Compound: Telithromycin
SMILES: O=C1O[C@@H]([C@]2(OC(=O)N([C@@H]2[C@H](C(=O)[C@H](C)C[C@]([C@@H]([C@H](C([C@H]1C)=O)C)O[C@@H]3O[C@@H](C[C@@H]([C@H]3O)N(C)C)C)(OC)C)C)CCCCn4cnc(c4)-c5cnccc5)C)CC
InChIKey: LJVAJPDWBABPEJ-PNUFFHFMSA-N
Synonyms: Telithromycin, Ketek, 191114-48-4, HMR-3647, HMR3647, Levviax, RU-66647, telithromycine, telitromicina, KI8H7H19WL, DTXSID3046455, NSC-758940, DTXCID1026455, RU66647, (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, 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))-, telithromycinum, (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, RefChem:56921, J01FA15, (1S,2R,5R,7R,8R,9S,11R,13R,14R)-8-((2S,3R,4S,6R)-4-dimethylamino-3-hydroxy-6-methyl-oxan-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, (3aR,4S,7R,9R,10R,11R,13R,15R,15aR)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl)oxy)-4-ethyl-11-methoxy-3a,7,9,11,13,15-hexamethyl-1-(4-(4-(pyridin-3-yl)-1H-imidazol-1-yl)butyl)-tetradecahydro-1H-oxacyclotetradeca(4,3-d)(1,3)oxazole-2,6,8,14-tetrone, (1S,2R,5R,7R,8R,9R,11R,13R,14S)-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, HMR 3647, UNII-KI8H7H19WL, 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)-, RU 66647, MFCD00943561, (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, CAS-191114-48-4, C43H65N5O10, Telithromycin [USAN:INN:BAN], HSDB 7359, NCGC00164575-01, Telithromycin - 95%, Telithromycin (Ketek)?, Telithromycin (Standard), GlyTouCan:G09927EK, TELITHROMYCIN [MI], TELITHROMYCIN [INN], TELITHROMYCIN [JAN], SCHEMBL5100, CHEMBL1136, TELITHROMYCIN [HSDB], TELITHROMYCIN [USAN], TELITHROMYCIN [VANDF], TELITHROMYCIN [MART.], TELITHROMYCIN [WHO-DD], orb1689974, SCHEMBL29497351, TELITHROMYCIN [EMA EPAR], CHEBI:29688, HY-A0062R, GLXC-10284, TELITHROMYCIN [ORANGE BOOK], G09927EK, HY-A0062, Tox21_111454, Tox21_112203, BDBM50378137, MSK161460, DB00976, NSC 758940, HMR-3647;RU-66647, 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, AT164862, DA-68029, Q2736135, BRD-K82240271-001-01-8, (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-methyl-tetrahydropyran-2-yl]oxy-2-ethyl-9-methoxy-1,5,7,9,11,13-hexamethyl-15-[4-[4-(3-pyridyl)imidazol-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)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-11-methoxy-3a,7,9,11,13,15-hexamethyl-1-(4-(4-(pyridin-3-yl)-1H-imidazol-1-yl)butyl)octahydro-2H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(1H,7H,9H)-tetraone, (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, 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)-|A-D-xylo-hexopyranosyl]oxy]-, (3aS,4R,7R,9R,10R,11R,13R,15R,15aR)-, 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)-
Theoretical properties:
molecular_formula: C43H65N5O10
molecular_weight: 812.0 g/mol
exact_mass: 811.47314329 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 13
rotatable_bond_count: 11
heavy_atom_count: 58
topological_polar_surface_area: 172 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: White to off-white crystalline powder
color: White to off-white crystalline powder
melting_point: 176-188 °C
Descriptions:
pubchem: Telithromycin is an amino sugar.
chembl: TELITHROMYCIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Telithromycin is the first ketolide antibiotic to enter clinical use and is sold under the brand name of Ketek. It is used to treat community acquired pneumonia of mild to moderate severity. After significant safety concerns, the US Food and Drug Administration sharply curtailed the approved uses of the drug in early 2007.
Telithromycin is a semi-synthetic erythromycin derivative. It is created by substituting a ketogroup for the cladinose sugar and adding a carbamate ring in the lactone ring. An alkyl-aryl moiety is attached to this carbamate ring. Furthermore, the oxygen at the 6 position is methylated, as is the case with clarithromycin, to achieve better acid-stability.
It was patented in 1994 and approved for medical use in 2001.