Contezolid
- Product Name
- Contezolid
- CAS No.
- 1112968-42-9
- Chemical Name
- Contezolid
- Synonyms
- MRX-1;MRX-I;Contezolid;Contezolid(MRX-1);Contezolid (MRX I);Ciprofol Impurity 8;(S)-5-((Isoxazol-3-ylamino)methyl)-3-(2,3,5-trifluoro-4-(4-oxo-3,4-dihydropyridin-1(2H)-yl)phenyl)oxazolidin-2-one;4(1H)-Pyridinone, 2,3-dihydro-1-[2,3,6-trifluoro-4-[(5S)-5-[(3-isoxazolylamino)methyl]-2-oxo-3-oxazolidinyl]phenyl]-
- CBNumber
- CB33152206
- Molecular Formula
- C18H15F3N4O4
- Formula Weight
- 408.33
- MOL File
- 1112968-42-9.mol
Contezolid Property
- Boiling point:
- 610.4±55.0 °C(Predicted)
- Density
- 1.528±0.06 g/cm3(Predicted)
- storage temp.
- -20°C Freezer, Under inert atmosphere
- solubility
- Chloroform (Slightly), DMSO (Very Slightly)
- form
- Solid
- pka
- 1.86±0.50(Predicted)
- color
- White to Off-White
- InChI
- InChI=1S/C18H15F3N4O4/c19-12-7-13(15(20)16(21)17(12)24-4-1-10(26)2-5-24)25-9-11(29-18(25)27)8-22-14-3-6-28-23-14/h1,3-4,6-7,11H,2,5,8-9H2,(H,22,23)/t11-/m0/s1
- InChIKey
- SULYVXZZUMRQAX-NSHDSACASA-N
- SMILES
- C1N(C2=C(F)C=C(N3C[C@H](CNC4C=CON=4)OC3=O)C(F)=C2F)C=CC(=O)C1
N-Bromosuccinimide Price
- Product number
- 453559
- Product name
- Lascufloxacin
- Packaging
- 500ug
- Price
- $403
- Updated
- 2021/12/16
Contezolid Chemical Properties,Usage,Production
Description
Contezolid (trade name Youxitai) is an oral oxazolidinone antibacterial drug developed by Shanghai MicuRx Pharmaceutical Co. Ltd. Contezolid is designed to overcome the myelosuppression and monoamine oxidase (MAO) inhibition limitations of the structurally similar linezolid.
Uses
Lascufloxacin is an intermediate used in the preparation of quinolonecarboxylic acid deriatives as antibacterial agents.
Application
Contezolid is used to treat complicated skin and soft tissue infections caused by multidrug-resistant Gram-positive bacteria, including methicillin-susceptible Staphylococcus aureus (MSSA), methicillin-resistant Staphylococcus aureus (MRSA), Streptococcus pyogenes, group B Streptococci, and vancomycin-resistant Enterococci.
Synthesis
The synthesis reported by Pharmacia began with a SNAr reaction between polyfluorinated nitrobenzene 4.1 and piperidin-4-one 4.2 to afford 4.3 in very high yield (Fig. 1.4). The silyl enol ether gave 4.4, which was then followed by the Tsuji method to afford the α,β-unsaturated ketone in very high yield. Subsequent reduction of the nitro group afforded the aryl amine 4.5. Treatment of 4.5 with isobutyl chloroformate afforded the carbamate 4.6, which was then treated with an optically pure epoxide 4.7 to afford the oxazolidinone 4.8. Mesylation of the free alcohol followed by substitution with an N-Boc aminoisoxazole 4.9 afforded the Boc-protected contizolamide 4.10. Simple removal of the Boc group with acid afforded the contizolamide (4).
in vivo
Oral absorption of Contezolid (MRX-I) occurrs rapidly in mouse, rat, and dog, with peak plasma concentrations observed at 0.5?2.6 h postdose. In mouse, rat, and dog, respectively, PK parameters are determined as follows: dose-normalized Cmax/dose was 524, 1065, and 259 ng/mL/(mg/kg); dose-normalized AUC0?t/dose was 1654, 3703, and 1664 ng?h/mL/(mg/kg); T1/2 is 1, 1.5, and 3 h; and the oral bioavailability is 69%, 109%, and 37%[2].
Contezolid (MRX-I) exhibits no obvious toxicity[2].
Contezolid (MRX-I, 100 mg/kg, once daily) significantly reduced the bacterial load in lungs compared to the untreated early and late controls[3].
| Animal Model: | BALB/c mice infected intranasally with M. tuberculosis Erdman[3]. |
| Dosage: | 100, 50 (twice), 25 (twice) mg/kg. |
| Administration: | Gavage, once or twice daily, five days per week for four weeks. |
| Result: | Significantly reduced the CFU recovered from the lungs compared to the early and late control mice (P < 0.05). Twice daily MRX-I at 50mg/kg and 25 mg/kg were significantly better than the late control mice (P < 0.05). Once daily MRX-I at 100 mg/kg was significantly better than twice daily 50 mg/kg and 25 mg/kg (P < 0.05). There was no statistical difference between twice daily 50 mg/kg of MRX-I and 25mg/kg (P > 0.05). |
| Animal Model: | Rats[2]. |
| Dosage: | 20, 100, and 200/300 mg/kg/day. |
| Administration: | Orally twice daily. |
| Result: | No mortality was observed. |
IC 50
Oxazolidinone