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Merck
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Key Documents

C9742

Sigma-Aldrich

克拉霉素

≥95% (HPLC)

同義詞:

6-O-methyl erythromycin

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About This Item

經驗公式(希爾表示法):
C38H69NO13
CAS號碼:
分子量::
747.95
MDL號碼:
分類程式碼代碼:
51102829
PubChem物質ID:
NACRES:
NA.76

品質等級

化驗

≥95% (HPLC)

形狀

powder

抗生素活性譜

Gram-negative bacteria
Gram-positive bacteria

作用方式

protein synthesis | interferes

SMILES 字串

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

InChI 密鑰

AGOYDEPGAOXOCK-KCBOHYOISA-N

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一般說明

Chemical structure: macrolide

應用

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.

生化/生理作用

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.
克拉霉素是一种大环内酯类抗生素,能干扰细菌蛋白质的合成。克拉霉素是红霉素的酸稳定形式,对革兰氏阴性细菌特别有效。它的半衰期很短,但是其代谢产物 14-羟基克拉霉素对某些细菌的活性几乎是克拉霉素的两倍。

準備報告

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

其他說明

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

象形圖

Exclamation mark

訊號詞

Warning

危險聲明

危險分類

Acute Tox. 4 Oral

儲存類別代碼

11 - Combustible Solids

水污染物質分類(WGK)

WGK 1

閃點(°F)

Not applicable

閃點(°C)

Not applicable

個人防護裝備

dust mask type N95 (US), Eyeshields, Gloves


分析證明 (COA)

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Masahito Ogawa et al.
Journal of the American College of Cardiology, 51(20), 1977-1985 (2008-05-17)
Clarithromycin (CAM), a major macrolide antibiotic, has many biological functions, including matrix metalloproteinases (MMPs) regulation. However, little is known about the effect of CAM in heart transplantation via MMP-9. The purpose of this study was to clarify the role of
Barbara Gierlikowska et al.
Frontiers in pharmacology, 11, 1339-1339 (2020-10-06)
Phagocytosis is a crucial element of innate immune defense involved in bacterial killing. The aim of our study was to evaluate the influence of alantolactone on phagocytosis and cytokines release by THP1-derived macrophages. We assessed whether antimicrobial compound alantolactone (a
Ilknur Basyigit et al.
The Annals of pharmacotherapy, 38(9), 1400-1405 (2004-07-15)
Clarithromycin is an antimicrobial agent that can be used for treatment of chronic obstructive pulmonary disease (COPD) exacerbations with bronchodilator therapy. However, it has also been shown that clarithromycin has antiinflammatory effects by the inhibition of cytokine production. To evaluate
Stuart Schembri et al.
BMJ (Clinical research ed.), 346, f1235-f1235 (2013-03-26)
To study the association of clarithromycin with cardiovascular events in the setting of acute exacerbations of chronic obstructive pulmonary disease and community acquired pneumonia. Analysis of two prospectively collected datasets. Chronic obstructive pulmonary disease dataset including patients admitted to one
Stig Lyngbæk et al.
European journal of preventive cardiology, 21(10), 1275-1284 (2013-06-01)
Low prevalence of detectable cardiac troponin in healthy people and low-risk patients previously curtailed its use. With a new high-sensitive cardiac troponin assay (hs-cTnT), concentrations below conventional detection may have prognostic value, notably in combination with N-terminal pro-B-type natriuretic peptide

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