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N3538

Sigma-Aldrich

Nateglinide

≥98% (HPLC), solid

Synonym(s):

Fastic, N-[(trans-4-Isopropylcyclohexyl)carbonyl]-D-phenylalanine, Starlix, Starsis

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About This Item

Empirical Formula (Hill Notation):
C19H27NO3
CAS Number:
105816-04-4
Molecular Weight:
317.42
MDL number:
MFCD00875706
UNSPSC Code:
12352200
PubChem Substance ID:
329818636
NACRES:
NA.77

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

human ... ABCC8(6833) , KCNJ11(3767)

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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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
Toshiyuki Takanohashi et al.
European journal of drug metabolism and pharmacokinetics, 37(1), 9-15 (2011-10-21)
Nateglinide and mitiglinide are immediate short-acting insulinotropic agents. Both are administered preprandially to control postprandial hyperglycemia. Glinide drugs are characterized by immediate onset as well as rapid disappearance of effect as compared with sulfonylurea drugs. We examined the rapidity of
[Glinides].
Tomoya Mita et al.
Nihon rinsho. Japanese journal of clinical medicine, 70 Suppl 3, 608-613 (2012-07-10)
A S Abdelmoneim et al.
Diabetes, obesity & metabolism, 14(2), 130-138 (2011-09-20)
Insulin secretagogues promote insulin release by binding to sulfonylurea receptors on pancreatic β-cells (SUR1). However, these drugs also bind to receptor isoforms on cardiac myocytes (SUR2A) and vascular smooth muscle (SUR2B). Binding to SUR2A/SUR2B may inhibit ischaemic preconditioning, an endogenous
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