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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=C(OCC3(O)CCN(CC3)C4=CC5=C(C=C4F)C(=O)C(=CN5C6CC6)C(O)=O)C(F)=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
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2.24 ng/mL
1000 mg 2 times / day multiple, oral
dose: 1000 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
CADAZOLID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
3.28 ng/mL
3000 mg 2 times / day multiple, oral
dose: 3000 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
CADAZOLID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
2.64 ng/mL
3000 mg single, oral
dose: 3000 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CADAZOLID plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
1.82 ng/mL
300 mg 2 times / day multiple, oral
dose: 300 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
CADAZOLID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
17.68 ng × h/mL
1000 mg 2 times / day multiple, oral
dose: 1000 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
CADAZOLID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
25.03 ng × h/mL
3000 mg 2 times / day multiple, oral
dose: 3000 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
CADAZOLID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
125 ng × h/mL
3000 mg single, oral
dose: 3000 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CADAZOLID plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
13.36 ng × h/mL
300 mg 2 times / day multiple, oral
dose: 300 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
CADAZOLID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
14.17 h
1000 mg 2 times / day multiple, oral
dose: 1000 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
CADAZOLID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
13.02 h
3000 mg 2 times / day multiple, oral
dose: 3000 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
CADAZOLID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
14.08 h
300 mg 2 times / day multiple, oral
dose: 300 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
CADAZOLID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
PubMed

PubMed

TitleDatePubMed
In vitro activity of cadazolid against clinically relevant Clostridium difficile isolates and in an in vitro gut model of C. difficile infection.
2014 Mar
Cadazolid, a novel antibiotic with potent activity against Clostridium difficile: safety, tolerability and pharmacokinetics in healthy subjects following single and multiple oral doses.
2014 Mar
Susceptibility of Clostridium difficile isolates from a Phase 2 clinical trial of cadazolid and vancomycin in C. difficile infection.
2016 Jan
Patents

Sample Use Guides

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
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
Created
by admin
on Wed Jul 05 22:48:48 UTC 2023
Edited
by admin
on Wed Jul 05 22:48:48 UTC 2023
Record UNII
2OEA2UN10Y
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CADAZOLID
INN   USAN   WHO-DD  
USAN   INN  
Official Name English
cadazolid [INN]
Common Name English
Cadazolid [WHO-DD]
Common Name English
ACT-179811
Code English
3-QUINOLINECARBOXYLIC ACID, 1-CYCLOPROPYL-6-FLUORO-7-(4-((2-FLUORO-4-((5R)-5-(HYDROXYMETHYL)-2-OXO-3-OXAZOLIDINYL)PHENOXY)METHYL)-4-HYDROXY-1-PIPERIDINYL)-1,4-DIHYDRO-4-OXO-
Common Name English
CADAZOLID [USAN]
Common Name English
1-CYCLOPROPYL-6-FLUORO-7-(4-((2-FLUORO-4-((R)-5-HYDROXYMETHYL-2-OXOOXAZOLIDIN-3-YL)PHENOXY)METHYL)-4-HYDROXYPIPERIDIN-1-YL)-4-OXO-1,4-DIHYDROQUINOLINE-3-CARBOXYLIC ACID
Systematic Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 592917
Created by admin on Wed Jul 05 22:48:48 UTC 2023 , Edited by admin on Wed Jul 05 22:48:48 UTC 2023
NCI_THESAURUS C258
Created by admin on Wed Jul 05 22:48:48 UTC 2023 , Edited by admin on Wed Jul 05 22:48:48 UTC 2023
Code System Code Type Description
DRUG BANK
DB11847
Created by admin on Wed Jul 05 22:48:48 UTC 2023 , Edited by admin on Wed Jul 05 22:48:48 UTC 2023
PRIMARY
PUBCHEM
44242317
Created by admin on Wed Jul 05 22:48:48 UTC 2023 , Edited by admin on Wed Jul 05 22:48:48 UTC 2023
PRIMARY
ChEMBL
CHEMBL3707376
Created by admin on Wed Jul 05 22:48:48 UTC 2023 , Edited by admin on Wed Jul 05 22:48:48 UTC 2023
PRIMARY
USAN
CD-147
Created by admin on Wed Jul 05 22:48:48 UTC 2023 , Edited by admin on Wed Jul 05 22:48:48 UTC 2023
PRIMARY
EVMPD
SUB184432
Created by admin on Wed Jul 05 22:48:48 UTC 2023 , Edited by admin on Wed Jul 05 22:48:48 UTC 2023
PRIMARY
INN
9377
Created by admin on Wed Jul 05 22:48:48 UTC 2023 , Edited by admin on Wed Jul 05 22:48:48 UTC 2023
PRIMARY
EPA CompTox
DTXSID10145234
Created by admin on Wed Jul 05 22:48:48 UTC 2023 , Edited by admin on Wed Jul 05 22:48:48 UTC 2023
PRIMARY
WIKIPEDIA
Cadazolid
Created by admin on Wed Jul 05 22:48:48 UTC 2023 , Edited by admin on Wed Jul 05 22:48:48 UTC 2023
PRIMARY
NCI_THESAURUS
C118642
Created by admin on Wed Jul 05 22:48:48 UTC 2023 , Edited by admin on Wed Jul 05 22:48:48 UTC 2023
PRIMARY
CAS
1025097-10-2
Created by admin on Wed Jul 05 22:48:48 UTC 2023 , Edited by admin on Wed Jul 05 22:48:48 UTC 2023
PRIMARY
FDA UNII
2OEA2UN10Y
Created by admin on Wed Jul 05 22:48:48 UTC 2023 , Edited by admin on Wed Jul 05 22:48:48 UTC 2023
PRIMARY
SMS_ID
100000170453
Created by admin on Wed Jul 05 22:48:48 UTC 2023 , Edited by admin on Wed Jul 05 22:48:48 UTC 2023
PRIMARY
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TARGET ORGANISM->INHIBITOR
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ACTIVE MOIETY