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MedKoo Cat#: 319569 | Name: Epetraborole HCl
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Description:

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

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
Epetraborole HCl
CAS#1234563-16-6 (HCl)

Theoretical Analysis

MedKoo Cat#: 319569

Name: Epetraborole HCl

CAS#: 1234563-16-6 (HCl)

Chemical Formula: C11H17BClNO4

Exact Mass: 0.0000

Molecular Weight: 273.52

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 Quantity
10mg USD 150.00 Ready to ship
25mg USD 250.00 Ready to ship
50mg USD 450.00 Ready to ship
100mg USD 750.00 Ready to ship
200mg USD 1,250.00 Ready to ship
500mg USD 2,850.00 Ready to ship
1g USD 4,550.00 Ready to ship
2g USD 6,950.00 Ready to ship
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Related CAS #
1234563-16-6 (HCl) 1093643-37-8 (free base) 1234563-15-5 (R-mandelate)
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)
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/
Solvent mg/mL mM
Solubility
DMSO 200.0 731.21
Water 28.0 102.37
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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.

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
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.
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.