Azythromycin

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Azythromycin are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Azythromycin?

The molecule Azythromycin presents a molecular formula of C38H72N2O12 and its IUPAC name is (2S,3S,4R,5S,8S,10S,11S,12R,13S,14R)-11-[(2R,3S,4R,6S)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-3,4,10-trihydroxy-13-[(2S,4S,5R,6R)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan-15-one.

Azithromycin is a macrolide antibiotic used to treat bacterial infections. It is a derivative of erythromycin, and is structurally similar to clarithromycin and telithromycin. Azithromycin was first discovered in 1980, and was approved for use in the United States in 1992. It exists as a generic medication and is sold under the brand names Zithromax and Zmax..

Azithromycin is used to treat a wide variety of bacterial infections, including bronchitis, pneumonia, and infections of the ear, sinus, skin, and throat. It is also used to treat certain sexually transmitted infections, such as chlamydia and gonorrhea. Azithromycin is generally well-tolerated, and side effects are rare. However, some people may experience diarrhea, nausea, vomiting, abdominal pain, or headache..

Azithromycin belongs to a class of antibiotics called macrolides, which are bacteriostatic agents that inhibit protein synthesis in bacteria. Azithromycin works by binding to the 50S ribosomal subunit of susceptible bacteria and inhibiting bacterial protein synthesis. This results in the death of the bacteria..

Azithromycin is effective against a wide variety of bacteria, including Streptococcus pneumoniae, Haemophilus influenzae, Moraxella catarrhalis, and Chlamydia trachomatis. Azithromycin has also been shown to be effective against certain sexually transmitted infections, such as chlamydia and gonorrhea..

Azithromycin is typically taken as a once-daily dose, or as directed by a healthcare provider. It is important to take azithromycin exactly as prescribed, and to finish the entire course of therapy even if you are feeling better. If you stop taking azithromycin too soon, the bacteria may not be completely eradicated, and the infection may return..

Azithromycin exists as a tablet, suspension, or intravenous (IV) formulation. The IV formulation is typically used for patients who are unable to take oral medications, or for those who have a more severe infection..

Azithromycin is generally well-tolerated, with few side effects. The most common side effects include diarrhea, nausea, vomiting, abdominal pain, and headache. Azithromycin is a safe and effective antibiotic, and exists as a generic medication..

3D structure

Cartesian coordinates

Geometry of Azythromycin in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Azythromycin MQTOSJVFKKJCRP-HHZDEWPHSA-N chemical compound 2D structure molecule svg
Azythromycin

 

Molecule descriptors

 
IUPAC name(2S,3S,4R,5S,8S,10S,11S,12R,13S,14R)-11-[(2R,3S,4R,6S)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-3,4,10-trihydroxy-13-[(2S,4S,5R,6R)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan-15-one
InChI codeInChI=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+/m0/s1
InChI KeyMQTOSJVFKKJCRP-HHZDEWPHSA-N
SMILESCC[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]2O[C@@H](C)C[C@@H](N(C)C)[C@@H]2O)[C@@](C)(O)C[C@H](C)CN(C)[C@@H](C)[C@@H](O)[C@]1(C)O

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (2S,3S,4R,5S,8S,10S,11S,12R,13S,14R)-11-[(2R,3S,4R,6S)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-3,4,10-trihydroxy-13-[(2S,4S,5R,6R)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan-15-one
  • Azythromycin

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • CHEBI:176304

Physico-Chemical properties

IUPAC name(2S,3S,4R,5S,8S,10S,11S,12R,13S,14R)-11-[(2R,3S,4R,6S)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-3,4,10-trihydroxy-13-[(2S,4S,5R,6R)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan-15-one
Molecular formulaC38H72N2O12
Molecular weight748.984
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity200.78
LogP1.8
Topological polar surface area180.1

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.