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Namespace Prefixes

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Statements

Subject Item
n2:DB01261
rdf:type
n4:Drug
n4:description
Sitagliptin is a new oral hypoglycemic (anti-diabetic drug) of the new dipeptidyl peptidase-4 (DPP-4) inhibitor class of drugs. This enzyme-inhibiting drug is to be used either alone or in combination with metformin or a thiazolidinedione for control of type 2 diabetes mellitus. The drug works to competitively inhibit a protein/enzyme, dipeptidyl peptidase 4 (DPP-4), that results in an increased amount of active incretins (GLP-1 and GIP), reduced amount of release of glucagon (diminishes its release) and increased release of insulin.
n4:dosage
n16:271B6083-363D-11E5-9242-09173F13E4C5 n16:271B6084-363D-11E5-9242-09173F13E4C5 n16:271B6085-363D-11E5-9242-09173F13E4C5 n16:271B6086-363D-11E5-9242-09173F13E4C5 n16:271B6087-363D-11E5-9242-09173F13E4C5 n16:271B6088-363D-11E5-9242-09173F13E4C5
n4:generalReferences
# Herman GA, Stevens C, Van Dyck K, Bergman A, Yi B, De Smet M, Snyder K, Hilliard D, Tanen M, Tanaka W, Wang AQ, Zeng W, Musson D, Winchell G, Davies MJ, Ramael S, Gottesdiener KM, Wagner JA: Pharmacokinetics and pharmacodynamics of sitagliptin, an inhibitor of dipeptidyl peptidase IV, in healthy subjects: results from two randomized, double-blind, placebo-controlled studies with single oral doses. Clin Pharmacol Ther. 2005 Dec;78(6):675-88. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/16338283 # Herman GA, Bergman A, Liu F, Stevens C, Wang AQ, Zeng W, Chen L, Snyder K, Hilliard D, Tanen M, Tanaka W, Meehan AG, Lasseter K, Dilzer S, Blum R, Wagner JA: Pharmacokinetics and pharmacodynamic effects of the oral DPP-4 inhibitor sitagliptin in middle-aged obese subjects. J Clin Pharmacol. 2006 Aug;46(8):876-86. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/16855072 # Karasik A, Aschner P, Katzeff H, Davies MJ, Stein PP: Sitagliptin, a DPP-4 inhibitor for the treatment of patients with type 2 diabetes: a review of recent clinical trials. Curr Med Res Opin. 2008 Feb;24(2):489-96. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/18182122 # Pratley RE, Salsali A: Inhibition of DPP-4: a new therapeutic approach for the treatment of type 2 diabetes. Curr Med Res Opin. 2007 Apr;23(4):919-31. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/17407649 # Bergman A, Ebel D, Liu F, Stone J, Wang A, Zeng W, Chen L, Dilzer S, Lasseter K, Herman G, Wagner J, Krishna R: Absolute bioavailability of sitagliptin, an oral dipeptidyl peptidase-4 inhibitor, in healthy volunteers. Biopharm Drug Dispos. 2007 Sep;28(6):315-22. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/17575559 # Richter B, Bandeira-Echtler E, Bergerhoff K, Lerch C: Emerging role of dipeptidyl peptidase-4 inhibitors in the management of type 2 diabetes. Vasc Health Risk Manag. 2008;4(4):753-68. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/19065993
n4:group
investigational approved
n4:halfLife
12.4 hours
n4:indication
For use as an adjunct to diet and exercise to improve glycemic control in patients with type 2 diabetes mellitus. Also for use in patients with type 2 diabetes mellitus to improve glycemic control in combination with metformin or a PPARγ agonist (e.g., thiazolidinediones) when the single agent alone, with diet and exercise, does not provide adequate glycemic control.
owl:sameAs
n19:DB01261 n27:DB01261
dcterms:title
Sitagliptin
adms:identifier
n8:0006-0221-31 n9:715 n10:3571948 n11:DB01261 n12:13513 n13:40237 n14:PA164748978 n15:Sitagliptin n23:4369359 n24:46505822
n4:mechanismOfAction
Sitagliptin is a highly selective DPP-4 inhibitor, which is believed to exert its actions in patients with type 2 diabetes by slowing the inactivation of incretin hormones, thereby increasing the concentration and prolonging the action of these hormones. Incretin hormones, including glucagon-like peptide-1 (GLP-1) and glucose-dependent insulinotropic polypeptide (GIP), are released by the intestine throughout the day, and levels are increased in response to a meal. These hormones are rapidly inactivated by the enzyme, DPP-4. The incretins are part of an endogenous system involved in the physiologic regulation of glucose homeostasis. When blood glucose concentrations are normal or elevated, GLP-1 and GIP increase insulin synthesis and release from pancreatic beta cells by intracellular signaling pathways involving cyclic AMP. GLP-1 also lowers glucagon secretion from pancreatic alpha cells, leading to reduced hepatic glucose production. By increasing and prolonging active incretin levels, sitagliptin increases insulin release and decreases glucagon levels in the circulation in a glucose-dependent manner. These changes lead to a decrease in hemoglobin A1c (HbA1c)levels, as well as a lower fasting and postprandial glucose concentration. Sitagliptin demonstrates selectivity for DPP-4 and does not inhibit DPP-8 or DPP-9 activity in vitro at concentrations approximating those from therapeutic doses.
n4:packager
n17:271B6077-363D-11E5-9242-09173F13E4C5 n17:271B607A-363D-11E5-9242-09173F13E4C5 n17:271B607B-363D-11E5-9242-09173F13E4C5 n17:271B6078-363D-11E5-9242-09173F13E4C5 n17:271B6079-363D-11E5-9242-09173F13E4C5 n17:271B607C-363D-11E5-9242-09173F13E4C5 n17:271B607D-363D-11E5-9242-09173F13E4C5
n4:patent
n6:6303661 n6:7326708 n6:2536251 n6:2450740
n4:routeOfElimination
Approximately 79% of sitagliptin is excreted unchanged in the urine with metabolism being a minor pathway of elimination. Following administration of an oral [14C]sitagliptin dose to healthy subjects, approximately 100% of the administered radioactivity was eliminated in feces (13%) or urine (87%) within one week of dosing. Elimination of sitagliptin occurs primarily via renal excretion and involves active tubular secretion.
n4:synonym
Sitagliptin phosphate Sitagliptine Sitagliptan Sitagliptina Sitagliptinum MK-0431 (2R)-4-OXO-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine
n4:volumeOfDistribution
* 198 L [healthy subjects]
n4:foodInteraction
Can be administered without regard to food
n4:mixture
n30:271B6075-363D-11E5-9242-09173F13E4C5 n30:271B6076-363D-11E5-9242-09173F13E4C5
n4:proteinBinding
The fraction of sitagliptin reversibly bound to plasma proteins is low (38%).
n4:synthesisReference
Nurit Perlman, Marina Etinger, Valerie Niddam-Hildesheim, Mili Abramov, "Preparation of sitagliptin intermediate." U.S. Patent US20090192326, issued July 30, 2009.
n21:hasConcept
n22:M0480815
foaf:page
n26:januvia.htm n31:sitagliptin.html
n4:IUPAC-Name
n5:271B608D-363D-11E5-9242-09173F13E4C5
n4:InChI
n5:271B6093-363D-11E5-9242-09173F13E4C5
n4:Molecular-Formula
n5:271B6092-363D-11E5-9242-09173F13E4C5
n4:Molecular-Weight
n5:271B608F-363D-11E5-9242-09173F13E4C5
n4:Monoisotopic-Weight
n5:271B6090-363D-11E5-9242-09173F13E4C5
n4:SMILES
n5:271B6091-363D-11E5-9242-09173F13E4C5
n4:Water-Solubility
n5:271B608B-363D-11E5-9242-09173F13E4C5
n4:logP
n5:271B6089-363D-11E5-9242-09173F13E4C5 n5:271B608C-363D-11E5-9242-09173F13E4C5 n5:271B60A2-363D-11E5-9242-09173F13E4C5
n4:logS
n5:271B608A-363D-11E5-9242-09173F13E4C5
n28:hasATCCode
n29:A10BH01
n4:H-Bond-Acceptor-Count
n5:271B6099-363D-11E5-9242-09173F13E4C5
n4:H-Bond-Donor-Count
n5:271B609A-363D-11E5-9242-09173F13E4C5
n4:InChIKey
n5:271B6094-363D-11E5-9242-09173F13E4C5
n4:Polar-Surface-Area--PSA-
n5:271B6095-363D-11E5-9242-09173F13E4C5
n4:Polarizability
n5:271B6097-363D-11E5-9242-09173F13E4C5
n4:Refractivity
n5:271B6096-363D-11E5-9242-09173F13E4C5
n4:Rotatable-Bond-Count
n5:271B6098-363D-11E5-9242-09173F13E4C5
n4:absorption
Rapidly absorbed following oral administration, with an absolute bioavailability of 87%.
n4:affectedOrganism
Humans and other mammals
n4:casRegistryNumber
486460-32-6
n4:category
n4:clearance
* renal cl=350 mL/min [Healthy subjects receiving 100 mg oral dose]
n4:containedIn
n20:271B607E-363D-11E5-9242-09173F13E4C5 n20:271B6081-363D-11E5-9242-09173F13E4C5 n20:271B6082-363D-11E5-9242-09173F13E4C5 n20:271B607F-363D-11E5-9242-09173F13E4C5 n20:271B6080-363D-11E5-9242-09173F13E4C5
n4:Bioavailability
n5:271B609E-363D-11E5-9242-09173F13E4C5
n4:Ghose-Filter
n5:271B60A0-363D-11E5-9242-09173F13E4C5
n4:MDDR-Like-Rule
n5:271B60A1-363D-11E5-9242-09173F13E4C5
n4:Number-of-Rings
n5:271B609D-363D-11E5-9242-09173F13E4C5
n4:Physiological-Charge
n5:271B609C-363D-11E5-9242-09173F13E4C5
n4:Rule-of-Five
n5:271B609F-363D-11E5-9242-09173F13E4C5
n4:Traditional-IUPAC-Name
n5:271B608E-363D-11E5-9242-09173F13E4C5
n4:pKa--strongest-basic-
n5:271B609B-363D-11E5-9242-09173F13E4C5