(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-1-oxacyclotetradecane-2,10-dione

• ChemBase编号: 153977
• 分子式: C38H69NO13
• 平均质量: 747.95336
• 单一同位素质量: 747.47689127
• 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]1C[C@@]([C@H]([C@@H](O1)C)O)(C)OC)C)O[C@H]1[C@@H]([C@H](C[C@H](O1)C)N(C)C)O)(C)OC)C)C)O)(C)O
• Canonical SMILES: CC[C@@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@H]([C@@H](O2)C)O)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@@H]([C@H]2O)N(C)C)[C@](C[C@H](C(=O)[C@@H]([C@H]([C@]1(C)O)O)C)C)(C)OC
• 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
• InChIKey: AGOYDEPGAOXOCK-KCBOHYOISA-N

名称和登记号

名称

• IUPAC标准名: (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-1-oxacyclotetradecane-2,10-dione
• IUPAC传统名: clarithromycin
• 别名: Clarithromycin

登记号

• CAS号: 81103-11-9
• MDL号: MFCD00865140
• PubChem SID: 162248116
• PubChem CID: 84029

理论计算性质

• Acid pKa: 12.458389
• 质子受体: 13
• 质子供体: 4
• LogD (pH = 5.5): 0.4510266
• LogD (pH = 7.4): 2.2163913
• Log P: 3.2395153
• 摩尔折射率: 190.7883 cm^3
• 极化性: 77.6621 Å^3
• 极化表面积: 182.91 Å^2
• 可自由旋转的化学键: 8
• 里宾斯基五规则: false

分子性质

安全信息

• RTECS编号: KF4997000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 22
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥95% (HPLC)
• 适用性: suitable for 1694 per US EPA
• Pharmacopeia Traceability: traceable to BP 833; traceable to PhEur Y0000320; traceable to USP 1134379
• Empirical Formula (Hill Notation): C38H69NO13

详细说明

Sigma Aldrich - C9742

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
Clarithromycin is a macrolide antibiotic. It prevents bacterial growth by interfering with protein synthesis. Clarithromycin is an acid-stable version of erythromycin and is particularly effective against gram-negative bacteria.3 It has a short half-life4, however its metabolite, 14-hydroxy clarithromycin is nearly twice as active as clarithromycin against certain bacteria.5
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.
Application
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 suppression1. Clarithromycin has been used to study inflammatory markers in chronic obstructive pulmonary disease (COPD)2. It is used to study bacterial protein synthesis and peptide translation.

Sigma Aldrich - 16632

Biochem/physiol Actions
Clarithromycin is a macrolide antibiotic. It prevents bacterial growth by interfering with protein synthesis. Clarithromycin is an acid-stable version of erythromycin and is particularly effective against gram-negative bacteria.1 It has a short half-life2, however its metabolite, 14-hydroxy clarithromycin is nearly twice as active as clarithromycin against certain bacteria.3