| Stereochemistry | ABSOLUTE |
| Molecular Formula | C21H21F2N3O7 |
| Molecular Weight | 465.4041 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC[C@H](O)C(=O)N1CCC(=CC1)C2=C(F)C=C(C=C2F)N3C[C@H](COC4=NOC=C4)OC3=O
InChI
InChIKey=HBUJYEUPIIJJOS-PBHICJAKSA-N
InChI=1S/C21H21F2N3O7/c22-15-7-13(26-9-14(33-21(26)30)11-31-18-3-6-32-24-18)8-16(23)19(15)12-1-4-25(5-2-12)20(29)17(28)10-27/h1,3,6-8,14,17,27-28H,2,4-5,9-11H2/t14-,17+/m1/s1
| Molecular Formula | C21H21F2N3O7 |
| Molecular Weight | 465.4041 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Posizolid (AZD2563 or AZD5847) is an oxazolidinone, identified from an antibiotic research programme which aimed to synthesise agents that inhibited all Gram-positive bacteria, including multiresistant strains likely to be encountered clinically. Oxazolidinones bind to the 50S ribosomal subunit and inhibit the initiation phase of translation. Posizolid had been in phase II clinical trials for the treatment of tuberculosis. However, this study was discontinued.
Originator
Approval Year
Cmax
AUC
T1/2
Sourcing
PubMed
Patents
Sample Use Guides
Phase 2 trial doses and schedules (500 mg once daily, 500 mg twice daily, 1200 mg once daily, and 800 mg twice daily) in subjects with newly-diagnosed sputum smear positive pulmonary tuberculosis.
Route of Administration:
Oral
Posizolid (AZD2563 or AZD5847) was tested against uncommonly isolated Gram-positive species to establish the breadth of its spectrum. By reference broth microdilution methods, 120 strains were tested (48 Corynebacterium spp., 10 species; 27 Listeria spp., 2 species; 11 Micrococcus spp., 2 species; 23 Bacillus spp., 3 species; 6 Stomatococcus mucilaginosus and one strain each of 5 other species) against AZD2563 and compared to eight other agents. The AZD2563/linezolid MIC(50;) % inhibited at < or =4 microg/mL were: for corynebacteria (0.25/0.25 microg/mL; 100/100%), Listeria spp. (2/2 microg/mL; 100/100%), Micrococcus spp. (1/1 microg/mL; 100/100%), Bacillus spp. (0.5/1 microg/mL; 100/100%), and S mucilaginosus (0.5/1 microg/mL; 100/100%). Using the MIC(90) values, AZD2563 was slightly more potent than linezolid (two-fold). Only four genus- species groups had AZD2563 MICs of strains at 2 microg/mL (Aerococcus, Leuconostoc, Listeria, Rhodococcus), all other isolates were inhibited by < or = 1 microg/mL.
