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QuickView for Clarithromycin (compound)


PubChem
Name: Clarithromycin
PubChem Compound ID: 10147055
Description: A semisynthetic macrolide antibiotic derived from ERYTHROMYCIN that is active against a variety of microorganisms. It can inhibit protein synthesis in bacteria by reversibly binding to the 50S ribosomal subunits. This inhibits the translocation of aminoacyl transfer-RNA and prevents peptide chain elongation.
Molecular formula: C38H69NO13
Molecular weight: 747.953 g/mol
DrugBank
Identification
Name: Clarithromycin
Name (isomeric): DB01211
Drug Type: small molecule
Description: A semisynthetic macrolide antibiotic derived from ERYTHROMYCIN that is active against a variety of microorganisms. It can inhibit protein synthesis in bacteria by reversibly binding to the 50S ribosomal subunits. This inhibits the translocation of aminoacyl transfer-RNA and prevents peptide chain elongation.
Synonyms:
Clathromycin; CLA; Clarithromycine
Brand: Veclam, Biaxin, Zeclar, Klaricid, Klacid, Biaxin XL, Naxy, Macladin
Category: Protein Synthesis Inhibitors, Anti-Bacterial Agents, Other Macrolides, Macrolides
CAS number: 81103-11-9
Pharmacology
Indication: An alternative medication for the treatment of acute otitis media caused by <i>H. influenzae, M. catarrhalis, or S. pneumoniae</i> in patients with a history of type I penicillin hypersensitivity. Also for the treatment of pharyngitis and tonsillitis caused by susceptible <i>Streptococcus pyogenes</i>, as well as respiratory tract infections including acute maxillary sinusitis, acute bacterial exacerbations of chronic bronchitis, mild to moderate community-acquired pneuomia, Legionnaires' disease, and pertussis. Other indications include treatment of uncomplicated skin or skin structure infections, helicobacter pylori infection, duodenal ulcer disease, bartonella infections, early Lyme disease, and encephalitis caused by <i>Toxoplasma gondii</i> (in HIV infected patients in conjunction with pyrimethamine). Clarithromycin may also decrease the incidence of cryptosporidiosis, prevent the occurence of α-hemolytic (viridans group) streptococcal endocarditis, as well as serve as a primary prevention for <i>Mycobacterium avium</i> complex (MAC) bacteremia or disseminated infections (in adults, adolescents, and children with advanced HIV infection).
Pharmacology:
Clarithromycin is a macrolide antibiotic whose spectrum of activity includes many gram-positive (Staphylococcus aureus, S. pneumoniae, and S. pyogenes) and gram-negative aerobic bacteria (Haemophilus influenzae, H. parainfluenzae, and Moraxella catarrhalis), many anaerobic bacteria, some mycobacteria, and some other organisms includin...
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Mechanism of Action:
Clarithromycin is first metabolized to 14-OH clarithromycin, which is active and works synergistically with its parent compound. Like other macrolides, it then penetrates 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 pol...
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Absorption: Clarithromycin is well-absorbed, acid stable and may be taken with food.
Protein binding: ~ 70% protein bound
Biotransformation: Hepatic - predominantly metabolized by CYP3A4 resulting in numerous drug interactions.
Route of elimination: After a 250 mg tablet every 12 hours, approximately 20% of the dose is excreted in the urine as clarithromycin, while after a 500 mg tablet every 12 hours, the urinary excretion of clarithromycin is somewhat greater, approximately 30%.
Half Life: 3-4 hours
Toxicity: Symptoms of toxicity include diarrhea, nausea, abnormal taste, dyspepsia, and abdominal discomfort. Transient hearing loss with high doses has been observed. Pseudomembraneous colitis has been reported with clarithromycin use. Allergic reactions ranging from urticaria and mild skin eruptions to rare cases of anaphylaxis and Stevens-Johnson syndrome have also occurred. Rare cases of severe hepatic dysfunctions also have been reported. Hepatic failure is usually reversible, but fatalities have been reported. Clarithromycin may also cause tooth decolouration which may be removed by dental cleaning. Fetal abnormalities, such as cardiovascular defects, cleft palate and fetal growth retardation, have been observed in animals. Clarithromycin may cause QT prolongation.
Affected organisms: Enteric bacteria and other eubacteria
Interactions
Food interaction:
Biaxin XL - take with a meal, taking it on an empty stomach is associated with total product exposure 30% inferior to that observed when administered with food.
Biaxin - take without regard to meals (however absorption appears to be improved when drug is taken with food).
Drug interaction:
TamoxifenClarithromycin may increase the serum concentration of Tamoxifen by decreasing its metabolism. Monitor for increased adverse/toxic effects of Tamoxifen.
DarunavirIncreased levels of clarithromycin
EletriptanThe macrolide, clarithromycin, may increase the effect and toxicity of eletriptan.
DihydroergotamineRisk of ergotism and severe ischemia with this association
AlprazolamThe macrolide, clarithromycin, may increase the effect of the benzodiazepine, alprazolam.
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