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Namespace Prefixes

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Statements

Subject Item
n2:DB00412
rdf:type
n3:Drug
n3:description
Rosiglitazone is an anti-diabetic drug in the thiazolidinedione class of drugs. It is marketed by the pharmaceutical company GlaxoSmithKline as a stand-alone drug (Avandia) and in combination with metformin (Avandamet) or with glimepiride (Avandaryl). Like other thiazolidinediones, the mechanism of action of rosiglitazone is by activation of the intracellular receptor class of the peroxisome proliferator-activated receptors (PPARs), specifically PPARγ. Rosiglitazone is a selective ligand of PPARγ, and has no PPARα-binding action. Apart from its effect on insulin resistance, it appears to have an anti-inflammatory effect: nuclear factor kappa-B (NFκB) levels fall and inhibitor (IκB) levels increase in patients on rosiglitazone. Recent research has suggested that rosiglitazone may also be of benefit to a subset of patients with Alzheimer's disease not expressing the ApoE4 allele. This is the subject of a clinical trial currently underway.
n3:dosage
n13:271B46A0-363D-11E5-9242-09173F13E4C5 n13:271B46A1-363D-11E5-9242-09173F13E4C5 n13:271B46A2-363D-11E5-9242-09173F13E4C5 n13:271B46A3-363D-11E5-9242-09173F13E4C5 n13:271B46A4-363D-11E5-9242-09173F13E4C5 n13:271B46A5-363D-11E5-9242-09173F13E4C5
n3:generalReferences
# Mohanty P, Aljada A, Ghanim H, Hofmeyer D, Tripathy D, Syed T, Al-Haddad W, Dhindsa S, Dandona P: Evidence for a potent antiinflammatory effect of rosiglitazone. J Clin Endocrinol Metab. 2004 Jun;89(6):2728-35. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/15181049 # Kahn SE, Haffner SM, Heise MA, Herman WH, Holman RR, Jones NP, Kravitz BG, Lachin JM, O'Neill MC, Zinman B, Viberti G: Glycemic durability of rosiglitazone, metformin, or glyburide monotherapy. N Engl J Med. 2006 Dec 7;355(23):2427-43. Epub 2006 Dec 4. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/17145742
n3:group
investigational approved
n3:halfLife
3-4 hours (single oral dose, independent of dose)
n3:indication
Rosiglitazone is indicated as an adjunct to diet and exercise to improve glycemic control in adults with type 2 diabetes mellitus.
n3:manufacturer
n6:271B469B-363D-11E5-9242-09173F13E4C5 n6:271B469C-363D-11E5-9242-09173F13E4C5
owl:sameAs
n5:DB00412 n9:DB00412
dcterms:title
Rosiglitazone
adms:identifier
n19:PA451283 n20:0029-3158-18 n21:BRL n22:1056 n23:D00596 n24:1056 n26:DB00412 n27:28681 n28:50122 n33:Rosiglitazone
n3:mechanismOfAction
Rosiglitazone acts as a highly selective and potent agonist at peroxisome proliferator activated receptors (PPAR) in target tissues for insulin action such as adipose tissue, skeletal muscle, and liver. Activation of PPAR-gamma receptors regulates the transcription of insulin-responsive genes involved in the control of glucose production, transport, and utilization. In this way, rosiglitazone enhances tissue sensitivity to insulin.
n3:packager
n6:271B4693-363D-11E5-9242-09173F13E4C5 n6:271B4694-363D-11E5-9242-09173F13E4C5 n6:271B4691-363D-11E5-9242-09173F13E4C5 n6:271B4692-363D-11E5-9242-09173F13E4C5 n6:271B4697-363D-11E5-9242-09173F13E4C5 n6:271B4698-363D-11E5-9242-09173F13E4C5 n6:271B4695-363D-11E5-9242-09173F13E4C5 n6:271B4696-363D-11E5-9242-09173F13E4C5 n6:271B4699-363D-11E5-9242-09173F13E4C5 n6:271B469A-363D-11E5-9242-09173F13E4C5 n6:271B468B-363D-11E5-9242-09173F13E4C5 n6:271B468C-363D-11E5-9242-09173F13E4C5 n6:271B4689-363D-11E5-9242-09173F13E4C5 n6:271B468A-363D-11E5-9242-09173F13E4C5 n6:271B468F-363D-11E5-9242-09173F13E4C5 n6:271B4690-363D-11E5-9242-09173F13E4C5 n6:271B468D-363D-11E5-9242-09173F13E4C5 n6:271B468E-363D-11E5-9242-09173F13E4C5
n3:patent
n12:7358366 n12:2143849 n12:5002953 n12:1328452
n3:routeOfElimination
Following oral or intravenous administration of [14C]rosiglitazone maleate, approximately 64% and 23% of the dose was eliminated in the urine and in the feces, respectively.
n3:synonym
Rosiglitazonum (±)-5-[p-[2-(methyl-2-pyridylamino)ethoxy]benzyl]-2,4-thiazolidinedione (RS)-5-{4-[2-(Methyl-2-pyridylamino)ethoxy]benzyl}-2,4-thiazolidinedion Rosiglitazon Rosiglitazone Rosiglitazona
n3:toxicity
Side effects include fluid retention, congestive heart failure (CHF), liver disease
n3:volumeOfDistribution
* 17.6 L [oral volume of distribution Vss/F] * 13.5 L [population mean, pediatric patients]
n7:hasAHFSCode
n25:68-20-28
n3:mixture
n11:271B4685-363D-11E5-9242-09173F13E4C5 n11:271B4686-363D-11E5-9242-09173F13E4C5 n11:271B4683-363D-11E5-9242-09173F13E4C5 n11:271B4684-363D-11E5-9242-09173F13E4C5 n11:271B4681-363D-11E5-9242-09173F13E4C5 n11:271B4682-363D-11E5-9242-09173F13E4C5 n11:271B467F-363D-11E5-9242-09173F13E4C5 n11:271B4680-363D-11E5-9242-09173F13E4C5 n11:271B467D-363D-11E5-9242-09173F13E4C5 n11:271B467E-363D-11E5-9242-09173F13E4C5 n11:271B467B-363D-11E5-9242-09173F13E4C5 n11:271B467C-363D-11E5-9242-09173F13E4C5 n11:271B4687-363D-11E5-9242-09173F13E4C5 n11:271B4688-363D-11E5-9242-09173F13E4C5
n3:proteinBinding
99.8% bound to plasma proteins, primarily albumin.
n3:salt
n3:synthesisReference
Manne Reddy, "Amorphous form of rosiglitazone maleate and process for preparation thereof." U.S. Patent US20040242658, issued December 02, 2004.
n16:hasConcept
n17:M0237199
foaf:page
n15:cx1532.shtml n29:rosiglitazone.html n32:rosigl.htm
n3:IUPAC-Name
n10:271B46AA-363D-11E5-9242-09173F13E4C5
n3:InChI
n10:271B46B0-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n10:271B46AF-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n10:271B46AC-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n10:271B46AD-363D-11E5-9242-09173F13E4C5
n3:SMILES
n10:271B46AE-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n10:271B46A8-363D-11E5-9242-09173F13E4C5
n3:logP
n10:271B46A9-363D-11E5-9242-09173F13E4C5 n10:271B46A6-363D-11E5-9242-09173F13E4C5 n10:271B46C1-363D-11E5-9242-09173F13E4C5
n3:logS
n10:271B46A7-363D-11E5-9242-09173F13E4C5
n7:hasATCCode
n8:A10BG02
n3:H-Bond-Acceptor-Count
n10:271B46B6-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n10:271B46B7-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n10:271B46B1-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n10:271B46B2-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n10:271B46B4-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n10:271B46B3-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n10:271B46B5-363D-11E5-9242-09173F13E4C5
n3:absorption
The absolute bioavailability of rosiglitazone is 99%. Peak plasma concentrations are observed about 1 hour after dosing. Administration of rosiglitazone with food resulted in no change in overall exposure (AUC), but there was an approximately 28% decrease in C<sub>max</sub> and a delay in T<sub>max</sub> (1.75 hours). These changes are not likely to be clinically significant; therefore, rosiglitazone may be administered with or without food. Maximum plasma concentration (Cmax) and the area under the curve (AUC) of rosiglitazone increase in a dose-proportional manner over the therapeutic dose range.
n3:affectedOrganism
Humans and other mammals
n3:casRegistryNumber
122320-73-4
n3:clearance
* Oral clearance (CL) = 3.03 ± 0.87 L/hr [1 mg Fasting] * Oral CL = 2.89 ± 0.71 L/hr [2 mg Fasting] * Oral CL = 2.85 ± 0.69 L/hr [8 mg Fasting] * Oral CL = 2.97 ± 0.81 L/hr [8 mg Fed] * 3.15 L/hr [Population mean, Pediatric patients]
n3:containedIn
n31:271B469D-363D-11E5-9242-09173F13E4C5 n31:271B469E-363D-11E5-9242-09173F13E4C5 n31:271B469F-363D-11E5-9242-09173F13E4C5
n3:Bioavailability
n10:271B46BC-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n10:271B46BE-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n10:271B46BF-363D-11E5-9242-09173F13E4C5
n3:Melting-Point
n10:271B46C0-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n10:271B46BB-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n10:271B46BA-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n10:271B46BD-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n10:271B46AB-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-acidic-
n10:271B46B8-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
n10:271B46B9-363D-11E5-9242-09173F13E4C5