Cethromycin

Title: Cethromycin
CAS Registry Number: 205110-48-1
CAS Name: (3aS,4R,7R,9R,10R,11R,13R,15R,15aR)-4-Ethyloctahydro-3a,7,9,11,13,15-hexamethyl-11-[[3-(3-quinolinyl)-2-propenyl]oxy]-10-[[3,4,6-trideoxy-3-(dimethylamino)-b-D-xylohexopyranosyl]oxy]-2H-oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(1H,7H,9H)-tetrone
Manufacturers' Codes: A-195773; ABT-773
Molecular Formula: C42H59N3O10
Molecular Weight: 765.93
Percent Composition: C 65.86%, H 7.76%, N 5.49%, O 20.89%
Literature References: Semisynthetic macrolide antibiotic of the ketolide class; structurally similar to telithromycin, q.v. Prepn: Y. S. Or et al., WO 9809978; eidem, US 5866549 (1998, 1999 both to Abbott); eidem, J. Med. Chem. 43, 1045 (2000). Improved prepn: D. J. Plata et al., Tetrahedron 60, 10171 (2004). Comparative in vitro antibacterial spectrum: A. M. Nilius et al., Antimicrob. Agents Chemother. 45, 2163 (2001). Mechanism of action study: W. S. Champney, J. Pelt, Curr. Microbiol. 45, 155 (2002). HPLC-MS determn in biological samples: Q. Ren et al., J. Chromatogr. Sci. 41, 494 (2003). Clinical pharmacokinetics: M. W. Pletz et al., Antimicrob. Agents Chemother. 47, 1129 (2003). Reviews of development and therapeutic potential: L. E. Lawrence, Curr. Opin. Invest. Drugs 2, 766-772 (2001); T. J. Dougherty, J. F. Barrett, Expert Opin. Invest. Drugs 10, 343-351 (2001).
Properties: White crystalline solid, mp 211-213°.
Melting point: mp 211-213°
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); Macrolides.
Cetiedil Cetotiamine Cetoxime Cetraric Acid Cetraxate

Cethromycin
Cethromycin.png
Systematic (IUPAC) name
(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
Clinical data
Legal status Phase III Clinical Trials in US
Routes Oral
Pharmacokinetic data
Bioavailability Between 35.8 and 60 % in animal studies.
Metabolism Liver
Half-life 1.6, 3.0, 4.5, 5.9 and 6 hours. Mouse, Monkey, Rat, Dog and Human respectively.
Excretion 7.0% urine 87.2% faeces
Identifiers
CAS number 205110-48-1 YesY
ATC code None
PubChem CID 5282045
ChemSpider 23258189 N
UNII J0086219X6 YesY
KEGG D02391 N
Chemical data
Formula C42H59N3O10 
Mol. mass 765.931 g/mol
Physical data
Melt. point 211–213 °C (412–415 °F)
 N (what is this?)  (verify)

Cethromycin (initially known as ABT-773[1][2]) is a ketolide antibiotic undergoing research for the treatment of community acquired pneumonia (CAP)[1][3][4][5] and for the prevention of post-exposure inhalational anthrax, and was given an "orphan drug" status for this indication.[6] Originally discovered and developed by Abbott, it was acquired by Advanced Life Sciences Inc. for further development.

On October 1, 2008 Advanced Life Sciences submitted a New Drug Application (NDA) to Food and Drug Administration (FDA) for cethromycin to treat mild-to-moderate community acquired pneumonia.[7]

On December 3, 2008 Advanced Life Sciences announced that this New Drug Application has been accepted for filing by the FDA.[8]