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Clarithromycin

Catalog No. C9742 Name Sigma Aldrich
CAS Number 81103-11-9 Website http://www.sigmaaldrich.com
M. F. C38H69NO13 Telephone 1-800-521-8956
M. W. 747.95336 Fax
Purity ≥95% (HPLC) Email
Storage Chembase ID: 153977

SYNONYMS

IUPAC name
(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-14-ethyl-12,13-dihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-7-methoxy-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecane-2,10-dione
IUPAC Traditional name
clarithromycin

DATABASE IDS

MDL Number MFCD00865140
CAS Number 81103-11-9

PROPERTIES

Empirical Formula (Hill Notation) C38H69NO13
Purity ≥95% (HPLC)
Suitability suitable for 1694 per US EPA
GHS Pictograms GHS07
GHS Signal Word Warning
GHS Hazard statements H302
European Hazard Symbols Harmful Harmful (Xn)
MSDS Link Download
Personal Protective Equipment dust mask type N95 (US), Eyeshields, Gloves
Risk Statements 22
RTECS KF4997000
German water hazard class 3

DETAILS

Description (English)
Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
Clarithromycin is a macrolide antibiotic. It prevents bacterial growth by interfering with protein synthesis. Clarithromycin is an acid-stable version of erythromycin and is particularly effective against gram-negative bacteria.3 It has a short half-life4, however its metabolite, 14-hydroxy clarithromycin is nearly twice as active as clarithromycin against certain bacteria.5
Clarithromycin inhibits bacterial protein synthesis by binding to the bacterial 50S ribosomal subunit. Binding inhibits peptidyl transferase activity and interferes with amino acid translocation. Clarithromycin is first metabolized to 14-OH clarithromycin, which is active and works synergistically with its parent compound. Clarithromycin penetrates the bacteria cell wall and reversibly binds to domain V of the 23S ribosomal RNA of the 50S subunit of the bacterial ribosome, blocking translocation of aminoacyl transfer-RNA and polypeptide synthesis. Clarithromycin also inhibits the hepatic microsomal CYP3A4 isoenzyme and P-glycoprotein, an energy-dependent drug efflux pump.
Application
Clarithromycin is a semisynthetic macrolide antibiotic that is derived from erythromycin. Clarithromycin may be bacteriostatic or bactericidal depending on the organism and drug concentration . Clarithromycin may be used to attenuate cardiac transplantation rejection via matrix metalloproteinase suppression1. Clarithromycin has been used to study inflammatory markers in chronic obstructive pulmonary disease (COPD)2. It is used to study bacterial protein synthesis and peptide translation.
Description (简体中文)
Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
Clarithromycin is a macrolide antibiotic. It prevents bacterial growth by interfering with protein synthesis. Clarithromycin is an acid-stable version of erythromycin and is particularly effective against gram-negative bacteria.3 It has a short half-life4, however its metabolite, 14-hydroxy clarithromycin is nearly twice as active as clarithromycin against certain bacteria.5
Clarithromycin inhibits bacterial protein synthesis by binding to the bacterial 50S ribosomal subunit. Binding inhibits peptidyl transferase activity and interferes with amino acid translocation. Clarithromycin is first metabolized to 14-OH clarithromycin, which is active and works synergistically with its parent compound. Clarithromycin penetrates the bacteria cell wall and reversibly binds to domain V of the 23S ribosomal RNA of the 50S subunit of the bacterial ribosome, blocking translocation of aminoacyl transfer-RNA and polypeptide synthesis. Clarithromycin also inhibits the hepatic microsomal CYP3A4 isoenzyme and P-glycoprotein, an energy-dependent drug efflux pump.
Application
Clarithromycin is a semisynthetic macrolide antibiotic that is derived from erythromycin. Clarithromycin may be bacteriostatic or bactericidal depending on the organism and drug concentration . Clarithromycin may be used to attenuate cardiac transplantation rejection via matrix metalloproteinase suppression1. Clarithromycin has been used to study inflammatory markers in chronic obstructive pulmonary disease (COPD)2. It is used to study bacterial protein synthesis and peptide translation.

REFERENCES