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Details

Stereochemistry ABSOLUTE
Molecular Formula C29H29F2N3O8
Molecular Weight 585.5527
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CADAZOLID

SMILES

OC[C@H]1CN(C(=O)O1)C2=CC(F)=C(OCC3(O)CCN(CC3)C4=CC5=C(C=C4F)C(=O)C(=CN5C6CC6)C(O)=O)C=C2

InChI

InChIKey=XWFCFMXQTBGXQW-GOSISDBHSA-N
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

HIDE SMILES / InChI

Molecular Formula C29H29F2N3O8
Molecular Weight 585.5527
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Cadazolid is a new antibiotic in development for the treatment of Clostridium difficile-associated diarrhea. Cadazolid is active against all (including linezolid- and moxifloxacin-resistant) Clostridium difficile strains. In phase I and II clinical trials, cadazolid was shown to be safe, well tolerated, and efficacious positioning itself as a potential future viable therapeutic option for CDI. Using a series of macromolecular labeling, in vitro transcription/translation, and topoisomerase studies, it was determined that protein synthesis inhibition via the oxazolidinone moiety is the primary mechanism of action of cadazolid. Cadazolid is in phase III clinical trials by Actelion Pharmaceuticals for the treatment of Clostridium difficile infection. The US FDA has designated cadazolid as both a Qualified Infectious Disease Product (QIDP) and a Fast Track development program for this indication.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
1.82 ng/mL
300 mg 2 times / day multiple, oral
CADAZOLID plasma
Homo sapiens
3.28 ng/mL
3000 mg 2 times / day multiple, oral
CADAZOLID plasma
Homo sapiens
2.24 ng/mL
1000 mg 2 times / day multiple, oral
CADAZOLID plasma
Homo sapiens
2.64 ng/mL
3000 mg single, oral
CADAZOLID plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
13.36 ng × h/mL
300 mg 2 times / day multiple, oral
CADAZOLID plasma
Homo sapiens
25.03 ng × h/mL
3000 mg 2 times / day multiple, oral
CADAZOLID plasma
Homo sapiens
17.68 ng × h/mL
1000 mg 2 times / day multiple, oral
CADAZOLID plasma
Homo sapiens
125 ng × h/mL
3000 mg single, oral
CADAZOLID plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
14.08 h
300 mg 2 times / day multiple, oral
CADAZOLID plasma
Homo sapiens
13.02 h
3000 mg 2 times / day multiple, oral
CADAZOLID plasma
Homo sapiens
14.17 h
1000 mg 2 times / day multiple, oral
CADAZOLID plasma
Homo sapiens

PubMed

Sample Use Guides

In Vivo Use Guide
Single and multiple (twice daily for 10 days) oral doses of cadazolid between 30 mg and 3000 mg, or placebo, were tested in a total of 64 healthy male subjects. Cadazolid was well tolerated up to 3000 mg given twice daily for 10 days.
Route of Administration: Oral
In Vitro Use Guide
Cadazolid was active against all (including linezolid- and moxifloxacin-resistant) C. difficile strains (MIC90 0.125, range 0.03-0.25 mg/L).
Substance Class Chemical
Record UNII
2OEA2UN10Y
Record Status Validated (UNII)
Record Version