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50-63-5,MFCD00069852
Catalog No.:AA0034IX

50-63-5 | Chloroquine diphosphate

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10g
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25g
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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA0034IX
Chemical Name:
Chloroquine diphosphate
CAS Number:
50-63-5
Molecular Formula:
C18H30ClN3O7P2
Molecular Weight:
497.8472
MDL Number:
MFCD00069852
SMILES:
OP(=O)(OP(=O)(O)O)O.CCN(CCCC(Nc1ccnc2c1ccc(c2)Cl)C)CC
Properties
Properties
 
BP:
460.6°C at 760 mmHg  
Form:
Solid  
MP:
200°C(dec.)(lit.)  
Solubility:
H2O: 50 mg/mL, clear  
Storage:
Inert atmosphere;Room Temperature;  

Computed Properties
 
Complexity:
359  
Covalently-Bonded Unit Count:
3  
Heavy Atom Count:
32  
Hydrogen Bond Acceptor Count:
11  
Hydrogen Bond Donor Count:
7  
Rotatable Bond Count:
8  
Undefined Atom Stereocenter Count:
1  

Literature

Title: miRNA‑145 inhibits myocardial infarction‑induced apoptosis through autophagy via Akt3/mTOR signaling pathway in vitro and in vivo.

Journal: International journal of molecular medicine 20180901

Title: Chloroquine upregulates TRAIL/TRAILR2 expression and potentiates doxorubicin anti-tumor activity in thioacetamide-induced hepatocellular carcinoma model.

Journal: Chemico-biological interactions 20180105

Title: Hydroxychloroquine attenuates cigarette smoke induced autophagic signaling in the mouse ovary.

Journal: Reproductive toxicology (Elmsford, N.Y.) 20160601

Title: The relationship between Cd-induced autophagy and lysosomal activation in WRL-68 cells.

Journal: Journal of applied toxicology : JAT 20151101

Title: Elucidating mechanisms of toxicity using phenotypic data from primary human cell systems--a chemical biology approach for thrombosis-related side effects.

Journal: International journal of molecular sciences 20150101

Title: Second generation steroidal 4-aminoquinolines are potent, dual-target inhibitors of the botulinum neurotoxin serotype A metalloprotease and P. falciparum malaria.

Journal: Journal of medicinal chemistry 20140522

Title: Quinoline-pyrimidine hybrids: synthesis, antiplasmodial activity, SAR, and mode of action studies.

Journal: Journal of medicinal chemistry 20140123

Title: 3,5-bis(benzylidene)-4-piperidones and related N-acyl analogs: a novel cluster of antimalarials targeting the liver stage of Plasmodium falciparum.

Journal: Bioorganic & medicinal chemistry 20131201

Title: Synthesis of novel analogs of 2-pyrazoline obtained from [(7-chloroquinolin-4-yl)amino]chalcones and hydrazine as potential antitumor and antimalarial agents.

Journal: European journal of medicinal chemistry 20130901

Title: Ileal apical sodium-dependent bile acid transporter protein levels are down-regulated through ubiquitin-dependent protein degradation induced by bile acids.

Journal: European journal of pharmacology 20130815

Title: 4-Amino-7-chloroquinolines: probing ligand efficiency provides botulinum neurotoxin serotype A light chain inhibitors with significant antiprotozoal activity.

Journal: Journal of medicinal chemistry 20130725

Title: Resistance of colon cancer to 5-fluorouracil may be overcome by combination with chloroquine, an in vivo study.

Journal: Anti-cancer drugs 20120801

Title: Role of curcumin on chloroquine phosphate-induced reproductive toxicity.

Journal: Drug and chemical toxicology 20120401

Title: Evaluation of drugs with specific organ toxicities in organ-specific cell lines.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20120301

Title: Design and synthesis of small molecular dual inhibitor of falcipain-2 and dihydrofolate reductase as antimalarial agent.

Journal: Bioorganic & medicinal chemistry letters 20120115

Title: Blood parasites mediate morph-specific maintenance costs in a colour polymorphic wild bird.

Journal: Journal of evolutionary biology 20110801

Title: In-vitro culture of Plasmodium falciparum: utility of modified (RPNI) medium for drug-sensitivity studies using SYBR Green I assay.

Journal: Experimental parasitology 20110101

Title: Retinal toxicity associated with hydroxychloroquine and chloroquine: risk factors, screening, and progression despite cessation of therapy.

Journal: Archives of ophthalmology (Chicago, Ill. : 1960) 20110101

Title: Variant Plasmodium ovale isolated from a patient infected in Ghana.

Journal: Malaria journal 20110101

Title: Monitoring of clinical efficacy and in vitro sensitivity of Plasmodium vivax to chloroquine in area along Thai Myanmar border during 2009-2010.

Journal: Malaria journal 20110101

Title: Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.

Journal: Bioorganic & medicinal chemistry letters 20101101

Title: Antitumor and antimetastatic activities of chloroquine diphosphate in a murine model of breast cancer.

Journal: Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie 20101101

Title: Discovery of potent small-molecule inhibitors of multidrug-resistant Plasmodium falciparum using a novel miniaturized high-throughput luciferase-based assay.

Journal: Antimicrobial agents and chemotherapy 20100901

Title: Synthesis of novel alpha-pyranochalcones and pyrazoline derivatives as Plasmodium falciparum growth inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20100801

Title: Toxic epidermal necrolysis-like cutaneous lupus erythematosus: A series of three patients.

Journal: Acta dermato-venereologica 20100301

Title: A 4-aminoquinoline derivative that markedly sensitizes tumor cell killing by Akt inhibitors with a minimum cytotoxicity to non-cancer cells.

Journal: European journal of medicinal chemistry 20100201

Title: Synthesis and evaluation of phenylequine for antimalarial activity in vitro and in vivo.

Journal: Bioorganic & medicinal chemistry letters 20100201

Title: Modular synthesis and in vitro and in vivo antimalarial assessment of C-10 pyrrole mannich base derivatives of artemisinin.

Journal: Journal of medicinal chemistry 20100128

Title: [Monitoring delagil (chloroquine) efficacy against imported Plasmodium vivax strains].

Journal: Meditsinskaia parazitologiia i parazitarnye bolezni 20100101

Title: Genetic mapping of targets mediating differential chemical phenotypes in Plasmodium falciparum.

Journal: Nature chemical biology 20091001

Title: Seventy-five years of Resochin in the fight against malaria.

Journal: Parasitology research 20090901

Title: In utero exposure to chloroquine alters sexual development in the male fetal rat.

Journal: Toxicology and applied pharmacology 20090615

Title: New antimalarial and cytotoxic 4-nerolidylcatechol derivatives.

Journal: European journal of medicinal chemistry 20090601

Title: Amyloid-beta accumulation caused by chloroquine injections precedes ER stress and autophagosome formation in rat skeletal muscle.

Journal: Acta neuropathologica 20090501

Title: Synthesis, antimalarial activity, and preclinical pharmacology of a novel series of 4'-fluoro and 4'-chloro analogues of amodiaquine. Identification of a suitable 'back-up' compound for N-tert-butyl isoquine.

Journal: Journal of medicinal chemistry 20090409

Title: Lupus erythematosus tumidus: response to antimalarial treatment in 36 patients with emphasis on smoking.

Journal: Archives of dermatology 20090301

Title: Antirheumatic drug response signatures in human chondrocytes: potential molecular targets to stimulate cartilage regeneration.

Journal: Arthritis research & therapy 20090101

Title: [Diagnostic methods for chloroquine diphosphate induced retinopathy in systemic lupus erythematosus].

Journal: Arquivos brasileiros de oftalmologia 20090101

Title: Scar sarcoidosis with a 50-year interval between an accident and onset of lesions.

Journal: Dermatology online journal 20081115

Title: New ferrocenic pyrrolo[1,2-a]quinoxaline derivatives: synthesis, and in vitro antimalarial activity.

Journal: Bioorganic & medicinal chemistry 20081015

Title: Preparation and in vitro evaluation of liposomal chloroquine diphosphate loaded by a transmembrane pH-gradient method.

Journal: International journal of pharmaceutics 20080901

Title: The efficacy and selectivity of tumor cell killing by Akt inhibitors are substantially increased by chloroquine.

Journal: Bioorganic & medicinal chemistry 20080901

Title: [Effects of chloroquine diphosphate on proliferation and apoptosis of human leukemic K562 cells].

Journal: Zhongguo shi yan xue ye xue za zhi 20080801

Title: Antimalarial activity of novel pyrrolizidinyl derivatives of 4-aminoquinoline.

Journal: Bioorganic & medicinal chemistry letters 20080701

Title: Synthesis and structure-activity relationships of 4-pyridones as potential antimalarials.

Journal: Journal of medicinal chemistry 20080508

Title: Malaria--an experience at CMH Khuzdar (Balochistan).

Journal: Journal of the College of Physicians and Surgeons--Pakistan : JCPSP 20080401

Title: Increased yield of porcine circovirus-2 by a combined treatment of PK-15 cells with interferon-gamma and inhibitors of endosomal-lysosomal system acidification.

Journal: Archives of virology 20080101

Title: Azithromycin/chloroquine combination does not increase cardiac instability despite an increase in monophasic action potential duration in the anesthetized guinea pig.

Journal: The American journal of tropical medicine and hygiene 20071101

Title: [Light induced subacute cutaneous lupus erythematodes: diagnosis and management].

Journal: Der Hautarzt; Zeitschrift fur Dermatologie, Venerologie, und verwandte Gebiete 20071001

Title: [Effects of drugs known to trigger psoriasis on HaCaT keratinocytes].

Journal: Yao xue xue bao = Acta pharmaceutica Sinica 20071001

Title: Glycoconjugated peptide dendrimers-based nanoparticulate system for the delivery of chloroquine phosphate.

Journal: Biomaterials 20070801

Title: Capillary electrophoresis with end-column electrochemiluminescence for the analysis of chloroquine phosphate and the study on its interaction with human serum albumin.

Journal: Journal of chromatography. A 20070622

Title: Chloroquine increases low-density lipoprotein removal from plasma in systemic lupus patients.

Journal: Lupus 20070101

Title: 677C > T and 1298A > C MTHFR polymorphisms affect arechin treatment outcome in rheumatoid arthritis.

Journal: Pharmacological reports : PR 20070101

Title: [Administration of prostaglandins Ei and immunotherapy in management of various-genesis trophic ulcers].

Journal: Angiologiia i sosudistaia khirurgiia = Angiology and vascular surgery 20070101

Title: Influence of genotype, dose and sex on pruritogen-induced scratching behavior in the mouse.

Journal: Pain 20060901

Title: PEGylated peptide dendrimeric carriers for the delivery of antimalarial drug chloroquine phosphate.

Journal: Pharmaceutical research 20060301

Title: Nocardiosis in a patient with primary anti-phospholipid syndrome.

Journal: Rheumatology international 20060301

Title: Retinal nerve fibre layer thickness measurements in patients using chloroquine.

Journal: Clinical & experimental ophthalmology 20060301

Title: [Long-term results of treatment and prediction in patients with sarcoidosis].

Journal: Problemy tuberkuleza i boleznei legkikh 20060101

Title: [Rational therapeutic approach in rheumatoid arthritis].

Journal: Annales Academiae Medicae Stetinensis 20060101

Title: Spectrophotometric study of the reaction mechanism between DDQ Pi- and iodine sigma-acceptors and chloroquine and pyrimethamine drugs and their determination in pure and in dosage forms.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20051101

Title: [Occurrence of chloroquine-induced myopathy after low-dose treatment of rheumatoid arthritis for seven years].

Journal: Zeitschrift fur Rheumatologie 20050501

Title: Synthesis of some cryptolepine analogues, assessment of their antimalarial and cytotoxic activities, and consideration of their antimalarial mode of action.

Journal: Journal of medicinal chemistry 20050407

Title: [Acute chloroquine intoxication--rare, but always serious: case reports and literature review].

Journal: Przeglad lekarski 20050101

Title: Chloroquine for the maintenance of remission of autoimmune hepatitis: results of a pilot study.

Journal: Arquivos de gastroenterologia 20050101

Title: Toward a novel metal-based chemotherapy against tropical diseases. 7. Synthesis and in vitro antimalarial activity of new gold-chloroquine complexes.

Journal: Journal of medicinal chemistry 20041007

Title: In vitro and in vivo antimalarial studies of Striga hermonthica and Tapinanthus sessilifolius extracts.

Journal: African journal of medicine and medical sciences 20040301

Title: [Insanovin aerosol therapy in the treatment of bronchial asthma].

Journal: Problemy tuberkuleza i boleznei legkikh 20040101

Title: [The functional status of circulating lymphoid and phagocytic cells in patients with tropical malaria, living in the endemic areas of Guinea].

Journal: Meditsinskaia parazitologiia i parazitarnye bolezni 20040101

Title: Kinetics of DNA binding with chloroquine phosphate using capacitive sensing method.

Journal: Biosensors & bioelectronics 20031215

Title: Enhancement of the antiplasmodial activity of quassin by transformation into a gamma-lactone.

Journal: Journal of natural products 20031101

Title: Selective lack of the C16:0 fatty acid isoform of sulfatide in pancreas of type II diabetic animal models.

Journal: APMIS : acta pathologica, microbiologica, et immunologica Scandinavica 20030901

Title: Synthesis of ethyl 5-phenyl-6-oxa-1-azabicyclo[3.1.0]hexane-2-carboxylate derivatives and evaluation of their antimalarial activities.

Journal: Journal of medicinal chemistry 20030605

Title: Antimalarial dihydroisocoumarins produced by Geotrichum sp., an endophytic fungus of Crassocephalum crepidioides.

Journal: Journal of natural products 20030501

Title: [Toxic lesions of the organ of vision caused by chloroquine derivatives].

Journal: Vestnik oftalmologii 20030101

Title: [Clinico-functional efficacy of medicinal and photon stabilization of cell membrane in patients with angina pectoris].

Journal: Klinicheskaia meditsina 20030101

Title: Isolation and in vitro antiplasmodial activities of alkaloids from Teclea trichocarpa: in vivo antimalarial activity and X-ray crystal structure of normelicopicine.

Journal: Journal of natural products 20020701

Title: Synthesis and evaluation of cryptolepine analogues for their potential as new antimalarial agents.

Journal: Journal of medicinal chemistry 20010913

Title: Bioactive acridone alkaloids from Swinglea glutinosa.

Journal: Journal of natural products 20010901

Title: Phomoxanthones A and B, novel xanthone dimers from the endophytic fungus Phomopsis species.

Journal: Journal of natural products 20010801

Title: Longterm beneficial effect of chloroquine diphosphate on lipoprotein profile in lupus patients with and without steroid therapy.

Journal: The Journal of rheumatology 20010401

Title: Analysis of chromatin structural transitions by means of intercalator dyes.

Journal: Doklady. Biochemistry and biophysics 20010101

Title: Chloroquine neuromyopathy.

Journal: Clinical neuropathology 19960101

Title: Restrictive cardiomyopathy caused by chloroquine.

Journal: British heart journal 19930501

Title: Chloroquine-induced cardiomyopathy.

Journal: Archives of pathology & laboratory medicine 19871001

Title: Alterations of auditory evoked potentials during the course of chloroquine treatment.

Journal: Acta oto-laryngologica 19850101

Title: Chloroquine ototoxicity--a reversible phenomenon?

Journal: The Journal of laryngology and otology 19790801

Title: Motor polyneuroapthy and nystagmus associated with chloroquine phosphate.

Journal: Postgraduate medical journal 19790801

Title: Cardiac arrest after intravenous chloroquine injection.

Journal: The Journal of tropical medicine and hygiene 19790201

Title: Complete heart block due to chronic chloroquine toxicity managed with permanent pacemaker.

Journal: British medical journal 19780429

Title: Chloroquine induced involuntary movements.

Journal: British medical journal 19770409

Title: Letter: Visual defect from chloroquine phosphate.

Journal: Archives of dermatology 19750801

Title: Supplemental folates in the therapy of Plasmodium falciparum malaria.

Journal: JAMA 19701228

Title: Simultaneous drug reactions in the same patient. Chloroquine-Primaquine sensitivity.

Journal: JAMA 19700427

Title: Chloroquine: ophthalmological safety, and clinical assessment in rheumatoid arthritis.

Journal: British medical journal 19680907

Title: Chloroquine seizures. Report of four cases.

Journal: JAMA 19680603

Title: Said A, et al. Chloroquine promotes IL-17 production by CD4+ T cells via p38-dependent IL-23 release by monocyte-derived Langerhans-like cells. J Immunol. 2014 Dec 15;193(12):6135-43.

Title: Tuomela J, et al. Chloroquine has tumor-inhibitory and tumor-promoting effects in triple-negative breast cancer. Oncol Lett. 2013 Dec;6(6):1665-1672.

Title: Mohamed FE, et al. Effect of toll-like receptor 7 and 9 targeted therapy to prevent the development of hepatocellular carcinoma. Liver Int. 2014 Jul 2. doi: 10.1111/liv.12626.

Title: Colson P, et al. Chloroquine and hydroxychloroquine as available weapons to fight COVID-19. Int J Antimicrob Agents. 2020;55(4):105932.

Title: Wang M, et al. Remdesivir and chloroquine effectively inhibit the recently emerged novel coronavirus (2019-nCoV) in vitro. Cell Res. 2020 Mar;30(3):269-271.

Title: Savarino A, et al. The anti-HIV-1 activity of chloroquine. J Clin Virol. 2001;20(3):131-135.

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Tags:50-63-5 Molecular Formula|50-63-5 MDL|50-63-5 SMILES|50-63-5 Chloroquine diphosphate