(3R,4S,5S,6R,7R,9R,10Z,11S,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-3,5,7,9,11,13-hexamethyl-10-(2,4,7-trioxa-1-azaoctan-1-ylidene)-1-oxacyclotetradecan-2-one

• ChemBase编号: 658
• 分子式: C41H76N2O15
• 平均质量: 837.04654
• 单一同位素质量: 836.52456974
• SMILES: [C@@H]1([C@@](C[C@H](/C(=N/OCOCCOC)/[C@@H]([C@H]([C@]([C@H](OC(=O)[C@@H]([C@H]([C@@H]1C)O[C@H]1C[C@]([C@H]([C@@H](O1)C)O)(OC)C)C)CC)(C)O)O)C)C)(O)C)O[C@H]1[C@@H]([C@H](C[C@H](O1)C)N(C)C)O
• Canonical SMILES: COCCOCO/N=C\1/[C@H](C)C[C@@](C)(O)[C@H](O[C@@H]2O[C@H](C)C[C@@H]([C@H]2O)N(C)C)[C@@H](C)[C@H](O[C@@H]2O[C@@H](C)[C@@H]([C@](C2)(C)OC)O)[C@H](C(=O)O[C@@H]([C@@]([C@@H]([C@H]1C)O)(C)O)CC)C
• InChI: InChI=1S/C41H76N2O15/c1-15-29-41(10,49)34(45)24(4)31(42-53-21-52-17-16-50-13)22(2)19-39(8,48)36(58-38-32(44)28(43(11)12)18-23(3)54-38)25(5)33(26(6)37(47)56-29)57-30-20-40(9,51-14)35(46)27(7)55-30/h22-30,32-36,38,44-46,48-49H,15-21H2,1-14H3/b42-31-/t22-,23-,24+,25+,26-,27+,28+,29-,30+,32-,33+,34-,35+,36-,38+,39-,40-,41-/m1/s1
• InChIKey: RXZBMPWDPOLZGW-HEWSMUCTSA-N

名称和登记号

名称

• IUPAC标准名: (3R,4S,5S,6R,7R,9R,10Z,11S,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-3,5,7,9,11,13-hexamethyl-10-(2,4,7-trioxa-1-azaoctan-1-ylidene)-1-oxacyclotetradecan-2-one; (3R,4S,5S,6R,7R,9R,11S,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-3,5,7,9,11,13-hexamethyl-10-(2,4,7-trioxa-1-azaoctan-1-ylidene)-1-oxacyclotetradecan-2-one
• IUPAC传统名: (Z)-roxithromycin; roxiβ
• 商标名: ROX; Rulid; Rulide; Surlid
• 别名: Roxithromycin

登记号

• CAS号: 80214-83-1
• PubChem SID: 160964121
• PubChem CID: 5480431; 6915744
• CHEBI ID: 48935
• ATC码: J01FA06
• CHEMBL: 1214185
• Chemspider ID: 5291557
• DrugBank ID: DB00778
• KEGG ID: D01710
• 美国药典/FDA物质标识码: 21KOF230FA
• 维基百科标题: Roxithromycin

理论计算性质

JChem

• 可自由旋转的化学键: 13
• 里宾斯基五规则: false
• Acid pKa: 12.454023
• 质子受体: 16
• 质子供体: 5
• LogD (pH = 5.5): -0.23886713
• LogD (pH = 7.4): 1.3162447
• Log P: 2.9999793
• 摩尔折射率: 211.2376 cm^3
• 极化性: 85.90249 Å^3
• 极化表面积: 216.89 Å^2

ALOGPS 2.1

• 溶解度: 1.87e-01 g/l
• Log P: 2.9
• LOG S: -3.65

分子性质

理化性质

• 溶解度: 0.0189 mg/L at 25 oC (SRC PhysProp estimated -- MEYLAN,WM et al. (1996))
• 疏水性(logP): 1.7

药理学性质

• 半衰期: 11 hours
• 代谢: Liver, peak concentration averaging 2 hours after ingestion.
• 妊娠期药物分类: ? (USA) ; B1 (Aus)

详细说明

DrugBank - DB00778

• Drug Groups: approved
• Description: Roxithromycin is a semi-synthetic macrolide antibiotic. It is very similar in composition, chemical structure and mechanism of action to erythromycin, azithromycin, or clarithromycin. Roxithromycin prevents bacteria from growing, by interfering with their protein synthesis. Roxithromycin binds to the subunit 50S of the bacterial ribosome, and thus inhibits the translocation of peptides. Roxithromycin has similar antimicrobial spectrum as erythromycin, but is more effective against certain gram-negative bacteria, particularly Legionella pneumophila. It can treat respiratory tract, urinary and soft tissue infections.
• Indication: Used to treat respiratory tract, urinary and soft tissue infections.
• Pharmacology: Roxithromycin is a semi-synthetic macrolide antibiotic. It is very similar in composition, chemical structure and mechanism of action to erythromycin, azithromycin, or clarithromycin. Roxithromycin has the following antibacterial spectrum in vitro: Streptococcus agalactiae, Streptococcus pneumoniae (Pneumococcus), Neisseria meningitides (Meningococcus), Listeria monocytogenes, Mycoplasma pneumoniae, Chlamydia trachomatis, Ureaplasma urealyticum, Legionella pneumophila, Helicobacter (Campylobacter), Gardnerella vaginalis, Bordetella pertussis, Moraxella catarrhalis (Branhamella Catarrhalis), and Haemophilus ducreyi. Roxithromycin is highly concentrated in polymorphonuclear leukocytes and macrophages, achieving intracellular concentrations greater than those outside the cell. Roxithromycin enhances the adhesive and chemotactic functions of these cells which in the presence of infection produce phagocytosis and bacterial lysis. Roxithromycin also possesses intracellular bactericidal activity.
• Toxicity: Most common side-effects are gastrointestinal; diarrhoea, nausea, abdominal pain and vomiting. Less common side-effects include headaches, rashes, abnormal liver function values and alteration in senses of smell and taste.
• Affected Organisms: Enteric bacteria and other eubacteria
• Biotransformation: Hepatic. Roxithromycin is only partially metabolised, more than half the parent compound being excreted unchanged. Three metabolites have been identified in urine and faeces: the major metabolite is descladinose roxithromycin, with N-mono and N-di-demethyl roxithromycin as minor metabolites. The respective percentage of roxithromycin and these three metabolites is similar in urine and faeces.
• Absorption: Very rapidly absorbed and diffused into most tissues and phagocytes.
• Half Life: 12 hours
• Protein Binding: 96%, mainly to alpha1-acid glycoproteins
• References: [Link] ; Gentry LO: Roxithromycin, a new macrolide antibiotic, in the treatment of infections in the lower respiratory tract: an overview. J Antimicrob Chemother. 1987 Nov;20 Suppl B:145-52. [Pubmed]
• External Links: Wikipedia

参考文献

• Link
• Gentry LO: Roxithromycin, a new macrolide antibiotic, in the treatment of infections in the lower respiratory tract: an overview. J Antimicrob Chemother. 1987 Nov;20 Suppl B:145-52. Pubmed