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152-53-4,MFCD00035308
Catalog No.:AA003P1C

152-53-4 | Cycloguanil hydrochloride

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1mg
97%
in stock  
$7.00   $5.00
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5mg
95%
in stock  
$24.00   $17.00
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25mg
95%
in stock  
$48.00   $34.00
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100mg
97%
in stock  
$65.00   $46.00
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250mg
97%
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$110.00   $77.00
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  • Technical Information
  • Properties
  • Upstream Synthesis Route
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Upstream Synthesis Route
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA003P1C
Chemical Name:
Cycloguanil hydrochloride
CAS Number:
152-53-4
Molecular Formula:
C11H15Cl2N5
Molecular Weight:
288.1763
MDL Number:
MFCD00035308
SMILES:
Clc1ccc(cc1)N1C(=NC(=NC1(C)C)N)N.Cl
NSC Number:
3074
Properties
Properties
 
Form:
Solid  
MP:
210-215 °C  
Storage:
Inert atmosphere;-20 ℃;  

Computed Properties
 
Complexity:
355  
Covalently-Bonded Unit Count:
2  
Heavy Atom Count:
18  
Hydrogen Bond Acceptor Count:
1  
Hydrogen Bond Donor Count:
3  
Rotatable Bond Count:
1  

Upstream Synthesis Route

[1]SyntheticCommunications,2002,vol.32,#14,p.2089-2100

[1]JournalofMedicinalChemistry,2000,vol.43,#14,p.2738-2744

[2]BioorganicandMedicinalChemistryLetters,2009,vol.19,#19,p.5644-5647

[1]JournalofMedicinalChemistry,1984,vol.27,#2,p.129-143

Downstream Synthesis Route

[1]JournalofHeterocyclicChemistry,1993,vol.30,p.849-854

[2]BioorganicandMedicinalChemistryLetters,2009,vol.19,p.5644-5647

[1]JournalofMedicinalChemistry,1984,vol.27,p.129-143

[1]JournalofMedicinalChemistry,2000,vol.43,p.2738-2744

[2]BioorganicandMedicinalChemistryLetters,2009,vol.19,p.5644-5647

[1]SyntheticCommunications,2002,vol.32,p.2089-2100

Literature

Title: Cloning and heterologous expression of Plasmodium ovale dihydrofolate reductase-thymidylate synthase gene.

Journal: Parasitology international 20120601

Title: Exploring QSAR, pharmacophore mapping and docking studies and virtual library generation for cycloguanil derivatives as PfDHFR-TS inhibitors.

Journal: Medicinal chemistry (Shariqah (United Arab Emirates)) 20110501

Title: Fitness trade-offs in the evolution of dihydrofolate reductase and drug resistance in Plasmodium falciparum.

Journal: PloS one 20110101

Title: Quantitative structure-activity relationships for cycloguanil analogs as PfDHFR inhibitors using mathematical molecular descriptors.

Journal: SAR and QSAR in environmental research 20100401

Title: Shape- and chemical feature-based 3D-pharmacophore model generation and virtual screening: identification of potential leads for P. falciparum DHFR enzyme inhibition.

Journal: Chemical biology & drug design 20100101

Title: 3D-QSAR analysis of cycloguanil derivatives as inhibitors of A16V + S108T mutant Plasmodium falciparum dihydrofolate reductase enzyme.

Journal: Journal of molecular graphics & modelling 20091101

Title: Effects of genetic variation at the CYP2C19/CYP2C9 locus on pharmacokinetics of chlorcycloguanil in adult Gambians.

Journal: Pharmacogenomics 20090901

Title: Structure-activity relationship and comparative docking studies for cycloguanil analogs as PfDHFR-TS inhibitors.

Journal: Journal of chemical information and modeling 20090701

Title: Interactions between cycloguanil derivatives and wild type and resistance-associated mutant Plasmodium falciparum dihydrofolate reductases.

Journal: Journal of computer-aided molecular design 20090401

Title: A novel in silico approach to drug discovery via computational intelligence.

Journal: Journal of chemical information and modeling 20090401

Title: Synthesis and bioevaluation of hybrid 4-aminoquinoline triazines as a new class of antimalarial agents.

Journal: Bioorganic & medicinal chemistry letters 20081215

Title: Effect of folate derivatives on the activity of antifolate drugs used against malaria and cancer.

Journal: Parasitology research 20080501

Title: Role of specific cytochrome P450 isoforms in the conversion of phenoxypropoxybiguanide analogs in human liver microsomes to potent antimalarial dihydrotriazines.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20080201

Title: Escalating Plasmodium falciparum antifolate drug resistance mutations in Macha, rural Zambia.

Journal: Malaria journal 20080101

Title: The role of tryptophan-48 in catalysis and binding of inhibitors of Plasmodium falciparum dihydrofolate reductase.

Journal: International journal for parasitology 20070601

Title: Effect of honey on CYP3A4, CYP2D6 and CYP2C19 enzyme activity in healthy human volunteers.

Journal: Basic & clinical pharmacology & toxicology 20070401

Title: Simultaneous determination of monodesethylchloroquine, chloroquine, cycloguanil and proguanil on dried blood spots by reverse-phase liquid chromatography.

Journal: Journal of pharmaceutical and biomedical analysis 20070219

Title: Amino acid mutations in Plasmodium vivax DHFR and DHPS from several geographical regions and susceptibility to antifolate drugs.

Journal: The American journal of tropical medicine and hygiene 20061001

Title: Multiple synergistic interactions between atovaquone and antifolates against Plasmodium falciparum in vitro: a rational basis for combination therapy.

Journal: Acta tropica 20060301

Title: Population pharmacokinetic and pharmacodynamic modelling of the antimalarial chemotherapy chlorproguanil/dapsone.

Journal: British journal of clinical pharmacology 20060301

Title: Sensitive method for the quantitative determination of proguanil and its metabolites in rat blood and plasma by liquid chromatography-mass spectrometry.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20060118

Title: Plasmodium falciparum: interaction of shikimate analogues with antimalarial drugs.

Journal: Experimental parasitology 20051101

Title: A simple dual selection for functionally active mutants of Plasmodium falciparum dihydrofolate reductase with improved solubility.

Journal: Protein engineering, design & selection : PEDS 20051001

Title: Susceptibility studies of Malaysian Plasmodium falciparum clones to type II antifolate drugs after 3 years of continuous in vitro culture.

Journal: Chemotherapy 20051001

Title: The pharmacokinetics and pharmacodynamics of atovaquone and proguanil for the treatment of uncomplicated falciparum malaria in third-trimester pregnant women.

Journal: European journal of clinical pharmacology 20050901

Title: Stoichiometric selection of tight-binding inhibitors by wild-type and mutant forms of malarial (Plasmodium falciparum) dihydrofolate reductase.

Journal: Analytical chemistry 20050301

Title: Syntheses of 2,4,6-trisubstituted triazines as antimalarial agents.

Journal: Bioorganic & medicinal chemistry letters 20050201

Title: In vitro recrudescence of Plasmodium falciparum parasites suppressed to dormant state by atovaquone alone and in combination with proguanil.

Journal: Transactions of the Royal Society of Tropical Medicine and Hygiene 20050101

Title: Novel alleles of Plasmodium falciparum dhfr that confer resistance to chlorcycloguanil.

Journal: Molecular and biochemical parasitology 20050101

Title: The chemotherapy of rodent malaria. LXII. Drug combinations to impede the selection of drug resistance, part 5: rates of development of resistance to some inhibitors of folate metabolism and to artesunate.

Journal: Annals of tropical medicine and parasitology 20041201

Title: Short communication: Prevalence of mutations associated with resistance to atovaquone and to the antifolate effect of proguanil in Plasmodium falciparum isolates from northern Ghana.

Journal: Tropical medicine & international health : TM & IH 20040301

Title: Inhibitors of multiple mutants of Plasmodium falciparum dihydrofolate reductase and their antimalarial activities.

Journal: Journal of medicinal chemistry 20040129

Title: Susceptibility of Plasmodium falciparum to the drugs used to treat severe malaria (quinine) and to prevent malaria (mefloquine, cycloguanil) in Comoros Union and Madagascar.

Journal: South African medical journal = Suid-Afrikaanse tydskrif vir geneeskunde 20040101

Title: Concordance between proguanil phenotype and CYP2C19 genotype in Chinese.

Journal: European journal of clinical pharmacology 20031101

Title: Pregnancy and use of oral contraceptives reduces the biotransformation of proguanil to cycloguanil.

Journal: European journal of clinical pharmacology 20031001

Title: DHFR and DHPS genotypes of Plasmodium falciparum isolates from Gabon correlate with in vitro activity of pyrimethamine and cycloguanil, but not with sulfadoxine-pyrimethamine treatment efficacy.

Journal: The Journal of antimicrobial chemotherapy 20030701

Title: The mechanisms of resistance to antimalarial drugs in Plasmodium falciparum.

Journal: Fundamental & clinical pharmacology 20030401

Title: Synthesis of solution-phase combinatorial library of 4,6-diamino-1,2-dihydro-1,3,5-triazine and identification of new leads against A16V+S108T mutant dihydrofolate reductase of Plasmodium falciparum.

Journal: Bioorganic & medicinal chemistry 20030117

Title: Different mutation patterns of atovaquone resistance to Plasmodium falciparum in vitro and in vivo: rapid detection of codon 268 polymorphisms in the cytochrome b as potential in vivo resistance marker.

Journal: Malaria journal 20030101

Title: Pharmacodynamic interactions among atovaquone, proguanil and cycloguanil against Plasmodium falciparum in vitro.

Journal: Transactions of the Royal Society of Tropical Medicine and Hygiene 20030101

Title: [Presence of pyrimethamine and cycloguanil resistance genotype in West Africa? Evidence of a single mutation 59Arg in the dhfr gene of Plasmodium falciparum].

Journal: Acta medica portuguesa 20030101

Title: In vitro sensitivity of Plasmodium falciparum to amodiaquine compared with other major antimalarials in Madagascar.

Journal: Parassitologia 20021201

Title: Molecular modeling of wild-type and antifolate resistant mutant Plasmodium falciparum DHFR.

Journal: Biophysical chemistry 20020802

Title: Profile and evolution of the chemosusceptibility of falciparum malaria imported into France in 2000.

Journal: Euro surveillance : bulletin Europeen sur les maladies transmissibles = European communicable disease bulletin 20020701

Title: Time-dependent pharmacokinetics and drug metabolism of atovaquone plus proguanil (Malarone) when taken as chemoprophylaxis.

Journal: European journal of clinical pharmacology 20020401

Title: Novel alleles of the Plasmodium falciparum dhfr highly resistant to pyrimethamine and chlorcycloguanil, but not WR99210.

Journal: Molecular and biochemical parasitology 20010928

Title: Homology modeling of wild type and pyrimethamine/cycloguanil-cross resistant mutant type Plasmodium falciparum dihydrofolate reductase. A model for antimalarial chemotherapy resistance.

Journal: Biophysical chemistry 20010724

Title: Analysis of proguanil and its metabolites by application of the sweeping technique in micellar electrokinetic chromatography.

Journal: Journal of chromatography. A 20010504

Title: Genome comparison of progressively drug resistant Plasmodium falciparum lines derived from drug sensitive clone.

Journal: Memorias do Instituto Oswaldo Cruz 20010401

Title: [Gene point mutation in the dihydrofolate reductase-thymidylate synthase gene of Plasmodium falciparum].

Journal: Zhongguo ji sheng chong xue yu ji sheng chong bing za zhi = Chinese journal of parasitology & parasitic diseases 20010101

Title: In vitro effects of artemisinin ether, cycloguanil hydrochloride (alone and in combination with sulfadiazine), quinine sulfate, mefloquine, primaquine phosphate, trifluoperazine hydrochloride, and verapamil on Toxoplasma gondii.

Journal: Antimicrobial agents and chemotherapy 19940601

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Journal: Journal of medicinal chemistry 19841201

Title: Matthaei J, et al. OCT1 Deficiency Affects Hepatocellular Concentrations and Pharmacokinetics of Cycloguanil, the Active Metabolite of the Antimalarial Drug Proguanil. Clin Pharmacol Ther. 2019 Jan;105(1):190-200.

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