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MedKoo Cat#: 318352 | Name: Nateglinide
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Nateglinide is a drug for the treatment of type 2 diabetes. Nateglinide belongs to the meglitinide class of blood glucose-lowering drugs.

Chemical Structure

Nateglinide
Nateglinide
CAS#105816-04-4

Theoretical Analysis

MedKoo Cat#: 318352

Name: Nateglinide

CAS#: 105816-04-4

Chemical Formula: C19H27NO3

Exact Mass: 317.1991

Molecular Weight: 317.42

Elemental Analysis: C, 71.89; H, 8.57; N, 4.41; O, 15.12

Price and Availability

Size Price Availability Quantity
500mg USD 275.00
1g USD 465.00
2g USD 665.00
5g USD 950.00
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Related CAS #
No Data
Synonym
DJN 608; DJN-608l; DJN608; Nateglinide; Fastic; Starlix
IUPAC/Chemical Name
(R)-2-((1r,4R)-4-isopropylcyclohexanecarboxamido)-3-phenylpropanoic acid
InChi Key
OELFLUMRDSZNSF-BRWVUGGUSA-N
InChi Code
InChI=1S/C19H27NO3/c1-13(2)15-8-10-16(11-9-15)18(21)20-17(19(22)23)12-14-6-4-3-5-7-14/h3-7,13,15-17H,8-12H2,1-2H3,(H,20,21)(H,22,23)/t15-,16-,17-/m1/s1
SMILES Code
O=C(O)[C@@H](CC1=CC=CC=C1)NC([C@H]2CC[C@H](C(C)C)CC2)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Nateglinide, a D-phenylalanine derivative, is an orally active and short-acting insulinotropic agent and a DPP IV inhibitor.
In vitro activity:
Nateglinide inhibited SUR1/Kir6.2 channels with high and low affinities (K(i) = 75 nM and 114 microM) but SUR2A/Kir6.2 and SUR2B/Kir6.2 channels only with low affinity (K(i) = 105 and 111 microM, respectively). Nateglinide inhibited the K(ATP) current mediated by Kir6.2 lacking C-terminal 26 amino acids only with low affinity (K(i) = 290 microM) in the absence of SUR. Reference: J Pharmacol Exp Ther. 2003 Mar;304(3):1025-32. https://pubmed.ncbi.nlm.nih.gov/12604678/
In vivo activity:
Because K(ATP) channels are widely distributed in cardiovascular (CV) tissues, this study assessed the tissue specificity of NAT by examining its effect on K(ATP) channels in enzymatically isolated rat beta-cells, rat cardiac myocytes, and smooth muscle cells from porcine coronary artery and rat aorta with the patch-clamp method. NAT (nateglinide) was found to inhibit K(ATP) channels in the cells from porcine coronary artery and rat aorta with IC(50)s of 2.3 and 0. 3 mM, respectively, compared with 7.4 microM in rat beta-cells, indicating a respective 311- and 45-fold selectivity (p <.01) for beta-cells.
Solvent mg/mL mM
Solubility
DMF 30.0 94.51
DMSO 56.2 177.00
Ethanol 46.5 146.49
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 317.42 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Nishi K, Imoto S, Beppu T, Uchibori S, Yano A, Ishima YU, Ikeda T, Tsukigawa K, Otagiri M, Yamasaki K. The Nitrated Form of Nateglinide Induces Apoptosis in Human Pancreatic Cancer Cells Through a Caspase-dependent Mechanism. Anticancer Res. 2022 Mar;42(3):1333-1338. doi: 10.21873/anticanres.15601. PMID: 35220224. 2. Chachin M, Yamada M, Fujita A, Matsuoka T, Matsushita K, Kurachi Y. Nateglinide, a D-phenylalanine derivative lacking either a sulfonylurea or benzamido moiety, specifically inhibits pancreatic beta-cell-type K(ATP) channels. J Pharmacol Exp Ther. 2003 Mar;304(3):1025-32. doi: 10.1124/jpet.102.044917. PMID: 12604678. 3. Duffy NA, Green BD, Irwin N, Gault VA, McKillop AM, O'Harte FP, Flatt PR. Effects of antidiabetic drugs on dipeptidyl peptidase IV activity: nateglinide is an inhibitor of DPP IV and augments the antidiabetic activity of glucagon-like peptide-1. Eur J Pharmacol. 2007 Jul 30;568(1-3):278-86. doi: 10.1016/j.ejphar.2007.05.010. Epub 2007 May 13. PMID: 17573070. 4. Hu S, Wang S, Dunning BE. Tissue selectivity of antidiabetic agent nateglinide: study on cardiovascular and beta-cell K(ATP) channels. J Pharmacol Exp Ther. 1999 Dec;291(3):1372-9. PMID: 10565863.
In vitro protocol:
1. Nishi K, Imoto S, Beppu T, Uchibori S, Yano A, Ishima YU, Ikeda T, Tsukigawa K, Otagiri M, Yamasaki K. The Nitrated Form of Nateglinide Induces Apoptosis in Human Pancreatic Cancer Cells Through a Caspase-dependent Mechanism. Anticancer Res. 2022 Mar;42(3):1333-1338. doi: 10.21873/anticanres.15601. PMID: 35220224. 2. Chachin M, Yamada M, Fujita A, Matsuoka T, Matsushita K, Kurachi Y. Nateglinide, a D-phenylalanine derivative lacking either a sulfonylurea or benzamido moiety, specifically inhibits pancreatic beta-cell-type K(ATP) channels. J Pharmacol Exp Ther. 2003 Mar;304(3):1025-32. doi: 10.1124/jpet.102.044917. PMID: 12604678.
In vivo protocol:
1. Duffy NA, Green BD, Irwin N, Gault VA, McKillop AM, O'Harte FP, Flatt PR. Effects of antidiabetic drugs on dipeptidyl peptidase IV activity: nateglinide is an inhibitor of DPP IV and augments the antidiabetic activity of glucagon-like peptide-1. Eur J Pharmacol. 2007 Jul 30;568(1-3):278-86. doi: 10.1016/j.ejphar.2007.05.010. Epub 2007 May 13. PMID: 17573070. 2. Hu S, Wang S, Dunning BE. Tissue selectivity of antidiabetic agent nateglinide: study on cardiovascular and beta-cell K(ATP) channels. J Pharmacol Exp Ther. 1999 Dec;291(3):1372-9. PMID: 10565863.
1: Campbell IW. Nateglinide--current and future role in the treatment of patients with type 2 diabetes mellitus. Int J Clin Pract. 2005 Oct;59(10):1218-28. Review. PubMed PMID: 16178991. 2: Phillips LS, Dunning BE. Nateglinide (Starlix): update on a new antidiabetic agent. Int J Clin Pract. 2003 Jul-Aug;57(6):535-41. Review. PubMed PMID: 12918894. 3: Tentolouris N, Voulgari C, Katsilambros N. A review of nateglinide in the management of patients with type 2 diabetes. Vasc Health Risk Manag. 2007;3(6):797-807. Review. PubMed PMID: 18200800; PubMed Central PMCID: PMC2350129. 4: Israel MK, Istvan E, Baron MA. Safety and efficacy of nateglinide/metformin combination therapy in the treatment of type 2 diabetes. Vasc Health Risk Manag. 2008;4(6):1167-78. Review. PubMed PMID: 19337530; PubMed Central PMCID: PMC2663444. 5: Scheen AJ. Drug-drug and food-drug pharmacokinetic interactions with new insulinotropic agents repaglinide and nateglinide. Clin Pharmacokinet. 2007;46(2):93-108. Review. PubMed PMID: 17253883.