Epetraborole HCl | GSK2251052 | AN3365 | CAS#1234563-16-6 | 1093643-37-8 | 1234563-15-5 | leucyl-tRNA synthetase inhibitor

Epetraborole HCl
featured

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

MedKoo CAT#: 319569

CAS#: 1234563-16-6 (HCl)

Description: Epetraborole, also known as GSK2251052 and AN3365, is a potent and selective leucyl-tRNA synthetase inhibitor. Epetraborole was in development for the treatment of infections caused by multidrug-resistant Gram-negative pathogens. GSK2251052 is a novel boron-containing antibiotic that inhibits bacterial leucyl tRNA synthetase. All Clostridium perfringens strains had GSK2251052 MICs of >32 μg/ml.

Chemical Structure

Epetraborole HCl

CAS# 1234563-16-6 (HCl)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 319569
Name: Epetraborole HCl
CAS#: 1234563-16-6 (HCl)
Chemical Formula: C11H17BClNO4
Exact Mass: 0.00
Molecular Weight: 273.520
Elemental Analysis: C, 48.30; H, 6.26; B, 3.95; Cl, 12.96; N, 5.12; O, 23.40

Price and Availability

Size	Price	Availability
10mg	USD 150	Ready to ship
25mg	USD 250	Ready to ship
50mg	USD 450	Ready to ship
100mg	USD 750	Ready to ship
200mg	USD 1250	Ready to ship
500mg	USD 2850	Ready to ship
1g	USD 4550	Ready to ship
2g	USD 6950	Ready to ship
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Epetraborole hydrochloride; GSK-2251052; GSK 2251052; GSK2251052; AN3365; AN 3365; AN-3365; GSK-052; GSK 052; GSK052;

IUPAC/Chemical Name: (S)-3-(Aminomethyl)-7-(3-hydroxypropoxy)-1-hydroxy-1,3-dihydro-2,1-benzoxaborole hydrochloride

InChi Key: DADYQGIQOBJGIW-HNCPQSOCSA-N

InChi Code: InChI=1S/C11H16BNO4.ClH/c13-7-10-8-3-1-4-9(16-6-2-5-14)11(8)12(15)17-10;/h1,3-4,10,14-15H,2,5-7,13H2;1H/t10-;/m1./s1

SMILES Code: OB1O[C@H](CN)C2=CC=CC(OCCCO)=C21.[H]Cl

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).

HS Tariff Code: 2934.99.9001

More Info: Related CAS#: CAS#1234563-16-6 (EpetraboroleHCl); CAS#1093643-37-8 (Epetraborole free base) CAS#1234563-15-5 (Epetraborole R-mandelate)

Product Data:

Product Data

Certificate of Analysis:

View CoA: current batch, Lot#BBC60822

QC Data:

View QC data: current batch, Lot#BBC60822

Safety Data Sheet (SDS):

View Safety Data Sheet (SDS)

Instruction:

View handling instruction

Biological target:	Epetraborole hydrochloride is a novel leucyl-tRNA synthetase (LeuRS) inhibitor.
In vitro activity:	AN3365 (MIC50/90, 0.5/1 μg/ml) demonstrated potent activity against Enterobacteriaceae, inhibiting all isolates at ≤2 μg/ml, except for one Proteus vulgaris strain (MIC, 4 μg/ml). Furthermore, the overall MIC distribution of AN3365 remained constant (MIC50, 0.5 μg/ml) across the tested Enterobacteriaceae species, groups of organisms, and resistant subsets. However, slightly higher AN3365 MIC results were observed for P. mirabilis isolates (MIC50/90, 1/1 μg/ml), suggesting that this species may be less susceptible to this compound than other wild-type strains. In addition, KPC-producing K. pneumoniae strains also exhibited higher MIC50 results (1 μg/ml) than the respective susceptible counterparts. Reference: Antimicrob Agents Chemother. 2013 Jun; 57(6): 2849–2857. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3716140/
In vivo activity:	In vivo efficacy of ETB was also validated in Danio rerio (zebrafish; hereafter referred to as ZF) of infection. To determine whether ETB has the ability to treat Mab infected ZF as a therapeutic agent. ETB in vivo efficacy was evaluated in ZF after infection with Mab subsp. abscessus CIP104536T R variant that express mWasabi green fluorescence (hereafter referred to as MabR-mWasabi) at concentrations of 6.25, 12.5, 25, and 50 µM. As shown in Figure 4A, MabR-mWasabi was disseminated and localized inside of ZF, especially in the head when the DMSO was treated. However, the mWasabi fluorescent signal was significantly reduced in the ETB treated condition. In more detail, a significant mWasabi reduction in the MabR-mWasabi infected ZF head was observed at 25 μM ETB. Furthermore, almost no mWasabi protein signals were detected in the ZF when MabR-mWasabi infected ZF were treated with 25 and 50 μM ETB. Reference: Int J Mol Sci. 2021 Jun; 22(11): 5936. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8199016/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	200.0	731.21
	Water	28.0	102.37

Preparing Stock Solutions

The following data is based on the product molecular weight 273.52 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.

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

Formulation protocol:	1. Mendes RE, Alley MR, Sader HS, Biedenbach DJ, Jones RN. Potency and spectrum of activity of AN3365, a novel boron-containing protein synthesis inhibitor, tested against clinical isolates of Enterobacteriaceae and nonfermentative Gram-negative bacilli. Antimicrob Agents Chemother. 2013 Jun;57(6):2849-57. doi: 10.1128/AAC.00160-13. Epub 2013 Mar 18. PMID: 23507283; PMCID: PMC3716140. 2. Kim T, Hanh BT, Heo B, Quang N, Park Y, Shin J, Jeon S, Park JW, Samby K, Jang J. A Screening of the MMV Pandemic Response Box Reveals Epetraborole as a New Potent Inhibitor against Mycobacterium abscessus. Int J Mol Sci. 2021 May 31;22(11):5936. doi: 10.3390/ijms22115936. PMID: 34073006; PMCID: PMC8199016.
In vitro protocol:	1. Mendes RE, Alley MR, Sader HS, Biedenbach DJ, Jones RN. Potency and spectrum of activity of AN3365, a novel boron-containing protein synthesis inhibitor, tested against clinical isolates of Enterobacteriaceae and nonfermentative Gram-negative bacilli. Antimicrob Agents Chemother. 2013 Jun;57(6):2849-57. doi: 10.1128/AAC.00160-13. Epub 2013 Mar 18. PMID: 23507283; PMCID: PMC3716140.
In vivo protocol:	1. Kim T, Hanh BT, Heo B, Quang N, Park Y, Shin J, Jeon S, Park JW, Samby K, Jang J. A Screening of the MMV Pandemic Response Box Reveals Epetraborole as a New Potent Inhibitor against Mycobacterium abscessus. Int J Mol Sci. 2021 May 31;22(11):5936. doi: 10.3390/ijms22115936. PMID: 34073006; PMCID: PMC8199016.

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.

Mass

Concentration

Volume

M. Wt* g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

Volume (to add to vial)

Mass (in vial)

Desired Reconstitution Concentration

Dilution Calculator

Calculate the dilution required to prepare a stock solution.

Concentration 1

Volume 1

Concentration 2

Volume 2

1: O'Dwyer K, Spivak AT, Ingraham K, Min S, Holmes DJ, Jakielaszek C, Rittenhouse S, Kwan AL, Livi GP, Sathe G, Thomas E, Van Horn S, Miller LA, Twynholm M, Tomayko J, Dalessandro M, Caltabiano M, Scangarella-Oman NE, Brown JR. Bacterial resistance to leucyl-tRNA synthetase inhibitor GSK2251052 develops during treatment of complicated urinary tract infections. Antimicrob Agents Chemother. 2015 Jan;59(1):289-98. doi: 10.1128/AAC.03774-14. Epub 2014 Oct 27. PubMed PMID: 25348524; PubMed Central PMCID: PMC4291364.

2: Wu L, Vogt FG, Liu DQ. Flow-injection MS/MS for gas-phase chiral recognition and enantiomeric quantitation of a novel boron-containing antibiotic (GSK2251052A) by the mass spectrometric kinetic method. Anal Chem. 2013 May 21;85(10):4869-74. doi: 10.1021/ac401079x. Epub 2013 May 7. PubMed PMID: 23650921.

3: Tenero D, Bowers G, Rodvold KA, Patel A, Kurtinecz M, Dumont E, Tomayko J, Patel P. Intrapulmonary pharmacokinetics of GSK2251052 in healthy volunteers. Antimicrob Agents Chemother. 2013 Jul;57(7):3334-9. doi: 10.1128/AAC.02483-12. Epub 2013 May 6. PubMed PMID: 23650164; PubMed Central PMCID: PMC3697385.

4: Ross JE, Scangarella-Oman N, Jones RN. Determination of disk diffusion and MIC quality control guidelines for GSK2251052: a novel boron-containing antibacterial. Diagn Microbiol Infect Dis. 2013 Apr;75(4):437-9. doi: 10.1016/j.diagmicrobio.2013.01.007. Epub 2013 Feb 23. PubMed PMID: 23461830.

5: Goldstein EJ, Citron DM, Tyrrell KL, Merriam CV. Comparative in vitro activities of GSK2251052, a novel boron-containing leucyl-tRNA synthetase inhibitor, against 916 anaerobic organisms. Antimicrob Agents Chemother. 2013 May;57(5):2401-4. doi: 10.1128/AAC.02580-12. Epub 2013 Mar 4. PubMed PMID: 23459482; PubMed Central PMCID: PMC3632912.

6: Bowers GD, Tenero D, Patel P, Huynh P, Sigafoos J, O'Mara K, Young GC, Dumont E, Cunningham E, Kurtinecz M, Stump P, Conde JJ, Chism JP, Reese MJ, Yueh YL, Tomayko JF. Disposition and metabolism of GSK2251052 in humans: a novel boron-containing antibiotic. Drug Metab Dispos. 2013 May;41(5):1070-81. doi: 10.1124/dmd.112.050153. Epub 2013 Feb 25. PubMed PMID: 23439661.

7: Sutcliffe JA. Antibiotics in development targeting protein synthesis. Ann N Y Acad Sci. 2011 Dec;1241:122-52. doi: 10.1111/j.1749-6632.2011.06323.x. Review. PubMed PMID: 22191530.

Your view history

Epetraborole HCl featured