Cadazolid

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

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]

References

  1. 1 2 3 Boschert S (19 September 2012). "Promising C. difficile Antibiotic in Pipeline". Internal Medicine News. International Medical News Group. Retrieved 22 May 2013.
  2. 1 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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