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Namespace Prefixes

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Statements

Subject Item
n2:DB01016
rdf:type
n3:Drug
n3:description
Glyburide is an oral antihyperglycemic agent used for the treatment of non-insulin-dependent diabetes mellitus (NIDDM). It belongs to the sulfonylurea class of insulin secretagogues, which act by stimulating &beta; cells of the pancreas to release insulin. Sulfonylureas increase both basal insulin secretion and meal-stimulated insulin release. Medications in this class differ in their dose, rate of absorption, duration of action, route of elimination and binding site on their target pancreatic &beta; cell receptor. Sulfonylureas also increase peripheral glucose utilization, decrease hepatic gluconeogenesis and may increase the number and sensitivity of insulin receptors. Sulfonylureas are associated with weight gain, though less so than insulin. Due to their mechanism of action, sulfonylureas may cause hypoglycemia and require consistent food intake to decrease this risk. The risk of hypoglycemia is increased in elderly, debilitated and malnourished individuals. Glyburide has been shown to decrease fasting plasma glucose, postprandial blood glucose and glycosolated hemoglobin (HbA1c) levels (reflective of the last 8-10 weeks of glucose control). Glyburide appears to be completely metabolized, likely in the liver. Although its metabolites exert a small hypoglycemic effect, their contribution to glyburide's hypoglycemic effect is thought to be clinically unimportant. Glyburide metabolites are excreted in urine and feces in approximately equal proportions. The half-life of glyburide appears to be unaffected in those with a creatinine clearance of greater than 29 ml/min/1.73m<sup>2</sup>.
n3:dosage
n23:271B5291-363D-11E5-9242-09173F13E4C5 n23:271B5292-363D-11E5-9242-09173F13E4C5 n23:271B528D-363D-11E5-9242-09173F13E4C5 n23:271B528E-363D-11E5-9242-09173F13E4C5 n23:271B528F-363D-11E5-9242-09173F13E4C5 n23:271B5290-363D-11E5-9242-09173F13E4C5
n3:generalReferences
# Monami M, Luzzi C, Lamanna C, Chiasserini V, Addante F, Desideri CM, Masotti G, Marchionni N, Mannucci E: Three-year mortality in diabetic patients treated with different combinations of insulin secretagogues and metformin. Diabetes Metab Res Rev. 2006 Nov-Dec;22(6):477-82. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/16634115
n3:group
approved
n3:halfLife
1.4-1.8 hours (unchanged drug only); 10 hours (metabolites included). Duration of effect is 12-24 hours.
n3:indication
Indicated as an adjunct to diet to lower the blood glucose in patients with NIDDM whose hyperglycemia cannot be satisfactorily controlled by diet alone.
n3:manufacturer
n4:271B5266-363D-11E5-9242-09173F13E4C5 n4:271B5267-363D-11E5-9242-09173F13E4C5 n4:271B5265-363D-11E5-9242-09173F13E4C5 n4:271B526A-363D-11E5-9242-09173F13E4C5 n4:271B526B-363D-11E5-9242-09173F13E4C5 n4:271B5268-363D-11E5-9242-09173F13E4C5 n4:271B5269-363D-11E5-9242-09173F13E4C5 n4:271B526E-363D-11E5-9242-09173F13E4C5 n4:271B526C-363D-11E5-9242-09173F13E4C5 n4:271B526D-363D-11E5-9242-09173F13E4C5
owl:sameAs
n20:DB01016 n28:DB01016
dcterms:title
Glyburide
adms:identifier
n7:3368 n8:DB01016 n9:5441 n10:2414 n11:C07022 n12:2414 n13:PA449782 n14:3488 n15:D00336 n16:0378-1113-01 n17:46509154 n27:Glibenclamide
n3:mechanismOfAction
Sulfonylureas such as glyburide bind to ATP-sensitive potassium channels 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.
n3:packager
n4:271B5232-363D-11E5-9242-09173F13E4C5 n4:271B522F-363D-11E5-9242-09173F13E4C5 n4:271B5230-363D-11E5-9242-09173F13E4C5 n4:271B522D-363D-11E5-9242-09173F13E4C5 n4:271B522E-363D-11E5-9242-09173F13E4C5 n4:271B522B-363D-11E5-9242-09173F13E4C5 n4:271B522C-363D-11E5-9242-09173F13E4C5 n4:271B5229-363D-11E5-9242-09173F13E4C5 n4:271B522A-363D-11E5-9242-09173F13E4C5 n4:271B5264-363D-11E5-9242-09173F13E4C5 n4:271B5262-363D-11E5-9242-09173F13E4C5 n4:271B5263-363D-11E5-9242-09173F13E4C5 n4:271B5260-363D-11E5-9242-09173F13E4C5 n4:271B5261-363D-11E5-9242-09173F13E4C5 n4:271B525E-363D-11E5-9242-09173F13E4C5 n4:271B525F-363D-11E5-9242-09173F13E4C5 n4:271B525C-363D-11E5-9242-09173F13E4C5 n4:271B525D-363D-11E5-9242-09173F13E4C5 n4:271B525A-363D-11E5-9242-09173F13E4C5 n4:271B525B-363D-11E5-9242-09173F13E4C5 n4:271B5258-363D-11E5-9242-09173F13E4C5 n4:271B5259-363D-11E5-9242-09173F13E4C5 n4:271B5256-363D-11E5-9242-09173F13E4C5 n4:271B5257-363D-11E5-9242-09173F13E4C5 n4:271B5254-363D-11E5-9242-09173F13E4C5 n4:271B5255-363D-11E5-9242-09173F13E4C5 n4:271B5252-363D-11E5-9242-09173F13E4C5 n4:271B5253-363D-11E5-9242-09173F13E4C5 n4:271B5250-363D-11E5-9242-09173F13E4C5 n4:271B5251-363D-11E5-9242-09173F13E4C5 n4:271B524E-363D-11E5-9242-09173F13E4C5 n4:271B524F-363D-11E5-9242-09173F13E4C5 n4:271B524C-363D-11E5-9242-09173F13E4C5 n4:271B524D-363D-11E5-9242-09173F13E4C5 n4:271B524A-363D-11E5-9242-09173F13E4C5 n4:271B524B-363D-11E5-9242-09173F13E4C5 n4:271B5248-363D-11E5-9242-09173F13E4C5 n4:271B5249-363D-11E5-9242-09173F13E4C5 n4:271B5247-363D-11E5-9242-09173F13E4C5 n4:271B5245-363D-11E5-9242-09173F13E4C5 n4:271B5246-363D-11E5-9242-09173F13E4C5 n4:271B5243-363D-11E5-9242-09173F13E4C5 n4:271B5244-363D-11E5-9242-09173F13E4C5 n4:271B5241-363D-11E5-9242-09173F13E4C5 n4:271B5242-363D-11E5-9242-09173F13E4C5 n4:271B523F-363D-11E5-9242-09173F13E4C5 n4:271B5240-363D-11E5-9242-09173F13E4C5 n4:271B523D-363D-11E5-9242-09173F13E4C5 n4:271B523E-363D-11E5-9242-09173F13E4C5 n4:271B523B-363D-11E5-9242-09173F13E4C5 n4:271B523C-363D-11E5-9242-09173F13E4C5 n4:271B5239-363D-11E5-9242-09173F13E4C5 n4:271B523A-363D-11E5-9242-09173F13E4C5 n4:271B5237-363D-11E5-9242-09173F13E4C5 n4:271B5238-363D-11E5-9242-09173F13E4C5 n4:271B5235-363D-11E5-9242-09173F13E4C5 n4:271B5236-363D-11E5-9242-09173F13E4C5 n4:271B5233-363D-11E5-9242-09173F13E4C5 n4:271B5234-363D-11E5-9242-09173F13E4C5 n4:271B5231-363D-11E5-9242-09173F13E4C5
n3:routeOfElimination
Glyburide is excreted as metabolites in the bile and urine, approximately 50% by each route. This dual excretory pathway is qualitatively different from that of other sulfonylureas, which are excreted primarily in the urine.
n3:synonym
5-chloro-N-(2-(4-((((Cyclohexylamino)carbonyl)amino)sulfonyl)phenyl)ethyl)-2-methoxybenzamide 1-(P-(2-(5-chloro-2-Methoxybenzamido)ethyl)benzenesulfonyl)-3-cyclohexylurea Glibenclamidum 1-((P-(2-(5-chloro-O-Anisamido)ethyl)phenyl)sulfonyl)-3-cyclohexylurea Glynase Micronase Glibenclamida Diabeta Glibenclamide Glyburide
n3:toxicity
Oral rat LD<sub>50</sub>: > 20,000 mg/kg. Oral mouse LD<sub>50</sub>: 3250 mg/kg.
n3:volumeOfDistribution
Steady state V<sub>d</sub>=0.125 L/kg; V<sub>d</sub> during elimination phase=0.155 L/kg.
n21:hasAHFSCode
n26:68-20-20
n3:foodInteraction
Take 30-60 minutes before breakfast. Avoid alcohol.
n3:mixture
n30:271B5228-363D-11E5-9242-09173F13E4C5 n30:271B5226-363D-11E5-9242-09173F13E4C5 n30:271B5227-363D-11E5-9242-09173F13E4C5
n3:proteinBinding
Unchanged drug is ~99% bound to serum proteins; 4-trans-hydroxyglyburide is greater than 97% bound to serum proteins. Protein binding is primarily nonionic making glyburide and is less likely to displace or be displaced by drugs that bind via an ionic mechanism.
n3:synthesisReference
Suresh Gidwani, "Solid oral dosage form of metformin and glyburide and the method of preparation thereof." U.S. Patent US20040175421, issued September 09, 2004.
n24:hasConcept
n25:M0009265
foaf:page
n32:glybur.htm
n3:IUPAC-Name
n5:271B5297-363D-11E5-9242-09173F13E4C5
n3:InChI
n5:271B529D-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n5:271B529C-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n5:271B5299-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n5:271B529A-363D-11E5-9242-09173F13E4C5
n3:SMILES
n5:271B529B-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n5:271B52AD-363D-11E5-9242-09173F13E4C5 n5:271B5295-363D-11E5-9242-09173F13E4C5
n3:logP
n5:271B5293-363D-11E5-9242-09173F13E4C5 n5:271B5296-363D-11E5-9242-09173F13E4C5 n5:271B52AF-363D-11E5-9242-09173F13E4C5
n3:logS
n5:271B5294-363D-11E5-9242-09173F13E4C5 n5:271B52B0-363D-11E5-9242-09173F13E4C5
n21:hasATCCode
n22:A10BB01
n3:H-Bond-Acceptor-Count
n5:271B52A3-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n5:271B52A4-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n5:271B529E-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n5:271B529F-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n5:271B52A1-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n5:271B52A0-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n5:271B52A2-363D-11E5-9242-09173F13E4C5
n3:absorption
Significant absorption within 1 hour and peak plasma levels are reached in 2 to 4 hours. Onset of action occurs within one hour.
n3:affectedOrganism
Humans and other mammals
n3:casRegistryNumber
10238-21-8
n3:category
n3:clearance
78 ml/hr/kg in healthy adults. Clearance may be substantially decreased in those with severe renal impairment.
n3:containedIn
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n3:Bioavailability
n5:271B52A9-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n5:271B52AB-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n5:271B52AC-363D-11E5-9242-09173F13E4C5
n3:Melting-Point
n5:271B52AE-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n5:271B52A8-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n5:271B52A7-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n5:271B52AA-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n5:271B5298-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-acidic-
n5:271B52A5-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
n5:271B52A6-363D-11E5-9242-09173F13E4C5