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Namespace Prefixes

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Statements

Subject Item: n2:DB00560
rdf:type: n3:Drug
n3:description: Tigecycline is a glycylcycline antibiotic developed and marketed by Wyeth under the brand name Tygacil. It was given a U.S. Food and Drug Administration (FDA) fast-track approval and was approved on June 17, 2005. It was developed in response to the growing prevalence of antibiotic resistance in bacteria such as Staphylococcus aureus.
n3:dosage: n28:271B47AE-363D-11E5-9242-09173F13E4C5 n28:271B47AF-363D-11E5-9242-09173F13E4C5 n28:271B47B0-363D-11E5-9242-09173F13E4C5
n3:generalReferences: # Rose WE, Rybak MJ: Tigecycline: first of a new class of antimicrobial agents. Pharmacotherapy. 2006 Aug;26(8):1099-110. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/16863487 # Kasbekar N: Tigecycline: a new glycylcycline antimicrobial agent. Am J Health Syst Pharm. 2006 Jul 1;63(13):1235-43. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/16790575
n3:group: approved
n3:halfLife: 27-43 hours
n3:indication: For the treatment of infections caused by susceptible strains of the designated microorganisms in the following conditions: Complicated skin and skin structure infections caused by Escherichia coli, Enterococcus faecalis (vancomycin-susceptible isolates only), Staphylococcus aureus (methicillin-susceptible and -resistant isolates), Streptococcus agalactiae, Streptococcus anginosus grp. (includes S. anginosus, S. intermedius, and S. constellatus), Streptococcus pyogenes and Bacteroides fragilis. Complicated intra-abdominal infections caused by Citrobacter freundii, Enterobacter cloacae, Escherichia coli, Klebsiella oxytoca, Klebsiella pneumoniae, Enterococcus faecalis (vancomycin-susceptible isolates only), Staphylococcus aureus (methicillin-susceptible isolates only), Streptococcus anginosus grp. (includes S. anginosus, S. intermedius, and S. constellatus), Bacteroides fragilis, Bacteroides thetaiotaomicron, Bacteroides uniformis, Bacteroides vulgatus, Clostridium perfringens, and Peptostreptococcus micros.
n3:manufacturer: n5:271B47AD-363D-11E5-9242-09173F13E4C5
owl:sameAs: n7:DB00560 n19:DB00560
dcterms:title: Tigecycline
adms:identifier: n10:46509041 n11:D01079 n12:5282044 n13:DB00560 n14:C12012 n15:149836 n16:4445273 n23:Tigecycline n26:PA164746412
n3:mechanismOfAction: Tigecycline, a glycylcycline, inhibits protein translation in bacteria by binding to the 30S ribosomal subunit and blocking entry of amino-acyl tRNA molecules into the A site of the ribosome. This prevents incorporation of amino acid residues into elongating peptide chains. Tigecycline carries a glycylamido moiety attached to the 9-position of minocycline. The substitution pattern is not present in any naturally occurring or semisynthetic tetracycline and imparts certain microbiologic properties to tigecycline. Tigecycline is not affected by the two major tetracycline resistance mechanisms, ribosomal protection and efflux. Accordingly, tigecycline has demonstrated in vitro and in vivo activity against a broad spectrum of bacterial pathogens. There has been no cross resistance observed between tigecycline and other antibiotics. Tigecycline is not affected by resistance mechanisms such as beta-lactamases (including extended spectrum beta-lactamases), target site modifications, macrolide efflux pumps or enzyme target changes (e.g. gyrase/topoisomerase). In vitro studies have not demonstrated antagonism between tigecycline and other commonly used antibacterial drugs. In general, tigecycline is considered bacteriostatic.
n3:packager: n5:271B47AB-363D-11E5-9242-09173F13E4C5 n5:271B47AC-363D-11E5-9242-09173F13E4C5 n5:271B47AA-363D-11E5-9242-09173F13E4C5
n3:patent: n27:RE40086 n27:RE40183 n27:2079692
n3:synonym: Tigeciclina (4S,4AS,5ar,12as)-9-(2-(tert-butylamino)acetamido)-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide Tigecyclinum Tigecycline
n3:toxicity: Since glycylcyclines are similar to tetracyclines, they share many of the same side effects and contraindications as tetracyclines. These side effects may include nausea/vomiting, headache, photosensitivity, discoloration of growing teeth, and fetal damage.
n17:hasAHFSCode: n22:08-12-24
n3:proteinBinding: 71% to 89%
n3:synthesisReference: Mahdi Fawzi, Tianmin Zhu, Syed Shah, "Tigecycline compositons and methods of preparation." U.S. Patent US20060247181, issued November 02, 2006.
n20:hasConcept: n21:M0305009
foaf:page: n25:tygacil.htm n29:tigecycline.html
n3:IUPAC-Name: n4:271B47B5-363D-11E5-9242-09173F13E4C5
n3:InChI: n4:271B47BB-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula: n4:271B47BA-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight: n4:271B47B7-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight: n4:271B47B8-363D-11E5-9242-09173F13E4C5
n3:SMILES: n4:271B47B9-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility: n4:271B47B3-363D-11E5-9242-09173F13E4C5
n3:logP: n4:271B47B4-363D-11E5-9242-09173F13E4C5 n4:271B47CB-363D-11E5-9242-09173F13E4C5 n4:271B47B1-363D-11E5-9242-09173F13E4C5
n3:logS: n4:271B47B2-363D-11E5-9242-09173F13E4C5
n17:hasATCCode: n18:J01AA12
n3:H-Bond-Acceptor-Count: n4:271B47C1-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count: n4:271B47C2-363D-11E5-9242-09173F13E4C5
n3:InChIKey: n4:271B47BC-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-: n4:271B47BD-363D-11E5-9242-09173F13E4C5
n3:Polarizability: n4:271B47BF-363D-11E5-9242-09173F13E4C5
n3:Refractivity: n4:271B47BE-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count: n4:271B47C0-363D-11E5-9242-09173F13E4C5
n3:affectedOrganism: Enteric bacteria and other eubacteria
n3:casRegistryNumber: 220620-09-7
n3:category
n3:Bioavailability: n4:271B47C7-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter: n4:271B47C9-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule: n4:271B47CA-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings: n4:271B47C6-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge: n4:271B47C5-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five: n4:271B47C8-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name: n4:271B47B6-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-acidic-: n4:271B47C3-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-: n4:271B47C4-363D-11E5-9242-09173F13E4C5