An internal standard for the quantification of sitagliptin
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(±)-Sitagliptin-d4 (hydrochloride)

Item No. 25042

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-amino-1-[5,6-dihydro-5,6-d2-3-(trifluoromethyl)-1,2,4-triazolo[4,3-α]pyrazin-7(8H)-yl-5,6-d2]-4-(2,4,5-trifluorophenyl)-1-butanone, monohydrochloride
CAS Number
2749855-96-5
Molecular Formula
C16H11D4F6N5O • HCl
Formula Weight
447.8
Purity
≥99% deuterated forms (d1-d4)
Formulation
A solid
Solubility(Learn about Variance in Solubility)
Water: Soluble
SMILES
FC1=CC(CC(N)CC(N2CC3=NN=C(C(F)(F)F)N3C([2H])([2H])C2([2H])[2H])=O)=C(F)C=C1F.Cl
InChi Code
InChI=1S/C16H15F6N5O.ClH/c17-10-6-12(19)11(18)4-8(10)3-9(23)5-14(28)26-1-2-27-13(7-26)24-25-15(27)16(20,21)22;/h4,6,9H,1-3,5,7,23H2;1H/i1D2,2D2;
InChi Key
PNXSHNOORJKXDW-PBCJVBLFSA-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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    Cayman Chemical
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    OBESITY RESEARCH SOLUTIONS
    Product Description

    (±)-Sitagliptin-d4 is intended for use as an internal standard for the quantification of sitagliptin by GC- or LC-MS. Sitagliptin is a mixture of the dipeptidyl peptidase 4 (DPP-4) inhibitor (–)-sitagliptin (Item No. 13252) and (+)-sitagliptin, also known as sitagliptin impurity E, a potential impurity found in commercial preparations of (–)-sitagliptin.1 (–)-Sitagliptin is a potent inhibitor of DPP-4 (IC50 = 18 nM).2 It is selective for DPP-4 over DPP-8 (IC50 = 48 µM) as well as several other peptidases, including DPP-9, DPP-2, and amino peptidase P.2,3 (–)-Sitagliptin improves glucose tolerance in insulin-resistant Zucker fatty and high-fat diet fed rats as well as ob/ob and high-fat diet fed mice.4 It also reduces hyperglycemia in mice fed a high-fat diet with diabetes induced by streptozotocin (Item No. 13104). Formulations containing (–)-sitagliptin have been used in the treatment of type 2 diabetes mellitus.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kothari, H.M., Dave, M.G., Pandey, B., et al. Process for preparation of (2R)-4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro [1,2,4]-triazolo[4,3-α]pyrazin-7(8H)-yl]-L-(2,4,5-trifluorophenyl)butan-2-amine and new impurities in preparation thereof. (2013).

    2. Biftu, T., Feng, D., Qian, X., et al. (3R)-4-[(3R)-3-Amino-4-(2,4,5-trifluorophenyl)butanoyl]-3-(2,2,2-trifluoroethyl)-1,4-diazepan-2-one, a selective dipeptidyl peptidase IV inhibitor for the treatment of type 2 diabetes. Bioorg. Med. Chem. Lett. 17(1), 49-52 (2007).

    3. Kim, D., Kowalchick, J.E., Edmondson, S.D., et al. Triazolopiperazine-amides as dipeptidyl peptidase IV inhibitors: Close analogs of JANUVIAT (sitagliptin phosphate). Bioorg. Med. Chem. Lett. 17(12), 3373-3377 (2007).

    4. Ahrén, B. DPP-4 inhibitors. Best Pract. Res. Clin. Endocrinol. Metab. 21(4), 517-533 (2007).