An internal standard for the quantification of daclatasvir
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Unlabeled Version(s)
23730Daclatasvir
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Daclatasvir-d6

Item No. 29077

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N,N′-[[1,1′-biphenyl]-4,4′-diylbis[1H-imidazole-5,2-diyl-(2S)-2,1-pyrrolidinediyl[(1S)-1-(1-methylethyl)-2-oxo-2,1-ethanediyl]]]bis-carbamic acid, C,C′-di(methyl-d3) ester
CAS Number
1801709-41-0
Molecular Formula
C40H44D6N8O6
Formula Weight
744.9
Purity
≥99% deuterated forms (d1-d6)
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: solubleMethanol: soluble
SMILES
O=C([C@H](C(C)C)NC(OC([2H])([2H])[2H])=O)N1CCC[C@H]1C2=NC=C(C(C=C3)=CC=C3C4=CC=C(C5=CN=C([C@@H]6CCCN6C([C@@H](NC(OC([2H])([2H])[2H])=O)C(C)C)=O)N5)C=C4)N2
InChi Code
InChI=1S/C40H50N8O6/c1-23(2)33(45-39(51)53-5)37(49)47-19-7-9-31(47)35-41-21-29(43-35)27-15-11-25(12-16-27)26-13-17-28(18-14-26)30-22-42-36(44-30)32-10-8-20-48(32)38(50)34(24(3)4)46-40(52)54-6/h11-18,21-24,31-34H,7-10,19-20H2,1-6H3,(H,41,43)(H,42,44)(H,45,51)(H,46,52)/t31-,32-,33-,34-/m0/s1/i5D3,6D3
InChi Key
FKRSSPOQAMALKA-GXBFPSLASA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Daclatasvir-d6 is intended for use as an internal standard for the quantification of daclatasvir (Item No. 23730) by GC- or LC-MS. Daclatasvir is a first generation direct-acting inhibitor of hepatitis C virus (HCV) non-structural protein 5A (NS5A; Kds = 8 and 210 nM for the NS5A33-202 and NS5A26-202 residues of HCV genotype 1b, respectively).1,2 It potently inhibits HCV replication in multiple HCV replicon genotypes (EC50s = 9-146 pM) with the highest potency in genotypes 1b and 4a (EC50s = 9 and 12 pM, respectively).1 Daclatasvir disrupts the subcellular localization of NS5A in Huh7.5 cells and inhibits viral RNA synthesis and virion assembly and secretion when used at a concentration of 1 nM in HCV-infected Huh7 cells.3,4 Daclatasvir also inhibits organic anion transport polypeptides 1B1 (OAT1B1) and OAT1B3 (IC50s = 1.5 and 3.27 µM, respectively).5 Formulations containing daclatasvir have been used alone and in combination with NS3/4A and NS5B inhibitors in the treatment of HCV.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Gao, M., Nettles, R.E., Belema, M., et al. Chemical genetics strategy identifies an HCV NS5A inhibitor with a potent clinical effect. Nature 465(7294), 96-100 (2010).

    2. Ascher, D.B., Wielens, J., Nero, T.L., et al. Potent hepatitis C inhibitors bind directly to NS5A and reduce its affinity for RNA. Sci. Rep. 4, 4765 (2014).

    3. Lee, C., Ma, H., Hang, J.Q., et al. The hepatitis C virus NS5A inhibitor (BMS-790052) alters the subcellular localization of the NS5A non-structural viral protein. Virology 414(1), 10-18 (2011).

    4. Guedj, J., Dahari, H., Rong, L., et al. Modeling shows that the NS5A inhibitor daclatasvir has two modes of action and yields a shorter estimate of the hepatitis C virus half-life. Proc. Natl. Acad. Sci. USA 110(10), 3991-3996 (2013).

    5. Furihata, T., Matsumoto, S., Fu, Z., et al. Different interaction profiles of direct-acting anti-hepatitis C virus agents with human organic anion transporting polypeptides. Antimicrob. Agents Chemother. 58(8), 4555-4565 (2014).