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BAL30072

BAL30072

  • CAT Number: I003906
  • CAS Number: 941285-15-0
  • Molecular Formula: C16H18N6O10S2
  • Molecular Weight: 518.472
  • Purity: ≥95%
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BAL30072 is a monocyclic β-lactam belonging to the monosulfactam class used for the treatment of infections caused by Gram-negative bacteria. BAL30072 carries a dihydroxypyridone moiety in its oxyiminoacyl side chain that may allow it to exploit iron-uptake systems to gain accelerated entry into bacteria. BAL30072 has previously been shown to have strong antimicrobial activity against most aerobic Gram-negative bacilli.

Catalog Number I003906
CAS Number 941285-15-0
Synonyms

BAL30072; BAL 30072; BAL-30072; UNII-LY97ZJM4QX;;4-Thiazoleacetamide, 2-amino-alpha-(((1,4-dihydro-1,5-dihydroxy-4-oxo-2-pyridinyl)methoxy)imino)-N-((3S)-2,2-dimethyl-4-oxo-1-(Sulfooxy)-3-azetidinyl)-, (alphaz)-

Molecular Formula

C16H18N6O10S2

Purity 95%
Solubility Soluble in DMSO, not in water
Storage store at -20°C
IUPAC Name [(3S)-3-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(1,5-dihydroxy-4-oxopyridin-2-yl)methoxyimino]acetyl]amino]-2,2-dimethyl-4-oxoazetidin-1-yl] hydrogen sulfate
InChI InChI=1S/C16H18N6O10S2/c1-16(2)12(14(26)22(16)32-34(28,29)30)19-13(25)11(8-6-33-15(17)18-8)20-31-5-7-3-9(23)10(24)4-21(7)27/h3-4,6,12,24,27H,5H2,1-2H3,(H2,17,18)(H,19,25)(H,28,29,30)/b20-11-/t12-/m1/s1
InChIKey KLFSEZJCLYBFKQ-WXYNYTDUSA-N
SMILES CC1(C(C(=O)N1OS(=O)(=O)O)NC(=O)C(=NOCC2=CC(=O)C(=CN2O)O)C3=CSC(=N3)N)C
Reference

</br>1:Urinary Concentrations and Antibacterial Activity of BAL30072, a Novel Siderophore Monosulfactam, against Uropathogens after Intravenous Administration in Healthy Subjects. Straubinger M, Blenk H, Naber KG, Wagenlehner FM.Antimicrob Agents Chemother. 2016 May 23;60(6):3309-15. doi: 10.1128/AAC.02425-15. Print 2016 Jun. PMID: 26976871 Free PMC Article</br>2:In vitro activity of the siderophore monosulfactam BAL30072 against contemporary Gram-negative pathogens from New York City, including multidrug-resistant isolates. Landman D, Singh M, El-Imad B, Miller E, Win T, Quale J.Int J Antimicrob Agents. 2014 Jun;43(6):527-32. doi: 10.1016/j.ijantimicag.2014.02.017. Epub 2014 Apr 13. PMID: 24796217 </br>3:In vitro activity of the novel monosulfactam BAL30072 alone and in combination with meropenem versus a diverse collection of important Gram-negative pathogens. Hornsey M, Phee L, Stubbings W, Wareham DW.Int J Antimicrob Agents. 2013 Oct;42(4):343-6. doi: 10.1016/j.ijantimicag.2013.05.010. Epub 2013 Jul 7. PMID: 23837926 </br>4:Activity of BAL30072 alone or combined with β-lactamase inhibitors or with meropenem against carbapenem-resistant Enterobacteriaceae and non-fermenters. Mushtaq S, Woodford N, Hope R, Adkin R, Livermore DM.J Antimicrob Chemother. 2013 Jul;68(7):1601-8. doi: 10.1093/jac/dkt050. Epub 2013 Feb 28. PMID: 23449829 </br>5:Involvement of Fe uptake systems and AmpC β-lactamase in susceptibility to the siderophore monosulfactam BAL30072 in Pseudomonas aeruginosa. van Delden C, Page MG, Köhler T.Antimicrob Agents Chemother. 2013 May;57(5):2095-102. doi: 10.1128/AAC.02474-12. Epub 2013 Feb 19. PMID: 23422914 Free PMC Article</br>6:Combined effects of the siderophore monosulfactam BAL30072 and carbapenems on multidrug-resistant Gram-negative bacilli. Hofer B, Dantier C, Gebhardt K, Desarbre E, Schmitt-Hoffmann A, Page MG.J Antimicrob Chemother. 2013 May;68(5):1120-9. doi: 10.1093/jac/dks527. Epub 2013 Jan 22. PMID: 23344577 </br>7:In vitro activity of the siderophore monosulfactam BAL30072 against meropenem-non-susceptible Acinetobacter baumannii. Higgins PG, Stefanik D, Page MG, Hackel M, Seifert H.J Antimicrob Chemother. 2012 May;67(5):1167-9. doi: 10.1093/jac/dks009. Epub 2012 Feb 1. PMID: 22294643 </br>8:[BAL30072–an iron complexing beta lactam antibiotic against multidrug-resistant gram negative bacteria]. Schmitz J.Pharm Unserer Zeit. 2011 Mar;40(2):98-9. German. No abstract available. PMID: 21630531 </br>9:In vitro activity of BAL30072 against Burkholderia pseudomallei. Mima T, Kvitko BH, Rholl DA, Page MG, Desarbre E, Schweizer HP.Int J Antimicrob Agents. 2011 Aug;38(2):157-9. doi: 10.1016/j.ijantimicag.2011.03.019. Epub 2011 May 18. PMID: 21596528 Free PMC Article</br>10:In vivo and in vitro activity of the siderophore monosulfactam BAL30072 against Acinetobacter baumannii. Russo TA, Page MG, Beanan JM, Olson R, Hujer AM, Hujer KM, Jacobs M, Bajaksouzian S, Endimiani A, Bonomo RA.J Antimicrob Chemother. 2011 Apr;66(4):867-73. doi: 10.1093/jac/dkr013. Epub 2011 Feb 13. PMID: 21393224 Free PMC Article

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