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MedKoo Cat#: 574602 | Name: Brobactam Sodium

Description:

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

Brobactam Sodium Salt is a β-lactamase inhibitor.

Chemical Structure

Brobactam Sodium
Brobactam Sodium
CAS#73335-78-1 (sodium)

Theoretical Analysis

MedKoo Cat#: 574602

Name: Brobactam Sodium

CAS#: 73335-78-1 (sodium)

Chemical Formula: C8H9BrNNaO3S

Exact Mass: 300.9384

Molecular Weight: 302.12

Elemental Analysis: C, 31.80; H, 3.00; Br, 26.45; N, 4.64; Na, 7.61; O, 15.89; S, 10.61

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Related CAS #
26631-90-3 (free acid) 73335-78-1 (sodium)
Synonym
6β-Bromopenicillanic Acid Sodium Salt; BRL 25214 Sodium Salt; Brobactam Sodium Salt;
IUPAC/Chemical Name
(2S,5R,6R)-6-Bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid Sodium Salt
InChi Key
GDQBTVSBACSUEH-ZXSAOVMCSA-M
InChi Code
InChI=1S/C8H10BrNO3S.Na/c1-8(2)4(7(12)13)10-5(11)3(9)6(10)14-8;/h3-4,6H,1-2H3,(H,12,13);/q;+1/p-1/t3-,4+,6-;/m1./s1
SMILES Code
O=C([C@@H](C(C)(C)S[C@]1([H])[C@@H]2Br)N1C2=O)[O-].[Na+]
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
>3 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 302.12 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
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PMID: 8807798. 5: Woodcock JM, Wolstenholme MR, Andrews JM, Wise R. Determination of 6-beta- bromopenicillanic acid (brobactam) in human serum by high-performance liquid chromatography (HPLC) using solid phase extraction for sample preparation. J Antimicrob Chemother. 1994 Jan;33(1):157-61. doi: 10.1093/jac/33.1.157. PMID: 8157556. 6: 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. doi: 10.1128/AAC.33.11.1915. PMID: 2558614; PMCID: PMC172787. 7: 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. doi: 10.1093/jac/33.6.1117. PMID: 7928805. 8: 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. doi: 10.1128/AAC.41.2.374. PMID: 9021194; PMCID: PMC163716. 9: 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. doi: 10.1111/j.1574-6968.1994.tb07016.x. PMID: 8056282. 10: 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. doi: 10.1098/rstb.1980.0048. PMID: 6109326. 11: 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. PMID: 2123390. 12: Neu HC. beta-Lactamase inhibitory activity of iodopenicillanate and bromopenicillanate. Antimicrob Agents Chemother. 1983 Jan;23(1):63-6. doi: 10.1128/AAC.23.1.63. PMID: 6299186; PMCID: PMC184618. 13: 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. doi: 10.7164/antibiotics.38.75. PMID: 2982779. 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. doi: 10.1093/jac/7.5.531. PMID: 6267005. 15: Neu HC. The role of beta-lactamase inhibitors in chemotherapy. Pharmacol Ther. 1985;30(1):1-18. doi: 10.1016/0163-7258(85)90044-0. PMID: 3018803. 16: De Meester F, Matagne A, Dive G, Frère JM. Unexpected influence of ionic strength on branched-pathway interactions between beta-lactamases and beta- halogenopenicillanates. Biochem J. 1989 Jan 1;257(1):245-9. doi: 10.1042/bj2570245. PMID: 2537624; PMCID: PMC1135562. 17: 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. doi: 10.1016/s0014-827x(02)01261-2. PMID: 12361234. 18: Danelon G, Mascaretti O, Radice M, Power P, Calcagno ML, Mata EG, Gutkind G. Comparative in-vitro activities of GD-40 and other beta-lactamase inhibitors against TEM-1 and SHV-2 beta-lactamases. J Antimicrob Chemother. 1998 Feb;41(2):313-5. doi: 10.1093/jac/41.2.313. PMID: 9533481. 19: 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. doi: 10.1042/bj2470029. PMID: 2825657; PMCID: PMC1148364. 20: 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. doi: 10.1042/bj1870797. PMID: 6331385; PMCID: PMC1162464.