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-ULQDDVLXSA-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-/m0/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 |
|||
Target ID: CHEMBL3397 |
125.0 µM [IC50] | ||
Target ID: CHEMBL3622 |
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 Date9.7735678E11 |
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 |
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: |
|
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 |
|---|---|---|
| Effectiveness of nateglinide on in vitro insulin secretion from rat pancreatic islets desensitized to sulfonylureas. | 2001 |
|
| Glucose-dependent and glucose-sensitizing insulinotropic effect of nateglinide: comparison to sulfonylureas and repaglinide. | 2001 |
|
| [Interrelations of the pancreas exocrine and endocrine functions in chronic alcohol pancreatitis]. | 2002 |
|
| Insulin secretagogues. | 2002 |
|
| Study of the insulinotropic effect of the novel antihyperglycemic agent KAD-1229 using HIT T15 cells, a hamster's insulinoma cell line. | 2002 |
|
| Control of post-prandial hyperglycemia--an essential part of good diabetes treatment and prevention of cardiovascular complications. | 2002 Apr |
|
| [Postprandial hyperglycemia. II. Pharmacological approaches]. | 2002 Apr |
|
| [Differential type 2 diabetes therapy based on pathophysiological aspects]. | 2002 Aug |
|
| No effect of the novel antidiabetic agent nateglinide on the pharmacokinetics and anticoagulant properties of warfarin in healthy volunteers. | 2002 Dec |
|
| Control of postprandial hyperglycemia: optimal use of short-acting insulin secretagogues. | 2002 Dec |
|
| Nateglinide improves early insulin secretion and controls postprandial glucose excursions in a prediabetic population. | 2002 Dec |
|
| [Detection of crystal polymorphs of nateglinide by DSC]. | 2002 Jan |
|
| New drugs 2002, part 1. | 2002 Jan |
|
| Efficacy and safety of nateglinide in the treatment of type II diabetes mellitus. | 2002 Jul |
|
| 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 |
|
| Preventing the progressive nature of type 2 diabetes. | 2002 Jul-Aug |
|
| [Islands cells are not activated quickly enough. Risk of obstruction of blood vessels]. | 2002 Jun 27 |
|
| [Glinides and glitazones in diabetes treatment. Are they really effective?]. | 2002 May 2 |
|
| [Dangerous postprandial glucose peaks. Risk for heart and blood vessels]. | 2002 May 23 |
|
| Therapeutic options for the management of type 2 diabetes mellitus. | 2002 Nov |
|
| Nateglinide suppresses postprandial hypertriglyceridemia in Zucker fatty rats and Goto-Kakizaki rats: comparison with voglibose and glibenclamide. | 2002 Nov |
|
| Decreased blood glucose excursion by nateglinide ameliorated neuropathic changes in Goto-Kakizaki rats, an animal model of non-obese type 2 diabetes. | 2002 Nov |
|
| Effects of nateglinide and glibenclamide on postprandial lipid and glucose metabolism in type 2 diabetes. | 2002 Nov-Dec |
|
| Health and economic effects of adding nateglinide to metformin to achieve dual control of glycosylated hemoglobin and postprandial glucose levels in a model of type 2 diabetes mellitus. | 2002 Oct |
|
| A 3-way crossover study to evaluate the pharmacokinetic interaction between nateglinide and diclofenac in healthy volunteers. | 2002 Oct |
|
| Transport and uptake of nateglinide in Caco-2 cells and its inhibitory effect on human monocarboxylate transporter MCT1. | 2002 Oct |
|
| [Management guideline for elderly diabetic patients]. | 2002 Sep |
|
| [Metformin--its regimen and effects]. | 2002 Sep |
|
| [Nateglinide]. | 2002 Sep |
|
| [Structures and mechanisms for non SU insulin secretagogues]. | 2002 Sep |
|
| [Adverse effects of oral hypoglycemic agents]. | 2002 Sep |
|
| Efficacy and safety of nateglinide in type 2 diabetic patients with modest fasting hyperglycemia. | 2002 Sep |
|
| Differential interactions of nateglinide and repaglinide on the human beta-cell sulphonylurea receptor 1. | 2002 Sep |
|
| Combination therapy with nateglinide and a thiazolidinedione improves glycemic control in type 2 diabetes. | 2002 Sep |
|
| Efficacy, tolerability and safety of nateglinide in combination with metformin. Results from a study under general practice conditions. | 2003 Aug |
|
| Pharmacokinetics of nateglinide and its metabolites in subjects with type 2 diabetes mellitus and renal failure. | 2003 Aug |
|
| Pharmacodynamics, insulinotropic action and hypoglycemic effect of nateglinide and glibenclamide in normal and diabetic rats. | 2003 Jan |
|
| [Nateglinide and mitiglinide]. | 2003 Jul |
|
| Effect of fluconazole on the pharmacokinetics and pharmacodynamics of nateglinide. | 2003 Jul |
|
| Should diabetic patients treated long-term with sulfonylureas be switched to nateglinide? | 2003 Jul 28 |
|
| Nateglinide (Starlix): update on a new antidiabetic agent. | 2003 Jul-Aug |
|
| [Meglitinide analogs: new insulinotropic agents for the treatment of non-insulin dependent diabetes]. | 2003 Jun |
|
| Addition of nateglinide to rosiglitazone monotherapy suppresses mealtime hyperglycemia and improves overall glycemic control. | 2003 Jun |
|
| Evaluation of the effects of nateglinide on postprandial glycemia in patients with type 2 diabetes mellitus: a multicenter, multinational, non-randomized, non-controlled Latin American study. | 2003 Jun |
|
| Rationale and options for combination therapy in the treatment of Type 2 diabetes. | 2003 Mar |
|
| The mechanisms underlying the unique pharmacodynamics of nateglinide. | 2003 Mar |
|
| 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 |
|
| Hypoglycemia due to nateglinide administration in diabetic patient with chronic renal failure. | 2003 Mar |
|
| [Differences between oral antidiabetics]. | 2003 Mar 20 |
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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Jul 07 00:15:57 UTC 2023
by
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on
Fri Jul 07 00:15:57 UTC 2023
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| Record UNII |
E9V3S85RHY
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| Record Status |
Validated (UNII)
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| Record Version |
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1457629
Created by
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E9V3S85RHY
Created by
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105816-05-5
Created by
admin on Fri Jul 07 00:15:57 UTC 2023 , Edited by admin on Fri Jul 07 00:15:57 UTC 2023
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ENANTIOMER -> ENANTIOMER |
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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