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

Details

Stereochemistry ABSOLUTE
Molecular Formula C12H15NO5S
Molecular Weight 285.316
Optical Activity ( + )
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FAROPENEM

SMILES

[H][C@]12SC(=C(N1C(=O)[C@]2([H])[C@@H](C)O)C(O)=O)[C@@]3([H])CCCO3

InChI

InChIKey=HGGAKXAHAYOLDJ-FHZUQPTBSA-N
InChI=1S/C12H15NO5S/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)/t5-,6-,7+,11-/m1/s1

HIDE SMILES / InChI

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
[Study on Streptococcus pneumoniae isolated from infants in widely-separated primary care facilities in Japan].
2001 May
[Comparative study on bacterial eradication rate and clinical efficacy of CDTR, CFPN, and FRPM for treatment of children with otitis media and lower respiratory tract infection due to Streptococcus pneumoniae and Haemophilus influenzae].
2001 May
[Epidemiological study on patients with pneumococcal respiratory tract infection in a Japanese health facility during the past year].
2001 May
Profound skin infection with bone involvement due to Nocardia asteroides in a patient with myelodysplastic syndrome.
2001 Oct
Activity of faropenem against resistant isolates of Streptococcus pneumoniae.
2001 Sep-Oct
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
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
In vitro activity of faropenem against respiratory pathogens.
2002 Mar
Antimicrobial susceptibility of major pathogens of orofacial odontogenic infections to 11 beta-lactam antibiotics.
2002 Oct
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
The in vitro effects of faropenem on lower respiratory tract pathogens isolated in the United Kingdom.
2003 Jun
In vitro activity of faropenem compared with eight agents against fourteen Gram-positive and Gram-negative bacteria by time-kill.
2003 Jun
Beta-lactamase stability of faropenem.
2003 Sep
The glycopeptide vancomycin does not enhance toll-like receptor 2 (TLR2) activation by Streptococcus pneumoniae.
2004 Jul
Mycobacterium peregrinum infection in a patient with AIDS.
2005 Mar
[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
The antimicrobial armamentarium: evaluating current and future treatment options.
2005 Oct
JPMorgan 24th Annual Healthcare Conference.
2006 Mar
Faropenem: review of a new oral penem.
2007 Apr
Efficacy and safety of faropenem in eradication therapy of Helicobacter pylori.
2007 Dec
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
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
Nationwide survey of the development of drug-resistance in the pediatric field: drug sensitivity of Haemophilus influenzae in Japan.
2009 Dec
A case of multidrug-resistant Salmonella enterica serovar Typhi treated with a bench to bedside approach.
2009 Feb 28
Minimum inhibitory concentration of carbapenems and tigecycline against Salmonella spp.
2009 Mar
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.
Name Type Language
FAROPENEM
INN   MI   WHO-DD  
INN  
Official Name English
faropenem [INN]
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)-,(5R,6S)
Common Name English
FROPENEM
Common Name English
FAROPENEM [MI]
Common Name English
(5R,6S)-6-((1R)-1-HYDROXYETHYL)-7-OXO-3-((2R)-TETRAHYDROFURAN-2-YL)-4-THIA-1-AZABICYCLO(3.2.0)HEPT-2-ENE-2-CARBOXYLIC ACID
Systematic Name English
Faropenem [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-ATC J01DI03
Created by admin on Fri Dec 15 15:30:06 GMT 2023 , Edited by admin on Fri Dec 15 15:30:06 GMT 2023
NCI_THESAURUS C260
Created by admin on Fri Dec 15 15:30:06 GMT 2023 , Edited by admin on Fri Dec 15 15:30:06 GMT 2023
WHO-VATC QJ01DI03
Created by admin on Fri Dec 15 15:30:06 GMT 2023 , Edited by admin on Fri Dec 15 15:30:06 GMT 2023
Code System Code Type Description
DRUG CENTRAL
1131
Created by admin on Fri Dec 15 15:30:06 GMT 2023 , Edited by admin on Fri Dec 15 15:30:06 GMT 2023
PRIMARY
SMS_ID
100000081763
Created by admin on Fri Dec 15 15:30:06 GMT 2023 , Edited by admin on Fri Dec 15 15:30:06 GMT 2023
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PUBCHEM
65894
Created by admin on Fri Dec 15 15:30:06 GMT 2023 , Edited by admin on Fri Dec 15 15:30:06 GMT 2023
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FDA UNII
F52Y83BGH3
Created by admin on Fri Dec 15 15:30:06 GMT 2023 , Edited by admin on Fri Dec 15 15:30:06 GMT 2023
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EVMPD
SUB07512MIG
Created by admin on Fri Dec 15 15:30:06 GMT 2023 , Edited by admin on Fri Dec 15 15:30:06 GMT 2023
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MERCK INDEX
m5246
Created by admin on Fri Dec 15 15:30:06 GMT 2023 , Edited by admin on Fri Dec 15 15:30:06 GMT 2023
PRIMARY Merck Index
MESH
C107057
Created by admin on Fri Dec 15 15:30:06 GMT 2023 , Edited by admin on Fri Dec 15 15:30:06 GMT 2023
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ChEMBL
CHEMBL556262
Created by admin on Fri Dec 15 15:30:06 GMT 2023 , Edited by admin on Fri Dec 15 15:30:06 GMT 2023
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NCI_THESAURUS
C72776
Created by admin on Fri Dec 15 15:30:06 GMT 2023 , Edited by admin on Fri Dec 15 15:30:06 GMT 2023
PRIMARY
EPA CompTox
DTXSID0046430
Created by admin on Fri Dec 15 15:30:06 GMT 2023 , Edited by admin on Fri Dec 15 15:30:06 GMT 2023
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DRUG BANK
DB12190
Created by admin on Fri Dec 15 15:30:06 GMT 2023 , Edited by admin on Fri Dec 15 15:30:06 GMT 2023
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CHEBI
51257
Created by admin on Fri Dec 15 15:30:06 GMT 2023 , Edited by admin on Fri Dec 15 15:30:06 GMT 2023
PRIMARY
INN
7086
Created by admin on Fri Dec 15 15:30:06 GMT 2023 , Edited by admin on Fri Dec 15 15:30:06 GMT 2023
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WIKIPEDIA
FAROPENEM
Created by admin on Fri Dec 15 15:30:06 GMT 2023 , Edited by admin on Fri Dec 15 15:30:06 GMT 2023
PRIMARY
CAS
106560-14-9
Created by admin on Fri Dec 15 15:30:06 GMT 2023 , Edited by admin on Fri Dec 15 15:30:06 GMT 2023
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