Roxithromycin

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

What is the Roxithromycin?

The molecule Roxithromycin presents a molecular formula of C25H38O5 and its IUPAC name is (3R,4S,5S,6R,7R,9R,11S,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-10-(2-methoxyethoxymethoxyimino)-3,5,7,9,11,13-hexamethyl-oxacyclotetradecan-2-one.

Roxithromycin is a semi-synthetic macrolide antibiotic. It is used to treat respiratory tract, urinary and soft tissue infections. Roxithromycin comes from from erythromycin, contains a keto group at the C-3 position and a hydroxyl group at the C-9 position. The molecular weight is 758.88. The melting point is about 158 °C. Roxithromycin is soluble in ethanol, methanol, and acetone, slightly soluble in water, and practically insoluble in chloroform and petroleum ether..

Roxithromycin is bacteriostatic and works by binding to the 50S ribosomal subunit of susceptible bacteria and inhibiting protein synthesis. It is active against a wide range of Gram-positive and Gram-negative bacteria including: .

Streptococcus pneumoniae.

Streptococcus pyogenes.

Streptococcus agalactiae.

Haemophilus influenzae.

Moraxella catarrhalis.

Roxithromycin is used to treat respiratory tract infections, urinary tract infections and soft tissue infections. It is generally well tolerated with the most common side effects being gastrointestinal upset and rash..

3D structure

Cartesian coordinates

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

2D drawing

 

Roxithromycin RYMZZMVNJRMUDD-HGQWONQESA-N chemical compound 2D structure molecule svg
Roxithromycin

 

Molecule descriptors

 
IUPAC name(3R,4S,5S,6R,7R,9R,11S,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-10-(2-methoxyethoxymethoxyimino)-3,5,7,9,11,13-hexamethyl-oxacyclotetradecan-2-one
InChI codeInChI=1S/C25H38O5/c1-6-25(4,5)24(28)30-21-12-15(2)11-17-8-7-16(3)20(23(17)21)10-9-19-13-18(26)14-22(27)29-19/h7-8,11,15-16,18-21,23,26H,6,9-10,12-14H2,1-5H3/t15-,16-,18+,19+,20-,21-,23-/m0/s1
InChI KeyRYMZZMVNJRMUDD-HGQWONQESA-N
SMILESCCC(C)(C)C(=O)O[C@H]1C[C@@H](C)C=C2C=C[C@H](C)[C@H](CC[C@@H]3C[C@@H](O)CC(=O)O3)[C@H]21

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.

  • (3R,4S,5S,6R,7R,9R,10Z,11S,12R,13S,14R)-6-[4-(Dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-(5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl)oxy-10-(2-methoxyethoxymethoxyimino)-3,5,7,9,11,13-hexamethyl-oxacyclotetradecan-2-one
  • (3R,4S,5S,6R,7R,9R,11S,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-10-(2-methoxyethoxymethoxyimino)-3,5,7,9,11,13-hexamethyl-oxacyclotetradecan-2-one
  • 80214-83-1
  • BCBcMAP01_000131
  • DSSTox_CID_21117
  • DSSTox_GSID_41117
  • DSSTox_RID_79628
  • DivK1c_000382
  • HMS2236F08
  • KBio1_000382
  • KBio2_002133
  • KBio2_004701
  • KBio2_007269
  • KBio3_002217
  • KBioGR_000779
  • KBioSS_002133
  • MLS001304008
  • NCGC00016942-01
  • NCGC00182077-02
  • NCGC00255408-01
  • NINDS_000382
  • Roxithromycin
  • SMP1_000054
  • SMR000718779
  • roxithromycin

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC261494713
  • CAS-80214-83-1
  • DTXSID8041117
  • CHEMBL1476500
  • CHEBI:48844
  • Tox21_110697
  • Tox21_113150
  • Tox21_301835
  • SPBio_001422
  • Spectrum_001653
  • Spectrum2_001551
  • Spectrum3_001159
  • Spectrum4_000200

Physico-Chemical properties

IUPAC name(3R,4S,5S,6R,7R,9R,11S,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-10-(2-methoxyethoxymethoxyimino)-3,5,7,9,11,13-hexamethyl-oxacyclotetradecan-2-one
Molecular formulaC25H38O5
Molecular weight418.566
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity118.47
LogP4.6
Topological polar surface area72.8

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.