Radezolid

Radezolid
Systematic (IUPAC) name

N-{[(5S)-3-(2-fluoro-4′-{[(1H-1,2,3-triazol-5-ylmethyl)amino]methyl}biphenyl-4-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide
Clinical data
Routes of administration	Intravenous infusion, oral
Legal status	Investigational
Identifiers
CAS Number	869884-78-6
ATC code	none
PubChem	CID 11224409
ChemSpider	9399462
UNII	53PC6LO35W^Y
ChEMBL	CHEMBL455461
Chemical data
Formula	C₂₂H₂₃FN₆O₃
Molar mass	438.455 g/mol
SMILES CC(=O)NC[C@H]1CN(C(=O)O1)c2ccc(c(c2)F)c3ccc(cc3)CNCc4cnn[nH]4

Radezolid (INN, codenamed RX-1741) is a novel oxazolidinone antibiotic being developed by Melinta Therapeutics, Inc. for the treatment of serious multi-drug–resistant infections. Radezolid has completed two phase-II clinical trials. One of these clinical trials was for uncomplicated skin and skin-structure infections (uSSSI) and the other clinical trial was for community acquired pneumonia (CAP).

References

Zhou J, Bhattacharjee A, Chen S, et al. (December 2008). "Design at the atomic level: design of biaryloxazolidinones as potent orally active antibiotics". Bioorg. Med. Chem. Lett. 18 (23): 6175–8. doi:10.1016/j.bmcl.2008.10.011. PMID 18947996.
Skripkin E, McConnell TS, DeVito J, et al. (October 2008). "Rχ-01, a new family of oxazolidinones that overcome ribosome-based linezolid resistance". Antimicrob. Agents Chemother. 52 (10): 3550–7. doi:10.1128/AAC.01193-07. PMC 2565890. PMID 18663023.
Lawrence L, Danese P, DeVito J, Franceschi F, Sutcliffe J (May 2008). "In vitro activities of the Rχ-01 oxazolidinones against hospital and community pathogens". Antimicrob. Agents Chemother. 52 (5): 1653–62. doi:10.1128/AAC.01383-07. PMC 2346622. PMID 18316525.
Hanselmann R, Job G, Johnson G, Lou R, Martynow JG, Reeve MM (2009). "Synthesis of an antibacterial compound containing a 1,4-substituted 1H-1,2,3-triazole- a scaleable alternative to the "click" reaction"". Organic Process Research and Development 14: 152–158. doi:10.1021/op900252a.
Franceschi F, Duffy EM (March 2006). "Structure-based drug design meets the ribosome". Biochem. Pharmacol. 71 (7): 1016–25. doi:10.1016/j.bcp.2005.12.026. PMID 16443192.
Ohlsen K (November 2009). "Novel antibiotics for the treatment of Staphylococcus aureus". Expert Rev. Clin. Pharmacol. 2 (6): 661–72. doi:10.1586/ecp.09.26.

External links

Radezolid at Rib-X Pharmaceuticals

Antibacterials: protein synthesis inhibitors (J01A, J01B, J01F, J01G, QJ01XQ)

30S

Aminoglycosides
(initiation inhibitors)

-mycin (Streptomyces)	Streptomycin^# Dihydrostreptomycin Neomycin^# Framycetin Paromomycin Ribostamycin Kanamycin^# Amikacin Arbekacin Bekanamycin Dibekacin Tobramycin Spectinomycin^# Hygromycin B Paromomycin

-micin (Micromonospora)	Gentamicin^# Netilmicin Sisomicin Isepamicin Verdamicin Astromicin

Tetracycline antibiotics
(tRNA binding)

Tetracyclines	Doxycycline^# Chlortetracycline Clomocycline Demeclocycline Lymecycline Meclocycline Metacycline Minocycline Oxytetracycline Penimepicycline Rolitetracycline Tetracycline

Glycylcyclines	Tigecycline

50S

Oxazolidinone
(initiation inhibitors)

Peptidyl transferase

Amphenicols	Chloramphenicol^# Azidamfenicol Thiamphenicol Florfenicol

Pleuromutilins	Retapamulin Tiamulin Valnemulin

MLS (transpeptidation/translocation)

Macrolides	Azithromycin^# Clarithromycin Dirithromycin Erythromycin^# Flurithromycin Josamycin Midecamycin Miocamycin Oleandomycin Rokitamycin Roxithromycin Spiramycin Troleandomycin Tylosin Ketolides Telithromycin Cethromycin Solithromycin^†

Lincosamides	Clindamycin^# Lincomycin Pirlimycin

Streptogramins	Pristinamycin Quinupristin/dalfopristin Virginiamycin

EF-G

Steroid antibacterials	Fusidic acid

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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