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Betamipron

CAS# 3440-28-6

Betamipron

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Chemical structure

Betamipron

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Chemical Properties of Betamipron

Cas No. 3440-28-6 SDF Download SDF
PubChem ID 71651 Appearance Powder
Formula C10H11NO3 M.Wt 193
Type of Compound N/A Storage Desiccate at -20°C
Synonyms N-Benzoyl-β-alanine; CS-443
Solubility DMSO : ≥ 43 mg/mL (222.57 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name 3-benzamidopropanoic acid
SMILES C1=CC=C(C=C1)C(=O)NCCC(=O)O
Standard InChIKey CWXYHOHYCJXYFQ-UHFFFAOYSA-N
Standard InChI InChI=1S/C10H11NO3/c12-9(13)6-7-11-10(14)8-4-2-1-3-5-8/h1-5H,6-7H2,(H,11,14)(H,12,13)
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Betamipron Dilution Calculator

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Preparing Stock Solutions of Betamipron

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 5.1813 mL 25.9067 mL 51.8135 mL 103.6269 mL 129.5337 mL
5 mM 1.0363 mL 5.1813 mL 10.3627 mL 20.7254 mL 25.9067 mL
10 mM 0.5181 mL 2.5907 mL 5.1813 mL 10.3627 mL 12.9534 mL
50 mM 0.1036 mL 0.5181 mL 1.0363 mL 2.0725 mL 2.5907 mL
100 mM 0.0518 mL 0.2591 mL 0.5181 mL 1.0363 mL 1.2953 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Betamipron

Betamipron is a chemical compound which is used together with Panipenem to inhibit Panipenem uptake into the renal tubule and prevent nephrotoxicity.

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References on Betamipron

Recent updates of carbapenem antibiotics.[Pubmed:28324783]

Eur J Med Chem. 2017 May 5;131:185-195.

Carbapenems are among the most commonly used and the most efficient antibiotics since they are relatively resistant to hydrolysis by most beta-lactamases, they target penicillin-binding proteins, and generally have broad-spectrum antibacterial effect. In this review, we described the initial discovery and development of carbapenems, chemical characteristics, in vitro/in vivo activities, resistance studies, and clinical investigations for traditional carbapenem antibiotics in the market; imipenem-cilastatin, meropenem, ertapenem, doripenem, biapenem, panipenem/Betamipron in addition to newer carbapenems such as razupenem, tebipenem, tomopenem, and sanfetrinem. We focused on the literature published from 2010 to 2016.

[Successful treatment with chloramphenicol in four pediatric cases of intractable bacterial meningitis].[Pubmed:27012107]

No To Hattatsu. 2016 Jan;48(1):29-33.

Chloramphenicol (CP) is recently one of the rarely-used antibiotics. In this study, we present four patients with intractable bacterial meningitis, who were successfully treated with CP and discuss the therapeutic indications of CP in these pediatric cases. The patients were diagnosed as bacterial meningitis at the ages ranging from 2 months to 1 year and 4 months. The causative organisms found in three of the patients were H. influenzae and in the fourth patient, S. pneumoniae. According to the microbial sensitivity tests, these organisms were highly sensitive to antibiotics including ceftriaxone, meropenem and/or panipenem/Betamipron. Treatment with these antibiotics was initially effective; however, recurrences of meningitis appeared in all patients. Administration of CP (100 mg/kg/day) started between the 11th and the 58th days, and was continued for 9 days up to 19 days. Their fever had disappeared within four days after the administration of CP, and it was confirmed that all patients completely recovered from meningitis. Two of the patients developed a mild degree of anemia, but soon recovered after the discontinuation of CP. None of them had neurological sequela. We recommend CP as one of the choices for the treatment of intractable bacterial meningitis.

Real-time monitoring of antimicrobial use density to reduce antimicrobial resistance through the promotion of antimicrobial heterogeneity in a haematology/oncology unit.[Pubmed:26071518]

J Antimicrob Chemother. 2015 Sep;70(9):2661-4.

BACKGROUND: In haematology/oncology units, the frequent and heavy use of broad-spectrum antimicrobials can lead to outbreaks of antimicrobial resistance. Increasing antimicrobial heterogeneity might be a useful strategy for preventing such resistance. METHODS: A real-time antimicrobial use density (AUD) monitoring system (RAMS) was developed to precisely assess antimicrobial heterogeneity. This study was prospectively conducted over a 39 month period and involved 970 patients. Patient-specific antimicrobial therapy with five carbapenems (meropenem, biapenem, panipenem/Betamipron, imipenem/cilastatin and doripenem) and four non-carbapenems (piperacillin/tazobactam, ceftazidime, cefozopran and cefepime) was prescribed in the first 12 months. A first-line antimicrobial was selected from among nine antimicrobials according to a predetermined schedule for the next 15 months. AUD-based antimicrobial selection was implemented using the RAMS during the last 12 months. We compared our findings for the RAMS period with those for the other periods to determine the effects of RAMS-based AUD monitoring on antimicrobial resistance. RESULTS: The mean absolute difference between the AUD values of carbapenems and non-carbapenems (AUD deviation) was 6.0% in the RAMS period (range 0.5%-15.8%) and antimicrobial heterogeneity (AUD deviation <10%) was achieved in 10 out of 12 months (83.3%). Furthermore, during the RAMS period, AUD deviation was significantly smaller and the frequency of outbreaks of antimicrobial-resistant strains other than Stenotrophomonas maltophilia was significantly decreased (from 7.9% to 3.5%; P < 0.01) compared with the other periods. CONCLUSIONS: The longer period of stable antimicrobial heterogeneity achieved by the RAMS strengthened its preventive effects against antimicrobial resistance. Optimal antimicrobial heterogeneity based on real-time AUD monitoring could reduce the frequency of outbreaks of antimicrobial resistance.

Antibiotic Susceptibilities of Pseudomonas aeruginosa Isolated from Blood Samples and Antibiotic Utilization in a University Hospital in Japan.[Pubmed:25991512]

Infect Dis Ther. 2015 Jun;4(2):213-8.

INTRODUCTION: Pseudomonas aeruginosa is one of the most important causes of nosocomial infection. Several reports indicated a correlation of antimicrobial usages and declined susceptibilities. In this report, we evaluated their relation in a tertiary care teaching hospital in Tokyo, Japan for 4 years. METHODS: We evaluated the susceptibilities of 149 strains of P. aeruginosa isolated from blood samples and consumption of anti-pseudomonal antibiotics as antimicrobial use density from 2009 to 2012 in the University of Tokyo Hospital in Tokyo, Japan. RESULTS: Usages of carbapenems and anti-pseudomonal cephalosporins decreased 44% and 31% from 2009 to 2011, and then increased 30% and 24% in 2012, respectively. Usage of piperacillin-tazobactam increased 87% from 2009 to 2012, which was introduced in the hospital in 2008. Consumption of fluoroquinolones and aminoglycoside remained low in those years. Susceptibilities to cephalosporins, carbapenems (except for panipenem-Betamipron), penicillins, and fluoroquinolones declined between 22% and 39% in 2010, increased in the range of 16-31% in 2011, and increased by 1-14% in 2012. Susceptibility of panipenem-Betamipron ranged between 25% and 32%. Susceptibility to aminoglycoside was more than 90% during this period. No relationship between antimicrobial usages and susceptibilities of P. aeruginosa was observed. CONCLUSION: Susceptibilities of P. aeruginosa did not correlate with the usage of antibiotics in our hospital. Several infection control measures and other factors might contribute to changing the susceptibilities of bacteria.

Mediastinitis of bronchogenic cyst caused by endobronchial ultrasound-guided transbronchial needle aspiration.[Pubmed:25473572]

Respirol Case Rep. 2014 Jun;2(2):73-5.

Here, we describe the case of a 56-year-old female patient who was diagnosed with an anterior mediastinal cyst measuring 26 x 16 mm in size. An endobronchial ultrasound-guided transbronchial needle aspiration was performed, and punctures occurred three times. The patient was then prescribed cefditoren pivoxil. Three days after the procedure, the patient developed infective mediastinitis. Panipenem/Betamipron, clindamycin, and human immunoglobulin were administered, and her symptoms improved over 2 weeks. Five months after developing mediastinitis, surgical resection of the cyst was performed with inverted L-shaped mini-sternotomy. The cystic lesion strongly adhered to the surrounding tissues. The final pathological diagnosis was a bronchogenic cyst. Endobronchial ultrasound-guided transbronchial needle aspiration is not a completely sterile procedure and can lead to severe infective complications in the mediastinum. Although this procedure may not be contraindication for use with mediastinal cystic lesions, physicians must take into account the risk of severe infective complications.

Severe acute otitis media caused by mucoid Streptococcus pyogenes in a previously healthy adult.[Pubmed:24727832]

Tohoku J Exp Med. 2014 Apr;232(4):301-4.

Streptococcus (S.) pyogenes is well recognized as the most common pathogen causing pharyngotonsillitis in school-age children. In Japan, mucoid Streptococcus pneumoniae is well known as a causative agent of severe acute otitis media (AOM); however, mucoid S. pyogenes has rarely been reported. To the best of our knowledge, this is the first report of an AOM patient caused by mucoid S. pyogenes in Japan. A 36-year-old previously healthy female was referred to our hospital with suspicion of cerebrospinal otorrhea due to increasing otalgia accompanied by headache following myringotomy. Bacterial cultures of middle ear secretions were performed, and mucoid-form colonies surrounded by zones of complete beta-hemolysis were produced on sheep's blood agar. Antigen-agglutination test results were positive for S. pyogenes, and thus the patient received treatment with panipenem-Betamipron 2.0 g/day for 10 days, which resolved nearly all symptoms. The bacteriological features of this strain were then investigated. The M-protein genotype encoded by the emm gene, the major virulence factor of S. pyogenes, was determined to be emm75. Generally, S. pyogenes forms colonies having non-mucoid matt appearances based on beta-hemolysis of sheep's blood agar. The mucoid phenotype results from abundant production of hyaluronic acid capsular polysaccharide, a key virulence determinant. emm75 is common in noninvasive, but less common in invasive disease. In conclusion, mucoid S. pyogenes can cause severe infection even in previously healthy persons. Emergence of mucoid S. pyogenes and drug resistance trends should be monitored in the future.

A retrospective cohort study of panipenem/betamipron for adult pneumococcal bacteremia at three teaching hospitals in Japan.[Pubmed:23203218]

J Infect Chemother. 2013 Aug;19(4):607-14.

Panipenem/Betamipron (PAPM/BP) may be highly effective for life-threatening Streptococcus pneumoniae infection. However, the efficacy of PAPM/BP for S. pneumoniae infections has not been compared with that of other antimicrobial agents. We retrospectively compared PAPM/BP with other carbapenems for treatment of life-threatening infections in newly hospitalized adults with pneumococcal bacteremia. Clinical information for cases of pneumococcal bacteremia was collected from three teaching hospitals in Japan from January 2003 to December 2010. In total, 17 patients who received PAPM/BP therapy and 34 treated with other carbapenems (27 with meropenem, 4 with imipenem/cilastatin, and 3 with biapenem) were identified. The mean age (71 vs. 70 years old), sex distribution (women, 29 vs. 21 %), Charlson comorbidity index (CCI) (1.5 vs. 1.6), and rates of septic shock (29 vs. 38 %), and meningitis (5.9 vs. 8.8 %) did not differ significantly between the two groups. The inpatient mortality rates were lower in the PAPM/BP group (12 vs. 44 %, p = 0.03). Multiple logistic regression analysis adjusted for age, sex, CCI, and severe sepsis/septic shock showed that use of other carbapenems was associated with higher in-hospital mortality, with an odds ratio of 6.922 (95 % CI, 1.171-40.92) compared to PAPM/BP therapy. Initial PAPM/BP therapy might have a therapeutic advantage over other carbapenems in treatment of severe Streptococcus pneumoniae infections.

[The clinical efficacy and safety of panipenem-betamipron in treatment of moderate to severe pulmonary infection].[Pubmed:22943829]

Zhonghua Nei Ke Za Zhi. 2012 Jul;51(7):547-50.

OBJECTIVE: To evaluate the clinical efficacy and safety of intravenous panipenem-Betamipron in the treatment of moderate to severe pulmonary infection. METHODS: An open, perspective, multicenter clinical trial was conducted. Among the enrolled 665 patients, 621 patients with moderate to severe pulmonary infection were treated with intravenous panipenem-Betamipron at a dose of 500 mg every 6 hours per day for 7 - 14 days. Among them, the community acquired pneumonia (CAP), hospital acquired pneumonia (HAP) and ventilator associated pneumonia (VAP) patients were 55.6% (345/621), 37.0% (230/621) and 7.4% (46/621), respectively. All the adverse events were recorded. RESULTS: The overall effective rate of panipenem-Betamipron was 84.4% with CAP of 91.9%, HAP of 76.1% and VAP of 69.6%. The effective rates in the patients with moderate and severe pulmonary infection were 87.5% and 82.8%, respectively. Bacterial separation rate was 54.8% and bacterial eradication rate was 80.9%. Bacterial eradication rates to pseudomonas aeruginosa, pneumobacillus, Escherichia coli. and acinetobacter baumannii were 74.7%, 95.6%, 89.5% and 50.9%, respectively. The adverse events rate was 1.8% (12/665). CONCLUSION: Intravenous panipenem-Betamipron is effective in treating moderate to severe pulmonary infection with low adverse events rate.

[Preliminary clinical evaluations of panipenem-betamipron in the treatment of hematological malignancy infections].[Pubmed:22490964]

Zhonghua Yi Xue Za Zhi. 2012 Feb 21;92(7):452-5.

OBJECTIVE: To evaluate the clinical efficacy and safety of intravenous panipenem-Betamipron in the treatment of hematological malignancies infections. METHODS: From October 2009 to December 2010, a total of 286 hematological malignancy infection patients were recruited into this open-label, perspective and multicenter clinical trial to receive an intravenous daily dose panipenem-Betamipron of 0.5 g every 6 or 8 hours for 7 - 14 days. All clinical change and adverse reactions were recorded. RESULTS: The total effective rate of panipenem-Betamipron in the treatment of hematological malignancy infections was 86.6% (206/238). The effective rates of septicemia, pulmonary infections, urinary tract infections, digestive canal infections, oral infections and other infections were 68.2% (15/22), 89.3% (100/112), 77.8% (14/18), 100% (22/22), 83.3% (10/12) and 86.5% (45/52) respectively. The overall bacterial eradication rate was 85.07% (57/67) and the rate of adverse reactions 5.9% (17/286). CONCLUSION: Panipenem-Betamipron is both safe and effective in the treatment of hematological malignancy infections.

[Four infants with upper urinary tract infection due to extended-spectrum bata lactamase (ESBL)-producing Escherichia coli].[Pubmed:22117375]

Kansenshogaku Zasshi. 2011 Sep;85(5):481-7.

Bacteria producing extended-spectrum beta lactamase (ESBL) are detected mainly in adult urinary specimens, and are believed to cause hospital-acquired infection due to their resistance to many drugs. The incidence of community-acquired infection due to such bacteria is increasing, but few cases of infant upper urinary tract infection (UUTI) have been reported in Japan. We treated four infants with UUTI caused by ESBL-producing Escherichia coli, as determined by genotyping. Using medical records, we retrospectively evaluated the clinical course, antibiotic use and efficacy, antimicrobial susceptibility results, and the presence of underlying disease. One of the four had been previously hospitalized for occult bacteremia. Two developed UUTI after antibiotic treatment, indicating that previous antibiotic use may have been a risk factor in these cases. We could not identify the infection route in all cases. Two of the four had bilateral vesicoureteral reflux (VUR). Renal scintigraphy was done in three. Although an initial dimercaptosuccinic acid (DMSA) defect was detected in all four, only one had renal scarring. E. coli isolates from all four showed PCR signals for blaCTX-M-; one isolate positive for the blaCTX-M3 group and three positive for blaCTX-M14. Antimicrobial susceptibility test results showed all isolates to be resistant to cephalosporins, but discrepancies existed between antimicrobial susceptibility results and actual clinical efficacy. Clinically, cefazolin (CEZ) was effective in two subjects and ceftazidime (CAZ) effective in one. Panipenem/Betamipron (PAPM/BP) was effective in one. None of the four developed sepsis or meningitis. Post hospitalization antibiotic prophylaxis showed that none of the four has had UUTI recur. Japan's ESBL-producing bacterial infection incidence is increasing, so medical professionals should watch for such UUTI even in first-case occurrence in infants.

Neonatal meningitis caused by Streptococcus gallolyticus subsp. pasteurianus.[Pubmed:22002578]

J Infect Chemother. 2012 Apr;18(2):265-8.

We encountered a case of neonatal meningitis caused by Streptococcus gallolyticus subsp. pasteurianus. The patient was an 8-day-old boy. Gram staining of the cerebrospinal fluid (CSF) revealed gram-positive cocci in pairs or in short chains. In culture, gamma-streptococcus-like colonies grew. The result of 16S rRNA sequence analysis identified S. gallolyticus subsp. pasteurianus. From these results, bacterial meningitis was diagnosed and, as a result of antimicrobial susceptibility testing, single-dose ampicillin therapy was given. Because inflammatory deterioration and spread was suspected from the CSF test results, this therapy was added by panipenem/Betamipron. In response to his recovery, antibiotic treatment was stopped and the boy was discharged. This bacterium was classified as S. gallolyticus subsp. pasteurianus in the latest report in 2003. Since this change, there have only been a few cases of neonatal meningitis caused by this bacterium. Here we report this rare case.

Carbapenems: past, present, and future.[Pubmed:21859938]

Antimicrob Agents Chemother. 2011 Nov;55(11):4943-60.

In this review, we summarize the current "state of the art" of carbapenem antibiotics and their role in our antimicrobial armamentarium. Among the beta-lactams currently available, carbapenems are unique because they are relatively resistant to hydrolysis by most beta-lactamases, in some cases act as "slow substrates" or inhibitors of beta-lactamases, and still target penicillin binding proteins. This "value-added feature" of inhibiting beta-lactamases serves as a major rationale for expansion of this class of beta-lactams. We describe the initial discovery and development of the carbapenem family of beta-lactams. Of the early carbapenems evaluated, thienamycin demonstrated the greatest antimicrobial activity and became the parent compound for all subsequent carbapenems. To date, more than 80 compounds with mostly improved antimicrobial properties, compared to those of thienamycin, are described in the literature. We also highlight important features of the carbapenems that are presently in clinical use: imipenem-cilastatin, meropenem, ertapenem, doripenem, panipenem-Betamipron, and biapenem. In closing, we emphasize some major challenges and urge the medicinal chemist to continue development of these versatile and potent compounds, as they have served us well for more than 3 decades.

Description

Betamipron is a chemical compound which is used together with Panipenem to inhibit Panipenem uptake into the renal tubule and prevent nephrotoxicity.

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