| Identification | Back Directory | [Name]
PNU 100480 | [CAS]
168828-58-8 | [Synonyms]
CS-2604
U-100480
Sutezolid
PNU 100480
PF-02341272
Sutezolid (PNU-100480)
Sutezolid >=98% (HPLC)
PNU-100480; U-100480; PF-02341272
Sutezolid (PNU-100480, PF-02341272)
PNU 100480 - PF 02341272 | U 100480 | Sutezolid
(S)-N-((3-(3-fluoro-4-thiomorpholinophenyl)-2-oxooxazolidin-5-yl)methyl)acetamide
(S)-N-[[3-[3-Fluoro-4-(4-thiomorpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]-acetamide
Acetamide, N-[[(5S)-3-[3-fluoro-4-(4-thiomorpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]-
(S)-N-((3-(3-fluoro-4-thiomorpholinophenyl)-2-oxooxazolidin-5-yl)methyl)acetamide(WXC06631) | [Molecular Formula]
C16H20FN3O3S | [MDL Number]
MFCD00937821 | [MOL File]
168828-58-8.mol | [Molecular Weight]
353.41 |
| Chemical Properties | Back Directory | [Melting point ]
186-187°C | [Boiling point ]
609.0±55.0 °C(Predicted) | [density ]
1.321±0.06 g/cm3(Predicted) | [storage temp. ]
room temp | [solubility ]
DMSO: soluble20mg/mL, clear | [form ]
powder | [pka]
15.53±0.46(Predicted) | [color ]
white to beige | [Optical Rotation]
[α]/D -8 to -12°, c = 1 in chloroform-d | [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 | [InChIKey]
FNDDDNOJWPQCBZ-ZDUSSCGKSA-N | [SMILES]
FC1=CC(N(C[C@H](CNC(C)=O)O2)C2=O)=CC=C1N3CCSCC3 |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
22 | [Safety Statements ]
45 | [WGK Germany ]
WGK 3 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral |
| Hazard Information | Back Directory | [Description]
PNU 100480 is an oxazolidinone antibiotic that is active against multidrug resistant tuberculosis. It inhibits the growth of M. tuberculosis replicating and nonreplicating strains (MIC = ~400 ng/ml for both) and of clinical isolates that are susceptible or resistant to a combination of isoniazid , rifampin (rifampicin; ), ethambutol , and streptomycin (; MICs = ≤0.0625-0.5 mg/L). It also inhibits the growth of P. insidiosum and P. aphanidermatum clinical isolates (MICs = 4-64 μg/ml). PNU 100480 (100 mg/kg per day) decreases the number of colony forming units (CFU) in the lung in a mouse model of systemic nonreplicating M. tuberculosis infection. | [Uses]
Sutezolid is an oxazolidinone antibacterial agent analog. Sutezolid is a promising antimycobacterial agent (tuberculostatic). | [Biochem/physiol Actions]
Sutezolid (PNU 100480) is an oxazolidinone antimicrobial. Sutezolid inhibits protein synthesis by inhibiting bacterial mRNA translation. Sutezolid is being investigated for the treatment of multiple drug–resistant and extensively drug-resistant tuberculosis. The compound is a less toxic and more potent derivative of linezolid. | [in vivo]
Sutezolid (PNU-100480) is a thiomorpholinyl analog of linezolid with superior efficacy against M. tuberculosis in the hollow-fiber, mouse, and whole-blood models[3]. | [IC 50]
Oxazolidinone | [storage]
Store at -20°C | [References]
[1] J W C ALFFENAAR. Susceptibility of clinical Mycobacterium tuberculosis isolates to a potentially less toxic derivate of linezolid, PNU-100480.[J]. Antimicrobial Agents and Chemotherapy, 2011, 55 3: 1287-1289. DOI: 10.1128/aac.01297-10
[2] MING ZHANG. In vitro and in vivo activities of three oxazolidinones against nonreplicating Mycobacterium tuberculosis.[J]. Antimicrobial Agents and Chemotherapy, 2014: 3217-3223. DOI: 10.1128/aac.02410-14
[3] ERICO S LORETO. In Vitro Activities of Miltefosine and Antibacterial Agents from the Macrolide, Oxazolidinone, and Pleuromutilin Classes against Pythium insidiosum and Pythium aphanidermatum.[J]. Antimicrobial Agents and Chemotherapy, 2018, 62 3. DOI: 10.1128/aac.01678-17 |
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Sigma-Aldrich
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