Chemical Property of Clarithromycin
Chemical Property:
- Appearance/Colour:Colourless crystalline needles
- Vapor Pressure:5.06E-30mmHg at 25°C
- Melting Point:217-220 °C
- Refractive Index:-92 ° (C=1, CHCl3)
- Boiling Point:805.478 °C at 760 mmHg
- PKA:pKa 8.99(H2O t=25.0 I=0.167) (Uncertain)
- Flash Point:440.937 °C
- PSA：182.91000
- Density:1.184 g/cm3
- LogP:2.43970
- Storage Temp.:-20°C Freezer
- Solubility.:Soluble in DMSO
- Water Solubility.:99.48mg/L(20 oC)
- XLogP3:3.2
- Hydrogen Bond Donor Count:4
- Hydrogen Bond Acceptor Count:14
- Rotatable Bond Count:8
- Exact Mass:747.47689126
- Heavy Atom Count:52
- Complexity:1190
- Purity/Quality:
-
99% up *data from raw suppliers
Clarithromycin *data from reagent suppliers
Safty Information:
- Pictogram(s):
Xn， 
Xi
- Hazard Codes:Xn,Xi
- Statements:
22-36/37/38
- Safety Statements:
26-36-60
- MSDS Files:
-
SDS file from LookChem
Useful:
- Drug Classes:Antiinfective Agents
- Canonical SMILES:CCC1C(C(C(C(=O)C(CC(C(C(C(C(C(=O)O1)C)OC2CC(C(C(O2)C)O)(C)OC)C)OC3C(C(CC(O3)C)N(C)C)O)(C)OC)C)C)O)(C)O
- Isomeric SMILES:CC[C@@H]1[C@@]([C@@H]([C@H](C(=O)[C@@H](C[C@@]([C@@H]([C@H]([C@@H]([C@H](C(=O)O1)C)O[C@H]2C[C@@]([C@H]([C@@H](O2)C)O)(C)OC)C)O[C@H]3[C@@H]([C@H](C[C@H](O3)C)N(C)C)O)(C)OC)C)C)O)(C)O
- Recent ClinicalTrials:Recurrence Rate Comparison Between Esomeprazole and Lansoprazole in Eradicating Helicobacter Pylori Infection Among Children
- Recent EU Clinical Trials:A RANDOMIZED CLINICAL TRIAL OF ORAL CLARITHROMYCIN IN COMMUNITY-ACQUIRED PNEUMONIA TO ATTENUATE INFLAMMATORY RESPONSES AND IMPROVE OUTCOMES (THE ACCESS TRIAL)
- Recent NIPH Clinical Trials:CAM (Clarithromycin) Effectivity for COVID-19 pneumonia which does not require oxygen administration; multicenter, randomized-controlled, open-label, 3-armed parallel group comparison, exploratory trial
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Chemical Structure
Clarithromycin, derived from erythromycin, contains a 14-membered macrocyclic lactone ring, similar to erythromycin and roxithromycin. In contrast, azithromycin contains a 15-membered macrocyclic ring.
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Mechanism of Action
Clarithromycin binds to the 50S bacterial ribosomal subunit of H. pylori, inhibiting protein synthesis and exerting a bacteriostatic effect. Resistance to clarithromycin arises from specific point mutations in the peptidyl transferase region of the bacterial 23S ribosomal RNA.
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Indications and Usage
Clarithromycin is a macrolide antibiotic commonly used to treat atypical pneumonia and infections caused by Helicobacter pylori. It acts as a strong inhibitor of the hepatic statin uptake transporters OATP1B1 and OATP1B3.
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Treatment of Helicobacter pylori Infections
Helicobacter pylori is a bacteria responsible for gastric conditions like gastritis, peptic ulcers, and gastric carcinoma. Clarithromycin has been a key component of H. pylori treatment due to its low minimal inhibitory concentration (MIC) and good mucosal diffusion. However, the efficacy of triple therapy involving clarithromycin is declining due to bacterial resistance.
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Antibiotic Resistance
Resistance to clarithromycin in H. pylori is caused by specific mutations in the 23S ribosomal RNA. This antibiotic resistance is recognized as a global health issue by organizations like the World Health Organization (WHO).
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Clinical Considerations
Clinicians must carefully manage drug interactions and antibiotic resistance when prescribing clarithromycin, particularly in the context of H. pylori eradication and concurrent statin therapy.
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Drug-Drug Interactions
Clarithromycin interacts with statins, affecting their metabolism. Strategies to manage these interactions include avoiding co-administration of certain statins (atorvastatin, lovastatin, simvastatin), considering dose adjustments or alternative antibiotics for other statins (pitavastatin, pravastatin), and cautious use of pravastatin with dose limitation.
