cadazolid
{{Short description|Chemical compound}}
{{Drugbox
| drug_name =
| 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
| image = Cadazolid.svg
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| width = 250
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| Drugs.com =
| MedlinePlus =
| pregnancy_AU =
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| legal_AU =
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| legal_US =
| legal_status = Investigational
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| protein_bound =
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| CAS_number = 1025097-10-2
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 2OEA2UN10Y
| KEGG = D11207
| ATCvet =
| ATC_prefix = none
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| ChemSpiderID = 30774277
| C=29 | H=29 | F=2 | N=3 | O=8
| 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
| StdInChI = 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
| StdInChIKey = XWFCFMXQTBGXQW-GOSISDBHSA-N
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Cadazolid is an experimental antibiotic of the oxazolidinone class made by Actelion Pharmaceuticals Ltd. which is effective against Clostridioides difficile, a major cause of drug resistant diarrhea in the elderly.{{cite web |url=http://www.internalmedicinenews.com/index.php?id=2049&type=98&tx_ttnews%5Btt_news%5D=137097&cHash=da03e20e36 |title=Promising C. difficile Antibiotic in Pipeline |last1=Boschert |first1=Sherry | name-list-style = vanc |date=19 September 2012 |website=Internal Medicine News |publisher= International Medical News Group |access-date=22 May 2013}} 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 the synthesis of proteins in the bacteria, thus inhibiting the production of toxins and the formation of spores.{{cite web |url=http://www1.actelion.com/en/scientists/development-pipeline/phase-2/cadazolid.page |title=Cadazolid |publisher=.actelion.com |access-date=2013-05-22 |archive-url=https://web.archive.org/web/20130609070712/http://www1.actelion.com/en/scientists/development-pipeline/phase-2/cadazolid.page |archive-date=2013-06-09 |url-status=dead }} Cadazolid progressed through to Phase III clinical trials, 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."{{Cite web|url=https://www.idorsia.com/media/news-details?newsId=2185240|title=Idorsia announces financial results for the first quarter 2018|date=April 19, 2018|website=Idorsia|access-date=April 27, 2018|archive-url=https://web.archive.org/web/20180428011732/https://www.idorsia.com/media/news-details?newsId=2185240|archive-date=April 28, 2018|url-status=dead}}
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Structure
The chemical structure of cadazolid combines the pharmacophores of oxazolidinone and fluoroquinolone antibiotics.
Clinical trials
In a study published in the journal Anaerobe, cadazolid has been shown to be effective in vitro against 133 strains of Clostridioides difficile all collected from Sweden.{{cite journal | vauthors = Rashid MU, Lozano HM, Weintraub A, Nord CE | title = In vitro activity of cadazolid against Clostridium difficile strains isolated from primary and recurrent infections in Stockholm, Sweden | journal = Anaerobe | volume = 20 | pages = 32–5 | date = April 2013 | pmid = 23454525 | doi = 10.1016/j.anaerobe.2013.02.003 }}
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.