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 |
---|---|---|---|---|
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 Date1984 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
|
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 |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
|
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 |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
|
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 |
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 |
healthy, 15 |
Disc. AE: Hypoglycaemia... AEs leading to discontinuation/dose reduction: Hypoglycaemia Sources: |
1 g single, oral Overdose |
unhealthy, 55 |
Disc. AE: Hypoglycaemic encephalopathy... AEs leading to discontinuation/dose reduction: Hypoglycaemic encephalopathy (grade 5) Sources: |
20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy, 56.6 (9.8) Health Status: unhealthy Age Group: 56.6 (9.8) Sex: M+F Sources: |
Disc. AE: Myocardial infarction, Abortion spontaneous... AEs leading to discontinuation/dose reduction: Myocardial infarction (serious, 0.17%) Sources: Abortion 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 Sources: |
unhealthy, >/=18 years Health Status: unhealthy Age Group: >/=18 years Sex: M+F Sources: |
Disc. AE: Hypoglycemia, Pyelonephritis... AEs leading to discontinuation/dose reduction: Hypoglycemia (0.7%) Sources: Pyelonephritis (0.25%) |
40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Cardiovascular disorder NOS... AEs leading to discontinuation/dose reduction: Cardiovascular disorder NOS (grade 5) Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Hypoglycaemia | Disc. AE | 375 mg single, oral Overdose |
healthy, 15 |
Hypoglycaemic encephalopathy | grade 5 Disc. AE |
1 g single, oral Overdose |
unhealthy, 55 |
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 Sources: |
unhealthy, 56.6 (9.8) Health Status: unhealthy Age Group: 56.6 (9.8) Sex: M+F Sources: |
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 Sources: |
unhealthy, 56.6 (9.8) Health Status: unhealthy Age Group: 56.6 (9.8) Sex: M+F Sources: |
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 Sources: |
unhealthy, >/=18 years Health Status: unhealthy Age Group: >/=18 years Sex: M+F Sources: |
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 Sources: |
unhealthy, >/=18 years Health Status: unhealthy Age Group: >/=18 years Sex: M+F Sources: |
Cardiovascular disorder NOS | grade 5 Disc. AE |
40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
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 |
---|---|---|
ION-pair liquid chromatography technique for the estimation of metformin in its multicomponent dosage forms. | 2001 Apr |
|
Differences in pharmacotherapy and in glucose control of type 2 diabetes patients in two neighbouring towns: a longitudinal population-based study. | 2001 Aug |
|
Identification of a null allele of CYP2C9 in an African-American exhibiting toxicity to phenytoin. | 2001 Dec |
|
[Effects of octreotide on serum and urine electrolytes in a patient with parathyroid carcinoma: clinical case]. | 2001 Jul-Aug |
|
Protein binding of glipizide using equilibrium dialysis technique: effects of hydrogen ion concentration, drug concentration and ionic strength. | 2001 Mar |
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Comparison between repaglinide and glipizide in Type 2 diabetes mellitus: a 1-year multicentre study. | 2001 May |
|
Phototoxicity to diuretics and antidiabetics in the cultured keratinocyte cell line HaCaT: evaluation by clonogenic assay and single cell gel electrophoresis Comet assay). | 2002 Apr |
|
Evaluation of Glyde File Prep in combination with sodium hypochlorite as a root canal irrigant. | 2002 Apr |
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Comparison of the effects of three insulinotropic drugs on plasma insulin levels after a standard meal. | 2002 Aug |
|
Pharmacokinetics and pharmacodynamics of extended-release glipizide GITS compared with immediate-release glipizide in patients with type II diabetes mellitus. | 2002 Jun |
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Screening, library-assisted identification and validated quantification of oral antidiabetics of the sulfonylurea-type in plasma by atmospheric pressure chemical ionization liquid chromatography-mass spectrometry. | 2002 Jun 15 |
|
Confounding factors in diagnosing brain death: a case report. | 2002 Jun 26 |
|
Improved glucose control decreases the interaction of plasma low-density lipoproteins with arterial proteoglycans. | 2002 Oct |
|
Cyclodextrin complex osmotic tablet for glipizide delivery. | 2002 Sep |
|
[Study of drug prescribing in patients older than 65 in Languedoc-Roussillon]. | 2002 Sep |
|
Nitric oxide induces hyperpolarization by opening ATP-sensitive K(+) channels in guinea pig spiral modiolar artery. | 2002 Sep |
|
Severe hypoglycemia from clarithromycin-sulfonylurea drug interaction. | 2002 Sep |
|
K(ATP) channels and pancreatic islet blood flow in anesthetized rats: increased blood flow induced by potassium channel openers. | 2003 Aug |
|
Small amounts of some drugs can be toxic to young children: one pill or one swallow can require aggressive treatment. | 2003 Jun |
|
Rapid increase in the use of oral antidiabetic drugs in the United States, 1990-2001. | 2003 Jun |
|
Treatment of feline diabetes mellitus using an alpha-glucosidase inhibitor and a low-carbohydrate diet. | 2003 Jun |
|
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 |
|
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 |
|
Efficacy of sulfonylureas with insulin in type 2 diabetes mellitus. | 2003 Nov |
|
Managing hemorrhagic shock: fluids on the way out--drugs on the way in? | 2003 Oct |
|
Beneficial metabolic effects of chronic glipizide in obese African Americans with impaired glucose tolerance: implications for primary prevention of type 2 diabetes. | 2004 Apr |
|
Development and evaluation of osmotically controlled oral drug delivery system of glipizide. | 2004 May |
|
The association of patient trust and self-care among patients with diabetes mellitus. | 2004 Nov 16 |
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
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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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NDF-RT |
N0000008054
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WHO-ATC |
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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X7WDT95N5C
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C29074
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X7WDT95N5C
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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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Related Record | Type | Details | ||
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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 |
URINE
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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 |
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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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