Contezolid acefosamil

For research use only. Not for therapeutic Use.

  • CAT Number: I025095
  • CAS Number: 1807365-35-0
  • Molecular Formula: C20H17F3N4NaO8P
  • Molecular Weight: 552.33
  • Purity: 98%
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Contezolid acefosamil(Cat No.:I025095)is an investigational prodrug of contezolid, a potent oxazolidinone antibiotic. It is designed to target Gram-positive bacteria, including resistant strains such as methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant enterococci (VRE). Upon administration, contezolid acefosamil is converted to its active form, contezolid, which inhibits bacterial protein synthesis by binding to the bacterial ribosome. This compound is being evaluated in clinical trials for the treatment of complicated skin and soft tissue infections (cSSSIs) and pneumonia, offering a promising alternative to existing antibiotics.


Catalog Number I025095
CAS Number 1807365-35-0
Synonyms

Contezolid acefosamil; MRX4; MRX 4; MRX-4

Molecular Formula C20H17F3N4NaO8P
Purity 98%
Target Neuronal Signaling
Solubility Soluble in DMSO
Appearance Solid powder
Storage Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
IUPAC Name sodium;acetyloxy-[1,2-oxazol-3-yl-[[(5R)-2-oxo-3-[2,3,5-trifluoro-4-(4-oxo-2,3-dihydropyridin-1-yl)phenyl]-1,3-oxazolidin-5-yl]methyl]amino]phosphinate
InChI InChI=1S/C20H18F3N4O8P.Na/c1-11(28)35-36(31,32)27(16-4-7-33-24-16)10-13-9-26(20(30)34-13)15-8-14(21)19(18(23)17(15)22)25-5-2-12(29)3-6-25;/h2,4-5,7-8,13H,3,6,9-10H2,1H3,(H,31,32);/q;+1/p-1/t13-;/m1./s1
InChIKey JANNTEAGZXJITO-BTQNPOSSSA-M
SMILES CC(=O)OP(=O)(N(C[C@H]1CN(C(=O)O1)C2=CC(=C(C(=C2F)F)N3CCC(=O)C=C3)F)C4=NOC=C4)[O-].[Na+]
Reference

1: Wu J, Cao G, Wu H, Chen Y, Guo B, Wu X, Yu J, Ni K, Qian J, Wang L, Wu J, Wang Y, Yuan H, Zhang J, Xi Y. Evaluation of the Effect of Contezolid (MRX-I) on the Corrected QT Interval in a Randomized, Double-Blind, Placebo- and Positive- Controlled Crossover Study in Healthy Chinese Volunteers. Antimicrob Agents Chemother. 2020 May 21;64(6):e02158-19. doi: 10.1128/AAC.02158-19. PMID: 32229495; PMCID: PMC7269508.
2: Wu J, Wu H, Wang Y, Chen Y, Guo B, Cao G, Wu X, Yu J, Wu J, Zhu D, Guo Y, Yuan H, Hu F, Zhang J. Tolerability and Pharmacokinetics of Contezolid at Therapeutic and Supratherapeutic Doses in Healthy Chinese Subjects, and Assessment of Contezolid Dosing Regimens Based on Pharmacokinetic/Pharmacodynamic Analysis. Clin Ther. 2019 Jun;41(6):1164-1174.e4. doi: 10.1016/j.clinthera.2019.04.025. Epub 2019 May 22. PMID: 31126694.
3: Shoen C, DeStefano M, Hafkin B, Cynamon M. In Vitro and In Vivo Activities of Contezolid (MRX-I) against Mycobacterium tuberculosis. Antimicrob Agents Chemother. 2018 Jul 27;62(8):e00493-18. doi: 10.1128/AAC.00493-18. PMID: 29784848; PMCID: PMC6105800.
4: Li L, Wu H, Chen Y, Yuan H, Wu J, Wu X, Zhang Y, Cao G, Guo B, Wu J, Zhao M, Zhang J. Population Pharmacokinetics Study of Contezolid (MRX-I), a Novel Oxazolidinone Antibacterial Agent, in Chinese Patients. Clin Ther. 2020 May;42(5):818-829. doi: 10.1016/j.clinthera.2020.03.020. Epub 2020 May 7. PMID: 32389326.
5: Carvalhaes CG, Duncan LR, Wang W, Sader HS. In Vitro Activity and Potency of the Novel Oxazolidinone Contezolid (MRX-I) Tested against Gram- Positive Clinical Isolates from the United States and Europe. Antimicrob Agents Chemother. 2020 Oct 20;64(11):e01195-20. doi: 10.1128/AAC.01195-20. PMID: 32778552; PMCID: PMC7577137.
6: Wu J, Wang K, Chen Y, Yuan H, Li L, Zhang J. Concentration-response modeling of ECG data from early-phase clinical studies to assess QT prolongation risk of contezolid (MRX-I), an oxazolidinone antibacterial agent. J Pharmacokinet Pharmacodyn. 2019 Dec;46(6):531-541. doi: 10.1007/s10928-019-09650-7. Epub 2019 Aug 13. PMID: 31410633.
7: Wright A, Deane-Alder K, Marschall E, Bamert R, Venugopal H, Lithgow T, Lupton DW, Belousoff MJ. Characterization of the Core Ribosomal Binding Region for the Oxazolidone Family of Antibiotics Using Cryo-EM. ACS Pharmacol Transl Sci. 2020 May 13;3(3):425-432. doi: 10.1021/acsptsci.0c00041. PMID: 32566908; PMCID: PMC7296538.
8: Baillie TA, Dalvie D, Rietjens IM, Cyrus Khojasteh S. Biotransformation and bioactivation reactions – 2015 literature highlights. Drug Metab Rev. 2016 May;48(2):113-38. doi: 10.1080/03602532.2016.1195404. PMID: 27362326.
9: Bassetti M, Del Puente F, Magnasco L, Giacobbe DR. Innovative therapies for acute bacterial skin and skin-structure infections (ABSSSI) caused by methicillin-resistant Staphylococcus aureus: advances in phase I and II trials. Expert Opin Investig Drugs. 2020 May;29(5):495-506. doi: 10.1080/13543784.2020.1750595. Epub 2020 Apr 19. PMID: 32242469.
10: Gordeev MF, Yuan ZY. New potent antibacterial oxazolidinone (MRX-I) with an improved class safety profile. J Med Chem. 2014 Jun 12;57(11):4487-97. doi: 10.1021/jm401931e. Epub 2014 Apr 16. PMID: 24694071.

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