Telithromycin

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

What is the Telithromycin?

The molecule Telithromycin presents a molecular formula of C43H65N5O10 and its IUPAC name is (1S,2R,5R,7R,8R,9R,11R,13R,14R)-8-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-9-methoxy-1,5,7,9,11,13-hexamethyl-15-[4-(4-pyridin-3-ylimidazol-1-yl)butyl]-3,17-dioxa-15-azabicyclo[12.3.0]heptadecane-4,6,12,16-tetrone.

Telithromycin (trade name Ketek) is an antibiotic used to treat respiratory infections. It is a semi-synthetic derivative of erythromycin, developed by Aventis. Ketek was approved by the FDA in 2004..

Telithromycin is indicated for the treatment of mild to moderate respiratory tract infections, including sinusitis, otitis media, and acute bacterial exacerbations of bronchitis. It has activity against a wide range of Gram-positive and Gram-negative bacteria, including Streptococcus pneumoniae, Haemophilus influenzae, Moraxella catarrhalis, and Legionella pneumophila..

The most common adverse effects of telithromycin are gastrointestinal, including nausea, vomiting, diarrhea, and abdominal pain. Other common side effects include headache, dizziness, and rash. Rare but serious side effects include liver damage, muscle weakness, and prolongation of the QT interval on electrocardiograms..

Telithromycin should not be used in people with myasthenia gravis, as it may worsen the condition. It should also be used with caution in people with renal impairment and in those taking other medications that can affect the QT interval..

3D structure

Cartesian coordinates

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

2D drawing

 

Telithromycin LJVAJPDWBABPEJ-PNUFFHFMSA-N chemical compound 2D structure molecule svg
Telithromycin

 

Molecule descriptors

 
IUPAC name(1S,2R,5R,7R,8R,9R,11R,13R,14R)-8-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-9-methoxy-1,5,7,9,11,13-hexamethyl-15-[4-(4-pyridin-3-ylimidazol-1-yl)butyl]-3,17-dioxa-15-azabicyclo[12.3.0]heptadecane-4,6,12,16-tetrone
InChI codeInChI=1S/C43H65N5O10/c1-12-33-43(8)37(48(41(53)58-43)19-14-13-18-47-23-31(45-24-47)30-16-15-17-44-22-30)27(4)34(49)25(2)21-42(7,54-11)38(28(5)35(50)29(6)39(52)56-33)57-40-36(51)32(46(9)10)20-26(3)55-40/h15-17,22-29,32-33,36-38,40,51H,12-14,18-21H2,1-11H3/t25-,26-,27+,28+,29-,32+,33-,36-,37-,38-,40+,42-,43-/m1/s1
InChI KeyLJVAJPDWBABPEJ-PNUFFHFMSA-N
SMILESCC[C@H]1OC(=O)[C@H](C)C(=O)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@H](N(C)C)[C@H]2O)[C@](C)(OC)C[C@@H](C)C(=O)[C@H](C)[C@H]2N(CCCCn3cnc(-c4cccnc4)c3)C(=O)O[C@]12C

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.

  • (1R,2R,4R,6R,7R,8R,10R,13R,14S)-7-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-13-ethyl-6-methoxy-2,4,6,8,10,14-hexamethyl-17-[4-[4-(3-pyridyl)imidazol-1-yl]butyl]-12,15-dioxa-17-azabicyclo[12.3.0]heptadecane-3,9,11,16-tetrone
  • (1S,2R,5R,7R,8R,9R,11R,13R,14R)-8-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-9-methoxy-1,5,7,9,11,13-hexamethyl-15-[4-(4-pyridin-3-ylimidazol-1-yl)butyl]-3,17-dioxa-15-azabicyclo[12.3.0]heptadecane-4,6,12,16-tetrone
  • (3aS,4R,7R,9R,10R,11R,13R,15R,15aR)-4-Ethyl-11-methoxy-3a,7,9,11,13,15-hexamethyl-1-(4-(4-(pyridin-3-yl)-1H-imidazol-1-yl)butyl)-10-((3,4,6-trideoxy-3-(dimethylamino)-b-d-xylo-hexopyranosyl)oxy)octahydro-2H-oxacyclotetradecino(4,3-d)oxazole-2,6,8,14(1H,7H,9H)-tetrone
  • (3aS,4R,7R,9R,10R,11R,13R,15R,15aR)-4-ethyl-11-methoxy-3a,7,9,11,13,15-hexamethyl-2,6,8,14-tetraoxo-1-{4-[4-(pyridin-3-yl)-1H-imidazol-1-yl]butyl}tetradecahydro-2H-oxacyclotetradecino[4,3-d][1,3]oxazol-10-yl 3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranoside
  • 11,12-Dideoxy-3-des(2,6-dideoxy-3-C,3-O-dimethyl-alpha-L-altropyranosyloxy)-6-O-methyl-3-oxo-12,11-(oxycarbonylimino)-N11-[4-[4-(3-pyridyl)imidazol-1-yl]butyl]erythromycin A
  • 191114-48-4
  • 2H-Oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(1H,7H,9H)-tetrone, 4-ethyloctahydro-11-methoxy-3a,7,9,11,13,15-hexamethyl-1-[4-[4-(3-pyridinyl)-1H-imidazol-1-yl]butyl]-10-[[3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyl]oxy]-, (3aS,4R,7R,9R,10R,11R,13R,15R,15aR)-
  • BDBM50378137
  • DB00976
  • DSSTox_CID_26455
  • DSSTox_GSID_46455
  • DSSTox_RID_81629
  • ERYTHROMYCIN,3-DE((2,6-DIDEOXY-3-C-METHYL-3-O-METHYL-.ALPHA.-L-RIBO-HEXOPYRANOSYL)OXY)-11,12-DIDEOXY-6-O-METHYL-3-OXO-12,11-(OXYCARBONYL((4-(4-(3-PYRIDINYL)-1H-IMIDAZOL-1-YL)BUTYL)IMINO)-
  • Erythromycin, 3-de((2,6-dideoxy-3-C-methyl-3-O-methyl-alpha-L-ribo-hexopyranosyl)oxy)-11,12-dideoxy-6-O-methyl-3-oxo-12,11-(oxycarbonyl((4-(4-(3-pyridinyl)-1H-imidazol-1-yl)butyl)imino))-
  • HMR 3647
  • HMR-3647
  • HMR-3647;RU-66647
  • HMR3647
  • HSDB 7359
  • HY-A0062
  • KI8H7H19WL
  • Ketek
  • Levviax
  • MFCD00943561
  • NCGC00164575-01
  • NSC 758940
  • NSC-758940
  • Q2736135
  • RU 66647
  • RU-66647
  • RU66647
  • Telithromycin

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC9574770
  • CAS-191114-48-4
  • UNII-KI8H7H19WL
  • DTXSID3046455
  • CHEMBL1136
  • CHEBI:29688
  • Tox21_111454
  • Tox21_112203
  • SCHEMBL5100

Physico-Chemical properties

IUPAC name(1S,2R,5R,7R,8R,9R,11R,13R,14R)-8-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-9-methoxy-1,5,7,9,11,13-hexamethyl-15-[4-(4-pyridin-3-ylimidazol-1-yl)butyl]-3,17-dioxa-15-azabicyclo[12.3.0]heptadecane-4,6,12,16-tetrone
Molecular formulaC43H65N5O10
Molecular weight812.004
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity221.38
LogP4.9
Topological polar surface area171.9

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.