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MedKoo Cat#: 584270 | Name: Brobactam free acid

Description:

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

Brobactam is a beta lactamase inhibitor and antibacterial.

Chemical Structure

Brobactam free acid
Brobactam free acid
CAS#26631-90-3 (free acid)

Theoretical Analysis

MedKoo Cat#: 584270

Name: Brobactam free acid

CAS#: 26631-90-3 (free acid)

Chemical Formula: C8H10BrNO3S

Exact Mass: 278.9565

Molecular Weight: 280.14

Elemental Analysis: C, 34.30; H, 3.60; Br, 28.52; N, 5.00; O, 17.13; S, 11.44

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
26631-90-3 (free acid) 73335-78-1 (sodium)
Synonym
Brobactam; BRL25214; BRL-25214; BRL25214;
IUPAC/Chemical Name
(2S,5R,6R)-6-Bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
InChi Key
DAVPSCAAXXVSFU-ALEPSDHESA-N
InChi Code
InChI=1S/C8H10BrNO3S/c1-8(2)4(7(12)13)10-5(11)3(9)6(10)14-8/h3-4,6H,1-2H3,(H,12,13)/t3-,4+,6-/m1/s1
SMILES Code
O=C([C@@H](C(C)(C)S[C@]1([H])[C@@H]2Br)N1C2=O)O
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
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

Preparing Stock Solutions

The following data is based on the product molecular weight 280.14 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
1: Melchior NH, Keiding J. In-vitro evaluation of ampicillin/brobactam and comparison with other beta-lactam antibiotics. J Antimicrob Chemother. 1991 Jan;27(1):29-40. PubMed PMID: 1646779. 2: Brun T, Péduzzi J, Caniça MM, Paul G, Névot P, Barthélémy M, Labia R. Characterization and amino acid sequence of IRT-4, a novel TEM-type enzyme with a decreased susceptibility to beta-lactamase inhibitors. FEMS Microbiol Lett. 1994 Jul 1;120(1-2):111-7. PubMed PMID: 8056282. 3: Christensen JJ, Keiding J, Bruun B. Antimicrobial susceptibility and beta-lactamase characterization of Branhamella catarrhalis isolates from 1983/1984 and 1988. APMIS. 1990 Nov;98(11):1039-44. PubMed PMID: 2123390. 4: Chanal CM, Sirot DL, Petit A, Labia R, Morand A, Sirot JL, Cluzel RA. Multiplicity of TEM-derived beta-lactamases from Klebsiella pneumoniae strains isolated at the same hospital and relationships between the responsible plasmids. Antimicrob Agents Chemother. 1989 Nov;33(11):1915-20. PubMed PMID: 2558614; PubMed Central PMCID: PMC172787. 5: Stobberingh EE, Houben AW, van Boven CP. In vitro activity of ampicillin alone and in combination with different concentrations of 6 beta-bromopenicillanic acid, clavulanic acid and mecillinam. Scand J Infect Dis. 1987;19(1):105-12. PubMed PMID: 3031812. 6: Caniça MM, Barthélémy M, Gilly L, Labia R, Krishnamoorthy R, Paul G. Properties of IRT-14 (TEM-45), a newly characterized mutant of TEM-type beta-lactamases. Antimicrob Agents Chemother. 1997 Feb;41(2):374-8. PubMed PMID: 9021194; PubMed Central PMCID: PMC163716. 7: Bedini A, Balsamini C, Di Giacomo B, Tontini A, Citterio B, Giorgi L, Di Modugno E, Tarzia G. Synthesis and biological evaluation of 6-bromo-6-substituted penicillanic acid derivatives as beta-lactamase inhibitors. Farmaco. 2002 Aug;57(8):663-9. PubMed PMID: 12361234. 8: Jastalska D, Lupicki W, Zapaśnik M, Pajchel G, Chojnowski W. [Changes in the sensitivity of clinical strains of Staphylococcus aureus caused by cefamandole, cefoperazone and 6-alpha-bromopenicillanic acid sulfone in vitro]. Pol Tyg Lek. 1987 May 4;42(18):552-6. Polish. PubMed PMID: 2819835. 9: Sirot D, Chanal C, Henquell C, Labia R, Sirot J, Cluzel R. Clinical isolates of Escherichia coli producing multiple TEM mutants resistant to beta-lactamase inhibitors. J Antimicrob Chemother. 1994 Jun;33(6):1117-26. PubMed PMID: 7928805. 10: Loosemore MJ, Cohen SA, Pratt RF. Inactivation of Bacillus cereus beta-lactamase I by 6 beta-bromopenicillanic acid: kinetics. Biochemistry. 1980 Aug 19;19(17):3990-5. PubMed PMID: 6250581. 11: Mariotte-Boyer S, Nicolas-Chanoine MH, Labia R. A kinetic study of NMC-A beta-lactamase, an Ambler class A carbapenemase also hydrolyzing cephamycins. FEMS Microbiol Lett. 1996 Sep 15;143(1):29-33. PubMed PMID: 8807798. 12: Orlek BS, Sammes PG, Knott-Hunziker V, Waley SG. On the chemistry of beta-lactamase inhibition by 6 beta-bromopenicillanic acid. J Chem Soc Perkin 1. 1980;10:2322-9. PubMed PMID: 6253512. 13: Knap AK, Pratt RF. Inactivation of the thiol RTEM-1 beta-lactamase by 6-beta-bromopenicillanic acid. Identity of the primary active-site nucleophile. Biochem J. 1987 Oct 1;247(1):29-33. PubMed PMID: 2825657; PubMed Central PMCID: PMC1148364. 14: Wise R, Andrews JM, Patel N. 6-beta-bromo- and 6-beta-iodo penicillanic acid, two novel beta-lactamase inhibitors. J Antimicrob Chemother. 1981 May;7(5):531-6. PubMed PMID: 6267005. 15: Knott-Hunziker V, Orlek BS, Sammes PG, Waley SG. Kinetics of inactivation of beta-lactamase I by 6 beta-bromopenicillanic acid. Biochem J. 1980 Jun 1;187(3):797-802. PubMed PMID: 6331385; PubMed Central PMCID: PMC1162464. 16: Changov LS, Vasileva-Lukanova BK, Agapova NN, Tsenkova MM, Mondeshka DM, Ivanova ZT. [A simple method of synthesis of S-sulfoxides of penicillanic acid and 6-alpha-bromo[chloro]-penicillanic acids]. Antibiot Khimioter. 1990 Aug;35(8):12-3. Russian. PubMed PMID: 2176073. 17: Joris B, De Meester F, Galleni M, Reckinger G, Coyette J, Frere JM, Van Beeumen J. The beta-lactamase of Enterobacter cloacae P99. Chemical properties, N-terminal sequence and interaction with 6 beta-halogenopenicillanates. Biochem J. 1985 May 15;228(1):241-8. PubMed PMID: 2988516; PubMed Central PMCID: PMC1144975. 18: Claes PJ, Vanderhaeghe H, Roets E, Thomis J, De Meester F, Piette JL. Synthesis of deuterium- and tritium-labeled 6 beta-bromopenicillanic acid. J Antibiot (Tokyo). 1985 Jan;38(1):75-82. PubMed PMID: 2982779. 19: Kissmeyer-Nielsen AM. Determination of 6 beta-bromopenicillanic acid (brobactam) in human serum and urine by high-performance liquid chromatography. J Chromatogr. 1988 Apr 29;426(2):425-30. PubMed PMID: 2839533. 20: Fisher J, Belasco JG, Charnas RL, Khosla S, Knowles JR. Beta-lactamase inactivation by mechanism-based reagents. Philos Trans R Soc Lond B Biol Sci. 1980 May 16;289(1036):309-19. PubMed PMID: 6109326.