An internal standard for the quantification of cycloguanil
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Unlabeled Version(s)
16861Cycloguanil (hydrochloride)
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Cycloguanil-d6 (hydrochloride)

Item No. 31496

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1-(4-chlorophenyl)-1,6-dihydro-6,6-dimethyl-d3-1,3,5-triazine-2,4-diamine, monohydrochloride
CAS Number
2712364-69-5
Synonyms
  • Chloroguanide Triazine-d6
Molecular Formula
C11H8ClD6N5 • HCl
Formula Weight
294.2
Purity
≥99% deuterated forms (d1-d6)
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: soluble
SMILES
ClC1=CC=C(N2C(N)=NC(N)=NC2(C([2H])([2H])[2H])C([2H])([2H])[2H])C=C1.Cl
InChi Code
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/i1D3,2D3;
InChi Key
MOUAPRKJJUXEIE-TXHXQZCNSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

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    Product Description

    Cycloguanil-d6 is intended for use as an internal standard for the quantification of cycloguanil (Item No. 16861) by GC- or LC-MS. Cycloguanil is the active metabolite of the antimalarial prodrug proguanil.1 Cycloguanil is formed from proguanil by the cytochrome P450 (CYP) isoforms CYP2C19 and CYP3A in human liver microsomes. It is an inhibitor of dihydrofolate reductase (DHFR; Kis = 1.5 and 0.79 nM for the P. falciparum and P. berghei enzymes, respectively).2,3 It is active against ten P. falciparum field isolates (IC50s = 0.12-1,400 µg/ml).2 Cycloguanil reduces parasitemia in a mouse model of P. berghei infection (ED50 = 2 mg/kg).4 It also reduces parasitemia in a rhesus monkey model of P. cynomolgi infection when administered at a dose of 0.3 mg/kg.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Birkett, D.J., Rees, D., Anderson, T., et al. In vitro proguanil activation to cycloguanil by human liver microsomes is mediated by CYP3A isoforms as well as by S-mephenytoin hydroxylase. Br. J. Clin. Pharmacol. 37(5), 413-420 (1994).

    2. Foote, S.J., Galatis, D., and Cowman, A.F. Amino acids in the dihydrofolate reductase-thymidylate synthase gene of Plasmodium falciparum involved in cycloguanil resistance differ from those involved in pyrimethamine resistance. Proc. Natl. Acad. Sci. USA 87(8), 3014-3017 (1990).

    3. Yuthavong, Y., Vilaivan, T., Chareonsethakul, N., et al. Development of a lead inhibitor for the A16V+S108T mutant of dihydrofolate reductase from the cycloguanil-resistant strain (T9/94) of Plasmodium falciparum. J. Med. Chem. 43(14), 2738-2744 (2000).

    4. Knight, D.J., and Peters, W. The antimalarial activity of N-benzyloxydihydrotriazines. I. The activity of clociguanil (BRL 50216) against rodent malaria, and studies on its mode of action. Ann. Trop. Med. Parasitol. 74(4), 393-404 (1980).

    5. Schmidt, L.H., Loo, T.L., Fradkin, R., et al. Antimalarial activities of triazine metabolites of chlorguanide and dichlorguanide. Proc. Soc. Exp. Biol. Med. 80(2), 367-370 (1952).