Cadazolid

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 works by inhibiting synthesis of proteins in the bacteria, thus inhibiting the production of toxins and the formation of spores.[2] Cadazolid progressed through to Phase III clinical trials,[1] but in its financial results for Q1 2018, Idorsia mentions that Actelion informed them that "following completion of Phase 3 data analysis of cadazolid - it has decided to discontinue the development of the compound."[3]

Cadazolid
Clinical data
ATC code
  • none
Legal status
Legal status
  • Investigational
Identifiers
  • 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
CAS Number
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC29H29F2N3O8
Molar mass585.561 g·mol−1
3D model (JSmol)
  • 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=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

Structure

The chemical structure of cadazolid combines the pharmacophores of oxazolidinone and fluoroquinolone antibiotics.[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.[4]

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]

See also

References
  1. Boschert S (19 September 2012). "Promising C. difficile Antibiotic in Pipeline". Internal Medicine News. International Medical News Group. Retrieved 22 May 2013.
  2. "Cadazolid". .actelion.com. Archived from the original on 2013-06-09. Retrieved 2013-05-22.
  3. "Idorsia announces financial results for the first quarter 2018". Idorsia. April 19, 2018. Archived from the original on April 28, 2018. Retrieved April 27, 2018.
  4. Rashid MU, Lozano HM, Weintraub A, Nord CE (April 2013). "In vitro activity of cadazolid against Clostridium difficile strains isolated from primary and recurrent infections in Stockholm, Sweden". Anaerobe. 20: 32–5. doi:10.1016/j.anaerobe.2013.02.003. PMID 23454525.
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