Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C19H27NO3 |
Molecular Weight | 317.4226 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)[C@H]1CC[C@@H](CC1)C(=O)N[C@H](CC2=CC=CC=C2)C(O)=O
InChI
InChIKey=OELFLUMRDSZNSF-BRWVUGGUSA-N
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
Molecular Formula | C19H27NO3 |
Molecular Weight | 317.4226 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: http://www.drugbank.ca/drugs/DB00731Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021204s014lbl.pdf
https://www.ncbi.nlm.nih.gov/pubmed/12764427
Sources: http://www.drugbank.ca/drugs/DB00731
Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021204s014lbl.pdf
https://www.ncbi.nlm.nih.gov/pubmed/12764427
Nateglinide is an oral antihyperglycemic agent used for the treatment of non-insulin-dependent diabetes mellitus (NIDDM). It belongs to the meglitinide class of short-acting insulin secretagogues, which act by binding to β cells of the pancreas to stimulate insulin release. Nateglinide is an amino acid derivative that induces an early insulin response to meals decreasing postprandial blood glucose levels. It should only be taken with meals and meal-time doses should be skipped with any skipped meal. Approximately one month of therapy is required before a decrease in fasting blood glucose is seen. Meglitnides may have a neutral effect on weight or cause a slight increase in weight. The average weight gain caused by meglitinides appears to be lower than that caused by sulfonylureas and insulin and appears to occur only in those naïve to oral antidiabetic agents. Due to their mechanism of action, meglitinides may cause hypoglycemia although the risk is thought to be lower than that of sulfonylureas since their action is dependent on the presence of glucose. In addition to reducing postprandial and fasting blood glucose, meglitnides have been shown to decrease glycosylated hemoglobin (HbA1c) levels, which are reflective of the last 8-10 weeks of glucose control. Meglitinides appear to be more effective at lowering postprandial blood glucose than metformin, sulfonylureas and thiazolidinediones. Nateglinide is extensively metabolized in the liver and excreted in urine (83%) and feces (10%). The major metabolites possess less activity than the parent compound. One minor metabolite, the isoprene, has the same potency as its parent compound.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1971 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21923736 |
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Target ID: CHEMBL3397 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20609060 |
125.0 µM [IC50] | ||
Target ID: CHEMBL3622 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20609060 |
946.0 µM [IC50] | ||
Target ID: CHEMBL2096972 Sources: http://www.drugbank.ca/drugs/DB00731 |
8.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Starlix Approved UseStarlix® (nateglinide) is indicated as an adjunct to diet and exercise to improve glycemic control in adults with type 2 diabetes mellitus. Launch Date2000 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
5690 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/11259325 |
120 mg single, oral dose: 120 mg route of administration: Oral experiment type: SINGLE co-administered: |
NATEGLINIDE blood | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
16.19 μg/mL |
120 mg single, intravenous dose: 120 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
NATEGLINIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
5.21 μg/mL |
120 mg single, oral dose: 120 mg route of administration: Oral experiment type: SINGLE co-administered: |
NATEGLINIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
10.45 mg × h/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12940610 |
90 mg single, oral dose: 90 mg route of administration: Oral experiment type: SINGLE co-administered: |
NATEGLINIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
17.72 μg × h/mL |
120 mg single, intravenous dose: 120 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
NATEGLINIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
13.33 μg × h/mL |
120 mg single, oral dose: 120 mg route of administration: Oral experiment type: SINGLE co-administered: |
NATEGLINIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.89 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12940610 |
90 mg single, oral dose: 90 mg route of administration: Oral experiment type: SINGLE co-administered: |
NATEGLINIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
1.88 h |
120 mg single, intravenous dose: 120 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
NATEGLINIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
1.58 h |
120 mg single, oral dose: 120 mg route of administration: Oral experiment type: SINGLE co-administered: |
NATEGLINIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
3420 mg single, oral Overdose |
unknown, 30 years |
Other AEs: Hypoglycemia... |
240 mg 3 times / day steady, oral Highest studied dose Dose: 240 mg, 3 times / day Route: oral Route: steady Dose: 240 mg, 3 times / day Sources: |
unhealthy, 59 years (range: 42–67 years) Health Status: unhealthy Age Group: 59 years (range: 42–67 years) Sex: M+F Sources: |
|
120 mg 3 times / day steady, oral Recommended Dose: 120 mg, 3 times / day Route: oral Route: steady Dose: 120 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Hypoglycemia... AEs leading to discontinuation/dose reduction: Hypoglycemia (0.3%) Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Hypoglycemia | 3420 mg single, oral Overdose |
unknown, 30 years |
|
Hypoglycemia | 0.3% Disc. AE |
120 mg 3 times / day steady, oral Recommended Dose: 120 mg, 3 times / day Route: oral Route: steady Dose: 120 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Pharmacokinetics and metabolism of nateglinide in humans. | 2001 Apr |
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Nateglinide for type 2 diabetes. | 2001 Apr 2 |
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FDA approves nateglinide for treatment of type 2 diabetes. | 2001 Feb 15 |
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[New glucose regulator. More comfort for the type 2 diabetic patient]. | 2001 Feb 8 |
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Mealtime glucose regulation with nateglinide in healthy volunteers: comparison with repaglinide and placebo. | 2001 Jan |
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[Fasting blood glucose has little value. Postprandial glucose indicates risk]. | 2001 Jan 11 |
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A new crystal form of nateglinide. | 2001 Jul |
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Randomized dose ranging study of the reduction of fasting and postprandial glucose in type 2 diabetes by nateglinide (A-4166). | 2001 Jul |
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The effects of mitiglinide (KAD-1229), a new anti-diabetic drug, on ATP-sensitive K+ channels and insulin secretion: comparison with the sulfonylureas and nateglinide. | 2001 Nov 9 |
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Effects of timing of administration and meal composition on the pharmacokinetic and pharmacodynamic characteristics of the short-acting oral hypoglycemic agent nateglinide in healthy subjects. | 2001 Oct |
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[New drugs]. | 2001 Sep |
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Study of the insulinotropic effect of the novel antihyperglycemic agent KAD-1229 using HIT T15 cells, a hamster's insulinoma cell line. | 2002 |
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Control of post-prandial hyperglycemia--an essential part of good diabetes treatment and prevention of cardiovascular complications. | 2002 Apr |
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[Differential type 2 diabetes therapy based on pathophysiological aspects]. | 2002 Aug |
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The effects of nateglinide following oral glucose load in impaired glucose tolerance subjects: rapid insulin stimulation by nateglinide in IGT subjects. | 2002 Dec |
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Type 2 diabetes management. | 2002 Jan |
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Improvement of glucose tolerance by nateglinide occurs through enhancement of early phase insulin secretion. | 2002 Jan |
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Post-load hyperglycaemia-an inappropriate therapeutic target. | 2002 Jan 12 |
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The pathophysiologic basis of efficacy and clinical experience with the new oral antidiabetic agents. | 2002 Jan-Feb |
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Efficacy and safety of nateglinide in the treatment of type II diabetes mellitus. | 2002 Jul |
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Preventing the progressive nature of type 2 diabetes. | 2002 Jul-Aug |
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Nateglinide improves glycaemic control when added to metformin monotherapy: results of a randomized trial with type 2 diabetes patients. | 2002 May |
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[Glinides and glitazones in diabetes treatment. Are they really effective?]. | 2002 May 2 |
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Nateglinide suppresses postprandial hypertriglyceridemia in Zucker fatty rats and Goto-Kakizaki rats: comparison with voglibose and glibenclamide. | 2002 Nov |
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Decreased blood glucose excursion by nateglinide ameliorated neuropathic changes in Goto-Kakizaki rats, an animal model of non-obese type 2 diabetes. | 2002 Nov |
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Transport and uptake of nateglinide in Caco-2 cells and its inhibitory effect on human monocarboxylate transporter MCT1. | 2002 Oct |
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Efficacy, tolerability and safety of nateglinide in combination with metformin. Results from a study under general practice conditions. | 2003 Aug |
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Pharmacokinetics of nateglinide and its metabolites in subjects with type 2 diabetes mellitus and renal failure. | 2003 Aug |
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Pharmacokinetics of nateglinide in renally impaired diabetic patients. | 2003 Feb |
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Pharmacodynamics, insulinotropic action and hypoglycemic effect of nateglinide and glibenclamide in normal and diabetic rats. | 2003 Jan |
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Nateglinide (Starlix): update on a new antidiabetic agent. | 2003 Jul-Aug |
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The role of oral antidiabetic agents: why and when to use an early-phase insulin secretion agent in Type II diabetes mellitus. | 2003 Mar |
|
Pharmacologic restoration of the early insulin response in pre-diabetic monkeys controls mealtime glucose excursions without peripheral hyperinsulinaemia. | 2003 Mar |
Sample Use Guides
The recommended starting and maintenance dose of Starlix, alone or in combination with metformin or a thiazolidinedione, is 120 mg three times daily before meals.
The 60-mg dose of Starlix, either alone or in combination with metformin or a thiazolidinedione, may be used in patients who are near goal HbA1C when treatment is initiated.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11716850
Nateglinide inhibits Kir6.2/SUR1 and Kir6.2/SUR2B channels at 100 nM, and inhibits Kir6.2/SUR2A channels at high concentrations (1 uM).
Substance Class |
Chemical
Created
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admin
on
Edited
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Mon Mar 31 18:23:33 GMT 2025
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Record UNII |
41X3PWK4O2
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Record Status |
Validated (UNII)
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NDF-RT |
N0000175428
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NCI_THESAURUS |
C98079
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NDF-RT |
N0000175448
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WHO-ATC |
A10BX03
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QA10BX03
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LIVERTOX |
NBK548227
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CHEMBL783
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31897
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105816-04-4
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6833
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41X3PWK4O2
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C060142
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NATEGLINIDE
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MM-15
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274332
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100000091326
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SUB09170MIG
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41X3PWK4O2
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Nateglinide
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7594
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C61858
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m7780
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758695
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1457607
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DB00731
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DTXSID9040687
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1886
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BINDER->LIGAND |
BINDING
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TARGET -> INHIBITOR | |||
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ENANTIOMER -> ENANTIOMER |
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TRANSPORTER -> SUBSTRATE | |||
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EXCRETED UNCHANGED |
AMOUNT EXCRETED
URINE
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METABOLITE -> PARENT |
MAJOR
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METABOLITE -> PARENT |
PLASMA
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METABOLITE ACTIVE -> PARENT |
PLASMA
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT |
Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Volume of Distribution | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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Tmax | PHARMACOKINETIC |
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