Faropenem sodium
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-03809 |
| CAS | 122547-49-3 |
| Molecular Weight | 307.30 |
| Molecular Formula | C12H14NO5SNa |
| Purity | >95% |
Online Inquiry
Description
Faropenem is an orally active beta-lactam antibiotic belonging to the penem group.
Specification
| Related CAS | 158365-51-6 (hemipentahydrate) 106560-14-9 (free acid) |
| Synonyms | 4-Thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 6-[(1R)-1-hydroxyethyl]-7-oxo-3-[(2R)-tetrahydro-2-furanyl]-, sodium salt (1:1), (5R,6S)-; 4-Thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 6-[(1R)-1-hydroxyethyl]-7-oxo-3-[(2R)-tetrahydro-2-furanyl]-, monosodium salt, (5R,6S)-; (5R,6S)-6-[(1R)-1-Hydroxyethyl]-7-oxo-3-[(2R)-2-tetrahydrofuryl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid sodium salt; ALP 201; 4-Thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 6-(1-hydroxyethyl)-7-oxo-3-(tetrahydro-2-furanyl)-, monosodium salt, [5R-[3(R*),5α,6α(R*)]]-; Farom; Fropenem; Furopenem; SUN 5555; SY 5555; Wy 49605 |
| Storage | Store at -20°C |
| IUPAC Name | sodium;(5R,6S)-6-[(1R)-1-hydroxyethyl]-7-oxo-3-[(2R)-oxolan-2-yl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate |
| Canonical SMILES | CC(C1C2N(C1=O)C(=C(S2)C3CCCO3)C(=O)[O-])O.[Na+] |
| InChI | InChI=1S/C12H15NO5S.Na/c1-5(14)7-10(15)13-8(12(16)17)9(19-11(7)13)6-3-2-4-18-6;/h5-7,11,14H,2-4H2,1H3,(H,16,17);/q;+1/p-1/t5-,6-,7+,11-;/m1./s1 |
| InChI Key | ICSAXRANXQSPQP-VUKDEKJYSA-M |
Properties
| Appearance | White to Light Brown Powder |
| Boiling Point | 570.2°C at 760 mmHg |
| Flash Point | 298.7ºC |
| Solubility | Soluble in DMSO, Water (20 mg/mL) |
| LogP | -1.02310 |
Reference Reading
1. Oral Faropenem Sodium - Implications for Antimicrobial Resistance and Treatment Effectiveness
Dhanya Dharmapalan, Sujith J Chandy Indian Pediatr. 2022 Nov 15;59(11):879-881.
Rising antimicrobial resistance (AMR) is causing therapeutic failures with antibiotics. Inappropriate use is a contributing factor. One such antibiotic on the radar is faropenem, a broad spectrum antibiotic approved in 2005 in India. Recently, faropenem sodium suspension was approved for use in children. There is a potential danger of overuse due to the convenience of oral administration. Other carbapenems such as meropenem are used parenterally. Overuse of faropenem may promote cross-resistance with other carbapenems making them ineffective.
2. Oral Faropenem Sodium - Implications for Antimicrobial Resistance and Treatment Effectiveness
Dhanya Dharmapalan, Sujith J Chandy Indian Pediatr. 2022 Sep 22;S097475591600460. Online ahead of print.
Rising antimicrobial resistance (AMR) is causing therapeutic failures with antibiotics. Inappropriate use is a contributing factor. One such antibiotic on the radar is faropenem, a broad spectrum antibiotic approved in 2005 in India. Recently, faropenem sodium suspension was approved for use in children. There is a potential danger of overuse due to the convenience of oral administration. Other carbapenems such as meropenem are used parenterally. Overuse of faropenem may promote cross- resistance with other carbapenems making them ineffective.
3. Profiling of β-lactam selectivity for penicillin-binding proteins in Streptococcus pneumoniae D39
Ozden Kocaoglu, Ho-Ching T Tsui, Malcolm E Winkler, Erin E Carlson Antimicrob Agents Chemother. 2015;59(6):3548-55. doi: 10.1128/AAC.05142-14. Epub 2015 Apr 6.
Selective fluorescent β-lactam chemical probes enable the visualization of the transpeptidase activity of penicillin-binding proteins (PBPs) at different stages of bacterial cell division. To facilitate the development of new fluorescent probes for PBP imaging, we evaluated 20 commercially available β-lactams for selective PBP inhibition in an unencapsulated derivative of the D39 strain of Streptococcus pneumoniae. Live cells were treated with β-lactam antibiotics at different concentrations and subsequently incubated with Bocillin FL (Boc-FL; fluorescent penicillin) to saturate uninhibited PBPs. Fluorophore-labeled PBPs were visualized by sodium dodecyl sulfate-polyacrylamide gel electrophoresis (SDS-PAGE) and fluorescence scanning. Among 20 compounds tested, carbapenems (doripenem and meropenem) were coselective for PBP1a, PBP2x, and PBP3, while six of the nine penicillin compounds were coselective for PBP2x and PBP3. In contrast, the seven cephalosporin compounds tested display variability in their PBP-binding profiles. Three cephalosporin compounds (cefoxitin, cephalexin, and cefsulodin) and the monobactam aztreonam exhibited selectivity for PBP3, while only cefuroxime (a cephalosporin) was selective for PBP2x. Treatment of S. pneumoniae cultures with a sublethal concentration of cefuroxime that inhibited 60% of PBP2x activity and less than 20% of the activity of other PBPs resulted in formation of elongated cells. In contrast, treatment of S. pneumoniae cultures with concentrations of aztreonam and cefoxitin that inhibited up to 70% of PBP3 activity and less than 30% of other PBPs resulted in no discernible morphological changes. Additionally, correlation of the MIC and IC50s for each PBP, with the exception of faropenem, amdinocillin (mecillinam), and 6-APA, suggests that pneumococcal growth inhibition is primarily due to the inhibition of PBP2x.
Recommended Products
| BBF-01829 | Deoxynojirimycin | Inquiry |
| BBF-03753 | Baicalin | Inquiry |
| BBF-02642 | Lactonamycin | Inquiry |
| BBF-00764 | Cerebroside C | Inquiry |
| BBF-05862 | Epirubicin | Inquiry |
| BBF-01825 | Loganin | 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 ╳
