Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C12H14NO5S.Na |
Molecular Weight | 307.298 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].[H][C@]12SC([C@H]3CCCO3)=C(N1C(=O)[C@]2([H])[C@@H](C)O)C([O-])=O
InChI
InChIKey=ICSAXRANXQSPQP-VUKDEKJYSA-M
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
Molecular Formula | C12H14NO5S |
Molecular Weight | 284.308 |
Charge | -1 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Molecular Formula | Na |
Molecular Weight | 22.9898 |
Charge | 1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including:
http://www.evaluategroup.com/Universal/View.aspx?type=Story&id=80189 | https://www.fda.gov/downloads/Drugs/GuidanceComplianceRegulatoryInformation/EnforcementActivitiesbyFDA/WarningLettersandNoticeofViolationLetterstoPharmaceuticalCompanies/ucm054149.pdf | https://www.ncbi.nlm.nih.gov/pubmed/12886052
Curator's Comment: description was created based on several sources, including:
http://www.evaluategroup.com/Universal/View.aspx?type=Story&id=80189 | https://www.fda.gov/downloads/Drugs/GuidanceComplianceRegulatoryInformation/EnforcementActivitiesbyFDA/WarningLettersandNoticeofViolationLetterstoPharmaceuticalCompanies/ucm054149.pdf | https://www.ncbi.nlm.nih.gov/pubmed/12886052
Faropenem is a unique antimicrobial penem being developed for oral administration. It markets it in two forms: faropenem sodium and faropenem medoxomil. The high binding affinities of faropenem to penicillin-binding proteins from gram-negative and gram-positive bacteria are mirrored by its pronounced and concentration-dependent bactericidal effect. It is usually used to treat a wide range of infections such as skin, respiratory and otorhinologic infections. The most commonly reported adverse reactions include diarrhea, abdominal pain, loose stool, rash and nausea. The FDA refused to approve faropenem – the applicant have to conduct new studies and clinical trials to prove the drug treats community-acquired pneumonia, bacterial sinusitis, chronic bronchitis, and skin infections.
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18298129
Curator's Comment: http://adisinsight.springer.com/drugs/800000539
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2354204 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12886052 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | Farom Approved UseDrug is indicated for the treatment of bacterial infections and respiratory tract infections, including acute exacerbations of chronic bronchitis (AECB), acute bacterial sinusitis (ABS) and community-acquired pneumonia (CAP). |
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Curative | Farom Approved UseDrug is indicated for the treatment of bacterial infections and respiratory tract infections, including acute exacerbations of chronic bronchitis (AECB), acute bacterial sinusitis (ABS) and community-acquired pneumonia (CAP). |
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Curative | Farom Approved UseDrug is indicated for the treatment of bacterial infections and respiratory tract infections, including acute exacerbations of chronic bronchitis (AECB), acute bacterial sinusitis (ABS) and community-acquired pneumonia (CAP). |
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Curative | Farom Approved UseDrug is indicated for the treatment of bacterial infections and respiratory tract infections, including acute exacerbations of chronic bronchitis (AECB), acute bacterial sinusitis (ABS), community-acquired pneumonia (CAP) and uncomplicated skin and skin structure infections. |
PubMed
Title | Date | PubMed |
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In vitro activity of faropenem and 21 other compounds against 385 different genetically characterized isolates of antibiotic-resistant Streptococcus pneumoniae. | 2001 Jul |
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Profound skin infection with bone involvement due to Nocardia asteroides in a patient with myelodysplastic syndrome. | 2001 Oct |
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[Pyogenic sacroiliitis in pregnancy]. | 2001 Sep |
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In vitro activity of faropenem against 5460 clinical bacterial isolates from Europe. | 2002 Aug |
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Comparative in vitro activity of faropenem against staphylococci. | 2002 Aug |
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[Triple therapy with faropenem, proton pump inhibitor (PPI), and amoxicillin for clarithromycin-resistant H. pylori eradication]. | 2002 Feb |
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A case of retropharyngeal abscess caused by penicillin-resistant Streptococcus pneumoniae. | 2002 May |
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Comparative in vitro activity of faropenem and 11 other antimicrobial agents against 405 aerobic and anaerobic pathogens isolated from skin and soft tissue infections from animal and human bites. | 2002 Sep |
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Resistance to beta-lactams--the permutations. | 2003 Dec |
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Target affinities of faropenem to and its impact on the morphology of gram-positive and gram-negative bacteria. | 2003 Jul |
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The art of fusion: from penams and cephems to penems. | 2003 Jun |
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Faropenem, a new oral penem: antibacterial activity against selected anaerobic and fastidious periodontal isolates. | 2003 Mar |
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Quantification of faropenem in human plasma by high-performance liquid chromatography. | 2005 |
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The antimicrobial armamentarium: evaluating current and future treatment options. | 2005 Oct |
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JPMorgan 24th Annual Healthcare Conference. | 2006 Mar |
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Efficacy and safety of faropenem in eradication therapy of Helicobacter pylori. | 2007 Dec |
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In vitro activities of faropenem, ertapenem, imipenem and meropenem against Borrelia burgdorferi s.l. | 2007 Jul |
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Genetic analysis of faropenem-resistant Enterococcus faecalis in urinary isolates. | 2008 Apr |
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Effects of treatment with antimicrobial agents on the human colonic microflora. | 2008 Dec |
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Region-dependent absorption of faropenem shared with foscarnet, a phosphate transporter substrate, in the rat small intestine. | 2008 Sep |
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The determinants of the antibiotic resistance process. | 2009 |
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A case of multidrug-resistant Salmonella enterica serovar Typhi treated with a bench to bedside approach. | 2009 Feb 28 |
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In vitro and in vivo efficacy of β-lactams against replicating and slowly growing/nonreplicating Mycobacterium tuberculosis. | 2013 Jun |
Patents
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12886052
Exposure of S. aureus to faropenem at minimum inhibitory concentrations (MICs) of 1/8 or 1/4 resulted in irregular septum formation. At 1x MIC or higher, a larger number of lysed cells were observed. Exposure of E. coli to 1/8x MIC or 1/4x MIC also induced changes in cellular shape; the normal rod-shaped form changed to a spherical form in a time-dependent manner. After exposure of E. coli to 1x MIC for 2 h, bulging-shaped E. coli cells were observed and after 4 h of exposure cell lysis was demonstrated. In the presence of 4x MIC, spheroplast-like forms and cell lysis were observed.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 19:12:48 UTC 2023
by
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on
Fri Dec 15 19:12:48 UTC 2023
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Record UNII |
7O46G914RQ
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Record Status |
Validated (UNII)
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Record Version |
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ACTIVE MOIETY |