An internal standard for the quantification of stavudine
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Unlabeled Version(s)
14975Stavudine
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Stavudine-13C-d3

Item No. 28887

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1-((2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl)-5-(methyl-13C-d3)pyrimidine-2,4(1H,3H)-dione
CAS Number
2750534-86-0
Molecular Formula
C9[13C]H9D3N2O4
Formula Weight
228.2
Purity
≥99% deuterated forms (d1-d3)
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Acetonitrile: solubleDMSO: solubleMethanol: solubleWater: soluble
SMILES
OC[C@H]1O[C@@H](N2C(NC(C([13C]([2H])([2H])[2H])=C2)=O)=O)C=C1
InChi Code
InChI=1S/C10H12N2O4/c1-6-4-12(10(15)11-9(6)14)8-3-2-7(5-13)16-8/h2-4,7-8,13H,5H2,1H3,(H,11,14,15)/t7-,8+/m0/s1/i1+1D3
InChi Key
XNKLLVCARDGLGL-SCMAVCFBSA-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

    Stavudine-13C-d3 is intended for use as an internal standard for the quantification of stavudine (Item No. 14975) by GC- or LC-MS. Stavudine is an inhibitor of HIV reverse transcriptase and a derivative of the nucleoside thymidine (Item No. 20519).1 It inhibits HIV-1 replication in human peripheral blood mononuclear cells (PBMCs; EC50 = 8.8 nM). Stavudine reduces the synthesis of HIV-specific antigen in MT-4 cells when used at concentrations ranging from 0.1 to 10 µg/ml and reduces HIV-induced plaque formation in MT-4 cells at 0.05 µg/ml.2 It reduces plasma- and cell-associated viral load in macaques infected with a highly pathogenic isolate of HIV-2.3 Stavudine induces sustained hind paw mechanical allodynia in a rat model of antiretroviral toxic neuropathy (ATN) when administered at a dose of 75 mg/kg twice weekly for five consecutive doses for a cumulative dose of 375 mg/kg.4 Formulations containing stavudine, in combination with other antiretrovirals, have been used in the treatment of HIV-1 infection.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Lin, T.-S., Schinazi, R.F., and Prusoff, W.H. Potent and selective in vitro activity of 3'-deoxythymidin-2'-ene (3'-deoxy-2',3'-didehydrothymidine) against human immunodeficiency virus. Biochem. Pharmacol. 36(17), 2713-2718 (1987).

    2. Hamamoto, Y., Nakashima, H., Matsui, T., et al. Inhibitory effect of 2',3'-didehydro-2',3'-dideoxynucleosides on infectivity, cytopathic effects, and replication of human immunodeficiency virus. Antimicrob. Agents Chemother. 31(6), 907-910 (1987).

    3. Watson, A., McClure, J., Ranchalis, J., et al. Early postinfection antiviral treatment reduces viral load and prevents CD4+ cell decline in HIV type 2-infected macaques. AIDS Res. Hum. Retroviruses 13(16), 1375-1381 (1997).

    4. Kuo, A., Nicholson, J.R., Corradini, L., et al. Establishment and characterisation of a stavudine (d4T)-induced rat model of antiretroviral toxic neuropathy (ATN) using behavioural and pharmacological methods. Inflammopharmacology 27(2), 387-396 (2019).