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152-53-4 | Cycloguanil hydrochloride
CAS No: 152-53-4 Catalog No: AG003P44 MDL No:MFCD00838855
Product Description
Catalog Number:
AG003P44
Chemical Name:
Cycloguanil hydrochloride
CAS Number:
152-53-4
Molecular Formula:
C11H15Cl2N5
Molecular Weight:
288.1763
MDL Number:
MFCD00838855
IUPAC Name:
1-(4-chlorophenyl)-6,6-dimethyl-1,3,5-triazine-2,4-diamine;hydrochloride
InChI:
InChI=1S/C11H14ClN5.ClH/c1-11(2)16-9(13)15-10(14)17(11)8-5-3-7(12)4-6-8;/h3-6H,1-2H3,(H4,13,14,15,16);1H
InChI Key:
MOUAPRKJJUXEIE-UHFFFAOYSA-N
SMILES:
Clc1ccc(cc1)N1C(=NC(=NC1(C)C)N)N.Cl
UNII:
5C8E0L7498
NSC Number:
3074
Properties
Complexity:
355
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
2
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
287.07g/mol
Formal Charge:
0
Heavy Atom Count:
18
Hydrogen Bond Acceptor Count:
1
Hydrogen Bond Donor Count:
3
Isotope Atom Count:
0
Molecular Weight:
288.176g/mol
Monoisotopic Mass:
287.07g/mol
Rotatable Bond Count:
1
Topological Polar Surface Area:
80A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
Literature
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|---|---|
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| Fitness trade-offs in the evolution of dihydrofolate reductase and drug resistance in Plasmodium falciparum. | PloS one 20110101 |
| Quantitative structure-activity relationships for cycloguanil analogs as PfDHFR inhibitors using mathematical molecular descriptors. | SAR and QSAR in environmental research 20100401 |
| Shape- and chemical feature-based 3D-pharmacophore model generation and virtual screening: identification of potential leads for P. falciparum DHFR enzyme inhibition. | Chemical biology & drug design 20100101 |
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| Effect of honey on CYP3A4, CYP2D6 and CYP2C19 enzyme activity in healthy human volunteers. | Basic & clinical pharmacology & toxicology 20070401 |
| Simultaneous determination of monodesethylchloroquine, chloroquine, cycloguanil and proguanil on dried blood spots by reverse-phase liquid chromatography. | Journal of pharmaceutical and biomedical analysis 20070219 |
| Amino acid mutations in Plasmodium vivax DHFR and DHPS from several geographical regions and susceptibility to antifolate drugs. | The American journal of tropical medicine and hygiene 20061001 |
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| The pharmacokinetics and pharmacodynamics of atovaquone and proguanil for the treatment of uncomplicated falciparum malaria in third-trimester pregnant women. | European journal of clinical pharmacology 20050901 |
| Stoichiometric selection of tight-binding inhibitors by wild-type and mutant forms of malarial (Plasmodium falciparum) dihydrofolate reductase. | Analytical chemistry 20050301 |
| Syntheses of 2,4,6-trisubstituted triazines as antimalarial agents. | Bioorganic & medicinal chemistry letters 20050201 |
| In vitro recrudescence of Plasmodium falciparum parasites suppressed to dormant state by atovaquone alone and in combination with proguanil. | Transactions of the Royal Society of Tropical Medicine and Hygiene 20050101 |
| Novel alleles of Plasmodium falciparum dhfr that confer resistance to chlorcycloguanil. | Molecular and biochemical parasitology 20050101 |
| 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. | Annals of tropical medicine and parasitology 20041201 |
| Short communication: Prevalence of mutations associated with resistance to atovaquone and to the antifolate effect of proguanil in Plasmodium falciparum isolates from northern Ghana. | Tropical medicine & international health : TM & IH 20040301 |
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| Susceptibility of Plasmodium falciparum to the drugs used to treat severe malaria (quinine) and to prevent malaria (mefloquine, cycloguanil) in Comoros Union and Madagascar. | South African medical journal = Suid-Afrikaanse tydskrif vir geneeskunde 20040101 |
| Concordance between proguanil phenotype and CYP2C19 genotype in Chinese. | European journal of clinical pharmacology 20031101 |
| Pregnancy and use of oral contraceptives reduces the biotransformation of proguanil to cycloguanil. | European journal of clinical pharmacology 20031001 |
| 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. | The Journal of antimicrobial chemotherapy 20030701 |
| The mechanisms of resistance to antimalarial drugs in Plasmodium falciparum. | Fundamental & clinical pharmacology 20030401 |
| 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. | Bioorganic & medicinal chemistry 20030117 |
| 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. | Malaria journal 20030101 |
| Pharmacodynamic interactions among atovaquone, proguanil and cycloguanil against Plasmodium falciparum in vitro. | Transactions of the Royal Society of Tropical Medicine and Hygiene 20030101 |
| [Presence of pyrimethamine and cycloguanil resistance genotype in West Africa? Evidence of a single mutation 59Arg in the dhfr gene of Plasmodium falciparum]. | Acta medica portuguesa 20030101 |
| In vitro sensitivity of Plasmodium falciparum to amodiaquine compared with other major antimalarials in Madagascar. | Parassitologia 20021201 |
| Molecular modeling of wild-type and antifolate resistant mutant Plasmodium falciparum DHFR. | Biophysical chemistry 20020802 |
| Profile and evolution of the chemosusceptibility of falciparum malaria imported into France in 2000. | Euro surveillance : bulletin Europeen sur les maladies transmissibles = European communicable disease bulletin 20020701 |
| Time-dependent pharmacokinetics and drug metabolism of atovaquone plus proguanil (Malarone) when taken as chemoprophylaxis. | European journal of clinical pharmacology 20020401 |
| Novel alleles of the Plasmodium falciparum dhfr highly resistant to pyrimethamine and chlorcycloguanil, but not WR99210. | Molecular and biochemical parasitology 20010928 |
| Homology modeling of wild type and pyrimethamine/cycloguanil-cross resistant mutant type Plasmodium falciparum dihydrofolate reductase. A model for antimalarial chemotherapy resistance. | Biophysical chemistry 20010724 |
| Analysis of proguanil and its metabolites by application of the sweeping technique in micellar electrokinetic chromatography. | Journal of chromatography. A 20010504 |
| Genome comparison of progressively drug resistant Plasmodium falciparum lines derived from drug sensitive clone. | Memorias do Instituto Oswaldo Cruz 20010401 |
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| Folate antagonists. 22. Antimalarial and antibacterial effects of 2,4-diamino-6-quinazolinesulfonamides. | Journal of medicinal chemistry 19841201 |
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