Sutezolid (also known as U-100480; U-480; PF-2341272; PNU-100480; PNU-480) is a novel, potent oxazolidinone antimicrobial agent being developed for the treatment of tuberculosis, especially drug-resistant tuberculosis. Sutezolid has potent activity in vitro and in a murine model of tuberculosis. PNU-100480 may have the potential to significantly shorten the duration of therapy for drug-susceptible as well as multidrug-resistant tuberculosis.
Physicochemical Properties
| Molecular Formula | C16H20N3O3FS |
| Molecular Weight | 353.4117 |
| Exact Mass | 353.121 |
| Elemental Analysis | C, 54.38; H, 5.70; F, 5.38; N, 11.89; O, 13.58; S, 9.07 |
| CAS # | 168828-58-8 |
| PubChem CID | 465951 |
| Appearance | A crystalline solid |
| Density | 1.321g/cm3 |
| Boiling Point | 609ºC at 760 mmHg |
| Flash Point | 322.1ºC |
| Vapour Pressure | 8.97E-15mmHg at 25°C |
| Index of Refraction | 1.584 |
| LogP | 2.361 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 4 |
| Heavy Atom Count | 24 |
| Complexity | 476 |
| Defined Atom Stereocenter Count | 1 |
| SMILES | O=C(O[C@H]1CNC(C)=O)N(C1)C2=CC(F)=C(N3CCSCC3)C=C2 |
| InChi Key | FNDDDNOJWPQCBZ-ZDUSSCGKSA-N |
| InChi Code | 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 |
| Chemical Name | (S)-N-((3-(3-fluoro-4-thiomorpholinophenyl)-2-oxooxazolidin-5-yl)methyl)acetamide |
| Synonyms | PNU 100480; PNU100480; U-100480; U 100480; U100480; PF-02341272; PF02341272; PF 02341272; PNU-100480; |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| Targets | Oxazolidinone |
| ln Vitro | PNU-100480, sutezolid, demonstrates remarkable in vitro efficacy against various clinical isolates of Mycobacterium avium complex (MICs ranging from 0.5 to 4 µg/mL)[1]. |
| ln Vivo | With better effectiveness against M. tuberculosis in hollow-fiber, mouse, and whole-blood models, sutezolid (PNU-100480) is a thiomorpholinyl analog of linezolid[3]. |
| References |
[1]. Identification of a novel oxazolidinone (U-100480) with potent antimycobacterial activity. J Med Chem. 1996;39(3):680-685. [2]. Sutezolid. In Kucers the Use of Antibiotics: A Clinical Review of Antibacterial, Antifungal, Antiparasitic, and Antiviral Drugs, Seventh Edition (pp. 2559-2563). CRC Press. [3]. Population pharmacokinetic/pharmacodynamic analysis of the bactericidal activities of sutezolid (PNU-100480) and its major metabolite against intracellular Mycobacterium tuberculosis in ex vivo whole-blood cultures of patients with pulmonary tuberculosis. Antimicrob Agents Chemother. 2014;58(6):3306-3311. [4]. PLoS One. 2014 Apr 14;9(4):e94462. |
| Additional Infomation | Sutezolid has been used in trials studying the treatment of Tuberculosis. |
Solubility Data
| Solubility (In Vitro) | DMSO : ~50 mg/mL (~141.48 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.07 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (7.07 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.5 mg/mL (7.07 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. Solubility in Formulation 4: 10% DMSO+40% PEG300+5% Tween-80+45% Saline: ≥ 2.5 mg/mL (7.07 mM) (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.8296 mL | 14.1479 mL | 28.2957 mL | |
| 5 mM | 0.5659 mL | 2.8296 mL | 5.6591 mL | |
| 10 mM | 0.2830 mL | 1.4148 mL | 2.8296 mL |