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(–)-Sitagliptin (phosphate)

Item № 13252
CAS № 654671-78-0
Purity ≥98%
product image
                (CAS 654671-78-0)
SIZE PRICE QUANTITY SUBTOTAL
CART TOTAL
     50 mg $29.00 0.00
     100 mg $49.00 0.00
     250 mg $102.00 0.00
     1 g $290.00 0.00

Pricing updated 2019-07-17. Prices are subject to change without notice.

Description
Synonyms
  • INN
  • MK-431
  • ONO-5435
  • (R)-Sitagliptin

(–)-Sitagliptin is a potent inhibitor of dipeptidyl peptidase 4 (DPP-4; IC50 = 18 nM).1 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.1,2 (–)-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.3 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.

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Technical Information
Formal Name
(3R)-3-amino-1-[5,6-dihydro-3-(trifluoromethyl)-1,2,4-triazolo[4,3-a]pyrazin-7(8H)-yl]-4-(2,4,5-trifluorophenyl)-1-butanone, monophosphate
CAS Number
654671-78-0
Synonyms
  • INN
  • MK-431
  • ONO-5435
  • (R)-Sitagliptin
Molecular Formula
C16H15F6N5O • H3PO4
Formula Weight
505.3
Purity
≥98%
Formulation
A crystalline solid
λmax
267 nm
SMILES
FC1=CC(C[C@@H](N)CC(N2CC3=NN=C(C(F)(F)F)N3CC2)=O)=C(F)C=C1F.O=P(O)(O)O
InChI Code
InChI=1S/C16H15F6N5O.H3O4P/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;1-5(2,3)4/h4,6,9H,1-3,5,7,23H2;(H3,1,2,3,4)/t9-;/m1./s1
InChI Key
IQFYVLUXQXSJJN-SBSPUUFOSA-N

Warning - this product is not for human or veterinary use.

Shipping & Storage
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Stability
≥ 2 years
Downloads & Resources
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Additional Information

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References & Product Citations
Product Description References

1. 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).

2. 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).

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

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