SUTEZOLID

Possibly Marketed Outside US

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

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	MOL RATIO 1 MOL RATIO (average)

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

Conditions

Conditions

Condition	Modality	Targets	Highest Phase	Product
Tuberculosis 83	Curative		Phase II 1,132	Unknown

C_max

Value	Dose	Analyte	Population
986 ng/mL	600 mg 2 times / day multiple, oral	SUTEZOLID plasma	Homo sapiens
1972 ng/mL	1200 mg 1 times / day multiple, oral	SUTEZOLID plasma	Homo sapiens
252.4 ng/mL	100 mg 2 times / day steady-state, oral	SUTEZOLID plasma	Homo sapiens
458.7 ng/mL	300 mg 2 times / day steady-state, oral	SUTEZOLID plasma	Homo sapiens
942.7 ng/mL	600 mg 2 times / day steady-state, oral	SUTEZOLID plasma	Homo sapiens
2016 ng/mL	1200 mg 1 times / day steady-state, oral	SUTEZOLID plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
6494 ng × h/mL	600 mg 2 times / day multiple, oral	SUTEZOLID plasma	Homo sapiens
7127 ng × h/mL	1200 mg 1 times / day multiple, oral	SUTEZOLID plasma	Homo sapiens
845.8 ng × h/mL	100 mg 2 times / day steady-state, oral	SUTEZOLID plasma	Homo sapiens
2133 ng × h/mL	300 mg 2 times / day steady-state, oral	SUTEZOLID plasma	Homo sapiens
4294 ng × h/mL	600 mg 2 times / day steady-state, oral	SUTEZOLID plasma	Homo sapiens
10100 ng × h/mL	1200 mg 1 times / day steady-state, oral	SUTEZOLID plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
2.725 h	100 mg 2 times / day steady-state, oral	SUTEZOLID plasma	Homo sapiens
2.55 h	300 mg 2 times / day steady-state, oral	SUTEZOLID plasma	Homo sapiens
2.925 h	600 mg 2 times / day steady-state, oral	SUTEZOLID plasma	Homo sapiens
3.38 h	1200 mg 1 times / day steady-state, oral	SUTEZOLID plasma	Homo sapiens

Doses

Doses

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Dose	Population	Adverse events
1200 mg 1 times / day multiple, oral Highest studied dose	unhealthy, ADULT

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PubMed

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Title	Date	PubMed
Activities of several novel oxazolidinones against Mycobacterium tuberculosis in a murine model.	1999 May	10223934

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Patents

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
Record UNII	3A71182L8P
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

SUTEZOLID

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

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Classification Tree

Code System

Code

Positive

EU-Orphan Drug

EU/3/11/897

Designated

FDA ORPHAN DRUG

328210

Antibacterial Agent

NCI_THESAURUS

C280

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Code System

Code

Type

Description

EPA CompTox

DTXSID20168611

PRIMARY

NSC

742407

PRIMARY

NCI_THESAURUS

C152482

PRIMARY

ChEMBL

CHEMBL288149

PRIMARY

DRUG BANK

DB11905

PRIMARY

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Related Record

Type

Details


					R0EM8D5HFD

MYCOBACTERIUM TUBERCULOSIS

TARGET ORGANISM->INHIBITOR

Comments:

Intracellular Mycobacteria

Qualification:

IC50

Amount:

70.4 ng/mL (average)


					R0EM8D5HFD

MYCOBACTERIUM TUBERCULOSIS

TARGET ORGANISM->INHIBITOR

Qualification:

MIC

Amount:

0.25 microgram/mL (average)

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Related Record

Type

Details


					C26337G9CY

Sutezolid sulfoxide

METABOLITE ACTIVE -> PARENT

Comments:

Metabolite 17 fold less potent in killing intracellular M. Tb.

Interaction Type:

MAJOR

Amount:

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Related Record

Type

Details


					3A71182L8P

SUTEZOLID

ACTIVE MOIETY

Comments:

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

Amount:

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SMILES

InChI

Description<div class="info-popup-container"><div><span class="pop-sub-key ">Sources:&nbsp;</span><span class="pop-sub-val"><span class="ext-link"><a target="_self" href="https://www.ncbi.nlm.nih.gov/pubmed/8576910/">https://www.ncbi.nlm.nih.gov/pubmed/8576910/</a></span></span></div></div>

Originator

Approval Year

Conditions

Cmax

AUC

T1/2

Doses

PubMed

Patents

Sample Use Guides

Description

C_max

T_1/2