C9742

Clarithromycin

≥95% (HPLC)

• Synonym(e): 6-O-methyl erythromycin
• Empirische Formel (Hill-System): C₃₈H₆₉NO₁₃
• CAS-Nummer: 81103-11-9
• Molekulargewicht: 747.95
• MDL-Nummer: MFCD00865140
• UNSPSC-Code: 51102829
• PubChem Substanz-ID: 329775082
• NACRES: NA.76

Eigenschaften

• Qualitätsniveau: 200
• Assay: ≥95% (HPLC)
• Form: powder
• Wirkungsspektrum von Antibiotika: Gram-negative bacteria; Gram-positive bacteria
• Wirkungsweise: protein synthesis | interferes
• SMILES String: O[C@@H]([C@@](O)(C)[C@@H](CC)OC([C@H](C)[C@H]1O[C@@H]2O[C@@H](C)[C@H](O)[C@](C)(OC)C2)=O)[C@@H](C)C([C@H](C)C[C@@](C)(OC)[C@H](O[C@@H]3O[C@H](C)C[C@H](N(C)C)[C@H]3O)[C@H]1C)=O
• 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
• InChIKey: AGOYDEPGAOXOCK-KCBOHYOISA-N

Beschreibung

Allgemeine Beschreibung

Chemical structure: macrolide

Anwendung

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 suppression. Clarithromycin has been used to study inflammatory markers in chronic obstructive pulmonary disease (COPD). It is used to study bacterial protein synthesis and peptide translation.

Biochem./physiol. Wirkung

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.

Clarithromycin ist ein Makrolid-Antibiotikum. Es verhindert das Bakterienwachstum durch Störung der Proteinsynthese. Clarithromycin ist eine säurestabile Variante von Erythromycin und ist besonders wirksam gegen gram-negative Bakterien. Es hat eine kurze Halbwertszeit, jedoch ist sein Metabolit 14-Hydroxyclarithromycin fast doppelt so wirksam wie Clarithromycin gegen bestimmte Bakterien.

Angaben zur Herstellung

Practically insoluble in water, soluble in acetone and methylene chloride, slightly soluble in methanol.

Sonstige Hinweise

Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place.

Sicherheitshinweise

• Piktogramme: GHS07
• Signalwort: Warning
• H-Sätze: H302
• P-Sätze: P264 - P270 - P301 + P312 - P501
• Gefahreneinstufungen: Acute Tox. 4 Oral
• Lagerklassenschlüssel: 11 - Combustible Solids
• WGK: WGK 1
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable
• Persönliche Schutzausrüstung: dust mask type N95 (US), Eyeshields, Gloves