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	1025097-10-2;
ChemSpider	30774277;
UNII	2OEA2UN10Y;
KEGG	D11207;
CompTox Dashboard (EPA)	DTXSID10145234 ;
Chemical and physical data
Formula	C29H29F2N3O8
Molar mass	585.561 g·mol−1
3D model (JSmol)	Interactive image;
	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

^ ^a ^b ^c Boschert, Sherry (19 September 2012). "Promising C. difficile Antibiotic in Pipeline". Internal Medicine News. International Medical News Group. Retrieved 22 May 2013.
^ ^a ^b "Cadazolid". .actelion.com. Archived from the original on 2013-06-09. Retrieved 2013-05-22.
^ "Idorsia announces financial results for the first quarter 2018". Idorsia. April 19, 2018.
^ Rashid, M. U.; Lozano, H. M.; Weintraub, A.; Nord, C. E. (2013-02-26). "Anaerobe - In vitro activity of cadazolid against Clostridium difficile strains isolated from primary and recurrent infections in Stockholm, Sweden". Anaerobe. 20: 32–35. doi:10.1016/j.anaerobe.2013.02.003. PMID 23454525.

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[www.internalmedicinenews.com-1] Boschert, Sherry (19 September 2012). "Promising C. difficile Antibiotic in Pipeline". Internal Medicine News. International Medical News Group. Retrieved 22 May 2013.

[Cadazolid-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.

[ScienceDirect-4] Rashid, M. U.; Lozano, H. M.; Weintraub, A.; Nord, C. E. (2013-02-26). "Anaerobe - In vitro activity of cadazolid against Clostridium difficile strains isolated from primary and recurrent infections in Stockholm, Sweden". Anaerobe. 20: 32–35. doi:10.1016/j.anaerobe.2013.02.003. PMID 23454525.

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