- Molecular NameClarithromycin
- SynonymCLA; Clarithromycine; Clathromycin
- Weight747.964
- Drugbank_IDDB01211
- ACS_NO81103-11-9
- Show 2D model
- LogP (experiment)3.16
- LogP (predicted, AB/LogP v2.0)3.2
- pka8.99
- LogD (pH=7, predicted)1.65
- Solubility (experiment)0.33 mg/L
- LogS (predicted, ACD/Labs)(ph=7)-0.22
- LogSw (predicted, AB/LogsW2.0)0.39
- Sw (mg/ml) (predicted, ACD/Labs)36.82
- No.of HBond Donors4
- No.of HBond Acceptors14
- No.of Rotatable Bonds8
- TPSA182.91
- StatusFDA approved
- AdministrationN/A
- PharmacologyA macrolide antibiotic used to treat pharyngitis, tonsillitis, acute maxillary sinusitis, acute bacterial exacerbation of chronic bronchitis, pneumonia (especially atypical pneumonias associated with Chlamydia pneumoniae or TWAR),
- Absorption_valueN/A
- Absorption (description)Clarithromycin is rapidly absorbed from the gastro-intestinal tract after oral administration with a bioavailability of about 55%.
- Caco_2N/A
- Bioavailability55.0
- Protein binding46.0
- Volume of distribution (VD)2.6 L/kg
- Blood/Plasma Partitioning ratio (D_blood)N/A
- MetabollsmIt undergoes first-pass metabolism. Pharmacokinetics are non-linear and dose dependent with high doses producing disproportionate increases in plasma concentrations owing to saturation of metabolic pathways. Widely distributed and tissue concentrations exceed plasma concentrations. Readily enters leukocytes and macrophages. It is distributed into breast milk. Undergoes extensive metabolism in the liver by demethylation, hydroxylation and hydrolysis. The principal metabolite is 14-hydroxyclarithromycin and this also has antibacterial activity.
- Half life3.3 h
- ExcretionAt steady state, about 20% and 30%, respectively of a 250 mg or 500 mg dose is excreted in the urine as unchanged drug. Excretion in urine and faeces occurs in a dose-dependent manner: at low doses the two fractions are similar; at high doses urinary excretion is predominant. Not significantly removed by haemodialysis or peritoneal dialysis.
- Urinary Excretion36
- Clerance7.3 ml/min/kg
- ToxicitySymptoms of toxicity include diarrhea, nausea, abnormal taste, dyspepsia, and abdominal discomfort. 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 occurred. Rare cases of severe hepatic dysfunctions also have been reported. Hepatic failure is usually reversible, but fatalities have been reported.
- LD50 (rat)N/A
- LD50 (mouse)N/A