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SML0306

Sigma-Aldrich

Biapenem

≥98% (HPLC)

Synonym(s):

6-[[(4R,5S,6S)-2-Carboxy-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-en-3-yl]thio]-6,7-dihydro-5H-pyrazolo[1,2-a][1,2,4]triazol-4-ium inner salt, Biapenern, CL 186-815, CL 186815, L 627, LJC 10627

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About This Item

Empirical Formula (Hill Notation):
C15H18N4O4S
CAS Number:
120410-24-4
Molecular Weight:
350.39
MDL number:
MFCD00864863
UNSPSC Code:
12352200
PubChem Substance ID:
329825311
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

H2O: ≥5 mg/mL (warmed)

storage temp.

−20°C

SMILES string

C[C@@H](O)[C@@H]1[C@H]2[C@@H](C)C(SC3Cn4cnc[n+]4C3)=C(N2C1=O)C([O-])=O

InChI

1S/C15H18N4O4S/c1-7-11-10(8(2)20)14(21)19(11)12(15(22)23)13(7)24-9-3-17-5-16-6-18(17)4-9/h5-11,20H,3-4H2,1-2H3/t7-,8-,10-,11-/m1/s1

InChI key

MRMBZHPJVKCOMA-YJFSRANCSA-N

Biochem/physiol Actions

Biapenem does not react to renal dihydropeptidase-I mediated hydrolysis in human. Biapenem is well absorbed by tissues and body fluids, following intravenous injection.
Biapenem is a broad spectrum, carbapenem-based antibiotic with activity against both Gram-positive and Gram-negative bacterial strains.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Caroline M Perry et al.
Drugs, 62(15), 2221-2234 (2002-10-17)
Biapenem is a new parenteral carbapenem antibacterial agent with a broad spectrum of in vitro antibacterial activity encompassing many Gram-negative and Gram-positive aerobic and anaerobic bacteria, including species producing beta-lactamases. Biapenem is more stable than imipenem, meropenem and panipenem to
Darija Viducic et al.
Antimicrobial agents and chemotherapy, 60(10), 5752-5764 (2016-07-20)
The ability of Pseudomonas aeruginosa to rapidly modulate its response to antibiotic stress and persist in the presence of antibiotics is closely associated with the process of cell-to-cell signaling. The alternative sigma factor RpoN (σ(54)) is involved in the regulation
Sharon H Ackerman et al.
PloS one, 8(1), e55136-e55136 (2013-02-02)
A general mechanism has been proposed for metallo β-lactamases (MβLs), in which deprotonation of a water molecule near the Zn ion(s) results in the formation of a hydroxide ion that attacks the carbonyl oxygen of the β-lactam ring. However, because
Antonella R Palacios et al.
Biomolecules, 10(6) (2020-06-07)
β-Lactam antibiotics are the most widely prescribed antibacterial drugs due to their low toxicity and broad spectrum. Their action is counteracted by different resistance mechanisms developed by bacteria. Among them, the most common strategy is the expression of β-lactamases, enzymes
Ming Xia et al.
Journal of pharmaceutical and biomedical analysis, 49(4), 937-944 (2009-03-13)
The stability of biapenem in aqueous solution was investigated. Forced degradation of biapenem was carried out under different concentrations, pH values and temperatures. The degradation products were determined by reverse-phase HPLC and identified by LC-MS/MS. One dimeric impurity was obtained
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