U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C38H72N2O12.2ClH
Molecular Weight 821.906
Optical Activity UNSPECIFIED
Defined Stereocenters 18 / 18
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AZITHROMYCIN DIHYDROCHLORIDE

SMILES

Cl.Cl.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=WUTMHODASJRZBL-KUJJYQHYSA-N
InChI=1S/C38H72N2O12.2ClH/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;2*1H/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 ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Pharyngeal colonization prevalence rates for Streptococcus pyogenes and Streptococcus pneumoniae in a respiratory chemoprophylaxis intervention study using azithromycin.
2000 Jan
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
Pilot study of the use of community volunteers to distribute azithromycin for trachoma control in Ghana.
2001
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
Six cases of confluent and reticulated papillomatosis alleviated by various antibiotics.
2001 Apr
Clindamycin suspension and endocarditis prophylaxis.
2001 Apr 28
Comparison of amoxicillin and azithromycin in the prevention of recurrent acute otitis media.
2001 Apr 6
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
Lack of an effect of azithromycin on the disposition of zidovudine and dideoxyinosine in HIV-infected patients.
2001 Feb
Antibiotic-resistance patterns of Helicobacter pylori in Croatia: cohort study.
2001 Feb
Evaluation of iron-phosphate as a source of internal lake phosphorus loadings.
2001 Feb 5
Antibiotic susceptibilities among recent clinical isolates of Haemophilus influenzae and Moraxella catarrhalis from fifteen countries.
2001 Jan
Acute community-acquired pneumonia: current diagnosis and treatment.
2001 Jan
Irreversible sensorineural hearing loss as a result of azithromycin ototoxicity. A case report.
2001 Jan
Activity of buforin II alone and in combination with azithromycin and minocycline against Cryptosporidium parvum in cell culture.
2001 Jan
Chlamydia pneumoniae infection in circulating human monocytes is refractory to antibiotic treatment.
2001 Jan 23
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
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
Persistently positive culture results in a patient with community-acquired pneumonia due to Legionella pneumophila.
2001 Jun 1
Hypersensitivity syndrome associated with azithromycin.
2001 Mar
Comparative in vitro activity of moxifloxacin by E-test against Streptococcus pyogenes.
2001 Mar 15
Azithromycin prophylaxis during a hospital outbreak of Mycoplasma pneumoniae pneumonia.
2001 Mar 15
Antibiotic treatment in acute Otitis Media promotes superinfection with resistant Streptococcus pneumoniae carried before initiation of treatment.
2001 Mar 15
Dose-escalation, phase I/II study of azithromycin and pyrimethamine for the treatment of toxoplasmic encephalitis in AIDS.
2001 Mar 30
The treatment of babesiosis.
2001 Mar 8
The treatment of babesiosis.
2001 Mar 8
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
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
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 Tue Oct 22 09:10:00 UTC 2019
Edited
by admin
on Tue Oct 22 09:10:00 UTC 2019
Record UNII
4WY75EB7AG
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AZITHROMYCIN DIHYDROCHLORIDE
Common Name English
1-OXA-6-AZACYCLOPENTADECAN-15-ONE, 13-((2,6-DIDEOXY-3-C-METHYL-3-O-METHYL-.ALPHA.-L-RIBO-HEXOPYRANOSYL)OXY)-2-ETHYL-3,4,10-TRIHYDROXY-3,5,6,8,10,12,14-HEPTAMETHYL-11-((3,4,6-TRIDEOXY-3-(DIMETHYLAMINO)-.BETA.-D-XYLO-HEXOPYRANOSYL)OXY)-, HYDROCHLORIDE (1:2
Systematic Name English
AZITHROMYCIN HYDROCHLORIDE [WHO-DD]
Common Name English
Code System Code Type Description
CAS
918525-68-5
Created by admin on Tue Oct 22 09:10:00 UTC 2019 , Edited by admin on Tue Oct 22 09:10:00 UTC 2019
NON-SPECIFIC STOICHIOMETRY
CAS
90581-31-0
Created by admin on Tue Oct 22 09:10:00 UTC 2019 , Edited by admin on Tue Oct 22 09:10:00 UTC 2019
PRIMARY
PUBCHEM
44468059
Created by admin on Tue Oct 22 09:10:00 UTC 2019 , Edited by admin on Tue Oct 22 09:10:00 UTC 2019
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY