CADAZOLID

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 Search

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24128668 | https://www.ncbi.nlm.nih.gov/pubmed/28286992 | https://www.pharmacodia.com/yaodu/html/v1/chemicals/92ae5cfef57d9ef9a523753e45fc9b0b.html

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 Target	Pharmacology	Condition	Potency
Clostridium difficile 3 Target ID: CHEMBL614965 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24128668	Inhibitor 8297
translation 13 Target ID: GO:0006412 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28286992 \| https://www.ncbi.nlm.nih.gov/pubmed/24277035	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Clostridium difficile infection 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26433782 https://www.ncbi.nlm.nih.gov/pubmed/26419191	Curative		Phase III 656	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
2.24 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24106141	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24106141	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26419191	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24106141	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

Value	Dose	Analyte	Population
17.68 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24106141	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24106141	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26419191	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24106141	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

T_1/2

Value	Dose	Analyte	Population
14.17 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24106141	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24106141	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24106141	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

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY34080	https://www.001chemical.com/chem/search?q=DY34080
1PlusChem LLC	1P01EP8Z	https://www.1pchem.com/search?query=1P01EP8Z
Chem Scene	CS-6972	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-6972
ChemShuttle	186322	https://www.chemshuttle.com/catalogsearch/result/?q=186322
Excenen	EX-A1438	http://www.excenen.com/searchresultlist.php?id=EX-A1438
Hairui	CAXM018	http://www.hairuichem.com/en/product/search.do?q=CAXM018
MedChem Express	HY-100436	https://www.medchemexpress.com/search.html?q=HY-100436&ft=&fa=&fp=
MolPort	MolPort-046-033-609	https://www.molport.com/shop/molecule-link/MolPort-046-033-609
Molcore	MC34080	http://www.molcore.com/CatMC34080.html
Molnova	M17120	https://www.molnova.com/en/serch-list.html?keywords=M17120
ShangHai Biochempartner	BCP20623	http://www.biochempartner.com/search_BCP20623
TargetMol	T4020	https://www.targetmol.com/search?keyword=T4020
eMolecules	89941811	https://orderbb.emolecules.com/search/#?query=89941811
mcule	MCULE-3184828472	https://mcule.com/MCULE-3184828472/
mcule	MCULE-9923304125	https://mcule.com/MCULE-9923304125/

PubMed

Title	Date	PubMed
In vitro activity of cadazolid against clinically relevant Clostridium difficile isolates and in an in vitro gut model of C. difficile infection.	2014 Mar	24128668
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	24106141
Susceptibility of Clostridium difficile isolates from a Phase 2 clinical trial of cadazolid and vancomycin in C. difficile infection.	2016 Jan	26433782

Patents

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 Created by `admin` on `Fri Dec 15 15:17:40 UTC 2023` Edited by `admin` on `Fri Dec 15 15:17:40 UTC 2023`
Record UNII	2OEA2UN10Y
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CADAZOLID

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