Clarithromycin

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Clarithromycin
Category Antibiotics
Catalog number BBF-00648
CAS 81103-11-9
Molecular Weight 747.95
Molecular Formula C38H69NO13
Purity >98%

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Description

It is produced by the strain of erythromycin. Clarithromycin, a CYP3A4 inhibitor, is a macrolide antibiotic used to treat pharyngitis, tonsillitis, acute maxillary sinusitis, acute bacterial exacerbation of chronic bronchitis, pneumonia, skin and skin structure infections. It prevents bacteria from growing by interfering with their protein synthesis and binds to the subunit 50S of the bacterial ribosome and thus inhibits the translation of peptides. It has similar antimicrobial spectrum as erythromycin, but is more effective against certain Gram-negative bacteria, particularly Legionella pneumophila. It also has bactericidal effect on certain strains, such as Haemophilus influenzae, Streptococcus pneumoniae and Neisseria gonorrhoeae.

Specification

Synonyms Biaxin; 6-O-Methylerythromycin; Klaricid; Abbott-56268
Storage Store at -20°C
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-oxacyclotetradecane-2,10-dione
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
InChI InChI=1S/C38H69NO13/c1-15-26-38(10,45)31(42)21(4)28(40)19(2)17-37(9,47-14)33(52-35-29(41)25(39(11)12)16-20(3)48-35)22(5)30(23(6)34(44)50-26)51-27-18-36(8,46-13)32(43)24(7)49-27/h19-27,29-33,35,41-43,45H,15-18H2,1-14H3/t19-,20-,21+,22+,23-,24+,25+,26-,27+,29-,30+,31-,32+,33-,35+,36-,37-,38-/m1/s1
InChI Key AGOYDEPGAOXOCK-KCBOHYOISA-N
Source Semi-synthetic

Properties

Appearance Colorless Acicular Crystalline
Application Anti-bacterial agents
Antibiotic Activity Spectrum Gram-negative bacteria
Boiling Point 805.5°C at 760 mmHg
Melting Point 222-225°C
Density 1.18 g/cm3
Solubility Soluble in ethanol, methanol, DMF, DMSO

Reference Reading

1.UHPLC-QTOF MS screening of pharmaceuticals and their metabolites in treated wastewater samples from Athens.
Ibáñez M1, Borova V2, Boix C1, Aalizadeh R2, Bade R1, Thomaidis NS2, Hernández F3. J Hazard Mater. 2016 Mar 29. pii: S0304-3894(16)30302-8. doi: 10.1016/j.jhazmat.2016.03.078. [Epub ahead of print]
After consumption, pharmaceuticals are excreted as parent compounds and/or metabolites in urine and faeces. Some are not completely removed during wastewater treatments, forcing sewage treatment plants (STPs) to apply alternative technologies to guarantee quality of treated water. To monitor the removal efficiency of STPs, not only unchanged compounds and metabolites have to be taken into account, but also formation of possible transformation products (TPs). In this work, QTOF MS has been used for screening metabolites/TPs of pharmaceuticals in effluent wastewater from Athens. A customised database was built with the exact masses of metabolites reported in literature for the parent drugs found in an initial screening. Additionally, TPs identified in previous degradation experiments performed at our laboratory were included. Up to 34 metabolites/TPs were detected for omeprazole, venlafaxine, clindamycin, clarithromycin, clopidogrel or dipyrone, among others.
2.Hybrid Therapy Regimen for Helicobacter Pylori Eradication.
Song ZQ, Liu J, Zhou LY1. Chin Med J (Engl). 2016 20th Apr;129(8):992-999. doi: 10.4103/0366-6999.179803.
OBJECTIVE: Helicobacter pylori (H. pylori) eradication remains a challenge with increasing antibiotic resistance. Hybrid therapy has attracted widespread attention because of initial report with good efficacy and safety. However, many issues on hybrid therapy are still unclear such as the eradication efficacy, safety, compliance, influencing factors, correlation with antibiotic resistance, and comparison with other regimens. Therefore, a comprehensive review on the evidence of hybrid therapy for H. pylori infection was conducted.
3.Isolation of Mycobacterium kumamotonense from a patient with pulmonary infection and latent tuberculosis.
Kontos F1, Mavromanolakis DN, Zande MC, Gitti ZG. Indian J Med Microbiol. 2016 Apr-Jun;34(2):241-4. doi: 10.4103/0255-0857.180356.
Mycobacterium kumamotonense is a novel, slow-growing non-chromogenic nontuberculous mycobacterium, which belongs to Mycobacterium terrae complex. We report, for the first time in Greece, the isolation of M. kumamotonense from an immunocompetent patient with pulmonary infection and latent tuberculosis. M. kumamotonense was identified by sequencing analysis of 16S rDNA and 65-kDa heat shock protein genes while by commercial molecular assays it was misidentified as Mycobacterium celatum. Antibiotic susceptibility testing was performed by the reference broth microdilution method. The strain was susceptible to amikacin, clarithromycin, rifampin, ciprofloxacin, moxifloxacin, rifabutin, ethambutol and linezolid.
4.Rabeprazole, Minocycline, Amoxicillin, and Bismuth as First-Line and Second-Line Regimens for Helicobacter pylori Eradication.
Song Z1, Suo B1, Zhang L1, Zhou L1. Helicobacter. 2016 Apr 6. doi: 10.1111/hel.12313. [Epub ahead of print]
BACKGROUND: Because of general unavailability of tetracycline, common adverse effects, and complicated administration, the clinical application of bismuth quadruple therapy often faces difficulties. Whether the combination of minocycline and amoxicillin can replace tetracycline and metronidazole for Helicobacter pylori eradication remains unclear. This study was to determine the efficacy, compliance, and safety of rabeprazole, minocycline, amoxicillin, and bismuth (RMAB) therapy as first-line and second-line regimens.

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