• Tigecycline packaged and labeled.

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SKU: T022

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Description

Tigecycline is a broad spectrum glycylcycline antibiotic which was developed to combat infections caused by many leading multi-drug resistant organisms and approved by the FDA in June 2005. Tigecycline is a semisynthetic derivative of tetracycline, that is structurally similar to minocycline; however, it contains a large glycylamido group at the D-9 position. This substitution is thought to be the reason behind its broad-spectrum activity.

Tigecycline is a protein synthesis inhibitor, that show bacteriostatic activity against both gram-positive bacteria and gram-negative.  It was designed be less affected by the two major tetracycline-resistance mechanisms, ribosomal protection and efflux. Additionally, 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/topoisomerases). However, some ESBL-producing isolates may confer resistance to tigecycline via other resistance mechanisms. Tigecycline resistance in some bacteria (e.g. Acinetobacter calcoaceticus-Acinetobacter baumannii complex) is associated with multi-drug resistant (MDR) efflux pumps.

Tigecycline has recently shown anti-tumor properties and is being evaluated for Tigecycline’s inhibitory effects on several activating signaling pathways and abnormal mitochondrial function in cancer cells.

Tigecycline is soluble in water (0.45mg/mL) and DMSO (>3 mg/mL).

This product is considered a dangerous good. Quantities above 1 g may be subject to additional shipping fees. Please contact us for specific questions. 

    CAS Number

    220620-09-7

    Molecular Formula

    C29H39N5O8

    Molecular Weight

    585.65

    Mechanism of Action

    Tigecycline 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. In general, tigecycline is considered bacteriostatic; however, Tigecycline has demonstrated bactericidal activity against isolates of S. pneumoniae and L. pneumophila.

    Storage Conditions

    -20°C

    Tariff Code

    2941.30.0000

    Spectrum

    Tigecycline has broad spectrum activity against most Gram positive and Gram negative bacteria including multi-drug resistant organisms such as MRSA. Tigecycline has also been found to be effective against carbapenem resistant Enterobacteriaceae or CRE. CRE is a "superbug" which possesses NDM-1 or KPC genes which encode New Delhi Metallo-beta-lacamase or Klebsiella pneumoniae cabapenemase respectively; two enzymes which render nearly all beta-lactam antibiotics useless.

Applications

    Cancer Applications

    An increasing number of studies have emphasized the anti-tumor effects of Tigecycline. The inhibitory effects of tigecycline on cancer depend on activating several signaling pathways and abnormal mitochondrial function in cancer cells. Tigecycline has shown anti-tumor activity against different cancer types, including acute myeloid leukemia (AML), glioma, non-small cell lung cancer (NSCLC), among others.

    Microbiology Applications

    Tigecycline is commonly used in clinical in vitro microbiological antimicrobial susceptibility tests (panels, discs, and MIC strips) against Gram positive and Gram negative microbial isolates. Tigecycline has also shown high potency against high-resistant superbug strains. Medical microbiologists use AST results to recommend antibiotic treatment options for infected patients. Representative MIC values include:

    Staphylococcus aureus (methicillin resistant) 0.03 µg/mL-2 µg/mL

    Streptococcus pneumoniae 0.015 µg/mL – 2 µg/mL

    For a complete list of tigecycline MIC values, click here.

Specifications

    Form

    Powder

    Appearance

    Orange to orange-red colored crystalline powder

    Source

    Semi-synthetic

    Impurity Profile

    Bacterial Endotoxin: ≤1.75 EU/mg

    Water Content (Karl Fischer)

    Not more than 2.0%

    Optical Rotation

    -205° - -230°

    Assay

    (As Is): 98.0-102.0%

    Residue On Ignition

    Not more than 0.1%

    Heavy Metals

    Not more than 20 ppm

    Residual Solvents

    Meets requirements

References

    References

    Da Silva, L. M, et. al.. "Tigecycline: A Review of Properties, Applications, and Analytical Methods." Therapeutic Drug Monitoring 32.3 (2010): 282-88. Web. 10 Apr. 2013.

    Olson, M.W., et al. 2006. Antimicrob. Agents Chemother. 50, 2156.

    Greer, N.D. Tigecycline (Tygacil): The first in the glycylcycline class of antibiotics. Proc.(Bayl.Univ.Med.Cent.) 19, 155-161 (2006).

    Milatovic, D., Schmitz, F.J., Verhoef, J., et al. Activities of the glycylcycline tigecycline (GAR-936) against 1,924 recent European clinical bacterial isolates. Antimicrobial Agents and Chemotherapy 47(1), 400-404 (2003).

    Theriot, C.M., Schumacher, C.A., Bassis, C.M., et al. Effects of tigecycline and vancomycin administration on established Clostridium difficile infection. Antimicrob. Agents Chemother. 59(3), 1596-1604 (2015).

    Stein, G.E., and Craig, W.A., 2006. Clin. Infect Dis. 43, 518.

    Pankey, George A. "Tigecycline." Journal of Antimicrobial Chemotherapy 56.3 (2005): 470-80. Web. 10 Apr. 2013.

    Skrtic, M., et al. 2011. Cancer Cell 20, 674.

    Livermore, D.M., 2005. J. Antimicrob. Chemother. 56, 611.

    Theriot, C.M., Schumacher, C.A., Bassis, C.M., et al. Effects of tigecycline and vancomycin administration on established Clostridium difficile infection. Antimicrob. Agents Chemother. 59(3), 1596-1604 (2015).

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