Biapenem
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Biapenem
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CAS No:
120410-24-4
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Formula:
C15H18N4O4S
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Chemical Name:
Biapenem
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Synonyms:
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;5H-Pyrazolo[1,2-a][1,2,4]triazol-4-ium,6-[[2-carboxy-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-en-3-yl]thio]-6,7-dihydro-,inner salt,[4R-[4α,5β,6β(R*)]]-;1-Azabicyclo[3.2.0]heptane,5H-pyrazolo[1,2-a][1,2,4]triazol-4-ium deriv.;LJC 10627;L 627;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]-s-triazol-4-ium hydroxide,inner salt;CL 186815;Biapenem;Biapenern;CL 186-815;Omegacin;103939-78-2;133279-57-9
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Categories:
Active Pharmaceutical Ingredients > Synthetic Anti-infective Drugs
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CAS No:
Description
Off-White SolidBiapenem was introduced in Japan as a parenteral treatment for bacterial infections. This new 1-β-methylcarbapenem can be prepared by reaction of commercially available 4-nitrobenzyl protected β-methylcarbapenem enolphosphate with mercapto bicyclotriazolium chloride, obtained in 11 steps starting from hydrazine, followed by deprotection of the carboxylic acid function.
Biapenem is a carbapenem antibiotic in which the azetidine and pyrroline rings carry 1-hydroxymethyl and pyrazolo[1,2-a][1,2,4]triazolium-6-ylthio substituents respectively. It has a role as an antibacterial drug. It is a member of carbapenems, a pyrazolotriazole and an organic sulfide.|Biapenem has been used in trials studying the treatment of Bacterial Infections.|Biapenem is a 1-beta-methylcarbapenem antibiotic with a wide range of antibacterial activity. Biapenem has similar antibacterial activity to that of imipenem, but is more stable against human renal dehydropeptidase-I and with less neurotoxicity.
Biapenem Basic Attributes
350.39
350.104889
204-352-8
YR5U3L9ZH1
DTXSID5046435
C72620
J - Antiinfectives for systemic use
Characteristics
128
1.4
white to beige
265-271°C (dec.)
1.651
H2O: ≥5mg/mL (warmed)
-20°C Freezer
D20 -32.9° (c = 0.5)
Drug Information
Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection. (See all compounds classified as Anti-Infective Agents.)
3-((6,7-dihydro-5H-pyrazolo(1,2-a)(1,2,4)triazol-4-ium-6-yl)thio)-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo(3,2,0)hept-2-ene-2-carboxylate
Computed Properties
Molecular Weight:350.4
XLogP3:1.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:3
Exact Mass:350.10487624
Monoisotopic Mass:350.10487624
Topological Polar Surface Area:128
Heavy Atom Count:24
Complexity:609
Defined Atom Stereocenter Count:4
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
Biapenem is a carbapenem antibiotic that exerts its antibacterial effect by inhibiting the synthesis of bacterial cell walls. It has broad-spectrum antibacterial activity against gram-positive and gram-negative aerobic and anaerobic bacteria. Biapenem is stable to human renal dehydropeptidase-I (DHP-I) and can be administered alone without the need for combination with DHP-I inhibitors.
Registered Holders
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Amicogen(China) Biopharm Co., Ltd.
Active
China
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CSPC Zhongnuo PHARMACEUTICAL(Shijiazhuang) Co., Ltd.
Active
China
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Shandong Anhong Pharmaceutical Co., Ltd.
Active
China
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