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
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 |
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Target ID: CHEMBL2354204 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12886052 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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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) 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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[New orally active penem antibiotic: Farom]. | 2001 Dec |
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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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In vitro activity of faropenem and 20 other compounds against beta-lactamase-positive and -negative Moraxella catarrhalis and Haemophilus influenzae isolates and the effect of serum on faropenem MICs. | 2002 Jan |
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In vitro activity of faropenem against respiratory pathogens. | 2002 Mar |
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Successful treatment with faropenem and clarithromycin of pulmonary Mycobacterium abscessus infection. | 2002 Sep |
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Activity of faropenem, a new furanem, against European respiratory pathogens collected during 2000-2001: a comparison with other beta-lactam agents. | 2003 Jan |
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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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The in vitro effects of faropenem on lower respiratory tract pathogens isolated in the United Kingdom. | 2003 Jun |
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In vitro activity of faropenem compared with eight agents against fourteen Gram-positive and Gram-negative bacteria by time-kill. | 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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Comparative in vitro activity of faropenem and 11 other antimicrobial agents against 250 invasive Streptococcus pneumoniae isolates from France. | 2003 Sep |
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Activity of faropenem and imipenem for ciprofloxacin-resistant bacteria. | 2003 Sep |
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The influence of protein binding on the antibacterial activity of faropenem against Haemophilus influenzae. | 2004 Oct |
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In vitro investigation of the indirect pathogenicity of beta-lactamase-producing microorganisms in the nasopharyngeal microflora. | 2005 Apr |
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Activity of faropenem tested against Neisseria gonorrhoeae isolates including fluoroquinolone-resistant strains. | 2005 Dec |
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Mycobacterium peregrinum infection in a patient with AIDS. | 2005 Mar |
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[Investigation of Streptococcus pneumoniae and Haemophilus influenzae isolated from pediatric outpatients nationwide with a respiratory tract infection at the first consultation (2002-2003)--proportion of resistant strains and sensitivity to oral antibacterial agents]. | 2005 Nov |
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In vitro activity of beta-lactams, macrolides, telithromycin, and fluoroquinolones against clinical isolates of Streptococcus pneumoniae: correlation between drug resistance and genetic characteristics. | 2005 Oct |
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The antimicrobial armamentarium: evaluating current and future treatment options. | 2005 Oct |
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[Relationship between protein binding and antimicrobial activities of antibiotics against Streptococcus pneumoniae and Haemophilus influenzae]. | 2006 Oct |
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Faropenem: review of a new oral penem. | 2007 Apr |
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In vitro activities of faropenem, ertapenem, imipenem and meropenem against Borrelia burgdorferi s.l. | 2007 Jul |
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Activity of faropenem against cephalosporin-resistant Enterobacteriaceae. | 2007 May |
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Evaluation of the bioequivalence of two faropenem formulations in healthy Indian subjects. | 2008 |
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Faropenem medoxomil: A0026, BAY 56-6854, BAY 566854, faropenem daloxate, SUN 208, SUN A0026. | 2008 |
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Genetic analysis of faropenem-resistant Enterococcus faecalis in urinary isolates. | 2008 Apr |
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[Susceptibilities of bacteria isolated from patients with lower respiratory infectious diseases to antibiotics (2005)]. | 2008 Aug |
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Emerging therapies for the treatment of Helicobacter pylori infections. | 2008 Nov |
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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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Streptococcus pneumoniae serotype 3 among Costa Rican children with otitis media: clinical, epidemiological characteristics and antimicrobial resistance patterns. | 2009 Aug 14 |
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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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Antimicrobial development in the era of emerging resistance. | 2009 Jul |
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Pedal oedema: a rare side-effect of faropenem. | 2009 Oct |
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Human carboxymethylenebutenolidase as a bioactivating hydrolase of olmesartan medoxomil in liver and intestine. | 2010 Apr 16 |
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Quinolone and cephalosporin resistance in enteric Fever. | 2010 Sep |
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.
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C060114
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m5246
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SUB16432MIG
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122547-49-3
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DBSALT002150
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SUBSTANCE RECORD