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

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
[New orally active penem antibiotic: Farom].
2001 Dec
Profound skin infection with bone involvement due to Nocardia asteroides in a patient with myelodysplastic syndrome.
2001 Oct
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
Successful treatment with faropenem and clarithromycin of pulmonary Mycobacterium abscessus infection.
2002 Sep
Activity of faropenem, a new furanem, against European respiratory pathogens collected during 2000-2001: a comparison with other beta-lactam agents.
2003 Jan
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
Faropenem, a new oral penem: antibacterial activity against selected anaerobic and fastidious periodontal isolates.
2003 Mar
Comparative in vitro activity of faropenem and 11 other antimicrobial agents against 250 invasive Streptococcus pneumoniae isolates from France.
2003 Sep
Activity of faropenem and imipenem for ciprofloxacin-resistant bacteria.
2003 Sep
The influence of protein binding on the antibacterial activity of faropenem against Haemophilus influenzae.
2004 Oct
In vitro investigation of the indirect pathogenicity of beta-lactamase-producing microorganisms in the nasopharyngeal microflora.
2005 Apr
Activity of faropenem tested against Neisseria gonorrhoeae isolates including fluoroquinolone-resistant strains.
2005 Dec
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
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
[Relationship between protein binding and antimicrobial activities of antibiotics against Streptococcus pneumoniae and Haemophilus influenzae].
2006 Oct
Faropenem: review of a new oral penem.
2007 Apr
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
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
Streptococcus pneumoniae serotype 3 among Costa Rican children with otitis media: clinical, epidemiological characteristics and antimicrobial resistance patterns.
2009 Aug 14
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
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
Quinolone and cephalosporin resistance in enteric Fever.
2010 Sep
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 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 GMT 2023 , Edited by admin on Fri Dec 15 19:12:48 GMT 2023
PRIMARY
MESH
C060114
Created by admin on Fri Dec 15 19:12:48 GMT 2023 , Edited by admin on Fri Dec 15 19:12:48 GMT 2023
PRIMARY
EPA CompTox
DTXSID60924197
Created by admin on Fri Dec 15 19:12:48 GMT 2023 , Edited by admin on Fri Dec 15 19:12:48 GMT 2023
PRIMARY
MERCK INDEX
m5246
Created by admin on Fri Dec 15 19:12:48 GMT 2023 , Edited by admin on Fri Dec 15 19:12:48 GMT 2023
PRIMARY Merck Index
EVMPD
SUB16432MIG
Created by admin on Fri Dec 15 19:12:48 GMT 2023 , Edited by admin on Fri Dec 15 19:12:48 GMT 2023
PRIMARY
CAS
122547-49-3
Created by admin on Fri Dec 15 19:12:48 GMT 2023 , Edited by admin on Fri Dec 15 19:12:48 GMT 2023
PRIMARY
SMS_ID
100000091345
Created by admin on Fri Dec 15 19:12:48 GMT 2023 , Edited by admin on Fri Dec 15 19:12:48 GMT 2023
PRIMARY
PUBCHEM
23663972
Created by admin on Fri Dec 15 19:12:48 GMT 2023 , Edited by admin on Fri Dec 15 19:12:48 GMT 2023
PRIMARY
DRUG BANK
DBSALT002150
Created by admin on Fri Dec 15 19:12:48 GMT 2023 , Edited by admin on Fri Dec 15 19:12:48 GMT 2023
PRIMARY