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 |
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 |
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Effectiveness of nateglinide on in vitro insulin secretion from rat pancreatic islets desensitized to sulfonylureas. | 2001 |
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Glucose-dependent and glucose-sensitizing insulinotropic effect of nateglinide: comparison to sulfonylureas and repaglinide. | 2001 |
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Importance of early phase insulin secretion to intravenous glucose tolerance in subjects with type 2 diabetes mellitus. | 2001 Dec |
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Nateglinide therapy for type 2 diabetes mellitus. | 2001 Nov |
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Insulinotropic meglitinide analogues. | 2001 Nov 17 |
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[New molecules]. | 2001 Sep-Oct |
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Insulin secretagogues. | 2002 |
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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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[Postprandial hyperglycemia. II. Pharmacological approaches]. | 2002 Apr |
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[Differential type 2 diabetes therapy based on pathophysiological aspects]. | 2002 Aug |
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Repaglinide at a cellular level. | 2002 Dec |
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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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No effect of the novel antidiabetic agent nateglinide on the pharmacokinetics and anticoagulant properties of warfarin in healthy volunteers. | 2002 Dec |
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Control of postprandial hyperglycemia: optimal use of short-acting insulin secretagogues. | 2002 Dec |
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Restoring post-prandial insulin release in type 2 diabetes. | 2002 Feb |
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[Detection of crystal polymorphs of nateglinide by DSC]. | 2002 Jan |
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New drugs 2002, part 1. | 2002 Jan |
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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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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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[Islands cells are not activated quickly enough. Risk of obstruction of blood vessels]. | 2002 Jun 27 |
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Nateglinide, a new agent for postprandial glucose control in type 2 diabetes. | 2002 May |
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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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Current oral agents for type 2 diabetes. Many options, but which to choose when? | 2002 May |
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Comparison of insulinotrophic actions of nateglinide with glibenclamide dissociated from absorption in conscious dogs. | 2002 May |
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[Glinides and glitazones in diabetes treatment. Are they really effective?]. | 2002 May 2 |
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[Dangerous postprandial glucose peaks. Risk for heart and blood vessels]. | 2002 May 23 |
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Interaction of nateglinide with K(ATP) channel in beta-cells underlies its unique insulinotropic action. | 2002 May 3 |
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Effect of KAD-1229, a novel hypoglycaemic agent, on plasma glucose levels after meal load in type 2 diabetic rats. | 2002 May-Jun |
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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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[Nateglinide]. | 2002 Sep |
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[Structures and mechanisms for non SU insulin secretagogues]. | 2002 Sep |
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[Adverse effects of oral hypoglycemic agents]. | 2002 Sep |
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Efficacy and safety of nateglinide in type 2 diabetic patients with modest fasting hyperglycemia. | 2002 Sep |
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Differential interactions of nateglinide and repaglinide on the human beta-cell sulphonylurea receptor 1. | 2002 Sep |
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Combination therapy with nateglinide and a thiazolidinedione improves glycemic control in type 2 diabetes. | 2002 Sep |
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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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[Nateglinide and mitiglinide]. | 2003 Jul |
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[Pharmacological treatment of postprandial hyperglycemia in hypertensive patients with type 2 diabetes mellitus]. | 2003 Jul |
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Nateglinide (Starlix): update on a new antidiabetic agent. | 2003 Jul-Aug |
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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 |
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The mechanisms underlying the unique pharmacodynamics of nateglinide. | 2003 Mar |
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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 |
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The prevention of type 2 diabetes--lifestyle change or pharmacotherapy? A challenge for the 21st century. | 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
Fri Dec 15 16:16:10 GMT 2023
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on
Fri Dec 15 16:16:10 GMT 2023
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Record UNII |
41X3PWK4O2
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Record Status |
Validated (UNII)
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Record Version |
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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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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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