An internal standard for the quantification of dolutegravir
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Unlabeled Version(s)
22191Dolutegravir
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Dolutegravir-d5

Item No. 25755

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(4R,12aS)-N-((2,4-difluorophenyl-3,5,6-d3)methyl-d2)-7-hydroxy-4-methyl-6,8-dioxo-3,4,6,8,12,12a-hexahydro-2H-pyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazine-9-carboxamide
Molecular Formula
C20H14D5F2N3O5
Formula Weight
424.4
Purity
≥99% deuterated forms (d1-d5)
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 5 mg/mlDMSO: 2.5 mg/mlEthanol: Slightly Soluble
SMILES
FC1=C([2H])C(F)=C([2H])C([2H])=C1C([2H])([2H])NC(C2=CN(C[C@@](OCC[C@H]3C)([H])N3C4=O)C4=C(O)C2=O)=O
InChi Code
InChI=1S/C20H19F2N3O5/c1-10-4-5-30-15-9-24-8-13(17(26)18(27)16(24)20(29)25(10)15)19(28)23-7-11-2-3-12(21)6-14(11)22/h2-3,6,8,10,15,27H,4-5,7,9H2,1H3,(H,23,28)/t10-,15+/m1/s1/i2D,3D,6D,7D2
InChi Key
RHWKPHLQXYSBKR-DZYLKJILSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $933

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    Product Description

    Dolutegravir-d5 is intended for use as an internal standard for the quantification of dolutegravir (Item No. 22191) by GC- or LC-MS. Dolutegravir is a potent inhibitor of HIV integrase with an IC50 value of 2.7 nM for HIV-1 integrase-catalyzed strand transfer in vitro.1 It inhibits HIV-1 viral replication (EC50 = 0.51 nM) in peripheral blood mononuclear cells (PBMCs). The cytotoxic concentration (CC50) values for dolutegravir in unstimulated and stimulated PBMCs are 189 and 52 µM, respectively, resulting in a therapeutic index of at least 9,400. It prevents replication of several HIV-1 strains (EC50s = 0.36-2.1 nM) that are resistant to nucleoside reverse transcriptase inhibitors (NRTIs), non-nucleoside reverse transcriptase inhibitors (NNRTIs), and protease inhibitors and impairs their ability to infect CIP4 cells.1,2 Formulations containing dolutegravir have been used to treat HIV-1 infection in humans.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kobyayshi, M., Yoshinaga, T., Seki, T., et al. In vitro antiretroviral properties of S/GSK1349572, a next-generation HIV integrase inhibitor. Antimicrob. Agents and Chemother. 55(2), 813-821 (2011).

    2. Hare, S.A., Smith, S.J., Métifiot , M., et al. Structural and functional analyses of the second-generation integrase strand transfer inhibitor dolutegravir (S/GSK1349572). Mol. Pharmacol. 80(4), 565-572 (2011).

    3. Venter, W.D.F., Clayden, P., and Serenata, C. The ADVANCE study: a groundbreaking trial to evaluate a candidate universal antiretroviral regimen. Curr. Opin. HIV AIDS 12(4), 351-354 (2017).