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Details

Stereochemistry ABSOLUTE
Molecular Formula C12H14NO5S.Na
Molecular Weight 307.2996
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FAROPENEM SODIUM

SMILES

C[C@]([H])([C@@]1([H])C(=O)N2C(=C([C@@]3([H])CCCO3)S[C@]12[H])C(=O)[O-])O.[Na+]

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

HIDE SMILES / InChI

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

Molecular Formula C12H14NO5S
Molecular Weight 284.3098
Charge -1
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
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

Curator's Comment:: http://adisinsight.springer.com/drugs/800000539

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Farom

Approved Use

Drug 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 Use

Drug 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 Use

Drug 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 Use

Drug 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

PubMed

TitleDatePubMed
Chemical and microbiologic aspects of penems, a distinct class of beta-lactams: focus on faropenem.
2003 Nov
Beta-lactamase stability of faropenem.
2003 Sep
In vitro studies on the impact of human serum on the antibacterial effect of faropenem.
2004 Feb
Quantification of faropenem in human plasma by high-performance liquid chromatography.
2005
In vitro investigation of the indirect pathogenicity of beta-lactamase-producing microorganisms in the nasopharyngeal microflora.
2005 Apr
Investigational new drugs for the treatment of resistant pneumococcal infections.
2005 Aug
Activity of faropenem tested against Neisseria gonorrhoeae isolates including fluoroquinolone-resistant strains.
2005 Dec
In vitro evaluation of faropenem activity against anaerobic bacteria.
2005 Feb
Efficacy of a triple therapy with rabeprazole, amoxicillin, and faropenem as second-line treatment after failure of initial Helicobacter pylori eradication therapy.
2005 Mar-Apr
[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
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
The antimicrobial armamentarium: evaluating current and future treatment options.
2005 Oct
Faropenem medoxomil: a treatment option in acute bacterial rhinosinusitis.
2006 Dec
JPMorgan 24th Annual Healthcare Conference.
2006 Mar
Redefining penems.
2006 Mar 30
[Relationship between protein binding and antimicrobial activities of antibiotics against Streptococcus pneumoniae and Haemophilus influenzae].
2006 Oct
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 Oct
Clinical significance of overexpression of multiple RND-family efflux pumps in Bacteroides fragilis isolates.
2006 Sep
Faropenem: review of a new oral penem.
2007 Apr
Efficacy and safety of faropenem in eradication therapy of Helicobacter pylori.
2007 Dec
In vitro activities of faropenem, ertapenem, imipenem and meropenem against Borrelia burgdorferi s.l.
2007 Jul
Activity of faropenem against cephalosporin-resistant Enterobacteriaceae.
2007 May
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
Genetic analysis of faropenem-resistant Enterococcus faecalis in urinary isolates.
2008 Apr
[Susceptibilities of bacteria isolated from patients with lower respiratory infectious diseases to antibiotics (2005)].
2008 Aug
Effects of treatment with antimicrobial agents on the human colonic microflora.
2008 Dec
[Efficacy and safety of faropenem in pediatric patients with bacterial infectious diseases].
2008 Dec
[T serotypes distribution and antimicrobial susceptibility of Streptococcus pyogenes in children with pharyngotonsillitis in Asahikawa].
2008 Dec
Multidrug-resistant Gram-negative bacterial infections: the emerging threat and potential novel treatment options.
2008 Feb
Faropenem medoxomil.
2008 Jan
Determination of faropenem in human plasma and urine by liquid chromatography-tandem mass spectrometry.
2008 Jan
Emerging therapies for the treatment of Helicobacter pylori infections.
2008 Nov
Region-dependent absorption of faropenem shared with foscarnet, a phosphate transporter substrate, in the rat small intestine.
2008 Sep
The determinants of the antibiotic resistance process.
2009
[Antimicrobial activity of tebipenem against various clinical isolates from various specimen, mainly urinary tract].
2009 Apr
New antimicrobial molecules and new antibiotic strategies.
2009 Apr
Increase in pneumococcus macrolide resistance, United States.
2009 Aug
Streptococcus pneumoniae serotype 3 among Costa Rican children with otitis media: clinical, epidemiological characteristics and antimicrobial resistance patterns.
2009 Aug 14
Nationwide survey of the development of drug-resistance in the pediatric field: drug sensitivity of Haemophilus influenzae in Japan.
2009 Dec
Nationwide survey of the development of drug-resistant pathogens in the pediatric field: drug sensitivity of Streptococcus pneumoniae in Japan.
2009 Dec
A case of multidrug-resistant Salmonella enterica serovar Typhi treated with a bench to bedside approach.
2009 Feb 28
Antimicrobial development in the era of emerging resistance.
2009 Jul
Minimum inhibitory concentration of carbapenems and tigecycline against Salmonella spp.
2009 Mar
Pedal oedema: a rare side-effect of faropenem.
2009 Oct
Human carboxymethylenebutenolidase as a bioactivating hydrolase of olmesartan medoxomil in liver and intestine.
2010 Apr 16
Synthesis, characterization and antibacterial activities of some new ferrocene-containing penems.
2010 Mar
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 May 1
Quinolone and cephalosporin resistance in enteric Fever.
2010 Sep
In vitro and in vivo efficacy of β-lactams against replicating and slowly growing/nonreplicating Mycobacterium tuberculosis.
2013 Jun
Patents

Sample Use Guides

150 - 300 mg three times a day
Route of Administration: Oral
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 Sat Jun 26 11:20:02 UTC 2021
Edited
by admin
on Sat Jun 26 11:20:02 UTC 2021
Record UNII
7O46G914RQ
Record Status Validated (UNII)
Record Version
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Name Type Language
FAROPENEM SODIUM
MART.   WHO-DD  
Common Name English
FAROPENEM SODIUM [MART.]
Common Name English
WY-49605
Common Name English
SY-5555
Common Name English
SODIUM (+)-(5R,6S)-6-((1R)-1-HYDROXYETHYL)-7-OXO-3-((2R)-TETRAHYDRO-2-FURYL)-4-THIA-1-AZABICYCLO(3.2.0)HEPT-2-ENE-2-CARBOXYLATE
Systematic Name English
ALP-201
Common Name English
YM-044
Common Name English
FAROPENEM SODIUM SALT [MI]
Common Name English
SUN 5555
Common Name English
FUROPENEM
Brand Name English
FAROPENEM SODIUM [WHO-DD]
Common Name English
FAROPENEM SODIUM SALT
MI  
Common Name English
FAROM
Brand Name English
WY 49605
Common Name English
SUN-5555
Common Name English
SY 5555
Common Name English
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)-
Common Name English
Code System Code Type Description
FDA UNII
7O46G914RQ
Created by admin on Sat Jun 26 11:20:02 UTC 2021 , Edited by admin on Sat Jun 26 11:20:02 UTC 2021
PRIMARY
MESH
C060114
Created by admin on Sat Jun 26 11:20:02 UTC 2021 , Edited by admin on Sat Jun 26 11:20:02 UTC 2021
PRIMARY
MERCK INDEX
M5246
Created by admin on Sat Jun 26 11:20:02 UTC 2021 , Edited by admin on Sat Jun 26 11:20:02 UTC 2021
PRIMARY Merck Index
EVMPD
SUB16432MIG
Created by admin on Sat Jun 26 11:20:02 UTC 2021 , Edited by admin on Sat Jun 26 11:20:02 UTC 2021
PRIMARY
CAS
122547-49-3
Created by admin on Sat Jun 26 11:20:02 UTC 2021 , Edited by admin on Sat Jun 26 11:20:02 UTC 2021
PRIMARY
PUBCHEM
23663972
Created by admin on Sat Jun 26 11:20:02 UTC 2021 , Edited by admin on Sat Jun 26 11:20:02 UTC 2021
PRIMARY
DRUG BANK
DBSALT002150
Created by admin on Sat Jun 26 11:20:02 UTC 2021 , Edited by admin on Sat Jun 26 11:20:02 UTC 2021
PRIMARY
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SALT/SOLVATE -> PARENT
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