NAV

Radezolid

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Radezolid
DrugBank Accession Number
DB12339
Background

Radezolid has been used in trials studying the treatment of Abscess, Bacterial Skin Diseases, Streptococcal Infections, Infectious Skin Diseases, and Staphylococcal Skin Infections, among others.

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 438.463
Monoisotopic: 438.181566788
Chemical Formula
C22H23FN6O3
Synonyms
  • Radezolid
External IDs
  • AND RX-01_667
  • RX-013
  • RX-103
  • RX-1741
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
URibosome-binding protein 1
inhibitor
Humans
U50S ribosomal protein L1
binder
Staphylococcus aureus (strain NCTC 8325)
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
Integrate drug-drug
interactions in your software
AcenocoumarolThe risk or severity of bleeding can be increased when Radezolid is combined with Acenocoumarol.
AmbroxolThe risk or severity of methemoglobinemia can be increased when Radezolid is combined with Ambroxol.
ArticaineThe risk or severity of methemoglobinemia can be increased when Radezolid is combined with Articaine.
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Radezolid.
BenzocaineThe risk or severity of methemoglobinemia can be increased when Radezolid is combined with Benzocaine.
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Radezolid hydrochloride37CW568NXL869884-77-5UQKABVKLBIJYBI-FYZYNONXSA-N

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Biphenyls and derivatives
Direct Parent
Biphenyls and derivatives
Alternative Parents
Phenylmethylamines / Benzylamines / Aralkylamines / Fluorobenzenes / Aryl fluorides / Oxazolidinones / Triazoles / Carbamate esters / Heteroaromatic compounds / Dialkylamines
show 8 more
Substituents
1,2,3-triazole / Amine / Aralkylamine / Aromatic heteromonocyclic compound / Aryl fluoride / Aryl halide / Azacycle / Azole / Benzylamine / Biphenyl
show 24 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
53PC6LO35W
CAS number
869884-78-6
InChI Key
BTTNOGHPGJANSW-IBGZPJMESA-N
InChI
InChI=1S/C22H23FN6O3/c1-14(30)25-12-19-13-29(22(31)32-19)18-6-7-20(21(23)8-18)16-4-2-15(3-5-16)9-24-10-17-11-26-28-27-17/h2-8,11,19,24H,9-10,12-13H2,1H3,(H,25,30)(H,26,27,28)/t19-/m0/s1
IUPAC Name
N-{[(5S)-3-[2-fluoro-4'-({[(1H-1,2,3-triazol-5-yl)methyl]amino}methyl)-[1,1'-biphenyl]-4-yl]-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide
SMILES
CC(=O)NC[C@H]1CN(C(=O)O1)C1=CC=C(C(F)=C1)C1=CC=C(CNCC2=CN=NN2)C=C1

References

General References
Not Available
PubChem Compound
11224409
PubChem Substance
347828598
ChemSpider
9399462
ChEMBL
CHEMBL455461
ZINC
ZINC000040379938
PDBe Ligand
RD8
Wikipedia
Radezolid
PDB Entries
6wqq / 7s1i / 7s1j / 7s1k

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentAbscesses / Bacterial skin infections / Skin Diseases, Infectious / Staphylococcal Skin Infections / Streptococcal Infections1
2CompletedTreatmentCommunity Acquired Pneumonia (CAP)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.043 mg/mLALOGPS
logP1.23ALOGPS
logP1.29Chemaxon
logS-4ALOGPS
pKa (Strongest Acidic)8.56Chemaxon
pKa (Strongest Basic)7.46Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area112.24 Å2Chemaxon
Rotatable Bond Count8Chemaxon
Refractivity115.89 m3·mol-1Chemaxon
Polarizability45.19 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0002900000-f2b9228e465c69af2b67
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-2109000000-e51d7095806d1e38cfb6
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000b-1009400000-cdffa4188f3a68790a9d
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00bd-1009000000-5d25db3988037029034f
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0nni-4339200000-513b0fac76098b23fa38
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-7009300000-be0e88182ab279f00b43
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-192.201
predicted
DeepCCS 1.0 (2019)
[M+H]+194.59656
predicted
DeepCCS 1.0 (2019)
[M+Na]+200.5091
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Ribosome-binding protein 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Receptor activity
Specific Function
Acts as a ribosome receptor and mediates interaction between the ribosome and the endoplasmic reticulum membrane.
Gene Name
RRBP1
Uniprot ID
Q9P2E9
Uniprot Name
Ribosome-binding protein 1
Molecular Weight
152471.765 Da
References
  1. Shriwas O, Arya R, Mohanty S, Mohapatra P, Kumar S, Rath R, Kaushik SR, Pahwa F, Murmu KC, Majumdar SKD, Muduly DK, Dixit A, Prasad P, Nanda RK, Dash R: RRBP1 rewires cisplatin resistance in oral squamous cell carcinoma by regulating Hippo pathway. Br J Cancer. 2021 Jun;124(12):2004-2016. doi: 10.1038/s41416-021-01336-7. Epub 2021 Mar 24. [Article]
Details2. 50S ribosomal protein L1
Kind
Protein
Organism
Staphylococcus aureus (strain NCTC 8325)
Pharmacological action
Unknown
Actions
Binder
Curator comments
Radezolid binds to the 50s ribosomal subunit of different bacterial species, including S. aureus.
General Function
Binds directly to 23S rRNA. The L1 stalk is quite mobile in the ribosome, and is involved in E site tRNA release.
Specific Function
Rna binding
Gene Name
rplA
Uniprot ID
Q2G0P0
Uniprot Name
50S ribosomal protein L1
Molecular Weight
24708.165 Da
References
  1. Skripkin E, McConnell TS, DeVito J, Lawrence L, Ippolito JA, Duffy EM, Sutcliffe J, Franceschi F: R chi-01, a new family of oxazolidinones that overcome ribosome-based linezolid resistance. Antimicrob Agents Chemother. 2008 Oct;52(10):3550-7. doi: 10.1128/AAC.01193-07. Epub 2008 Jul 28. [Article]
  2. Lemaire S, Kosowska-Shick K, Appelbaum PC, Verween G, Tulkens PM, Van Bambeke F: Cellular pharmacodynamics of the novel biaryloxazolidinone radezolid: studies with infected phagocytic and nonphagocytic cells, using Staphylococcus aureus, Staphylococcus epidermidis, Listeria monocytogenes, and Legionella pneumophila. Antimicrob Agents Chemother. 2010 Jun;54(6):2549-59. doi: 10.1128/AAC.01724-09. Epub 2010 Apr 12. [Article]

Drug created at October 20, 2016 22:00 / Updated at March 14, 2023 09:13