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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

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
Azithromycin-induced hearing loss.
1999 Feb 15
Pharyngeal colonization prevalence rates for Streptococcus pyogenes and Streptococcus pneumoniae in a respiratory chemoprophylaxis intervention study using azithromycin.
2000 Jan
Anticryptosporidial activity of ranalexin, lasalocid and azithromycin alone and in combination in cell lines.
2000 Mar
Breakthrough pneumococcal bacteremia in patients being treated with azithromycin and clarithromycin.
2000 Oct
Potentially fatal interaction between azithromycin and disopyramide.
2000 Sep
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
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
Duration of clinical symptoms in female patients with acute urethral syndrome caused by Chlamydia trachomatis treated with azithromycin or doxycycline.
2001 Apr
Incidence and determinants of Pseudomonas aeruginosa infection among persons with HIV: association with hospital exposure.
2001 Apr
In vitro activity of telithromycin (HMR 3647) against 502 strains of anaerobic bacteria.
2001 Apr
Severe babesiosis in Long Island: review of 34 cases and their complications.
2001 Apr 15
Azithromycin: a new 15-membered macrolide.
2001 Feb
[Subacute infectious endocarditis due to the agent of cat scratch fever: Bartonella henselae].
2001 Feb
Treatment of cat-scratch disease.
2001 Feb
New approaches to the treatment of group A streptococcal pharyngitis.
2001 Feb
Rhodococcus equi and cytomegalovirus pneumonia in a renal transplant patient: diagnosis by fine-needle aspiration biopsy.
2001 Feb
Evaluation of iron-phosphate as a source of internal lake phosphorus loadings.
2001 Feb 5
Azithromycin monthly pulse vs daily doxycycline in the treatment of acne vulgaris.
2001 Jan
Irreversible sensorineural hearing loss as a result of azithromycin ototoxicity. A case report.
2001 Jan
Compliance issues related to the selection of antibiotic suspensions for children.
2001 Jan
Serum and WBC pharmacokinetics of 1500 mg of azithromycin when given either as a single dose or over a 3 day period in healthy volunteers.
2001 Jan
In vitro activity of ketolides HMR 3004 and HMR 3647 and seven other antimicrobial agents against Corynebacterium diphtheriae.
2001 Jan
Resolution of cyclosporine-induced gingival hyperplasia resistant to azithromycin by switching to tacrolimus.
2001 Jan
Activity of moxifloxacin by itself and in combination with ethambutol, rifabutin, and azithromycin in vitro and in vivo against Mycobacterium avium.
2001 Jan
Effect of azithromycin on murine arteriosclerosis exacerbated by Chlamydia pneumoniae.
2001 Jan 15
Malaria chemoprophylaxis in the age of drug resistance. I. Currently recommended drug regimens.
2001 Jul 15
The hidden impact of antibacterial resistance in respiratory tract infection. Re-evaluating current antibiotic therapy.
2001 Jun
[Pharmacological and pharmacokinetic properties of azithromycin (Zithromac), a novel 15-membered ring macrolide antibacterial agent].
2001 May
The effects of intravenous doxycycline therapy for rheumatoid arthritis: a randomized, double-blind, placebo-controlled trial.
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
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.
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