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Namespace Prefixes

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Statements

Subject Item
n2:DB01220
rdf:type
n3:Drug
n3:description
Rifaximin is a semisynthetic, rifamycin-based non-systemic antibiotic, meaning that the drug will not pass the gastrointestinal wall into the circulation as is common for other types of orally administered antibiotics. It is used to treat diarrhea caused by E. coli.
n3:dosage
n11:271B58A9-363D-11E5-9242-09173F13E4C5 n11:271B58AA-363D-11E5-9242-09173F13E4C5
n3:generalReferences
# Cottreau J, Baker SF, DuPont HL, Garey KW: Rifaximin: a nonsystemic rifamycin antibiotic for gastrointestinal infections. Expert Rev Anti Infect Ther. 2010 Jul;8(7):747-60. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/20586560 # Williams R, Bass N: Rifaximin, a nonabsorbed oral antibiotic, in the treatment of hepatic encephalopathy: antimicrobial activity, efficacy, and safety. Rev Gastroenterol Disord. 2005;5 Suppl 1:S10-8. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/15976747 # Koo HL, DuPont HL: Rifaximin: a unique gastrointestinal-selective antibiotic for enteric diseases. Curr Opin Gastroenterol. 2010 Jan;26(1):17-25. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/19881343 # Pakyz AL: Rifaximin: a new treatment for travelers' diarrhea. Ann Pharmacother. 2005 Feb;39(2):284-9. Epub 2004 Dec 14. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/15598963 # Jalan R: Rifaximin in hepatic encephalopathy: More than just a non-absorbable antibiotic? J Hepatol. 2010 May 31. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/20561708 # Lawrence KR, Klee JA: Rifaximin for the treatment of hepatic encephalopathy. Pharmacotherapy. 2008 Aug;28(8):1019-32. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/18657018 # Layer P, Andresen V: Review article: rifaximin, a minimally absorbed oral antibacterial, for the treatment of travellers' diarrhoea. Aliment Pharmacol Ther. 2010 Jun;31(11):1155-64. Epub 2010 Mar 11. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/20331580 # Ojetti V, Lauritano EC, Barbaro F, Migneco A, Ainora ME, Fontana L, Gabrielli M, Gasbarrini A: Rifaximin pharmacology and clinical implications. Expert Opin Drug Metab Toxicol. 2009 Jun;5(6):675-82. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/19442033 # Scarpignato C, Pelosini I: Rifaximin, a poorly absorbed antibiotic: pharmacology and clinical potential. Chemotherapy. 2005;51 Suppl 1:36-66. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/15855748 # Gillis JC, Brogden RN: Rifaximin. A review of its antibacterial activity, pharmacokinetic properties and therapeutic potential in conditions mediated by gastrointestinal bacteria. Drugs. 1995 Mar;49(3):467-84. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/7774516 # Koo HL, Dupont HL, Huang DB: The role of rifaximin in the treatment and chemoprophylaxis of travelers' diarrhea. Ther Clin Risk Manag. 2009;5:841-8. Epub 2009 Nov 2. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/19898648 # DuPont HL: Systematic review: prevention of travellers' diarrhoea. Aliment Pharmacol Ther. 2008 May;27(9):741-51. Epub 2008 Feb 14. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/18284650 # Romero-Gomez M: Pharmacotherapy of hepatic encephalopathy in cirrhosis. Expert Opin Pharmacother. 2010 Jun;11(8):1317-27. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/20384539 # Scarpignato C, Pelosini I: Experimental and clinical pharmacology of rifaximin, a gastrointestinal selective antibiotic. Digestion. 2006;73 Suppl 1:13-27. Epub 2006 Feb 8. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/16498249 # Pimentel M: Review of rifaximin as treatment for SIBO and IBS. Expert Opin Investig Drugs. 2009 Mar;18(3):349-58. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/19243285
n3:group
approved investigational
n3:halfLife
Approximately 6 hours.
n3:indication
For the treatment of patients (≥12 years of age) with travelers' diarrhea caused by noninvasive strains of <i>Escherichia coli</i>. Rifaximin is also designated an orphan drug by the Food and Drug Administration for the adjunctive treatment of hepatic encephalopathy to reduce blood ammonia concentrations and decrease severity of neurological manifestations.
owl:sameAs
n19:DB01220 n20:DB01220
dcterms:title
Rifaximin
adms:identifier
n9:PA164752443 n10:Rifaximin n21:DB01220 n22:D02554 n23:4940837 n24:6436173 n25:46508705 n27:65649-301-03
n3:mechanismOfAction
Rifaximin acts by inhibiting RNA synthesis in susceptible bacteria by binding to the beta-subunit of bacterial deoxyribonucleic acid (DNA)-dependent ribonucleic acid (RNA) polymerase enzyme. This results in the blockage of the translocation step that normally follows the formation of the first phosphodiester bond, which occurs in the transcription process.
n3:packager
n29:271B58A5-363D-11E5-9242-09173F13E4C5 n29:271B58A6-363D-11E5-9242-09173F13E4C5 n29:271B58A3-363D-11E5-9242-09173F13E4C5 n29:271B58A4-363D-11E5-9242-09173F13E4C5
n3:patent
n7:7045620
n3:routeOfElimination
In a mass balance study, after administration of 400 mg 14C-rifaximin orally to healthy volunteers, of the 96.94% total recovery, 96.62% of the administered radioactivity was recovered in feces almost exclusively as the unchanged drug and 0.32% was recovered in urine mostly as metabolites with 0.03% as the unchanged drug.Rifaximin accounted for 18% of radioactivity in plasma. This suggests that the absorbed rifaximin undergoes metabolism with minimal renal excretion of the unchanged drug
n3:synonym
Xifaxsan Rifamycin L 105SV Rifaximinum Rifaxidin Rifaximinun Rifaximina Rifaximin Rifamycin L 105 Rifaximine
n3:toxicity
LD<sub>50</sub> > 2 g/kg (orally, in rats)
n3:synthesisReference
Giuseppe Viscomi, Manuela Campana, Dario Braga, Donatella Confortini, Vincenzo Cannata, Paolo Righi, Goffredo Rosini, "Polymorphic forms of rifaximin, processes for their production and uses thereof." U.S. Patent US20050272754, issued December 08, 2005.
n13:hasConcept
n14:M0126046
foaf:page
n16:rifaximin.html n26:xif1703.shtml n28:xifaxan.htm
n3:IUPAC-Name
n4:271B58AF-363D-11E5-9242-09173F13E4C5
n3:InChI
n4:271B58B5-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n4:271B58B4-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n4:271B58B1-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n4:271B58B2-363D-11E5-9242-09173F13E4C5
n3:SMILES
n4:271B58B3-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n4:271B58AD-363D-11E5-9242-09173F13E4C5
n3:logP
n4:271B58AB-363D-11E5-9242-09173F13E4C5 n4:271B58AE-363D-11E5-9242-09173F13E4C5 n4:271B58C5-363D-11E5-9242-09173F13E4C5
n3:logS
n4:271B58AC-363D-11E5-9242-09173F13E4C5
n5:hasATCCode
n6:D06AX11 n6:A07AA11
n3:H-Bond-Acceptor-Count
n4:271B58BB-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n4:271B58BC-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n4:271B58B6-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n4:271B58B7-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n4:271B58B9-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n4:271B58B8-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n4:271B58BA-363D-11E5-9242-09173F13E4C5
n3:absorption
Low absorption in both the fasting state and when administered within 30 minutes of a high-fat breakfast.
n3:affectedOrganism
Enteric bacteria and other eubacteria
n3:casRegistryNumber
80621-81-4
n3:category
n3:containedIn
n17:271B58A7-363D-11E5-9242-09173F13E4C5 n17:271B58A8-363D-11E5-9242-09173F13E4C5
n3:Bioavailability
n4:271B58C1-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n4:271B58C3-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n4:271B58C4-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n4:271B58C0-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n4:271B58BF-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n4:271B58C2-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n4:271B58B0-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-acidic-
n4:271B58BD-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
n4:271B58BE-363D-11E5-9242-09173F13E4C5