Cadazolid

Cadazolid

Systematic (IUPAC) name
1-Cyclopropyl-6-fluoro-7-[4-({2-fluoro-4-[(5R)-5-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]phenoxy}methyl)-4-hydroxypiperidin-1-yl]-4-oxo-1,4-dihydroquinolin-3-carboxylic acid
Clinical data
Legal status	Investigational
Identifiers
CAS Number	1025097-10-2
ATC code	none
ChemSpider	30774277
Chemical data
Formula	C29H29F2N3O8
Molar mass	585.55 g/mol
SMILES OC(C1=CN(C2CC2)C3=C(C=C(F)C(N4CCC(COC5=C(F)C=C(N6C[C@H](CO)OC6=O)C=C5)(O)CC4)=C3)C1=O)=O
InChI InChI=1S/C29H29F2N3O8/c30-21-10-19-23(33(16-1-2-16)13-20(26(19)36)27(37)38)11-24(21)32-7-5-29(40,6-8-32)15-41-25-4-3-17(9-22(25)31)34-12-18(14-35)42-28(34)39/h3-4,9-11,13,16,18,35,40H,1-2,5-8,12,14-15H2,(H,37,38)/t18-/m1/s1 Key:XWFCFMXQTBGXQW-GOSISDBHSA-N

Cadazolid is an experimental antibiotic of the oxazolidinone class made by Actelion Pharmaceuticals Ltd. which is effective against Clostridium difficile, a major cause of drug resistant diarrhea in the elderly.^[1] Current drug treatments for this infection involve orally delivered antibiotics, principally fidaxomicin, metronidazole and vancomycin; the last two drugs are the principal therapeutic agents in use, but fail in approximately 20 to 45% of the cases. The drug is in Phase III trials.^[1] The drug works by inhibiting synthesis of proteins in the bacteria, thus inhibiting the production of toxins and the formation of spores.^[2]

Structure

The chemical structure of cadazolid combines the pharmacophores of oxazolidinone and fluoroquinolone.^[2]

Clinical trials

In a study published in the journal Anaerobe, cadazolid has been shown to be effective in vitro against 133 strains of Clostridium difficile all collected from Sweden.^[3]

In phase I tests, sixty four male patients reacted favourably to cadazolid which primarily acted and remained in the colon while displaying little toxicity even in regimes involving large doses.^[1]

References

1. Boschert, Sherry (19 Sep 2012). "Promising C. difficile Antibiotic in Pipeline". Internal Medicine News. International Medical News Group. Retrieved 22 May 2013.
2. "Cadazolid". .actelion.com. Retrieved 2013-05-22.
3. "Anaerobe - In vitro activity of cadazolid against Clostridium difficile strains isolated from primary and recurrent infections in Stockholm, Sweden". Anaerobe 20: 32–35. 2013-02-26. doi:10.1016/j.anaerobe.2013.02.003. Retrieved 2013-05-22.