Biapenem

Names

[ CAS No. ]:
120410-24-4

[ Name ]:
Biapenem

[Synonym ]:
Biapenem (JAN/USAN)
EINECS 204-352-8
5H-Pyrazolo[1,2-a][1,2,4]triazol-4-ium, 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-, inner salt
BiapeneM Crude
Biapenem [USAN:INN]
(4R,5S,6S)-3-(6,7-Dihydro-5H-pyrazolo[1,2-a][1,2,4]triazol-4-ium-6-ylsulfanyl)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
[4R-[4a,5b,6b(R*)]]-6-[[2-Carboxy-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-en-3-yl]thio]-6,7-dihydro-5 H-pyrazolo[1,2-a][1,2,4]triazol-4-ium inner salt
LJ C10627
omegacin
MFCD00864863
Biapenem
LJ C10,627
Biapenern
L-627

Biological Activity

[Description]:

Biapenem is a parenteral carbapenem antibacterial agent with a broad spectrum.Target: AntibacterialBiapenem is a carbapenem antibiotic of in vitro antibacterial activity encompassing many Gramnegative and Gram-positive aerobic and anaerobic bacteria, including species producing β-lactamases. Biapenem is more stable than imipenem, mero-penem and panipenem to hydrolysis by human renal dihydropeptidase-I (DHP-I), and therefore does not require the coadministration of a DHP-I inhibitor. In randomised, nonblind or double-blind clinical trials, biapenem showed good clinical and bacteriological efficacy (similar to that of imipenem/ cilastatin) in the treatment of adult patients with intra-abdominal infections, lower respiratory infections or complicated urinary tract infections.

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Bacterial

Research Areas >> Infection

[References]

[1]. Perry, C.M. and T. Ibbotson, Biapenem. Drugs, 2002. 62(15): p. 2221-34; discussion 2235.

[2]. Kasahara, S., et al., [Clinical effects of biapenem on febrile neutropenia in patients with hematological malignancy]. Jpn J Antibiot, 2008. 61(3): p. 115-21.

[Related Small Molecules]

Chemical & Physical Properties

[ Melting Point ]:
265-271°C (dec.)

[ Molecular Formula ]:
C₁₅H₁₈N₄O₄S

[ Molecular Weight ]:
350.393

[ Exact Mass ]:
350.104889

[ PSA ]:
127.67000

[ Index of Refraction ]:
1.651

[ Storage condition ]:
-20?C Freezer

Safety Information

[ RIDADR ]:
NONH for all modes of transport

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Nationwide surveillance of bacterial respiratory pathogens conducted by the surveillance committee of Japanese Society of Chemotherapy, the Japanese Association for Infectious Diseases, and the Japanese Society for Clinical Microbiology in 2010: General view of the pathogens' antibacterial susceptibility.

J. Infect. Chemother. 21 , 410-20, (2015)

The nationwide surveillance on antimicrobial susceptibility of bacterial respiratory pathogens from patients in Japan, was conducted by Japanese Society of Chemotherapy, Japanese Association for Infec...

Novel approach to optimize synergistic carbapenem-aminoglycoside combinations against carbapenem-resistant Acinetobacter baumannii.

Antimicrob. Agents Chemother. 59 , 2286-98, (2015)

Acinetobacter baumannii is among the most dangerous pathogens and emergence of resistance is highly problematic. Our objective was to identify and rationally optimize β-lactam-plus-aminoglycoside comb...

Biapenem inactivation by B2 metallo β-lactamases: energy landscape of the post-hydrolysis reactions.

PLoS ONE 7(1) , e30079, (2012)

The first line of defense by bacteria against β-lactam antibiotics is the expression of β-lactamases, which cleave the amide bond of the β-lactam ring. In the reaction of biapenem inactivation by B2 m...