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83905-01-5 molecular structure
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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 ID: 92
Molecular Formular: C38H72N2O12
Molecular Mass: 748.98448
Monoisotopic Mass: 748.50852575
SMILES and 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

Cite this record

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

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(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 Traditional name
azithromycin
Brand Name
Azenil
Azitromax
Aziwok
Aztrin
Hemomycin
Misultina
Mixoterin
Setron
Sumamed
Tobil
Tromix
Zeto
Zifin
Zithrax
Zithromax
Zitrim
Zitromax
Zitrotek
Vinzam
Zmax
Zitrocin
Azibiot
Azifine
Synonyms
Aritromicina [Spanish]
Azithramycine
Azithromycin Dihydrate
Azithromycine [French]
Azithromycinum [Latin]
Azithromycin
CAS Number
83905-01-5
PubChem SID
160963555
PubChem CID
55185

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 55185 external link
DrugBank DB00207 external link
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 12.428324  H Acceptors 13 
H Donor LogD (pH = 5.5) -4.14965 
LogD (pH = 7.4) -1.2309437  Log P 2.4447815 
Molar Refractivity 194.1082 cm3 Polarizability 79.00683 Å3
Polar Surface Area 180.08 Å2 Rotatable Bonds
Lipinski's Rule of Five false 
Log P 3.03  LOG S -3.16 
Solubility (Water) 5.14e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Bioassay(PubChem)
Solubility
slight expand Show data source
Hydrophobicity(logP)
4.02 [MCFARLAND,JW ET AL. (1997)] expand Show data source

DETAILS

DETAILS

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

REFERENCES

REFERENCES

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  • • 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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PATENTS

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