Details
Stereochemistry | ACHIRAL |
Molecular Formula | C21H27N5O4S |
Molecular Weight | 445.535 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=NC=C(N=C1)C(=O)NCCC2=CC=C(C=C2)S(=O)(=O)NC(=O)NC3CCCCC3
InChI
InChIKey=ZJJXGWJIGJFDTL-UHFFFAOYSA-N
InChI=1S/C21H27N5O4S/c1-15-13-24-19(14-23-15)20(27)22-12-11-16-7-9-18(10-8-16)31(29,30)26-21(28)25-17-5-3-2-4-6-17/h7-10,13-14,17H,2-6,11-12H2,1H3,(H,22,27)(H2,25,26,28)
Molecular Formula | C21H27N5O4S |
Molecular Weight | 445.535 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: http://www.drugbank.ca/drugs/DB01067Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/glipizide.html
Sources: http://www.drugbank.ca/drugs/DB01067
Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/glipizide.html
Glipizide, a second-generation sulfonylurea, is used with diet to lower blood glucose in patients with diabetes mellitus type II. The primary mode of action of glipizide in experimental animals appears to be the stimulation of insulin secretion from the beta cells of pancreatic islet tissue and is thus dependent on functioning beta cells in the pancreatic islets. In humans glipizide appears to lower the blood glucose acutely by stimulating the release of insulin from the pancreas, an effect dependent upon functioning beta cells in the pancreatic islets. In man, stimulation of insulin secretion by glipizide in response to a meal is undoubtedly of major importance. Fasting insulin levels are not elevated even on long-term glipizide administration, but the postprandial insulin response continues to be enhanced after at least 6 months of treatment. Some patients fail to respond initially, or gradually lose their responsiveness to sulfonylurea drugs, including glipizide. Sulfonylureas likely bind to ATP-sensitive potassium-channel receptors on the pancreatic cell surface, reducing potassium conductance and causing depolarization of the membrane. Depolarization stimulates calcium ion influx through voltage-sensitive calcium channels, raising intracellular concentrations of calcium ions, which induces the secretion, or exocytosis, of insulin. Glipizide is used as an adjunct to diet for the control of hyperglycemia and its associated symptomatology in patients with non-insulin-dependent diabetes mellitus (NIDDM; type II), formerly known as maturity-onset diabetes, after an adequate trial of dietary therapy has proved unsatisfactory. Glipizide is marketed by Pfizer under the brand name Glucotrol in the USA, where Pfizer sells Glucotrol in doses of 5 and 10 milligrams and Glucotrol XL (an extended release form of glipizide) in doses of 2.5, 5, and 10 milligrams. Other companies also market glipizide, most commonly extended release tablets of 5 and 10 milligrams.
Originator
Sources: http://imr.sagepub.com/content/1/7/608.full.pdf
Curator's Comment: first described by Ambrogi in 1971
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL235 Sources: http://www.drugbank.ca/drugs/DB01067 |
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Target ID: CHEMBL2071 Sources: http://www.drugbank.ca/drugs/DB01067 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | GLUCOTROL Approved UseGLUCOTROL is indicated as an adjunct to diet and exercise to improve glycemic control in
adults with type 2 diabetes mellitus. Launch Date4.52735992E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
523 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/16509763 |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
GLIPIZIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
465 ng/mL |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
GLIPIZIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1897 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/16509763 |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
GLIPIZIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1878 ng × h/mL |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
GLIPIZIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.65 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/16509763 |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
GLIPIZIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
3 h |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
GLIPIZIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.5% |
GLIPIZIDE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
375 mg single, oral Overdose Dose: 375 mg Route: oral Route: single Dose: 375 mg Co-administed with:: melformin, p.o(14.5 g; single) Sources: Page: p.565 |
healthy, 15 n = 1 Health Status: healthy Age Group: 15 Sex: F Population Size: 1 Sources: Page: p.565 |
Disc. AE: Hypoglycaemia... AEs leading to discontinuation/dose reduction: Hypoglycaemia Sources: Page: p.565 |
1 g single, oral Overdose Dose: 1 g Route: oral Route: single Dose: 1 g Co-administed with:: insulin, i.v(1600 u; single) Sources: Page: p.265 |
unhealthy, 55 n = 1 Health Status: unhealthy Condition: Type 2 diabetes mellitus Age Group: 55 Sex: M Population Size: 1 Sources: Page: p.265 |
Disc. AE: Hypoglycaemic encephalopathy... AEs leading to discontinuation/dose reduction: Hypoglycaemic encephalopathy (grade 5) Sources: Page: p.265 |
20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Co-administed with:: melformin, p.o(>/=1500 mg/day; 52 wk) Sources: Page: p.199 |
unhealthy, 56.6 (9.8) n = 584 Health Status: unhealthy Condition: Type 2 diabetes mellitus Age Group: 56.6 (9.8) Sex: M+F Population Size: 584 Sources: Page: p.199 |
Disc. AE: Myocardial infarction, Abortion spontaneous... AEs leading to discontinuation/dose reduction: Myocardial infarction (serious, 0.17%) Sources: Page: p.199Abortion spontaneous (serious, 0.17%) |
20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Co-administed with:: melformin, p.o(1500–2500mg/day) Sources: Page: p.2020 |
unhealthy, >/=18 years n = 408 Health Status: unhealthy Condition: Type 2 diabetes mellitus Age Group: >/=18 years Sex: M+F Population Size: 408 Sources: Page: p.2020 |
Disc. AE: Hypoglycemia, Pyelonephritis... AEs leading to discontinuation/dose reduction: Hypoglycemia (0.7%) Sources: Page: p.2020Pyelonephritis (0.25%) |
40 mg 1 times / day multiple, oral (total daily dose) Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: Page: p.3 |
unhealthy Health Status: unhealthy Condition: Type 2 diabetes mellitus Sources: Page: p.3 |
Disc. AE: Cardiovascular disorder NOS... AEs leading to discontinuation/dose reduction: Cardiovascular disorder NOS (grade 5) Sources: Page: p.3 |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Hypoglycaemia | Disc. AE | 375 mg single, oral Overdose Dose: 375 mg Route: oral Route: single Dose: 375 mg Co-administed with:: melformin, p.o(14.5 g; single) Sources: Page: p.565 |
healthy, 15 n = 1 Health Status: healthy Age Group: 15 Sex: F Population Size: 1 Sources: Page: p.565 |
Hypoglycaemic encephalopathy | grade 5 Disc. AE |
1 g single, oral Overdose Dose: 1 g Route: oral Route: single Dose: 1 g Co-administed with:: insulin, i.v(1600 u; single) Sources: Page: p.265 |
unhealthy, 55 n = 1 Health Status: unhealthy Condition: Type 2 diabetes mellitus Age Group: 55 Sex: M Population Size: 1 Sources: Page: p.265 |
Abortion spontaneous | serious, 0.17% Disc. AE |
20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Co-administed with:: melformin, p.o(>/=1500 mg/day; 52 wk) Sources: Page: p.199 |
unhealthy, 56.6 (9.8) n = 584 Health Status: unhealthy Condition: Type 2 diabetes mellitus Age Group: 56.6 (9.8) Sex: M+F Population Size: 584 Sources: Page: p.199 |
Myocardial infarction | serious, 0.17% Disc. AE |
20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Co-administed with:: melformin, p.o(>/=1500 mg/day; 52 wk) Sources: Page: p.199 |
unhealthy, 56.6 (9.8) n = 584 Health Status: unhealthy Condition: Type 2 diabetes mellitus Age Group: 56.6 (9.8) Sex: M+F Population Size: 584 Sources: Page: p.199 |
Pyelonephritis | 0.25% Disc. AE |
20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Co-administed with:: melformin, p.o(1500–2500mg/day) Sources: Page: p.2020 |
unhealthy, >/=18 years n = 408 Health Status: unhealthy Condition: Type 2 diabetes mellitus Age Group: >/=18 years Sex: M+F Population Size: 408 Sources: Page: p.2020 |
Hypoglycemia | 0.7% Disc. AE |
20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Co-administed with:: melformin, p.o(1500–2500mg/day) Sources: Page: p.2020 |
unhealthy, >/=18 years n = 408 Health Status: unhealthy Condition: Type 2 diabetes mellitus Age Group: >/=18 years Sex: M+F Population Size: 408 Sources: Page: p.2020 |
Cardiovascular disorder NOS | grade 5 Disc. AE |
40 mg 1 times / day multiple, oral (total daily dose) Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: Page: p.3 |
unhealthy Health Status: unhealthy Condition: Type 2 diabetes mellitus Sources: Page: p.3 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes | no (pharmacogenomic study) Comment: there were detectable differences between CYP2C19 EMs and PMs in the pharmacokinetics and pharmacodynamics of glipizide, but none of these differences were statistically significant |
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yes | weak (co-administration study) Comment: rifampin decreased the AUC(0-infinity) of glipizide by 22% (P <.05) and shortened its half-life from 3.0 to 1.9 hours (P =.01); pharmacogenomic studies also performed: CYP2C9 polymorphism significantly influences the pharmacokinetics and pharmacodynamics of glipizide, which needs to be considered in clinical practice |
PubMed
Title | Date | PubMed |
---|---|---|
Transdermal delivery of glibenclamide and glipizide: in vitro permeation studies through mouse skin. | 2002 Dec |
|
Control of postprandial hyperglycemia: optimal use of short-acting insulin secretagogues. | 2002 Dec |
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Pharmacogenetics affects dosing, efficacy, and toxicity of cytochrome P450-metabolized drugs. | 2002 Dec 15 |
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Metaglip and Avandamet for type 2 diabetes. | 2002 Dec 23 |
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Design and in vitro and in vivo evaluation of mucoadhesive microcapsules of glipizide for oral controlled release: a technical note. | 2003 |
|
Presentation and 5-year follow-up of type 2 diabetes mellitus in African-American and Caribbean-Hispanic adolescents. | 2003 |
|
Economic model of first-line drug strategies to achieve recommended glycaemic control in newly diagnosed type 2 diabetes mellitus. | 2003 |
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[Oral antidiabetic therapy and cardiovascular complications: theoretical problem or clinical evidence?]. | 2003 Apr 6 |
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Differential responsiveness of rat striatal nerve endings to the mitochondrial toxin 3-nitropropionic acid: implications for Huntington's disease. | 2003 Aug |
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K(ATP) channels and pancreatic islet blood flow in anesthetized rats: increased blood flow induced by potassium channel openers. | 2003 Aug |
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Effect of some penetration enhancers on the permeation of glibenclamide and glipizide through mouse skin. | 2003 Dec |
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Hypoglycemic activity of Urtica pilulifera in streptozotocin-diabetic rats. | 2003 Feb |
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Differential effects of K(ATP) channel blockers on [(3)H]-noradrenaline overflow after short- and long-term exposure to (+)-oxaprotiline or desipramine. | 2003 Feb |
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Kappa-opioid receptor stimulation contributes to aortic artery dilation through activation of K(ATP) channel in the rats. | 2003 Feb 25 |
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Blinding controlled-release tablets for clinical trials. | 2003 Jan |
|
Use of octreotide to treat prolonged sulfonylurea-induced hypoglycemia in a patient with chronic renal failure. | 2003 Jan |
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Diabetes medicine update. Old dogs, new tricks. | 2003 Jan-Feb |
|
Performance liquid chromatographic analysis of glipizide: application to in vitro and in vivo studies. | 2003 Jul |
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Glipizide treatment with short-term alcohol abuse resulting in subfulminant hepatic failure. | 2003 Jul |
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Combination agents for diabetes. | 2003 Jun |
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Insulin secretagogues, but not glucose, stimulate an increase in [Ca2+]i in the fetal human and porcine beta-cell. | 2003 Jun |
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Small amounts of some drugs can be toxic to young children: one pill or one swallow can require aggressive treatment. | 2003 Jun |
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Rapid increase in the use of oral antidiabetic drugs in the United States, 1990-2001. | 2003 Jun |
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Treatment of feline diabetes mellitus using an alpha-glucosidase inhibitor and a low-carbohydrate diet. | 2003 Jun |
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Modification of cardiovascular response of posterior hypothalamic adenosine A(2) receptor stimulation by adenylate cylase, guanylate cyclase and by K(ATP) channel blockade in anesthetized rats. | 2003 Jun 19 |
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Multicenter, randomized, double-masked, parallel-group assessment of simultaneous glipizide/metformin as second-line pharmacologic treatment for patients with type 2 diabetes mellitus that is inadequately controlled by a sulfonylurea. | 2003 Mar |
|
Barriers to self-monitoring of blood glucose among adults with diabetes in an HMO: a cross sectional study. | 2003 Mar 19 |
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[Differences between oral antidiabetics]. | 2003 Mar 20 |
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Effects of sulfonylurea hypoglycemic agents and adenosine triphosphate dependent potassium channel antagonists on ventricular arrhythmias in patients with decompensated heart failure. | 2003 May |
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Metabolic effects of chronic glipizide gastrointestinal therapeutic system on serum glucose, insulin secretion, insulin sensitivity, and hepatic insulin extraction in glucose-tolerant, first-degree relatives of African American patients with type 2 diabetes: new insights on mechanisms of action. | 2003 May |
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Light and scanning electron microscopic evaluation of Glyde File Prep in smear layer removal. | 2003 May |
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Improvements in glycemic control in type 2 diabetes patients switched from sulfonylurea coadministered with metformin to glyburide-metformin tablets. | 2003 May-Jun |
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Effects of rosiglitazone maleate when added to a sulfonylurea regimen in patients with type 2 diabetes mellitus and mild to moderate renal impairment: a post hoc analysis. | 2003 Nov |
|
Targeting postprandial hyperglycemia: a comparative study of insulinotropic agents in type 2 diabetes. | 2003 Nov |
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Efficacy of sulfonylureas with insulin in type 2 diabetes mellitus. | 2003 Nov |
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Risk of hypoglycaemia with oral antidiabetic agents in patients with Type 2 diabetes. | 2003 Oct |
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Managing hemorrhagic shock: fluids on the way out--drugs on the way in? | 2003 Oct |
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Parenteral administration of glipizide sodium salt, an inhibitor of adenosine triphosphate-sensitive potassium channels, prolongs short-term survival after severe controlled hemorrhage in rats. | 2003 Oct |
|
Weight uniformity of split tablets required by a Veterans Affairs policy. | 2003 Sep-Oct |
|
The role of sulphonylureas in the management of type 2 diabetes mellitus. | 2004 |
|
Repaglinide : a pharmacoeconomic review of its use in type 2 diabetes mellitus. | 2004 |
|
Beneficial metabolic effects of chronic glipizide in obese African Americans with impaired glucose tolerance: implications for primary prevention of type 2 diabetes. | 2004 Apr |
|
Cross-reactivity among p-amino group compounds in sulfonamide fixed drug eruption: diagnostic value of patch testing. | 2004 Aug |
|
Kinetics-effect relations of insulin-releasing drugs in patients with type 2 diabetes: brief overview. | 2004 Dec |
|
Induction of human CYP2C9 by rifampicin, hyperforin, and phenobarbital is mediated by the pregnane X receptor. | 2004 Feb |
|
Idiosyncratic toxicity associated with potentiated sulfonamides in the dog. | 2004 Jun |
|
Basal nitric oxide production contributes to membrane potential and vasotone regulation of guinea pig in vitro spiral modiolar artery. | 2004 Mar |
|
Simultaneous determination of glipizide and rosiglitazone unbound drug concentrations in plasma by equilibrium dialysis and liquid chromatography-tandem mass spectrometry. | 2004 Mar 5 |
|
Metformin-associated respiratory alkalosis. | 2004 May-Jun |
|
Detection of anti-diabetics in equine plasma and urine by liquid chromatography-tandem mass spectrometry. | 2004 Nov 5 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/glipizide.html
Initial dose: 5 mg orally once a day, 30 minutes before breakfast
Maintenance dose: Up to 40 mg in divided doses 30 minutes before a meal of adequate caloric content. Doses may be increased in intervals of 2.5 to 5 mg a day according to blood glucose response.
Maximum single dose: 15 mg
Maximum daily dose: 40 mg
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21977453
Glipizide (100 uM) increased PPARγ transcriptional activity in Cos7 cells
Substance Class |
Chemical
Created
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on
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Wed Jul 05 22:53:19 UTC 2023
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Record UNII |
X7WDT95N5C
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Record Status |
Validated (UNII)
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LIVERTOX |
460
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WHO-VATC |
QA10BB07
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N0000008054
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A10BB07
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N0000008054
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N0000175608
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N0000008054
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NCI_THESAURUS |
C97936
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29094-61-9
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1292507
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3478
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5384
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C29074
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CHEMBL1073
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DB01067
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1301
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759120
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M5747
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3090
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D005913
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6821
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Glipizide
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4821
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249-427-6
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SUB07927MIG
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100000090337
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Glipizide
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DTXSID0040676
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BINDER->LIGAND |
BINDING
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
EP
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TARGET -> INHIBITOR |
Sulfonylureas bind to and close ATP-sensitive K+ (KATP) channels on the cell membrane of pancreatic beta cells, which depolarizes the cell by preventing potassium from exiting. This depolarization opens voltage-gated Ca2+ channels. The rise in intracellular calcium leads to increased fusion of insulin granulae with the cell membrane, and therefore increased secretion of mature insulin.
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
USP
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Related Record | Type | Details | ||
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METABOLITE LESS ACTIVE -> PARENT | |||
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METABOLITE LESS ACTIVE -> PARENT |
Related Record | Type | Details | ||
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IMPURITY -> PARENT |
For the calculation of contents, multiply the peak areas by 1.3
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 |
For the calculation of contents, multiply the peak areas by 2.1
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
For the calculation of contents, multiply the peak areas by 1.7
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (GC)
EP
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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Volume of Distribution | PHARMACOKINETIC |
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