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 |
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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 Date9.7735678E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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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 |
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 unknown | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
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 unknown | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
3420 mg single, oral Overdose |
unknown, 30 years n = 1 Health Status: unknown Age Group: 30 years Sex: F Population Size: 1 Sources: |
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) n = 24 Health Status: unhealthy Condition: Type 2 diabetes Age Group: 59 years (range: 42–67 years) Sex: M+F Population Size: 24 Sources: |
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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 n = 2600 Health Status: unhealthy Condition: Type 2 diabetes Population Size: 2600 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 n = 1 Health Status: unknown Age Group: 30 years Sex: F Population Size: 1 Sources: |
|
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 n = 2600 Health Status: unhealthy Condition: Type 2 diabetes Population Size: 2600 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Glucose-dependent and glucose-sensitizing insulinotropic effect of nateglinide: comparison to sulfonylureas and repaglinide. | 2001 |
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Early insulin release effectively improves glucose tolerance: studies in two rodent models of type 2 diabetes mellitus. | 2001 Apr |
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Mealtime glucose regulation with nateglinide in healthy volunteers: comparison with repaglinide and placebo. | 2001 Jan |
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Postoperative management of the diabetic patient. | 2001 Sep |
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Improvement of glucose tolerance by nateglinide occurs through enhancement of early phase insulin secretion. | 2002 Jan |
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Gateways to clinical trials. | 2002 Jan-Feb |
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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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Nateglinide, but not repaglinide, stimulates growth hormone release in rat pituitary cells by inhibition of K channels and stimulation of cyclic AMP-dependent exocytosis. | 2002 Jul |
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[Metformin--its regimen and effects]. | 2002 Sep |
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Treatment of patients over 64 years of age with type 2 diabetes: experience from nateglinide pooled database retrospective analysis. | 2003 Jul |
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Addition of nateglinide to rosiglitazone monotherapy suppresses mealtime hyperglycemia and improves overall glycemic control. | 2003 Jun |
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Nateglinide, a D-phenylalanine derivative lacking either a sulfonylurea or benzamido moiety, specifically inhibits pancreatic beta-cell-type K(ATP) channels. | 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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on
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Wed Jul 05 23:43:14 UTC 2023
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Wed Jul 05 23:43:14 UTC 2023
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Record UNII |
41X3PWK4O2
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Record Status |
Validated (UNII)
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Classification Tree | Code System | Code | ||
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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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WHO-VATC |
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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Related Record | Type | Details | ||
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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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Related Record | Type | Details | ||
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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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Related Record | Type | Details | ||
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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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ORAL ADMINISTRATION |
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