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83905-01-5 分子结构
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(2R,3S,4R,5R,8R,10R,11R,13S,14R)-11-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-2-ethyl-3,4,10-trihydroxy-13-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan-15-one

ChemBase编号:92
分子式:C38H72N2O12
平均质量:748.98448
单一同位素质量:748.50852575
SMILES和InChIs

SMILES:
O([C@@H]1C([C@H](O[C@@H]2O[C@H]([C@H](O)[C@](OC)(C2)C)C)[C@H](C(=O)O[C@@H]([C@@](O)([C@H](O)[C@H](N(C[C@@H](C[C@]1(O)C)C)C)C)C)CC)C)C)[C@@H]1O[C@@H](C[C@H](N(C)C)[C@H]1O)C
Canonical SMILES:
CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@@H]2O[C@@H](C)[C@@H]([C@](C2)(C)OC)O)C(C)[C@@H](O[C@@H]2O[C@H](C)C[C@@H]([C@H]2O)N(C)C)[C@](C[C@H](CN([C@@H]([C@H]([C@]1(C)O)O)C)C)C)(C)O
InChI:
InChI=1S/C38H72N2O12/c1-15-27-38(10,46)31(42)24(6)40(13)19-20(2)17-36(8,45)33(52-35-29(41)26(39(11)12)16-21(3)48-35)22(4)30(23(5)34(44)50-27)51-28-18-37(9,47-14)32(43)25(7)49-28/h20-33,35,41-43,45-46H,15-19H2,1-14H3/t20-,21-,22?,23-,24-,25+,26+,27-,28+,29-,30+,31-,32+,33-,35+,36-,37-,38-/m1/s1
InChIKey:
MQTOSJVFKKJCRP-OHJWJPDZSA-N

引用这个纪录

CBID:92 http://www.chembase.cn/molecule-92.html

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
(2R,3S,4R,5R,8R,10R,11R,13S,14R)-11-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-2-ethyl-3,4,10-trihydroxy-13-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan-15-one
IUPAC传统名
azithromycin
商标名
Azenil
Azitromax
Aziwok
Aztrin
Hemomycin
Misultina
Mixoterin
Setron
Sumamed
Tobil
Tromix
Zeto
Zifin
Zithrax
Zithromax
Zitrim
Zitromax
Zitrotek
Vinzam
Zmax
Zitrocin
Azibiot
Azifine
别名
Aritromicina [Spanish]
Azithramycine
Azithromycin Dihydrate
Azithromycine [French]
Azithromycinum [Latin]
Azithromycin
CAS号
83905-01-5
PubChem SID
160963555
PubChem CID
55185

数据来源

数据来源

所有数据来源 商品来源 非商品来源
数据来源 数据ID
DrugBank DB00207 external link
PubChem 55185 external link
数据来源 数据ID 价格

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 12.428324  质子受体 13 
质子供体 LogD (pH = 5.5) -4.14965 
LogD (pH = 7.4) -1.2309437  Log P 2.4447815 
摩尔折射率 194.1082 cm3 极化性 79.00683 Å3
极化表面积 180.08 Å2 可自由旋转的化学键
里宾斯基五规则 false 
Log P 3.03  LOG S -3.16 
溶解度 5.14e-01 g/l 

分子性质

分子性质

理化性质 生物活性(PubChem)
溶解度
slight expand 查看数据来源
疏水性(logP)
4.02 [MCFARLAND,JW ET AL. (1997)] expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank
DrugBank -  DB00207 external link
Item Information
Drug Groups approved
Description Azithromycin is a semi-synthetic macrolide antibiotic of the azalide class. Like other macrolide antibiotics, azithromycin inhibits bacterial protein synthesis by binding to the 50S ribosomal subunit of the bacterial 70S ribosome. Binding inhibits peptidyl transferase activity and interferes with amino acid translocation during the process of translation. Its effects may be bacteriostatic or bactericidal depending of the organism and the drug concentration. Its long half life, which enables once daily dosing and shorter administration durations, is a property distinct from other macrolides.
Indication For the treatment of patients with mild to moderate infections caused by susceptible strains of the designated microorganisms in the specific conditions: H. influenzae, M. catarrhalis, S. pneumoniae, C. pneumoniae, M. pneumoniae, S. pyogenes, S. aureus, S. agal
Pharmacology Azithromycin, a semisynthetic antibiotic belonging to the macrolide subgroup of azalides, is used to treat STDs due to chlamydia and gonorrhea, community-acquired pneumonia, pelvic inflammatory disease, pediatric otitis media and pharyngitis, and Mycobacterium avium complex (MAC) in patients with advanced HIV disease. Similar in structure to erythromycin. azithromycin reaches higher intracellular concentrations than erythromycin, increasing its efficacy and duration of action.
Toxicity Potentially serious side effects of angioedema and cholestatic jaundice were reported
Affected Organisms
Enteric bacteria and other eubacteria
Biotransformation Hepatic. In vitro and in vivo studies to assess the metabolism of azithromycin have not been performed.
Absorption Bioavailability is 37% following oral administration. Absorption is not affected by food. Azithromycin is extensively distributed in tissues with tissue concentrations reaching up to 50 times greater than plasma concentrations. Drug becomes concentrated within macrophages and polymorphonucleocytes giving it good activity against Chlamydia trachomatis.
Half Life 68 hours
Protein Binding Serum protein binding is variable in the concentration range approximating human exposure, decreasing from 51% at 0.02 µg/mL to 7% at 2 µg/mL.
Elimination Biliary excretion of azithromycin, predominantly as unchanged drug, is a major route of elimination.
Distribution * 31.1 L/kg
Clearance * apparent plasma cl=630 mL/min [following single 500 mg oral and i.v. doses]
References
Noedl H, Krudsood S, Chalermratana K, Silachamroon U, Leowattana W, Tangpukdee N, Looareesuwan S, Miller RS, Fukuda M, Jongsakul K, Sriwichai S, Rowan J, Bhattacharyya H, Ohrt C, Knirsch C: Azithromycin combination therapy with artesunate or quinine for the treatment of uncomplicated Plasmodium falciparum malaria in adults: a randomized, phase 2 clinical trial in Thailand. Clin Infect Dis. 2006 Nov 15;43(10):1264-71. Epub 2006 Oct 12. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Noedl H, Krudsood S, Chalermratana K, Silachamroon U, Leowattana W, Tangpukdee N, Looareesuwan S, Miller RS, Fukuda M, Jongsakul K, Sriwichai S, Rowan J, Bhattacharyya H, Ohrt C, Knirsch C: Azithromycin combination therapy with artesunate or quinine for the treatment of uncomplicated Plasmodium falciparum malaria in adults: a randomized, phase 2 clinical trial in Thailand. Clin Infect Dis. 2006 Nov 15;43(10):1264-71. Epub 2006 Oct 12. Pubmed
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