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+].C[C@@H](O)[C@@H]1[C@H]2SC([C@H]3CCCO3)=C(N2C1=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 | Na |
| Molecular Weight | 22.98976928 |
| Charge | 1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| 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 |
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). |
|||
| 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). |
|||
| 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). |
|||
| 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. |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1.32 μg/mL |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
FAROPENEM plasma | Homo sapiens population: UNKNOWN age: CHILD sex: FEMALE / MALE food status: FED |
|
2.08 μg/mL |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
FAROPENEM plasma | Homo sapiens population: UNKNOWN age: CHILD sex: FEMALE / MALE food status: FED |
|
2.36 μg/mL |
150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered: |
FAROPENEM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
6.24 μg/mL |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
FAROPENEM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
7.37 μg/mL |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
FAROPENEM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
1.9 μg/mL |
200 mg 3 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
FAROPENEM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
2.02 μg/mL |
200 mg 3 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
FAROPENEM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
1.89 μg/mL |
200 mg 3 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
FAROPENEM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
6.24 μg/mL |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
FAROPENEM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
4.25 μg/mL |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
FAROPENEM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
3.49 μg/mL |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
FAROPENEM plasma | Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE / MALE food status: FED |
|
4.25 μg/mL |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
FAROPENEM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
4.1 μg × h/mL |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
FAROPENEM plasma | Homo sapiens population: UNKNOWN age: CHILD sex: FEMALE / MALE food status: FED |
|
5.89 μg × h/mL |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
FAROPENEM plasma | Homo sapiens population: UNKNOWN age: CHILD sex: FEMALE / MALE food status: FED |
|
3.95 μg × h/mL |
150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered: |
FAROPENEM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
11.73 μg × h/mL |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
FAROPENEM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
19.59 μg × h/mL |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
FAROPENEM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
4.18 μg × h/mL |
200 mg 3 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
FAROPENEM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
4.34 μg × h/mL |
200 mg 3 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
FAROPENEM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
4.14 μg × h/mL |
200 mg 3 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
FAROPENEM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
11.73 μg × h/mL |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
FAROPENEM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
9.75 μg × h/mL |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
FAROPENEM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
16.49 μg × h/mL |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
FAROPENEM plasma | Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE / MALE food status: FED |
|
9.75 μg × h/mL |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
FAROPENEM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1.66 h |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
FAROPENEM plasma | Homo sapiens population: UNKNOWN age: CHILD sex: FEMALE / MALE food status: FED |
|
1.14 h |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
FAROPENEM plasma | Homo sapiens population: UNKNOWN age: CHILD sex: FEMALE / MALE food status: FED |
|
0.76 h |
150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered: |
FAROPENEM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
0.85 h |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
FAROPENEM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
1.08 h |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
FAROPENEM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
0.96 h |
200 mg 3 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
FAROPENEM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
0.89 h |
200 mg 3 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
FAROPENEM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
0.93 h |
200 mg 3 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
FAROPENEM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
0.85 h |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
FAROPENEM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
1.01 h |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
FAROPENEM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
1.61 h |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
FAROPENEM plasma | Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE / MALE food status: FED |
|
1.01 h |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
FAROPENEM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
9.3% |
FAROPENEM serum | Homo sapiens |
Doses
| Dose | Population | Adverse events |
|---|---|---|
300 mg 2 times / day multiple, oral Recommended Dose: 300 mg, 2 times / day Route: oral Route: multiple Dose: 300 mg, 2 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Disc. AE: Diarrhea, Vomiting... Other AEs: Nausea... AEs leading to discontinuation/dose reduction: Diarrhea Other AEs:Vomiting Nausea Sources: |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Nausea | 300 mg 2 times / day multiple, oral Recommended Dose: 300 mg, 2 times / day Route: oral Route: multiple Dose: 300 mg, 2 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
|
| Diarrhea | Disc. AE | 300 mg 2 times / day multiple, oral Recommended Dose: 300 mg, 2 times / day Route: oral Route: multiple Dose: 300 mg, 2 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Vomiting | Disc. AE | 300 mg 2 times / day multiple, oral Recommended Dose: 300 mg, 2 times / day Route: oral Route: multiple Dose: 300 mg, 2 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| In vitro and in vivo efficacy of β-lactams against replicating and slowly growing/nonreplicating Mycobacterium tuberculosis. | 2013-06 |
|
| Quinolone and cephalosporin resistance in enteric Fever. | 2010-09 |
|
| High-throughput determination of faropenem in human plasma and urine by on-line solid-phase extraction coupled to high-performance liquid chromatography with UV detection and its application to the pharmacokinetic study. | 2010-05-01 |
|
| Human carboxymethylenebutenolidase as a bioactivating hydrolase of olmesartan medoxomil in liver and intestine. | 2010-04-16 |
|
| Synthesis, characterization and antibacterial activities of some new ferrocene-containing penems. | 2010-03 |
|
| Nationwide survey of the development of drug-resistance in the pediatric field: drug sensitivity of Haemophilus influenzae in Japan. | 2009-12 |
|
| Nationwide survey of the development of drug-resistant pathogens in the pediatric field: drug sensitivity of Streptococcus pneumoniae in Japan. | 2009-12 |
|
| Pedal oedema: a rare side-effect of faropenem. | 2009-10 |
|
| Streptococcus pneumoniae serotype 3 among Costa Rican children with otitis media: clinical, epidemiological characteristics and antimicrobial resistance patterns. | 2009-08-14 |
|
| Increase in pneumococcus macrolide resistance, United States. | 2009-08 |
|
| Antimicrobial development in the era of emerging resistance. | 2009-07 |
|
| [Antimicrobial activity of tebipenem against various clinical isolates from various specimen, mainly urinary tract]. | 2009-04 |
|
| New antimicrobial molecules and new antibiotic strategies. | 2009-04 |
|
| Minimum inhibitory concentration of carbapenems and tigecycline against Salmonella spp. | 2009-03 |
|
| A case of multidrug-resistant Salmonella enterica serovar Typhi treated with a bench to bedside approach. | 2009-02-28 |
|
| The determinants of the antibiotic resistance process. | 2009 |
|
| Effects of treatment with antimicrobial agents on the human colonic microflora. | 2008-12 |
|
| [Efficacy and safety of faropenem in pediatric patients with bacterial infectious diseases]. | 2008-12 |
|
| [T serotypes distribution and antimicrobial susceptibility of Streptococcus pyogenes in children with pharyngotonsillitis in Asahikawa]. | 2008-12 |
|
| Emerging therapies for the treatment of Helicobacter pylori infections. | 2008-11 |
|
| Region-dependent absorption of faropenem shared with foscarnet, a phosphate transporter substrate, in the rat small intestine. | 2008-09 |
|
| [Susceptibilities of bacteria isolated from patients with lower respiratory infectious diseases to antibiotics (2005)]. | 2008-08 |
|
| Genetic analysis of faropenem-resistant Enterococcus faecalis in urinary isolates. | 2008-04 |
|
| Multidrug-resistant Gram-negative bacterial infections: the emerging threat and potential novel treatment options. | 2008-02 |
|
| Faropenem medoxomil. | 2008-01 |
|
| Determination of faropenem in human plasma and urine by liquid chromatography-tandem mass spectrometry. | 2008-01 |
|
| Evaluation of the bioequivalence of two faropenem formulations in healthy Indian subjects. | 2008 |
|
| Faropenem medoxomil: A0026, BAY 56-6854, BAY 566854, faropenem daloxate, SUN 208, SUN A0026. | 2008 |
|
| Efficacy and safety of faropenem in eradication therapy of Helicobacter pylori. | 2007-12 |
|
| In vitro activities of faropenem, ertapenem, imipenem and meropenem against Borrelia burgdorferi s.l. | 2007-07 |
|
| Activity of faropenem against cephalosporin-resistant Enterobacteriaceae. | 2007-05 |
|
| Faropenem: review of a new oral penem. | 2007-04 |
|
| Faropenem medoxomil: a treatment option in acute bacterial rhinosinusitis. | 2006-12 |
|
| [Relationship between protein binding and antimicrobial activities of antibiotics against Streptococcus pneumoniae and Haemophilus influenzae]. | 2006-10 |
|
| Randomized double-blind study comparing 7- and 10-day regimens of faropenem medoxomil with a 10-day cefuroxime axetil regimen for treatment of acute bacterial sinusitis. | 2006-10 |
|
| Clinical significance of overexpression of multiple RND-family efflux pumps in Bacteroides fragilis isolates. | 2006-09 |
|
| Redefining penems. | 2006-03-30 |
|
| JPMorgan 24th Annual Healthcare Conference. | 2006-03 |
|
| Activity of faropenem tested against Neisseria gonorrhoeae isolates including fluoroquinolone-resistant strains. | 2005-12 |
|
| [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]. | 2005-11 |
|
| In vitro activity of beta-lactams, macrolides, telithromycin, and fluoroquinolones against clinical isolates of Streptococcus pneumoniae: correlation between drug resistance and genetic characteristics. | 2005-10 |
|
| The antimicrobial armamentarium: evaluating current and future treatment options. | 2005-10 |
|
| Investigational new drugs for the treatment of resistant pneumococcal infections. | 2005-08 |
|
| Efficacy of a triple therapy with rabeprazole, amoxicillin, and faropenem as second-line treatment after failure of initial Helicobacter pylori eradication therapy. | 2005-04-09 |
|
| In vitro investigation of the indirect pathogenicity of beta-lactamase-producing microorganisms in the nasopharyngeal microflora. | 2005-04 |
|
| Mycobacterium peregrinum infection in a patient with AIDS. | 2005-03 |
|
| In vitro evaluation of faropenem activity against anaerobic bacteria. | 2005-02 |
|
| Quantification of faropenem in human plasma by high-performance liquid chromatography. | 2005 |
|
| The influence of protein binding on the antibacterial activity of faropenem against Haemophilus influenzae. | 2004-10 |
|
| Bacterial resistance to antimicrobials in urinary isolates. | 2004-09 |
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
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| Record UNII |
7O46G914RQ
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Validated (UNII)
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DBSALT002150
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SOLVATE->ANHYDROUS |
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TARGET ORGANISM->INHIBITOR |
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SALT/SOLVATE -> PARENT |
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ACTIVE MOIETY |