Pravibismane

CAS
175880-68-9
Catalog Number
ACM175880689
Category
Others
Molecular Weight
694.48
Molecular Formula
C6H12Bi2S6

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Specification

Description
Pravibismane, also known as BisEDT, MBN 101, is an antibacterial agent against a broad range of gram-positive and gram-negative pathogens.liposomal bismuth-ethanedithiol-loaded tobramycin (LipoBiEDT-TOB reduced the production of quorum-sensing molecules and virulence factors and could highly improve the management of chronic pulmonary infection in cystic fibrosis patients.
Synonyms
Pravibismane; BisEDT; MBN 101; MBN-101; MBN101; Bismuth ethanedithiol
IUPAC Name
2,2'-[ethane-1,2-diylbis(sulfanediyl)]bis(1,3,2-dithiabismolane)
Canonical SMILES
[Bi]1(SCCS[Bi]2SCCS2)SCCS1
InChI
InChI=1S/3C2H6S2.2Bi/c3*3-1-2-4;;/h3*3-4H,1-2H2;;/q;;;2*+3/p-6
InChI Key
GUTNLKRPYCTIHX-UHFFFAOYSA-H
Solubility
Soluble in DMSO
Appearance
Solid powder
Shelf Life
>3 years if stored properly
Storage
Dry, dark and at 0-4 °C for short term (days to weeks) or -20 °C for long term (months to years).
Biological Target
Antibacterial agent against a broad range of gram-positive and gram-negative pathogens.
Drug Formulation
This drug may be formulated in DMSO
Elemental Analysis
C, 10.38; H, 1.74; Bi, 60.18; S, 27.70
Exact Mass
693.8871
HS Tariff Code
2934.99.9001
In Vitro Activity
B. multivorans and B. cenocepacia showed a wide range of susceptibilities to BTs. Bismuth ethanedithiol (BisEDT) was one of the more potent BTs against these organisms (MIC50 7.8 microM), and was selected for synergy studies. Selected strains were highly resistant to tobramycin. The addition of subinhibitory concentrations of BisEDT (2 microM) reduced the MIC and MBC of tobramycin against all strains, achieving synergy in many instances. The FIC index was in the range 0.28-0.66 and the FBC in the range 0.12-0.85. Most strains became susceptible to tobramycin at clinically achievable concentrations in the presence of non-toxic BisEDT levels.
Reference: Veloira WG, Domenico P, LiPuma JJ, Davis JM, Gurzenda E, Kazzaz JA. In vitro activity and synergy of bismuth thiols and tobramycin against Burkholderia cepacia complex. J Antimicrob Chemother. 2003 Dec;52(6):915-9. doi: 10.1093/jac/dkg471. Epub 2003 Oct 29. PMID: 14585856.
In Vivo Activity
The quorum-sensing signal molecule N-acyl homoserine lactone was monitored by using a biosensor organism. P. aeruginosa virulence factors were assessed spectrophotometrically. An agar beads model of chronic Pseudomonas lung infection in rats was used to evaluate the efficacy of the liposomal formulation in the reduction of bacterial count. The levels of active tobramycin in the lungs and the kidneys were evaluated by microbiological assay. LipoBiEDT-TOB was effective in disrupting both quorum-sensing signal molecules N-3-oxo-dodeccanoylhomoserine lactone and N-butanoylhomoserine lactone, as well as significantly (P < 0.05) reducing lipase, chitinase, and protease production. At 24 h after 3 treatments, the CFU counts in lungs of animals treated with LipoBiEDT-TOB were of 3 log(10) CFU/lung, comparated to 7.4 and 4.7 log(10) CFU/lung, respectively, in untreated lungs and in lungs treated with free antibiotic. The antibiotic concentration after the last dose of LipoBiEDT-TOB was 25.1 μg/lung, while no tobramycin was detected in the kidneys. As for the free antibiotic, we found 6.5 μg/kidney but could not detect any tobramycin in the lungs. Taken together, LipoBiEDT-TOB reduced the production of quorum-sensing molecules and virulence factors and could highly improve the management of chronic pulmonary infection in cystic fibrosis patients.
Reference: Alhariri M, Omri A. Efficacy of liposomal bismuth-ethanedithiol-loaded tobramycin after intratracheal administration in rats with pulmonary Pseudomonas aeruginosa infection. Antimicrob Agents Chemother. 2013 Jan;57(1):569-78. doi: 10.1128/AAC.01634-12. Epub 2012 Nov 12. PMID: 23147741; PMCID: PMC3535983.
Shipping
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.
Stock Solution Storage
0-4 °C for short term (days to weeks), or -20 °C for long term (months).
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