Vaborbactam

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

MedKoo CAT#: 319536

CAS#: 1360457-46-0

Description: Vaborbactam, also known as RPX7009, is a potent and selective beta-lactamase inhibitor. Vaborbactam shows broad-spectrum inhibitor, notably restoring the activity of carbapenems against KPC-producing strains. Combined with a carbapenem, Vaborbactam is a promising product for the treatment of multidrug resistant Gram-negative bacteria. For recent consecutive strains of Bacteroides species, the MIC(90) for biapenem-RPX7009 was 1 μg/ml, with a MIC(90) of 4 μg/ml for meropenem.


Price and Availability

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Price

1g
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Size
Price

2g
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Size
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5g
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Vaborbactam is not in stock, but may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 319536
Name: Vaborbactam
CAS#: 1360457-46-0
Chemical Formula: C12H16BNO5S
Exact Mass: 297.0842
Molecular Weight: 297.13
Elemental Analysis: C, 48.51; H, 5.43; B, 3.64; N, 4.71; O, 26.92; S, 10.79


Synonym: RPX-7009; RPX7009; RPX 7009; MP-7009; MP7009; MP 7009; REBO-07; MP-7; Vaborbactam

IUPAC/Chemical Name: 2-((3R,6S)-2-hydroxy-3-(2-(thiophen-2-yl)acetamido)-1,2-oxaborinan-6-yl)acetic acid

InChi Key: IOOWNWLVCOUUEX-WPRPVWTQSA-N

InChi Code: InChI=1S/C12H16BNO5S/c15-11(7-9-2-1-5-20-9)14-10-4-3-8(6-12(16)17)19-13(10)18/h1-2,5,8,10,18H,3-4,6-7H2,(H,14,15)(H,16,17)/t8-,10-/m0/s1

SMILES Code: O=C(O)C[C@@H]1CC[C@H](NC(CC2=CC=CS2)=O)B(O)O1


Technical Data

Appearance:
Solid powder

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:
Soluble in DMSO, not in water

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


References

1: Sgrignani J, De Luca F, Torosyan H, Docquier JD, Duan D, Novati B, Prati F, Colombo G, Grazioso G. Structure-based approach for identification of novel phenylboronic acids as serine-β-lactamase inhibitors. J Comput Aided Mol Des. 2016 Sep 8. [Epub ahead of print] PubMed PMID: 27632226.

2: Griffith DC, Loutit JS, Morgan EE, Durso S, Dudley MN. A Phase 1 Study of the Safety, Tolerability, and Pharmacokinetics of the Beta-lactamase inhibitor Vaborbactam (RPX7009) in Healthy Adult Subjects. Antimicrob Agents Chemother. 2016 Aug 15. pii: AAC.00568-16. [Epub ahead of print] PubMed PMID: 27527080.

3: Falagas ME, Mavroudis AD, Vardakas KZ. The antibiotic pipeline for multi-drug resistant gram negative bacteria: what can we expect? Expert Rev Anti Infect Ther. 2016 Aug;14(8):747-63. doi: 10.1080/14787210.2016.1204911. PubMed PMID: 27400643.

4: Castanheira M, Rhomberg PR, Flamm RK, Jones RN. Effect of the β-Lactamase Inhibitor Vaborbactam Combined with Meropenem against Serine Carbapenemase-Producing Enterobacteriaceae. Antimicrob Agents Chemother. 2016 Aug 22;60(9):5454-8. doi: 10.1128/AAC.00711-16. Print 2016 Sep. PubMed PMID: 27381386; PubMed Central PMCID: PMC4997822.

5: Bush K. A resurgence of β-lactamase inhibitor combinations effective against multidrug-resistant Gram-negative pathogens. Int J Antimicrob Agents. 2015 Nov;46(5):483-93. doi: 10.1016/j.ijantimicag.2015.08.011. Epub 2015 Sep 25. Review. PubMed PMID: 26498989.

6: Kern WV. [New antibacterial agents on the market and in the pipeline]. Internist (Berl). 2015 Nov;56(11):1255-63. Review. German. PubMed PMID: 26475603.

7: Wenzler E, Gotfried MH, Loutit JS, Durso S, Griffith DC, Dudley MN, Rodvold KA. Meropenem-RPX7009 Concentrations in Plasma, Epithelial Lining Fluid, and Alveolar Macrophages of Healthy Adult Subjects. Antimicrob Agents Chemother. 2015 Dec;59(12):7232-9. doi: 10.1128/AAC.01713-15. Epub 2015 Sep 8. PubMed PMID: 26349830; PubMed Central PMCID: PMC4649232.

8: Bettiol E, Harbarth S. Development of new antibiotics: taking off finally? Swiss Med Wkly. 2015 Jul 31;145:w14167. doi: 10.4414/smw.2015.14167. eCollection 2015. PubMed PMID: 26230280.

9: Lapuebla A, Abdallah M, Olafisoye O, Cortes C, Urban C, Quale J, Landman D. Activity of Meropenem Combined with RPX7009, a Novel β-Lactamase Inhibitor, against Gram-Negative Clinical Isolates in New York City. Antimicrob Agents Chemother. 2015 Aug;59(8):4856-60. doi: 10.1128/AAC.00843-15. Epub 2015 Jun 1. PubMed PMID: 26033723; PubMed Central PMCID: PMC4505293.

10: Hecker SJ, Reddy KR, Totrov M, Hirst GC, Lomovskaya O, Griffith DC, King P, Tsivkovski R, Sun D, Sabet M, Tarazi Z, Clifton MC, Atkins K, Raymond A, Potts KT, Abendroth J, Boyer SH, Loutit JS, Morgan EE, Durso S, Dudley MN. Discovery of a Cyclic Boronic Acid β-Lactamase Inhibitor (RPX7009) with Utility vs Class A Serine Carbapenemases. J Med Chem. 2015 May 14;58(9):3682-92. doi: 10.1021/acs.jmedchem.5b00127. Epub 2015 Mar 17. PubMed PMID: 25782055.

11: Horcajada JP, Torre-Cisneros J, Peña C, Fariñas MC. Future alternatives for the treatment of infections caused by carbapenemase-producing Enterobacteriaceae: what is in the pipeline? Enferm Infecc Microbiol Clin. 2014 Dec;32 Suppl 4:56-60. doi: 10.1016/S0213-005X(14)70175-2. PubMed PMID: 25542053.

12: Toussaint KA, Gallagher JC. β-lactam/β-lactamase inhibitor combinations: from then to now. Ann Pharmacother. 2015 Jan;49(1):86-98. doi: 10.1177/1060028014556652. Epub 2014 Oct 31. Review. PubMed PMID: 25361682.

13: Drawz SM, Papp-Wallace KM, Bonomo RA. New β-lactamase inhibitors: a therapeutic renaissance in an MDR world. Antimicrob Agents Chemother. 2014;58(4):1835-46. doi: 10.1128/AAC.00826-13. Epub 2013 Dec 30. Review. PubMed PMID: 24379206; PubMed Central PMCID: PMC4023773.

14: Livermore DM, Mushtaq S. Activity of biapenem (RPX2003) combined with the boronate β-lactamase inhibitor RPX7009 against carbapenem-resistant Enterobacteriaceae. J Antimicrob Chemother. 2013 Aug;68(8):1825-31. doi: 10.1093/jac/dkt118. Epub 2013 Apr 10. PubMed PMID: 23580564.

15: Goldstein EJ, Citron DM, Tyrrell KL, Merriam CV. In vitro activity of Biapenem plus RPX7009, a carbapenem combined with a serine β-lactamase inhibitor, against anaerobic bacteria. Antimicrob Agents Chemother. 2013 Jun;57(6):2620-30. doi: 10.1128/AAC.02418-12. Epub 2013 Mar 25. PubMed PMID: 23529731; PubMed Central PMCID: PMC3716157.