ORANGE BOOK], CHLOROQUINE PHOSPHATE [EP MONOGRAPH], CHLOROQUINI PHOSPHAS [WHO-IP LATIN], DB-051808, C2301, Chloroquine diphosphate salt, solid, >=98%, CHLOROQUINE PHOSPHATE [USP MONOGRAPH], CS-0695021, EU-0100296, NS00078674, C 6628, D02125, D70732, EN300-100253, Chloroquine phosphate for peak identification CRS, F358020, SR-01000075548-1, SR-01000075548-3, SR-01000075548-5, Q27264629, F2173-1139, Z1541662176, 7-Chloro-4-[4-(diethylamino)-1-methylbutylamino]quinoline Bis(phosphate), 7-Chloro-4-[4-(diethylamino)-1-methylbutylamino]quinoline Diphosphate, Chloroquine phosphate, United States Pharmacopeia (USP) Reference Standard, N4-(7-Chloro-4-quinolyl)-N1,N1-diethyl-1,4-pentanediamine Diphosphate, 7-CHLORO-4-((4-(DIETHYLAMINO)-1-METHYLBUTYL)AMINO)QUINOLINE PHOSPHATE (1:2)., 7-CHLORO-N-[5-(DIETHYLAMINO)PENTAN-2-YL]QUINOLIN-4-AMINE, BIS(PHOSPHORIC ACID), Chloroquine phosphate, Pharmaceutical Secondary Standard, Certified Reference Material, N4-(7-Chloro-4-quinolinyl)-N1,N1-diethyl-1,4-pentanediamine diphosphate salt, N4-(7-chloro-4-quinolyl)-N1,N1-diethyl-pentane-1,4-diamine, phosphoric acid, Phosphoric acid--N~4~-(7-chloroquinolin-4-yl)-N~1~,N~1~-diethylpentane-1,4-diamine (2/1)

Bioactivity: Antimalarial 4-aminoquinoline agent; inhibitor of heme detoxification in Plasmodium parasites; lysosomotropic immunomodulatory agent

Solubility in Different Solvents

Solvent	Temperature [K]	Crystal form	Solubility [mg/mL]	Reference
1-Propanol	273.15	-	0.0138	[137]
1-Propanol	278.15	-	0.01793	[137]
1-Propanol	283.15	-	0.02342	[137]
1-Propanol	288.15	-	0.0296	[137]
1-Propanol	293.15	-	0.03683	[137]
1-Propanol	298.15	-	0.04441	[137]
1-Propanol	303.15	-	0.05376	[137]
1-Propanol	308.15	-	0.06476	[137]
1-Propanol	313.15	-	0.0779	[137]
Acetone	298.2	-	0.0293	[138]
Acetone	303.2	-	0.0319	[138]
Acetone	308.2	-	0.035	[138]
Acetone	313.2	-	0.0395	[138]
Acetone	318.2	-	0.0453	[138]
Acetone	323.2	-	0.0577	[138]
Acetone	328.1	-	0.07264	[138]
Acetonitrile	299.2	-	0.0234	[138]
Acetonitrile	303.2	-	0.0242	[138]
Acetonitrile	308.2	-	0.025	[138]
Acetonitrile	313.2	-	0.0258	[138]
Acetonitrile	318.2	-	0.0266	[138]
Acetonitrile	323.2	-	0.028	[138]
Acetonitrile	328.3	-	0.03075	[138]
Acetonitrile	333.3	-	0.0334	[138]
Dimethylformamide	273.15	-	0.0382	[137]
Dimethylformamide	278.15	-	0.05242	[137]
Dimethylformamide	283.15	-	0.0692	[137]
Dimethylformamide	288.15	-	0.0889	[137]
Dimethylformamide	293.15	-	0.1104	[137]
Dimethylformamide	298.15	-	0.1377	[137]
Dimethylformamide	303.15	-	0.1681	[137]
Dimethylformamide	308.15	-	0.2056	[137]
Dimethylformamide	313.15	-	0.248	[137]
Ethanol	273.15	-	0.03452	[137]
Ethanol	278.15	-	0.04458	[137]
Ethanol	283.15	-	0.05931	[137]
Ethanol	288.15	-	0.07756	[137]
Ethanol	293.15	-	0.09779	[137]
Ethanol	298.15	-	0.1217	[137]
Ethanol	298.2	-	0.1706	[138]
Ethanol	303.1	-	0.181	[138]
Ethanol	303.15	-	0.1473	[137]
Ethanol	308.15	-	0.1767	[137]
Ethanol	308.2	-	0.1982	[138]
Ethanol	313.1	-	0.217	[138]
Ethanol	313.15	-	0.2098	[137]
Ethanol	318.2	-	0.2347	[138]
Ethanol	323.2	-	0.26	[138]
Ethanol	328.1	-	0.2915	[138]
Ethanol	333.2	-	0.3093	[138]
Isopropanol	273.15	-	0.0074	[137]
Isopropanol	278.15	-	0.0103	[137]
Isopropanol	283.15	-	0.01384	[137]
Isopropanol	288.15	-	0.01817	[137]
Isopropanol	293.15	-	0.02313	[137]
Isopropanol	298.15	-	0.0295	[137]
Isopropanol	303.15	-	0.03688	[137]
Isopropanol	308.15	-	0.04531	[137]
Isopropanol	313.15	-	0.0541	[137]
Tetrahydrofuran	298.2	-	0.1975	[138]
Tetrahydrofuran	303.1	-	0.249	[138]
Tetrahydrofuran	308.1	-	0.3047	[138]
Tetrahydrofuran	313.1	-	0.3579	[138]
Tetrahydrofuran	318.0	-	0.4067	[138]
Tetrahydrofuran	323.2	-	0.4504	[138]
Tetrahydrofuran	328.2	-	0.4785	[138]
Tetrahydrofuran	333.2	-	0.5001	[138]
Water	298.2	-	254.8	[138]
Water	303.2	-	285.9	[138]
Water	308.2	-	322.5	[138]
Water	313.2	-	374.6	[138]
Water	318.1	-	462.5	[138]
Water	323.2	-	569.7	[138]
Water	328.3	-	714.1	[138]
Water	333.3	-	853.1	[138]

Molecule 3D descriptors

Descriptor	Value
PMI1	943.9345
PMI2	7293.6482
PMI3	7656.1811
NPR1	0.1233
NPR2	0.9526
RadiusOfGyration	3.9249
InertialShapeFactor	0.0010
Eccentricity	0.9924
Asphericity	0.6770
SpherocityIndex	0.1687
PBF	0.7361