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Details

Stereochemistry ABSOLUTE
Molecular Formula C38H72N2O12
Molecular Weight 748.9845
Optical Activity UNSPECIFIED
Defined Stereocenters 18 / 18
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AZITHROMYCIN ANHYDROUS

SMILES

CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]3O[C@H](C)C[C@@H]([C@H]3O)N(C)C)[C@](C)(O)C[C@@H](C)CN(C)[C@H](C)[C@@H](O)[C@]1(C)O

InChI

InChIKey=MQTOSJVFKKJCRP-BICOPXKESA-N
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

HIDE SMILES / InChI

Molecular Formula C38H72N2O12
Molecular Weight 748.9845
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 18 / 18
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Azithromycin is one of the world's best-selling antibiotics, used to treat or prevent certain bacterial infections: Acute bacterial exacerbations of chronic bronchitis in adults; acute bacterial sinusitis in adults; uncomplicated skin and skin structure infections in adults; urethritis and cervicitis in adults; genital ulcer disease in men; acute otitis media in pediatric patients; community-acquired pneumonia in adults and pediatric patients; pharyngitis/tonsillitis in adults and pediatric patients. Azithromycin should not be used in patients with pneumonia who are judged inappropriate for oral therapy because of moderate to severe illness or risk factors. A team of researchers at the Croatian pharmaceutical company Pliva, discovered azithromycin in 1980. It was patented in 1981. In 1986, Pliva and Pfizer signed a licensing agreement, which gave Pfizer exclusive rights for the sale of azithromycin in Western Europe and the United States. Pliva put its azithromycin on the market in Central and Eastern Europe under the brand name of Sumamed in 1988. Pfizer launched azithromycin under Pliva's license in other markets under the brand name Zithromax in 1991. 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.

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Antibiotic prophylaxis for intrauterine contraceptive device insertion.
2001
Comparative in vitro activity of thiamphenicol-glycinate and thiamphenicol-glycinate-acetylcysteinate and other antimicrobials against respiratory pathogens.
2001
Review of macrolides and ketolides: focus on respiratory tract infections.
2001
The SAFE strategy for the elimination of trachoma by 2020: will it work?
2001
Cost-effectiveness of trachoma control measures: comparing targeted household treatment and mass treatment of children.
2001
Comparison of two azithromycin distribution strategies for controlling trachoma in Nepal.
2001
[Skin eruptions due to azithromycin (Azadose-Zithromax) and infectious mononucleosis].
2001 Apr
Duration of clinical symptoms in female patients with acute urethral syndrome caused by Chlamydia trachomatis treated with azithromycin or doxycycline.
2001 Apr
Comparative efficacy of new investigational agents against Helicobacter pylori.
2001 Apr
In vitro activity of telithromycin (HMR 3647) against 502 strains of anaerobic bacteria.
2001 Apr
In vitro effects of azithromycin on Salmonella typhi: early inhibition by concentrations less than the MIC and reduction of MIC by alkaline pH and small inocula.
2001 Apr
Efficacy, safety and tolerability of 3 day azithromycin versus 10 day co-amoxiclav in the treatment of children with acute lower respiratory tract infections.
2001 Apr
Treatment alternatives for Mycobacterium kansasii.
2001 Apr
Can we eliminate trachoma?
2001 Apr
Azithromycin and pelvic inflammatory disease in the Northern Territory.
2001 Apr 2
Clindamycin suspension and endocarditis prophylaxis.
2001 Apr 28
[Isolation of Vibrio strains in French coastal waters and infection with Vibrio cholerae non-O1/non-O139].
2001 Apr 7
Oligella ureolytica in blood culture: contaminant or infection?
2001 Feb
Azithromycin: a new 15-membered macrolide.
2001 Feb
Identification of parasitoses in a child burial from Adak Island (Central Aleutian Islands, Alaska).
2001 Feb
[Subacute infectious endocarditis due to the agent of cat scratch fever: Bartonella henselae].
2001 Feb
Azithromycin monthly pulse vs daily doxycycline in the treatment of acne vulgaris.
2001 Jan
Buccal adherence of Pseudomonas aeruginosa in patients with cystic fibrosis under long-term therapy with azithromycin.
2001 Jan-Feb
Donovanosis: an update.
2001 Jul
Malaria chemoprophylaxis in the age of drug resistance. I. Currently recommended drug regimens.
2001 Jul 15
Inhibitory and bactericidal effects of telithromycin (HMR 3647, RU 56647) and five comparative antibiotics, used singly and in combination, against vancomycin-resistant and vancomycin-susceptible enterococci.
2001 Jul-Aug
The hidden impact of antibacterial resistance in respiratory tract infection. Re-evaluating current antibiotic therapy.
2001 Jun
A randomized controlled trial comparing amoxicillin and azithromycin for the treatment of Chlamydia trachomatis in pregnancy.
2001 Jun
Susceptibility of Canadian isolates of Haemophilus influenzae, Moraxella catarrhalis and Streptococcus pneumoniae to oral antimicrobial agents.
2001 Jun
The effect of azithromycin and clarithromycin on ex vivo interleukin-8 (IL-8) release from whole blood and IL-8 production by human alveolar macrophages.
2001 Jun
Insights into the mechanism of azithromycin interaction with an Escherichia coli functional ribosomal complex.
2001 Jun
Persistently positive culture results in a patient with community-acquired pneumonia due to Legionella pneumophila.
2001 Jun 1
Azithromycin-containing regimens for treatment of Mycobacterium avium complex lung disease.
2001 Jun 1
Macrolide therapy of group A streptococcal pharyngitis: 10 days of macrolide therapy (clarithromycin) is more effective in streptococcal eradication than 5 days (azithromycin).
2001 Jun 15
A family cluster of Chlamydia trachomatis infection.
2001 Jun 16
Postantibiotic suppression effect of macrolides on the expression of flagellin in Pseudomonas aeruginosa and Proteus mirabilis.
2001 Mar
Comparative serum bactericidal activity of clarithromycin and azithromycin against macrolide-sensitive and resistant strains of Streptococcus pneumoniae.
2001 Mar
Dose-escalation, phase I/II study of azithromycin and pyrimethamine for the treatment of toxoplasmic encephalitis in AIDS.
2001 Mar 30
Treatment outcomes in acute exacerbations of chronic bronchitis: comparison of macrolides and moxifloxacin from the patient perspective.
2001 Mar-Apr
[Experimental infection in mice by Plasmodium berghei: an evidence of antiparasitic action of azithromycin].
2001 Mar-Apr
[Pharmacological and pharmacokinetic properties of azithromycin (Zithromac), a novel 15-membered ring macrolide antibacterial agent].
2001 May
Azithromycin treatment of gingival hyperplasia in kidney transplant recipients is effective and safe.
2001 May
The effects of intravenous doxycycline therapy for rheumatoid arthritis: a randomized, double-blind, placebo-controlled trial.
2001 May
Inoculation of two genotypes of Hemobartonella felis (California and Ohio variants) to induce infection in cats and the response to treatment with azithromycin.
2001 May
[Chemoprophylaxis of meningococcal disease with azithromycin and ciprofloxacin].
2001 May
Decreased susceptibility to azithromycin and erythromycin mediated by a novel mtr(R) promoter mutation in Neisseria gonorrhoeae.
2001 May
The activity of 14-hydroxy clarithromycin, alone and in combination with clarithromycin, against penicillin- and erythromycin-resistant Streptococcus pneumoniae.
2001 May
When to suspect and how to monitor babesiosis.
2001 May 15
Solid-phase synthesis of macrolide analogues.
2001 May-Jun
A multicenter study of the antimicrobial susceptibility of Haemophilus influenzae, Streptococcus pneumoniae, and Moraxella catarrhalis isolated from patients with community-acquired lower respiratory tract infections in 1999 in Portugal.
2001 Spring
Patents

Sample Use Guides

In Vivo Use Guide
Community-acquired pneumonia (mild severity); Pharyngitis/tonsillitis (second-line therapy); Skin/skin structure (uncomplicated): 500 mg as a single dose on Day 1, followed by 250 mg once daily on Days 2 through 5. Acute bacterial exacerbations of chronic bronchitis (mild to moderate): 500 mg as a single dose on Day 1, followed by 250 mg once daily on Days 2 through 5 or 500 mg once daily for 3 days Acute bacterial sinusitis: 500 mg once daily for 3 days Genital ulcer disease (chancroid) Non-gonococcal urethritis and cervicitis: One single 1 gram dose. Gonococcal urethritis and cervicitis: One single 2 gram dose. Acute otitis media: 30 mg/kg as a single dose or 10 mg/kg once daily for 3 days or 10 mg/kg as a single dose on Day
Route of Administration: Oral
In Vitro Use Guide
Azithromycin can benefit treating allergic airway inflammation and remodeling. Azithromycin significantly reduced the inflammation score, peribronchial smooth muscle layer thickness, epithelial thickening and goblet cell metaplasia, and effectively suppressed apoptotic index (AI) of airway epithelium. Moreover, the increasing mRNA and protein expressions of Caspase-3 and Bax/Bcl-2 ratio in lung tissue were all significantly decreased in azithromycin-treated rats. In vitro, azithromycin significantly suppressed TGF-β1-induced BEAS-2B cells apoptosis and reversed TGF-β1 elevated Caspase-3 mRNA level and Bax/Bcl-2 ratio.
Substance Class Chemical
Created
by admin
on Mon Oct 21 22:33:20 UTC 2019
Edited
by admin
on Mon Oct 21 22:33:20 UTC 2019
Record UNII
J2KLZ20U1M
Record Status Validated (UNII)
Record Version
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Name Type Language
AZITHROMYCIN ANHYDROUS
Common Name English
ZITHROMAC
Brand Name English
ARUZILINA
Brand Name English
CP 62993
Code English
ZYTHROMAX
Brand Name English
HEMOMYCIN
Common Name English
N-METHYL-11-AZA-10-DEOXO-10-DIHYDROERYTHROMYCIN A
Common Name English
AZITHROCIN
Brand Name English
9-DEOXO-9A-AZA-9A-METHYL-9A-HOMOERYTHROMYCIN A
Common Name English
AZITHROMYCIN [HSDB]
Common Name English
ANHYDROUS AZITHROMYCIN
Common Name English
XZ 450
Code English
DURASITE
Brand Name English
XITHRONE
Common Name English
AZIROMYCIN
Common Name English
AZASITE
Brand Name English
CP-62,993
Code English
AZIWIN
Brand Name English
CP-62993
Code English
AZITHROMYCIN [INN]
Common Name English
SUMAMED
Brand Name English
XZ 405
Code English
AZITHROMYCIN [MI]
Common Name English
XZ-450
Code English
MACROZIT
Brand Name English
TROZOCINA
Brand Name English
Classification Tree Code System Code
WHO-ATC J01FA10
Created by admin on Mon Oct 21 22:33:20 UTC 2019 , Edited by admin on Mon Oct 21 22:33:20 UTC 2019
NDF-RT N0000175935
Created by admin on Mon Oct 21 22:33:20 UTC 2019 , Edited by admin on Mon Oct 21 22:33:20 UTC 2019
NCI_THESAURUS C261
Created by admin on Mon Oct 21 22:33:20 UTC 2019 , Edited by admin on Mon Oct 21 22:33:20 UTC 2019
Code System Code Type Description
HSDB
83905-01-5
Created by admin on Mon Oct 21 22:33:20 UTC 2019 , Edited by admin on Mon Oct 21 22:33:20 UTC 2019
PRIMARY
DRUG BANK
DB00207
Created by admin on Mon Oct 21 22:33:20 UTC 2019 , Edited by admin on Mon Oct 21 22:33:20 UTC 2019
PRIMARY
EPA CompTox
83905-01-5
Created by admin on Mon Oct 21 22:33:20 UTC 2019 , Edited by admin on Mon Oct 21 22:33:20 UTC 2019
PRIMARY
NCI_THESAURUS
C76213
Created by admin on Mon Oct 21 22:33:20 UTC 2019 , Edited by admin on Mon Oct 21 22:33:20 UTC 2019
PRIMARY
CAS
83905-01-5
Created by admin on Mon Oct 21 22:33:20 UTC 2019 , Edited by admin on Mon Oct 21 22:33:20 UTC 2019
PRIMARY
MERCK INDEX
M2177
Created by admin on Mon Oct 21 22:33:20 UTC 2019 , Edited by admin on Mon Oct 21 22:33:20 UTC 2019
PRIMARY Merck Index
INN
6197
Created by admin on Mon Oct 21 22:33:20 UTC 2019 , Edited by admin on Mon Oct 21 22:33:20 UTC 2019
PRIMARY
LactMed
83905-01-5
Created by admin on Mon Oct 21 22:33:20 UTC 2019 , Edited by admin on Mon Oct 21 22:33:20 UTC 2019
PRIMARY
EVMPD
SUB90954
Created by admin on Mon Oct 21 22:33:20 UTC 2019 , Edited by admin on Mon Oct 21 22:33:20 UTC 2019
PRIMARY
EVMPD
SUB05660MIG
Created by admin on Mon Oct 21 22:33:20 UTC 2019 , Edited by admin on Mon Oct 21 22:33:20 UTC 2019
PRIMARY
PUBCHEM
447043
Created by admin on Mon Oct 21 22:33:20 UTC 2019 , Edited by admin on Mon Oct 21 22:33:20 UTC 2019
PRIMARY
RXCUI
1299904
Created by admin on Mon Oct 21 22:33:20 UTC 2019 , Edited by admin on Mon Oct 21 22:33:20 UTC 2019
PRIMARY RxNorm
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
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ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC