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MedKoo Cat#: 146031 | Name: Ranbezolid

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Ranbezolid is an oxazolidinone class antibiotic primarily studied for its potential use in treating Gram-positive bacterial infections, particularly those caused by multi-drug-resistant pathogens. It works by inhibiting bacterial protein synthesis by binding to the 50S ribosomal subunit, preventing the formation of the initiation complex and halting translation. This mechanism effectively disrupts bacterial growth and replication, making it a valuable option for treating resistant infections such as methicillin-resistant Staphylococcus aureus (MRSA). Ranbezolid is being investigated for use in the treatment of serious bacterial infections, including pneumonia and skin infections, due to its potent antimicrobial activity.

Chemical Structure

Ranbezolid
Ranbezolid
CAS#392659-38-0

Theoretical Analysis

MedKoo Cat#: 146031

Name: Ranbezolid

CAS#: 392659-38-0

Chemical Formula: C21H24FN5O6

Exact Mass: 461.1700

Molecular Weight: 461.45

Elemental Analysis: C, 54.66; H, 5.24; F, 4.12; N, 15.18; O, 20.80

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Ranbezolid;
IUPAC/Chemical Name
(S)-N-((3-(3-fluoro-4-(4-((5-nitrofuran-2-yl)methyl)piperazin-1-yl)phenyl)-2-oxooxazolidin-5-yl)methyl)acetamide
InChi Key
PWHNTOQANLCTHN-KRWDZBQOSA-N
InChi Code
1S/C21H24FN5O6/c1-14(28)23-11-17-13-26(21(29)33-17)15-2-4-19(18(22)10-15)25-8-6-24(7-9-25)12-16-3-5-20(32-16)27(30)31/h2-5,10,17H,6-9,11-13H2,1H3,(H,23,28)/t17-/m0/s1
SMILES Code
CC(=O)NC[C@H]1CN(C(=O)O1)C2=CC(F)=C(C=C2)N3CCN(CC4=CC=C(O4)[N+]([O-])=O)CC3
Appearance
To be determined
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 -4 C for short term (days to weeks) or -20 C for long term(months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 461.45 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Kalia V, Miglani R, Purnapatre KP, Mathur T, Singhal S, Khan S, Voleti SR, Upadhyay DJ, Saini KS, Rattan A, Raj VS. Mode of action of Ranbezolid against staphylococci and structural modeling studies of its interaction with ribosomes. Antimicrob Agents Chemother. 2009 Apr;53(4):1427-33. doi: 10.1128/AAC.00887-08. Epub 2008 Dec 15. PMID: 19075051; PMCID: PMC2663096. 2: Ednie LM, Rattan A, Jacobs MR, Appelbaum PC. Antianaerobe activity of RBX 7644 (ranbezolid), a new oxazolidinone, compared with those of eight other agents. Antimicrob Agents Chemother. 2003 Mar;47(3):1143-7. doi: 10.1128/AAC.47.3.1143-1147.2003. PMID: 12604558; PMCID: PMC149336. 3: Naruganahalli KS, Shirumalla RK, Bansal V, Gupta JB, Das B, Ray A. Ranbezolid, a novel oxazolidinone antibacterial: in vivo characterisation of monoamine oxidase inhibitory potential in conscious rats. Eur J Pharmacol. 2006 Sep 18;545(2-3):167-72. doi: 10.1016/j.ejphar.2006.06.065. Epub 2006 Jul 5. PMID: 16899241. 4: Mathur T, Bhateja P, Pandya M, Fatma T, Rattan A. In vitro activity of RBx 7644 (ranbezolid) on biofilm producing bacteria. Int J Antimicrob Agents. 2004 Oct;24(4):369-73. doi: 10.1016/j.ijantimicag.2004.04.012. PMID: 15380263. 5: Mathur T, Kalia V, Barman TK, Singhal S, Khan S, Upadhyay DJ, Rattan A, Raj VS. Anti-anaerobic potential of ranbezolid: insight into its mechanism of action against Bacteroides fragilis. Int J Antimicrob Agents. 2013 Jan;41(1):36-40. doi: 10.1016/j.ijantimicag.2012.09.013. Epub 2012 Nov 9. PMID: 23142085. 6: Hoellman DB, Lin G, Ednie LM, Rattan A, Jacobs MR, Appelbaum PC. Antipneumococcal and antistaphylococcal activities of ranbezolid (RBX 7644), a new oxazolidinone, compared to those of other agents. Antimicrob Agents Chemother. 2003 Mar;47(3):1148-50. doi: 10.1128/AAC.47.3.1148-1150.2003. PMID: 12604559; PMCID: PMC149337. 7: Ndukwe ARN, Qin J, Wiedbrauk S, Boase NRB, Fairfull-Smith KE, Totsika M. In Vitro Activities of Oxazolidinone Antibiotics Alone and in Combination with C-TEMPO against Methicillin-Resistant Staphylococcus aureus Biofilms. Antibiotics (Basel). 2023 Dec 7;12(12):1706. doi: 10.3390/antibiotics12121706. PMID: 38136740; PMCID: PMC10741017. 8: Mathur T, Singhal S, Khan S, Bhateja P, Pandya M, Rattan A, Bhatnagar PK, Upadhyay DJ, Fatma T. Effect of oxazolidinone, RBx 7644 (ranbezolid), on inhibition of staphylococcal adherence to plastic surfaces. J Chemother. 2008 Aug;20(4):420-7. doi: 10.1179/joc.2008.20.4.420. PMID: 18676219. 9: Das B, Rudra S, Yadav A, Ray A, Rao AV, Srinivas AS, Soni A, Saini S, Shukla S, Pandya M, Bhateja P, Malhotra S, Mathur T, Arora SK, Rattan A, Mehta A. Synthesis and SAR of novel oxazolidinones: discovery of ranbezolid. Bioorg Med Chem Lett. 2005 Oct 1;15(19):4261-7. doi: 10.1016/j.bmcl.2005.06.063. PMID: 16054358. 10: Poulakou G, Giamarellou H. Investigational treatments for postoperative surgical site infections. Expert Opin Investig Drugs. 2007 Feb;16(2):137-55. doi: 10.1517/13543784.16.2.137. PMID: 17243935. 11: Bogdanovich T, Esel D, Kelly LM, Bozdogan B, Credito K, Lin G, Smith K, Ednie LM, Hoellman DB, Appelbaum PC. Antistaphylococcal activity of DX-619, a new des-F(6)-quinolone, compared to those of other agents. Antimicrob Agents Chemother. 2005 Aug;49(8):3325-33. doi: 10.1128/AAC.49.8.3325-3333.2005. PMID: 16048943; PMCID: PMC1196248. 12: Lin G, Credito K, Ednie LM, Appelbaum PC. Antistaphylococcal activity of dalbavancin, an experimental glycopeptide. Antimicrob Agents Chemother. 2005 Feb;49(2):770-2. doi: 10.1128/AAC.49.2.770-772.2005. PMID: 15673763; PMCID: PMC547276. 13: Credito K, Lin G, Ednie LM, Appelbaum PC. Antistaphylococcal activity of LBM415, a new peptide deformylase inhibitor, compared with those of other agents. Antimicrob Agents Chemother. 2004 Oct;48(10):4033-6. doi: 10.1128/AAC.48.10.4033-4036.2004. PMID: 15388473; PMCID: PMC521910. 14: Bozdogan B, Esel D, Whitener C, Browne FA, Appelbaum PC. Antibacterial susceptibility of a vancomycin-resistant Staphylococcus aureus strain isolated at the Hershey Medical Center. J Antimicrob Chemother. 2003 Nov;52(5):864-8. doi: 10.1093/jac/dkg457. Epub 2003 Oct 16. PMID: 14563898. 15: Rudra S, Yadav A, Raja Rao AV, Srinivas AS, Pandya M, Bhateja P, Mathur T, Malhotra S, Rattan A, Salman M, Mehta A, Cliffe IA, Das B. Synthesis and antibacterial activity of potent heterocyclic oxazolidinones and the identification of RBx 8700. Bioorg Med Chem Lett. 2007 Dec 15;17(24):6714-9. doi: 10.1016/j.bmcl.2007.10.061. Epub 2007 Oct 22. PMID: 17980588. 16: Hoellman DB, Pankuch GA, Appelbaum PC. Antistaphylococcal activity of CB-181963 (CAB-175), an experimental parenteral cephalosporin. Antimicrob Agents Chemother. 2004 Oct;48(10):4037-9. doi: 10.1128/AAC.48.10.4037-4039.2004. PMID: 15388474; PMCID: PMC521906. 17: Barman TK, Arora P, Rao M, Bhadauriya T, Upadhyay DJ. Utilization of Bombyx mori larvae as a surrogate animal model for evaluation of the anti-infective potential of oxazolidinones. J Infect Chemother. 2008 Apr;14(2):166-9. doi: 10.1007/s10156-008-0586-3. PMID: 18622683. 18: Mathur T, Singhal S, Khan S, Upadhyay D, Fatma T, Rattan A. Adverse effect of staphylococci slime on in vitro activity of glycopeptides. Jpn J Infect Dis. 2005 Dec;58(6):353-7. PMID: 16377866. 19: Sood R, Rao M, Singhal S, Rattan A. Activity of RBx 7644 and RBx 8700, new investigational oxazolidinones, against Mycobacterium tuberculosis infected murine macrophages. Int J Antimicrob Agents. 2005 Jun;25(6):464-8. doi: 10.1016/j.ijantimicag.2005.01.021. PMID: 15885988. 20: Das B, Rajarao AV, Rudra S, Yadav A, Ray A, Pandya M, Rattan A, Mehta A. Synthesis and biological activity of novel oxazolidinones. Bioorg Med Chem Lett. 2009 Nov 15;19(22):6424-8. doi: 10.1016/j.bmcl.2009.09.054. Epub 2009 Sep 17. PMID: 19811911.

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