U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of FAROPENEM SODIUM

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

HIDE SMILES / InChI

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

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
In vitro activity of faropenem and 21 other compounds against 385 different genetically characterized isolates of antibiotic-resistant Streptococcus pneumoniae.
2001 Jul
Profound skin infection with bone involvement due to Nocardia asteroides in a patient with myelodysplastic syndrome.
2001 Oct
[Pyogenic sacroiliitis in pregnancy].
2001 Sep
In vitro activity of faropenem against 5460 clinical bacterial isolates from Europe.
2002 Aug
Comparative in vitro activity of faropenem against staphylococci.
2002 Aug
[Triple therapy with faropenem, proton pump inhibitor (PPI), and amoxicillin for clarithromycin-resistant H. pylori eradication].
2002 Feb
A case of retropharyngeal abscess caused by penicillin-resistant Streptococcus pneumoniae.
2002 May
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
Resistance to beta-lactams--the permutations.
2003 Dec
Target affinities of faropenem to and its impact on the morphology of gram-positive and gram-negative bacteria.
2003 Jul
The art of fusion: from penams and cephems to penems.
2003 Jun
Faropenem, a new oral penem: antibacterial activity against selected anaerobic and fastidious periodontal isolates.
2003 Mar
Quantification of faropenem in human plasma by high-performance liquid chromatography.
2005
The antimicrobial armamentarium: evaluating current and future treatment options.
2005 Oct
JPMorgan 24th Annual Healthcare Conference.
2006 Mar
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
Genetic analysis of faropenem-resistant Enterococcus faecalis in urinary isolates.
2008 Apr
Effects of treatment with antimicrobial agents on the human colonic microflora.
2008 Dec
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
A case of multidrug-resistant Salmonella enterica serovar Typhi treated with a bench to bedside approach.
2009 Feb 28
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 Fri Dec 15 19:12:48 UTC 2023
Edited
by admin
on Fri Dec 15 19:12:48 UTC 2023
Record UNII
7O46G914RQ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FAROPENEM SODIUM
MART.   WHO-DD  
Common Name English
FAROPENEM SODIUM [MART.]
Common Name English
WY-49605
Common Name English
Faropenem sodium [WHO-DD]
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 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 Fri Dec 15 19:12:48 UTC 2023 , Edited by admin on Fri Dec 15 19:12:48 UTC 2023
PRIMARY
MESH
C060114
Created by admin on Fri Dec 15 19:12:48 UTC 2023 , Edited by admin on Fri Dec 15 19:12:48 UTC 2023
PRIMARY
EPA CompTox
DTXSID60924197
Created by admin on Fri Dec 15 19:12:48 UTC 2023 , Edited by admin on Fri Dec 15 19:12:48 UTC 2023
PRIMARY
MERCK INDEX
m5246
Created by admin on Fri Dec 15 19:12:48 UTC 2023 , Edited by admin on Fri Dec 15 19:12:48 UTC 2023
PRIMARY Merck Index
EVMPD
SUB16432MIG
Created by admin on Fri Dec 15 19:12:48 UTC 2023 , Edited by admin on Fri Dec 15 19:12:48 UTC 2023
PRIMARY
CAS
122547-49-3
Created by admin on Fri Dec 15 19:12:48 UTC 2023 , Edited by admin on Fri Dec 15 19:12:48 UTC 2023
PRIMARY
SMS_ID
100000091345
Created by admin on Fri Dec 15 19:12:48 UTC 2023 , Edited by admin on Fri Dec 15 19:12:48 UTC 2023
PRIMARY
PUBCHEM
23663972
Created by admin on Fri Dec 15 19:12:48 UTC 2023 , Edited by admin on Fri Dec 15 19:12:48 UTC 2023
PRIMARY
DRUG BANK
DBSALT002150
Created by admin on Fri Dec 15 19:12:48 UTC 2023 , Edited by admin on Fri Dec 15 19:12:48 UTC 2023
PRIMARY
Related Record Type Details
SOLVATE->ANHYDROUS
TARGET ORGANISM->INHIBITOR
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY