(1R,2R,4R,6S,7R,8R,10R,13R,14S)-7-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-13-ethyl-2,4,6,8,10,14-hexamethyl-6-[(E)-3-(3-quinolyl)allyloxy]-12,15-dioxa-17-azabicyclo[12.3.0]heptadecane-3,9,11,16-tetrone
Basic information
- CAS
205110-48-1- Standard SMILES
CC[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/c2cnc3ccccc3c2)C[C@@H](C)C(=O)[C@H](C)[C@H]2NC(=O)O[C@@]21C- InChIKey
PENDGIOBPJLVBT-HMMOOPTJSA-N- Molecular formula
- C42H59N3O10
- Average molar mass
- 765.9 g/mol
- Monoisotopic mass
- 765.42004509
Names & identifiers
- Preferred name
- (1R,2R,4R,6S,7R,8R,10R,13R,14S)-7-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-13-ethyl-2,4,6,8,10,14-hexamethyl-6-[(E)-3-(3-quinolyl)allyloxy]-12,15-dioxa-17-azabicyclo[12.3.0]heptadecane-3,9,11,16-tetrone
- IUPAC
- (1S,2R,5R,7R,8R,9S,11R,13R,14R)-8-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-1,5,7,9,11,13-hexamethyl-9-[(E)-3-quinolin-3-ylprop-2-enoxy]-3,17-dioxa-15-azabicyclo[12.3.0]heptadecane-4,6,12,16-tetrone
- English name
- CETHROMYCIN
- Molecular formula
- C42H59N3O10
- Molecular weight
- 765.93
Names & synonyms
C12020SCHEMBL1650649(1R,2R,4R,6S,7R,8R,10R,13R,14S)-7-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-13-ethyl-2,4,6,8,10,14-hexamethyl-6-[(E)-3-(3-quinolyl)allyloxy]-12,15-dioxa-17-azabicyclo[12.3.0]heptadecane-3,9,11,16-tetrone(1S,2R,5R,7R,8R,9R,11R,13R,14R)-2-Ethyl-1,5,7,9,11,13-Hexamethyl-9-[3-(3-quinolyl)-2(E)-propenyloxy]-8-[3,4,6-trideoxy-3-(dimethylamino)-beta-D-glucopyranosyloxy]-3,17-dioxa-15-azabicyclo[12.3.0]hepta(1S,2R,5R,7R,8R,9S,11R,13R,14R)-8-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-1,5,7,9,11,13-hexamethyl-9-[(E)-3-quinolin-3-ylprop-2-enoxy]-3,17-dioxa-15-azabicyclo[12.3.0]heptadecane-4,6,12,16-tetroneABT-773RestanzaA-195773CETHROMYCINAbbott-195773quinerythromycinCETHROMYCIN(ABT-773)
Show more names
11-Amino-11-deoxy-3-oxo-5-o-desosaminyl-6-o-[1'-(3'-quinolyl-2'-propenyl)] erythronolide A 11,12-cyclic carbamate
Properties
Computed structural properties
- XLogP
- 5.4
- Topological polar surface area
- 163 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 12
- Rotatable bonds
- 8
- Heavy atoms
- 55
- Formal charge
- 0
- Complexity
- 1,410
Physicochemical properties
- Melting point
- 211 · 211-213°
- Boiling point
- 927.1 · 927.1±65.0 °C(Predicted)
- Density
- 1.22 · 1.22±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · Store at -20°C
- form
- Solid
- pka
- 10.84 · 10.84±0.70(Predicted)
- color
- White to off-white
- FDA UNII
- 86219 X6 · J0086219X6
Chemistry & industry
Applications
DescriptionCethromycin (formerly ABT-773) is a ketolide antibiotic originally developed by Abbott in the late 1990s, but abandoned in 2002. Since 2004, Advanced Life Sciences has promoted current development of cethromycin. The ketolides are structurally derived from erythromycin A and are designed to overcome resistance to macrolides. One of the main features is the lack of the neutral sugar L-cladinose at position 3 of the erythonolide ring, which is replaced by a keto group (thus giving rise to the class name). Lack of the L-cladinose moiety results in better drug absorption and less gastric irritation through improved acid stability.
UsesAntibacterial.
Additional notes
DefinitionChEBI: Cethromycin is a macrolide antibiotic which displays in vitro activity against both gram-positive and gram-negative bacteria and is currently under investigation for the treatment of community-acquired pneumonia. The US Food and Drug Administration (FDA) have also granted orphan drug designation to cethromycin for the treatment of anthrax prophylaxis, tularemia, and plague (PDB entry: 1NWX). It has a role as an antibacterial drug and a protein synthesis inhibitor. It is a macrolide antibiotic, a member of quinolines and a monosaccharide derivative.
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