Imipenem Monohydrate
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-04641 |
| CAS | 74431-23-5 |
| Molecular Weight | 317.36 |
| Molecular Formula | C12H17N3O4S.H2O |
| Purity | 98% |
Ordering Information
| Catalog Number | Size | Price | Stock | Quantity |
|---|---|---|---|---|
| BBF-04641 | 500 mg | $199 | In stock |
Online Inquiry
Add to cartDescription
Imipenem is an intravenous β-lactam antibiotic. It is the first member of the carbapenem class of antibiotics. Imipenem is discovered via a lengthy trial-and-error search for a more stable version of the natural product thienamycin, which is produced by the bacterium Streptomyces cattleya. Imipenem has a broad spectrum of activity against aerobic and anaerobic, Gram-positive and Gram-negative bacteria. It is particularly important for its activity against Pseudomonas aeruginosa and the Enterococcus species, but it is not active against MRSA.
Specification
| Related CAS | 64221-86-9 (anhydrous) |
| Synonyms | (5R,6S)-6-[(1R)-1-hydroxyethyl]-3-[[2-[(iminomethyl)amino]ethyl]thio]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, monohydrate; N-Formimidoyl Thienamycin; MK-787; MK 787; MK787 |
| Shelf Life | 3 years |
| Storage | Store at -20°C |
| IUPAC Name | (5R,6S)-3-[2-(aminomethylideneamino)ethylsulfanyl]-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid;hydrate |
| Canonical SMILES | CC(C1C2CC(=C(N2C1=O)C(=O)O)SCCN=CN)O.O |
| InChI | InChI=1S/C12H17N3O4S.H2O/c1-6(16)9-7-4-8(20-3-2-14-5-13)10(12(18)19)15(7)11(9)17;/h5-7,9,16H,2-4H2,1H3,(H2,13,14)(H,18,19);1H2/t6-,7-,9-;/m1./s1 |
| InChI Key | GSOSVVULSKVSLQ-JJVRHELESA-N |
Properties
| Appearance | Off-white to Pale Yellow Solid |
| Application | Anti-Bacterial Agents |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
| Boiling Point | 567.3°C at 760 mmHg |
| Melting Point | 193-198°C |
| Solubility | Soluble in DMSO, Methanol |
Toxicity
| Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
| Mechanism Of Toxicity | Imipenem acts as an antimicrobial through the inhibition of cell wall synthesis of various gram-positive and gram-negative bacteria. This inhibition of cell wall synthesis in gram-negative bateria is attained by binding to pencillin binding proteins (PBPs). In E. coli and selected strains of P. aeruginosa, imipenem has shown to have the highest affinity to PBP-2, PBP-1a, and PBP-1b. This preferential binding to PBP-2 and PBP-1b results in the direct conversion of the individual cell to a spheroblast, which leads to rapid cell lysis and death without filament formation. |
Reference Reading
1.Primaxin in the treatment of acute bacterial pneumonia in adults.
Gebhart RJ;Duma RJ;Patterson PM;Bagett JW;Williams DS J Antimicrob Chemother. 1985 Feb;15(2):233-8.
Imipenem (N-Formimidoyl thienamycin) (MK-0787) is a new beta-lactam carbapenem antibiotic. When it is combined with the renal dipeptidase inhibitor cilastatin (MK-0791) the combination is known as primaxin. In this study 28 adult patients (24 males and 4 females) with acute bacterial pneumonia were treated with primaxin. Twenty-one patients were evaluable and 20 (95%) were clinically cured of their pneumonia. Bacteriological cures were demonstrated in 84% of the cases. One patient with a susceptible Pseudomonas aeruginosa failed. Major complications or toxic reactions included antibiotic associated diarrhoea in one patient; hypotension in one patient; increased grand mal seizures in one patient and elevated liver function studies in one patient. Results of this study suggest that primaxin will be useful in the treatment of a variety of serious Gram-positive and Gram-negative pneumonias. The true incidence of possible toxic reactions with this drug is not known at this time and awaits further experience.
2.[Fundamental and clinical studies on imipenem/cilastatin sodium in the field of pediatrics].
Nakashima T;Nakashima S;Hayakawa F;Miyachi Y;Hakamada S;Kuno K Jpn J Antibiot. 1986 Jul;39(7):1828-46.
Fundamental and clinical studies on imipenem/cilastatin sodium (MK-0787/MK-0791) were performed in pediatric patients with infections. Results obtained were summarized below. The mean plasma half-life of MK-0787 was 0.84 hour with a dosage of 10 mg/kg and 0.90 hour with a dosage of 20 mg/kg. Mean plasma half-lives of MK-0791 were 0.40 hour and 0.71 hour for dosages of 10 mg/kg and 20 mg/kg, respectively. Urinary recovery of both MK-0787 and MK-0791 was high. The antibacterial activity of MK-0787 against clinically isolated organisms was determined. The MK-0787 was bactericidal against a broad spectrum of both Gram-positive and Gram-negative pathogens. The MK-0787/MK-0791 was administered to 32 pediatric patients with various infections. The overall clinical efficacy rate was 96.9%. Side effects observed were loose stools in one patient, diarrhea in another and slight elevations of platelet and direct bilirubin, and eosinophilia were observed in 3 patients, respectively.
3.[Fundamental and clinical studies on imipenem/cilastatin sodium in the pediatric field].
Toyonaga Y;Sugita M;Tsuda T;Takahashi T;Hori M Jpn J Antibiot. 1986 Jul;39(7):1765-86.
Fundamental and clinical studies were performed on a newly developed carbapenem antibiotic, imipenem/cilastatin sodium (MK-0787/MK-0791), and results were summarized as follows. The antibacterial activity of MK-0787 at an inoculum of 10(6) cells/ml against strains of S. aureus which were sensitive or resistant to cefazolin (CEZ), E. coli, P. mirabilis, K. pneumoniae, S. marcescens and P. aeruginosa were determined and compared with activities of ceftazidime (CAZ), CEZ, cefmetazole (CMZ), ceftizoxime (CZX), latamoxef (LMOX), cefamandole (CMD), cefoperazone (CPZ), cefsulodin (CFS) and piperacillin (PIPC). The peak MIC of MK-0787 was less than or equal to 0.024 micrograms/ml against S. aureus, which were sensitive or resistant to CEZ, 0.10 micrograms/ml against E. coli, P. mirabilis, or K. pneumoniae, 0.39 micrograms/ml against S. marcescens and 1.56 micrograms/ml against P. aeruginosa. The antibacterial activity of MK-0787 against these bacteria was, on the whole, superior to that of CAZ, CEZ, CMZ, CZX, LMOX, CMD, CPZ, CFS or PIPC. The pharmacokinetics of MK-0787/MK-0791 was studied in 10 children at dose levels of 10 mg/10 mg/kg and 20 mg/20 mg/kg by a 30-minute intravenous drip infusion.
Spectrum
Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive
Experimental Conditions
Ionization Mode: Positive
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C12H17N3O4S
Molecular Weight (Monoisotopic Mass): 299.094 Da
Molecular Weight (Avergae Mass): 299.346 Da
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C12H17N3O4S
Molecular Weight (Monoisotopic Mass): 299.094 Da
Molecular Weight (Avergae Mass): 299.346 Da
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C12H17N3O4S
Molecular Weight (Monoisotopic Mass): 299.094 Da
Molecular Weight (Avergae Mass): 299.346 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C12H17N3O4S
Molecular Weight (Monoisotopic Mass): 299.094 Da
Molecular Weight (Avergae Mass): 299.346 Da
1H NMR Spectrum
Experimental Conditions
Solvent: D2O
Nucleus: 1H
Frequency: 100
Nucleus: 1H
Frequency: 100
Recommended Products
| BBF-01829 | Deoxynojirimycin | Inquiry |
| BBF-03753 | Baicalin | Inquiry |
| BBF-03755 | Actinomycin D | Inquiry |
| BBF-03754 | Castanospermine | Inquiry |
| BBF-00764 | Cerebroside C | Inquiry |
| BBF-01826 | Deoxymannojirimycin | Inquiry |
Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
