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Merck
CN

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

Key Documents

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Quality Level

100

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.
Biapenem is a broad spectrum, carbapenem-based antibiotic.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000476237
0000476240
0000476240
0000476237
0000473605

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Eiki Kikuchi et al.
Antimicrobial agents and chemotherapy, 53(7), 2799-2803 (2009-04-22)
The time above the MIC (T>MIC) is the pharmacokinetic/pharmacodynamic (PK/PD) parameter that correlates with the therapeutic efficacy of beta-lactam antibiotics. A prolonged infusion can provide plasma drug concentrations that remain above the MIC for a long period. The objective of
Fabio Simona et al.
The Journal of biological chemistry, 284(41), 28164-28171 (2009-08-13)
Metallo-beta-lactamases (MbetaLs) constitute an increasingly serious clinical threat by giving rise to beta-lactam antibiotic resistance. They accommodate in their catalytic pocket one or two zinc ions, which are responsible for the hydrolysis of beta-lactams. Recent x-ray studies on a member
Yan Bai et al.
Antimicrobial agents and chemotherapy, 59(3), 1466-1471 (2014-12-24)
The antimicrobial treatment of multidrug-resistant (MDR) Acinetobacter baumannii infections has become a great challenge for medical staff all over the world. Increasing numbers of MDR A. baumannii infections have been identified and reported, but effective clinical treatments for them are
Biapenem
<BIG>Perry CM and Ibbotson T</BIG>
Drugs, 52, 2221-2234 (2013)
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
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