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Details

Stereochemistry ABSOLUTE
Molecular Formula C16H20FN3O3S
Molecular Weight 353.412
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SUTEZOLID

SMILES

CC(=O)NC[C@H]1CN(C(=O)O1)C2=CC(F)=C(C=C2)N3CCSCC3

InChI

InChIKey=FNDDDNOJWPQCBZ-ZDUSSCGKSA-N
InChI=1S/C16H20FN3O3S/c1-11(21)18-9-13-10-20(16(22)23-13)12-2-3-15(14(17)8-12)19-4-6-24-7-5-19/h2-3,8,13H,4-7,9-10H2,1H3,(H,18,21)/t13-/m0/s1

HIDE SMILES / InChI
Molecular Formula C16H20FN3O3S
Molecular Weight 353.412
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Sutezolid (PNU-100480, PF-02341272) is an oxazolidinone antibiotic currently in development as a treatment for extensively drug-resistant tuberculosis. It is unaffected by mutations conferring resistance to standard TB drugs

Originator

Approval Year

Unknown
139594
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Phase II
1132
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Identification of a novel oxazolidinone (U-100480) with potent antimycobacterial activity.
1996 Feb 2
Activities of several novel oxazolidinones against Mycobacterium tuberculosis in a murine model.
1999 May
Short-course treatment regimen to identify potential antituberculous agents in a murine model of tuberculosis.
2004 Apr
Synthesis and in vitro antimycobacterial activity of novel 3-(1H-pyrrol-1-yl)-2-oxazolidinone analogues of PNU-100480.
2004 Mar 22
New small-molecule synthetic antimycobacterials.
2005 Jun
In vitro activities of PNU-100480 and linezolid against drug-susceptible and drug-resistant Mycobacterium tuberculosis isolates.
2013 Jul
Patents

Patents

05688792
1

Sample Use Guides

In Vivo Use Guide
600 mg twice daily (BID) for 14 days
Route of Administration: Oral
In Vitro Use Guide
U-100480 (SUTEZOLID) exhibited excellent in vitro activity against multiple clinical isolates of Mycobacterium avium complex (MIC's = 0.5-4 micrograms/mL).
Substance Class Chemical
Created
by admin
on Fri Dec 15 19:47:55 UTC 2023
Edited
by admin
on Fri Dec 15 19:47:55 UTC 2023
Record UNII
3A71182L8P
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SUTEZOLID
INN   USAN   WHO-DD  
INN   USAN  
Official Name English
U-100480
Code English
Sutezolid [WHO-DD]
Common Name English
ACETAMIDE, N-((3-(3-FLUORO-4-(4-THIOMORPHOLINYL)PHENYL)-2-OXO-5-OXAZOLIDINYL)METHYL)-, (S)-
Common Name English
PNU-100480
Code English
SUTEZOLID [USAN]
Common Name English
(S)-N-((3-(3-FLUORO-4-THIOMORPHOLINOPHENYL)-2-OXOOXAZOLIDIN-5-YL)METHYL)ACETAMIDE
Systematic Name English
N-({(5S)-3-[3-Fluoro-4-(thiomorpholin-4-yl)phenyl]-2-oxooxazolidin-5-yl}methyl) acetamide
Systematic Name English
sutezolid [INN]
Common Name English
U-480
Code English
U100480
Code English
OXAZOLIDININONE
Common Name English
NSC-742407
Code English
ACETAMIDE, N-(((5S)-3-(3-FLUORO-4-(4-THIOMORPHOLINYL)PHENYL)-2-OXO-5-OXAZOLIDINYL) METHYL)-
Common Name English
Classification Tree Code System Code
EU-Orphan Drug EU/3/11/897
Created by admin on Fri Dec 15 19:47:55 UTC 2023 , Edited by admin on Fri Dec 15 19:47:55 UTC 2023
FDA ORPHAN DRUG 328210
Created by admin on Fri Dec 15 19:47:55 UTC 2023 , Edited by admin on Fri Dec 15 19:47:55 UTC 2023
NCI_THESAURUS C280
Created by admin on Fri Dec 15 19:47:55 UTC 2023 , Edited by admin on Fri Dec 15 19:47:55 UTC 2023
Code System Code Type Description
EPA CompTox
DTXSID20168611
Created by admin on Fri Dec 15 19:47:55 UTC 2023 , Edited by admin on Fri Dec 15 19:47:55 UTC 2023
PRIMARY
NSC
742407
Created by admin on Fri Dec 15 19:47:55 UTC 2023 , Edited by admin on Fri Dec 15 19:47:55 UTC 2023
PRIMARY
NCI_THESAURUS
C152482
Created by admin on Fri Dec 15 19:47:55 UTC 2023 , Edited by admin on Fri Dec 15 19:47:55 UTC 2023
PRIMARY
ChEMBL
CHEMBL288149
Created by admin on Fri Dec 15 19:47:55 UTC 2023 , Edited by admin on Fri Dec 15 19:47:55 UTC 2023
PRIMARY
DRUG BANK
DB11905
Created by admin on Fri Dec 15 19:47:55 UTC 2023 , Edited by admin on Fri Dec 15 19:47:55 UTC 2023
PRIMARY
PUBCHEM
465951
Created by admin on Fri Dec 15 19:47:55 UTC 2023 , Edited by admin on Fri Dec 15 19:47:55 UTC 2023
PRIMARY
SMS_ID
100000182673
Created by admin on Fri Dec 15 19:47:55 UTC 2023 , Edited by admin on Fri Dec 15 19:47:55 UTC 2023
PRIMARY
USAN
XX-127
Created by admin on Fri Dec 15 19:47:55 UTC 2023 , Edited by admin on Fri Dec 15 19:47:55 UTC 2023
PRIMARY
CAS
168828-58-8
Created by admin on Fri Dec 15 19:47:55 UTC 2023 , Edited by admin on Fri Dec 15 19:47:55 UTC 2023
PRIMARY
WIKIPEDIA
SUTEZOLID
Created by admin on Fri Dec 15 19:47:55 UTC 2023 , Edited by admin on Fri Dec 15 19:47:55 UTC 2023
PRIMARY Sutezolid (PNU-100480, PF-02341272) is an oxazolidinone antibiotic currently in development as a treatment for extensively drug-resistant tuberculosis.
INN
9444
Created by admin on Fri Dec 15 19:47:55 UTC 2023 , Edited by admin on Fri Dec 15 19:47:55 UTC 2023
PRIMARY
FDA UNII
3A71182L8P
Created by admin on Fri Dec 15 19:47:55 UTC 2023 , Edited by admin on Fri Dec 15 19:47:55 UTC 2023
PRIMARY
Related Record Type Details
MYCOBACTERIUM TUBERCULOSIS
TARGET ORGANISM->INHIBITOR
Intracellular Mycobacteria
IC50
MYCOBACTERIUM TUBERCULOSIS
TARGET ORGANISM->INHIBITOR
MIC
Related Record Type Details
Structure of Sutezolid sulfoxide
METABOLITE ACTIVE -> PARENT
Metabolite 17 fold less potent in killing intracellular M. Tb.
MAJOR
Related Record Type Details
Structure of SUTEZOLID
ACTIVE MOIETY
Originator: Pharmacia Corporation; Developer: Sequella; Class: Acetamide, Amide, Antibacterial, Oxazolidinone, Small molecule, Thiamorpholine; Mechanism of Action: Protein 30S ribosomal subunit inhibitor; Highest Development Phase: No development reported for Tuberculosis; Most Recent Events: 27 Jul 2015 No recent reports on development identified - Phase-II for Tuberculosis (Treatment-naive) in South Africa (PO): 27 Jul 2015 No recent reports on development identified - Phase-I for Tuberculosis (In volunteers) in USA (PO): 09 Aug 2013 Pfizer terminates its involvement in the development of sutezolid
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