SKU: T015  / 
    CAS Number: 191114-48-4

    Telithromycin

    ₩478,772.25
    Telithromycin
    • Detailed Description

      CAS Number: 191114-48-4

      Molecular Formula: C43H65N5O10

      Molecular Weight: 812.00

      Mechanism of Action: Telithromycin is a very effective inhibitor of the translation function at the level of the 50S ribosomal subunit. It has been shown that 14‐ and 15‐membered ring macrolides are also able to inhibit a second cellular function, the assembly of the nascent 50S ribosomal subunit. Telithromycin, in addition, like many carbamate ketolides, is also able to inhibit the formation of the 30S ribosomal subunit.

      23S rRNA is composed of six domains. Domains V and II belong partly to the peptidyl transferase site, and erythromycin A interacts mainly with domain V.

      Telithromycin, like 14‐ and 15‐membered ring macrolides, interacts with the bacterial 23S rRNA. Interactions are limited to a region of domain V and additionally, for telithromycin, to domain II. The interaction with the 750 loop (position A‐752) of domain II is due to the C11–C12 carbamate chain.

      Storage Conditions: 2-8°C

      Tariff Code: 2941.90.3000

    • Applications

      Spectrum: Telithromycin shows activity against Gram-positive and Gram-negative bacteria, as well as mycoplasma. More specifically, Telithromycin retains its activity against erm-(MLS(B)) or mef-mediated macrolide-resistant Streptococcus pneumoniae and Streptococcus pyogenes and against Staphylococcus aureus resistant to macrolides through inducible MLS(B) mechanisms. Telithromycin also possesses high activity against the Gram-negative pathogens Haemophilus influenzae and Moraxella catarrhalis, regardless of beta-lactamase production. In vitro, it shows similar activity to azithromycin against H. influenzae, while in vivo its activity against H. influenzae is higher than that of azithromycin. Telithromycin's spectrum of activity also extends to the atypical, intracellular and cell-associated pathogens Legionella pneumophila, Mycoplasma pneumoniae and Chlamydia pneumoniae.

      Microbiology Applications: Telithromycin is commonly used in clinical in vitro microbiological antimicrobial susceptibility tests (panels, discs, and MIC strips) against gram positive microbial isolates. Medical microbiologists use AST results to recommend antibiotic treatment options.  Representative MIC values include:

      • Streptococcus pneumoniae 0.003 µg/mL – 0.5 µg/mL
      • Streptococcus pyogenes 0.015 µg/mL - 4 µg/mL
      • For a representative list of Telithromycin MIC values, click here.

    • Specifications

      Appearance: White or off-white crystalline powder

      Source: Semi-synthetic

    • Technical Data

      Solubility: Sparingly soluble in water.

    • References

      References:

      Ackermann G and  Rodloff AC (2003) Drugs of the 21st century: telithromycin (HMR 3647) - the first ketolide:  J. Antimicrob. Chemother. 51:497

      Araujo FG et al (1997) The ketolide antibiotics HMR-3647 and HMR 3004 are active against Toxoplasma gondii in vitro and in murine models of infection: Antimicrob. Agents Chemother. 41:2137

      Boswell FJ (1998)  The in vitro activity of HMR 3647, a new ketolide antimicrobial agent: J. Antimicrob. Chemother. 42:703

      Byoungduck P and Yu M (2015)  Hong-inducible expression of erm(B) by the ketolides telithromycin and cethromycin.  Int. J. Antimicrob. Agents 46:226

      Douthwaite S and Champney WS (2001)  Structures of ketolides and macrolides determine their mode of interaction with the ribosomal target site. J. Antimicrob. Chemother. 48 (Topic T1):1-8

      Fogarty CM et al (1006)  Telithromycin in the treatment of pneumococcal community-acquired respiratory tract infections: A review.  Int. J. Infect. Dis. 10 136

      Felmingham D, Zhanel G and Hoban D (2001)  Activity of the ketolide antibacterial telithromycin against typical community-acquired respiratory pathogens. J. Antimicrob. Ther.  48(Topic T1), 33-42

      Hansen LH, Mauvais, P and Douthwaite S (1999)  The macrolide-ketolide antibiotic binding site is formed by structures in domains II and V of 23S ribosomal RNA. Molecular Microbiol 31(2):623-631

      Lee JH, et al (2008)  Time-dependent effects of Klebsiella pneumonia endotoxin on the Telithromycin pharmacokinetics in rats; Restoration of the parameters in 96-hour KPLPS rats to the control levels: Pulm. Pharmacol. Ther. 21:860

      Lonks JR and Goldmann DA  (2005)  Telithromycin: A ketolide antibiotic for treatment of respiratory tract infections.  Clin. Inf. Dis. 40:1657

      Lovmar M and Tenson T (2003)  The mechanism of action of macrolides, lincosamides and streptogramin B reveals the nascent peptide exit path in the ribosome. J. Molec. Micro. 330(5):1005-1014

      Monaghan R and  Barrett JF (2008)  Benefit-risk assessment of Telithromycin in the treatment of community-acquired pneumonia: S.D. Brown; Drug Safety 31:561

      Wellington K and Noble S (2004)  Telithromycin Drugs 64:1683

      Zeitlinger M et al (2009)  Ketolides - the modern relatives of macrolides: The pharmacokinetic perspective.  Clin. Pharmacokinet. 48:23

      Vimberg V et al (2015)  ClpP-independent function of ClpX interferes with Telithromycin resistance conferred by msr(A) in Staphylococcus aureus. Antimicrob. Agents Chemother. 59:3611

       

    Telithromycin (Ketek, HMR 3647, RU 66647) is a semisynthetic antibacterial agent belonging to a class of compounds called ketolides, which are a variation on the existing class of antibiotics known as macrolides like erythromycin, whose structure includes a 14-molecule ring. Telithromycin was developed by the French pharmaceutical company Roussel Uclaf S.A., prior to 1997. 

    Telithromycin appears to be effective against macrolide-resistant Streptococcus pneumoniae. The defining differentiating characteristic of the ketolides, as opposed to other macrolides, is the removal of the neutral sugar, L-cladinose from the 3-position of the macrolide ring and the subsequent oxidation of the 3-hydroxyl to a 3-keto functional group.

    Telithromycin shows activity against Gram-positive and Gram-negative bacteria, as well as mycoplasma.  Telithromycin is a bacterial protein synthesis inhibitor that interacts with peptidyl transferase site of the 50S ribosomal subunit.  The main binding sites are with domains II and V of the 23S rRNA.

    Telithromycin is sparingly soluble in water and has a solubility of approximately 30mg/ml in organic solvents such as DMSO, ethanol, and dimethyl formamide (should be purged with inert gas).

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

    CAS Number: 191114-48-4

    Molecular Formula: C43H65N5O10

    Molecular Weight: 812.00

    Mechanism of Action: Telithromycin is a very effective inhibitor of the translation function at the level of the 50S ribosomal subunit. It has been shown that 14‐ and 15‐membered ring macrolides are also able to inhibit a second cellular function, the assembly of the nascent 50S ribosomal subunit. Telithromycin, in addition, like many carbamate ketolides, is also able to inhibit the formation of the 30S ribosomal subunit.

    23S rRNA is composed of six domains. Domains V and II belong partly to the peptidyl transferase site, and erythromycin A interacts mainly with domain V.

    Telithromycin, like 14‐ and 15‐membered ring macrolides, interacts with the bacterial 23S rRNA. Interactions are limited to a region of domain V and additionally, for telithromycin, to domain II. The interaction with the 750 loop (position A‐752) of domain II is due to the C11–C12 carbamate chain.

    Storage Conditions: 2-8°C

    Tariff Code: 2941.90.3000

    Spectrum: Telithromycin shows activity against Gram-positive and Gram-negative bacteria, as well as mycoplasma. More specifically, Telithromycin retains its activity against erm-(MLS(B)) or mef-mediated macrolide-resistant Streptococcus pneumoniae and Streptococcus pyogenes and against Staphylococcus aureus resistant to macrolides through inducible MLS(B) mechanisms. Telithromycin also possesses high activity against the Gram-negative pathogens Haemophilus influenzae and Moraxella catarrhalis, regardless of beta-lactamase production. In vitro, it shows similar activity to azithromycin against H. influenzae, while in vivo its activity against H. influenzae is higher than that of azithromycin. Telithromycin's spectrum of activity also extends to the atypical, intracellular and cell-associated pathogens Legionella pneumophila, Mycoplasma pneumoniae and Chlamydia pneumoniae.

    Microbiology Applications: Telithromycin is commonly used in clinical in vitro microbiological antimicrobial susceptibility tests (panels, discs, and MIC strips) against gram positive microbial isolates. Medical microbiologists use AST results to recommend antibiotic treatment options.  Representative MIC values include:

    • Streptococcus pneumoniae 0.003 µg/mL – 0.5 µg/mL
    • Streptococcus pyogenes 0.015 µg/mL - 4 µg/mL
    • For a representative list of Telithromycin MIC values, click here.

    Appearance: White or off-white crystalline powder

    Source: Semi-synthetic

    Solubility: Sparingly soluble in water.

    References:

    Ackermann G and  Rodloff AC (2003) Drugs of the 21st century: telithromycin (HMR 3647) - the first ketolide:  J. Antimicrob. Chemother. 51:497

    Araujo FG et al (1997) The ketolide antibiotics HMR-3647 and HMR 3004 are active against Toxoplasma gondii in vitro and in murine models of infection: Antimicrob. Agents Chemother. 41:2137

    Boswell FJ (1998)  The in vitro activity of HMR 3647, a new ketolide antimicrobial agent: J. Antimicrob. Chemother. 42:703

    Byoungduck P and Yu M (2015)  Hong-inducible expression of erm(B) by the ketolides telithromycin and cethromycin.  Int. J. Antimicrob. Agents 46:226

    Douthwaite S and Champney WS (2001)  Structures of ketolides and macrolides determine their mode of interaction with the ribosomal target site. J. Antimicrob. Chemother. 48 (Topic T1):1-8

    Fogarty CM et al (1006)  Telithromycin in the treatment of pneumococcal community-acquired respiratory tract infections: A review.  Int. J. Infect. Dis. 10 136

    Felmingham D, Zhanel G and Hoban D (2001)  Activity of the ketolide antibacterial telithromycin against typical community-acquired respiratory pathogens. J. Antimicrob. Ther.  48(Topic T1), 33-42

    Hansen LH, Mauvais, P and Douthwaite S (1999)  The macrolide-ketolide antibiotic binding site is formed by structures in domains II and V of 23S ribosomal RNA. Molecular Microbiol 31(2):623-631

    Lee JH, et al (2008)  Time-dependent effects of Klebsiella pneumonia endotoxin on the Telithromycin pharmacokinetics in rats; Restoration of the parameters in 96-hour KPLPS rats to the control levels: Pulm. Pharmacol. Ther. 21:860

    Lonks JR and Goldmann DA  (2005)  Telithromycin: A ketolide antibiotic for treatment of respiratory tract infections.  Clin. Inf. Dis. 40:1657

    Lovmar M and Tenson T (2003)  The mechanism of action of macrolides, lincosamides and streptogramin B reveals the nascent peptide exit path in the ribosome. J. Molec. Micro. 330(5):1005-1014

    Monaghan R and  Barrett JF (2008)  Benefit-risk assessment of Telithromycin in the treatment of community-acquired pneumonia: S.D. Brown; Drug Safety 31:561

    Wellington K and Noble S (2004)  Telithromycin Drugs 64:1683

    Zeitlinger M et al (2009)  Ketolides - the modern relatives of macrolides: The pharmacokinetic perspective.  Clin. Pharmacokinet. 48:23

    Vimberg V et al (2015)  ClpP-independent function of ClpX interferes with Telithromycin resistance conferred by msr(A) in Staphylococcus aureus. Antimicrob. Agents Chemother. 59:3611