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N3538

Sigma-Aldrich

Nateglinide

≥98% (HPLC), solid

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Synonym(s):
Fastic, N-[(trans-4-Isopropylcyclohexyl)carbonyl]-D-phenylalanine, Starlix, Starsis
Empirical Formula (Hill Notation):
C19H27NO3
CAS Number:
Molecular Weight:
317.42
MDL number:
PubChem Substance ID:

Quality Level

assay

≥98% (HPLC)

form

solid

color

white to off-white

solubility

DMSO: >5 mg/mL
H2O: insoluble

originator

Novartis

storage temp.

room temp

SMILES string

CC(C)[C@@H]1CC[C@H](CC1)C(=O)N[C@H](Cc2ccccc2)C(O)=O

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

InChI key

OELFLUMRDSZNSF-BRWVUGGUSA-N

Gene Information

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This Item
1457607Y0001437J3770
Nateglinide ≥98% (HPLC), solid

N3538

Nateglinide

Nateglinide United States Pharmacopeia (USP) Reference Standard

1457607

Nateglinide

Nateglinide European Pharmacopoeia (EP) Reference Standard

Y0001437

Nateglinide

JNJ7777120 ≥98% (HPLC)

J3770

JNJ7777120

form

solid

form

-

form

-

form

solid

storage temp.

room temp

storage temp.

-

storage temp.

2-8°C

storage temp.

room temp

solubility

DMSO: >5 mg/mL, H2O: insoluble

solubility

-

solubility

-

solubility

DMSO: >20 mg/mL, H2O: insoluble

color

white to off-white

color

-

color

-

color

white to off-white

originator

Novartis

originator

-

originator

-

originator

Johnson & Johnson

Biochem/physiol Actions

Nateglinide is a Kir6.2/SUR1 channel inhibitor and antidiabetic. It is selective for the SUR1 subtype, which is found on pancreatic islet cells. Nateglinide evokes KATP channel-dependent insulin secretion (50-200 μM) in the absence and presence of insulin.
Nateglinide is a short-acting insulin secretagogue useful in treating type 2 diabetes. It is an insulinotropic agent effective for postprandial hyperglycemia. Nateglinide restores prandial insulin levels in a glucose-dependent manner.

Features and Benefits

This compound is featured on the Potassium Channels page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Novartis. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Julia Kreis et al.
Health policy (Amsterdam, Netherlands), 104(1), 27-31 (2011-12-06)
In Germany, coverage decisions in the statutory health insurance (SHI) system are based on the principles of evidence-based medicine. Recently, an evidence assessment by the Institute for Quality and Efficiency in Health Care (IQWiG) of the oral antidiabetics of the
Carola Saloranta et al.
The Journal of clinical endocrinology and metabolism, 87(9), 4171-4176 (2002-09-06)
Nateglinide is a fast-acting insulin secretion agent that specifically targets postprandial hyperglycemia in patients with type 2 diabetes. The recent reduction in the diagnostic criteria for diabetes and improved understanding of the importance of early insulin secretion served as the
Julio Rosenstock et al.
Diabetes care, 27(6), 1265-1270 (2004-05-27)
A randomized, parallel-group, open-label, multicenter 16-week clinical trial compared efficacy and safety of repaglinide monotherapy and nateglinide monotherapy in type 2 diabetic patients previously treated with diet and exercise. Enrolled patients (n = 150) had received treatment with diet and
Jatinder Kaur et al.
Journal of medicinal chemistry, 55(17), 7883-7891 (2012-08-25)
A new group of hybrid nitric oxide-releasing type II antidiabetic drugs possessing a 1-(pyrrolidin-1-yl)diazen-1-ium-1,2-diolate (13 and 18), 1-(N,N-diethylamino)diazen-1-ium-1,2-diolate (14 and 19), or nitrooxyethyl (15 and 20) moiety attached to the carboxylic acid group of the type II antidiabetic drugs nateglinide
Jian Luo et al.
Metabolism: clinical and experimental, 62(1), 90-99 (2012-09-18)
To develop a rapid, easy and clinically relevant in vivo model to evaluate novel insulin secretagogues on human islets, we investigated the effect of insulin secretagogues on functional human islets in a humanized mouse model. Human islets were transplanted under

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