An internal standard for the quantification of desethylchloroquine
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Unlabeled Version(s)
30113Desethylchloroquine
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Desethylchloroquine-d4

Item No. 30907

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N4-(7-chloro-4-quinolinyl)-N1-ethyl-1,4-pentane-1,1,2,2-d4-diamine
CAS Number
1189971-72-9
Synonyms
  • N-Desethylchloroquine-d4
Molecular Formula
C16H18ClD4N3
Formula Weight
295.8
Purity
≥99% deuterated forms (d1-d4)
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: slightly solubleMethanol: slightly soluble
SMILES
CCNC([2H])([2H])C([2H])([2H])CC(C)NC1=CC=NC2=C1C=CC(Cl)=C2
InChi Code
InChI=1S/C16H22ClN3/c1-3-18-9-4-5-12(2)20-15-8-10-19-16-11-13(17)6-7-14(15)16/h6-8,10-12,18H,3-5,9H2,1-2H3,(H,19,20)/i4D2,9D2
InChi Key
MCYUUUTUAAGOOT-AUHPCMSFSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $375

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    Product Description

    Desethylchloroquine-d4 is intended for use as an internal standard for the quantification of desethylchloroquine (Item No. 30113) by GC- or LC-MS. Desethylchloroquine is an active metabolite of chloroquine (Item Nos. 14194 | 30708) and hydroxychloroquine (Item Nos. 17911 | 30709).1,2 It is formed from chloroquine and hydroxychloroquine by the cytochrome P450 (CYP) isoforms CYP2C8, CYP3A4, and CYP2D6. Desethylchloroquine (20 µM) inhibits Zika virus-induced plaque formation in Vero cells when used during viral entry or post-entry.3 It protects against the cytopathic effect (CPE) of Zika virus strains PLCal_ZV, MR 766, and PRVABC59 in Vero cells (EC50s = 7.01, 10.15, and 10.72 µM, respectively). Desethylchloroquine also inhibits the growth of the chloroquine-sensitive P. falciparum strain LA 136 with a reduction in activity against the multidrug-resistant P. falciparum Smith strain in vitro (IC50s = 7.8 and 210 ng/ml, respectively).4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Projean, D., Baune, B., Farinotti, R., et al. In vitro metabolism of chloroquine: Identification of CYP2C8, CYP3A4, and CYP2D6 as the main isoforms catalyzing N-desethylchloroquine formation. Drug Metab. Dispos. 31(6), 748-754 (2003).

    2. Paludetto, M.N., Kurkela, M., Kahma, H., et al. Hydroxychloroquine is metabolized by cytochrome P450 2D6, 3A4, and 2C8, and inhibits cytochrome P450 2D6, while its metabolites also inhibit cytochrome P450 3A in vitro. Drug Metab. Dispos. 51(3), 293-305 (2023).

    3. Han, Y., Pham, H.T., Xu, H., et al. Antimalarial drugs and their metabolites are potent Zika virus inhibitors. J. Med. Virol. 91(7), 1182-1190 (2019).

    4. Aderounmu, F.A. In vitro assessment of the antimalarial activity of chloroquine and its major metabolites. Ann. Trop. Med. Parasitol. 78(6), 581-585 (1984).