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Details

Stereochemistry ABSOLUTE
Molecular Formula C38H72N2O12.H2O
Molecular Weight 766.9998
Optical Activity UNSPECIFIED
Defined Stereocenters 18 / 18
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AZITHROMYCIN MONOHYDRATE

SMILES

O.[H][C@@]1(C[C@@](C)(OC)[C@@H](O)[C@H](C)O1)O[C@H]2[C@H](C)[C@@H](O[C@]3([H])O[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@](C)(O)[C@@H](CC)OC(=O)[C@@H]2C

InChI

InChIKey=HQUPLSLYZHKKQT-WVVFQGGUSA-N
InChI=1S/C38H72N2O12.H2O/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;1H2/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 H2O
Molecular Weight 18.0153
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C38H72N2O12
Molecular Weight 748.9845
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
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

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
ZITHROMAX
Curative
ZITHROMAX
Curative
ZITHROMAX
Curative
ZITHROMAX
Curative
ZITHROMAX
Curative
ZITHROMAX

Cmax

ValueDoseCo-administeredAnalytePopulation
0.39 μg/L
500 mg single, oral
AZITHROMYCIN ANHYDROUS serum
Homo sapiens
0.94 mg/L
2000 mg single, oral
AZITHROMYCIN ANHYDROUS serum
Homo sapiens
0.54 μg/mL
500 mg 1 times / day multiple, oral
AZITHROMYCIN ANHYDROUS serum
Homo sapiens
0.5 μg/mL
500 mg single, oral
AZITHROMYCIN ANHYDROUS unknown
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
0.94 mg × h/L
500 mg single, oral
AZITHROMYCIN ANHYDROUS serum
Homo sapiens
10 mg × h/L
2000 mg single, oral
AZITHROMYCIN ANHYDROUS serum
Homo sapiens
17.4 μg × h/mL
500 mg 1 times / day multiple, oral
AZITHROMYCIN ANHYDROUS serum
Homo sapiens
4.3 μg × h/mL
500 mg single, oral
AZITHROMYCIN ANHYDROUS unknown
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
71.8 h
500 mg 1 times / day multiple, oral
AZITHROMYCIN ANHYDROUS serum
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
71%
500 mg 1 times / day multiple, oral
AZITHROMYCIN ANHYDROUS serum
Homo sapiens
71%
500 mg single, oral
AZITHROMYCIN ANHYDROUS unknown
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

Drug as perpetrator​

Drug as victim

Tox targets

Sourcing

PubMed

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
Record UNII
JTE4MNN1MD
Record Status Validated (UNII)
Record Version