FAROPENEM SODIUM

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 Search

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
Sources: http://www.rad-ar.or.jp/siori/english/kekka.cgi?n=37321
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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial penicillin-binding protein 233 Target ID: CHEMBL2354204 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12886052	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Chronic bronchitis 51 Sources: http://www.rad-ar.or.jp/siori/english/kekka.cgi?n=37321	Curative	Approved 8429	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).
Community-acquired pneumonia 47 Sources: http://www.rad-ar.or.jp/siori/english/kekka.cgi?n=37321 https://www.ncbi.nlm.nih.gov/pubmed/18298129	Curative	Approved 8429	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).
Acute bacterial sinusitis 26 Sources: http://www.rad-ar.or.jp/siori/english/kekka.cgi?n=37321 https://www.ncbi.nlm.nih.gov/pubmed/18298129	Curative	Approved 8429	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).
Skin infections 59 Sources: http://www.rad-ar.or.jp/siori/english/kekka.cgi?n=37321	Curative	Approved 8429	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

Title	Date	PubMed
[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	12638154
Profound skin infection with bone involvement due to Nocardia asteroides in a patient with myelodysplastic syndrome.	2001 Oct	11732732
[Pyogenic sacroiliitis in pregnancy].	2001 Sep	11729713
In vitro activity of faropenem against 5460 clinical bacterial isolates from Europe.	2002 Aug	12161416
Comparative in vitro activity of faropenem against staphylococci.	2002 Aug	12161412
[Triple therapy with faropenem, proton pump inhibitor (PPI), and amoxicillin for clarithromycin-resistant H. pylori eradication].	2002 Feb	11979826
In vitro activity of faropenem against respiratory pathogens.	2002 Mar	11864964
[Faropenem 300 mg 3 times daily versus levofloxacin 100 mg 3 times daily in the treatment of urinary tract infections in patients with neurogenic bladder and/or benign prostatic hypertrophy].	2002 Nov	12508476
Effect of protein binding on the in vitro activity and pharmacodynamics of faropenem.	2002 Oct	12356797
Antimicrobial susceptibility of major pathogens of orofacial odontogenic infections to 11 beta-lactam antibiotics.	2002 Oct	12354209
Successful treatment with faropenem and clarithromycin of pulmonary Mycobacterium abscessus infection.	2002 Sep	12373490
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	12205068
Comparison of the efficacy and safety of faropenem daloxate and cefuroxime axetil for the treatment of acute bacterial maxillary sinusitis in adults.	2003 Apr	12709801
Resistance to beta-lactams--the permutations.	2003 Dec	14998075
Activity of faropenem, a new furanem, against European respiratory pathogens collected during 2000-2001: a comparison with other beta-lactam agents.	2003 Jan	12493818
Target affinities of faropenem to and its impact on the morphology of gram-positive and gram-negative bacteria.	2003 Jul	12886052
The art of fusion: from penams and cephems to penems.	2003 Jun	12815203
The in vitro effects of faropenem on lower respiratory tract pathogens isolated in the United Kingdom.	2003 Jun	12791474
In vitro activity of faropenem compared with eight agents against fourteen Gram-positive and Gram-negative bacteria by time-kill.	2003 Jun	12746376
Faropenem, a new oral penem: antibacterial activity against selected anaerobic and fastidious periodontal isolates.	2003 Mar	12615878
Beta-lactamase stability of faropenem.	2003 Sep	14504433
In vitro studies on the impact of human serum on the antibacterial effect of faropenem.	2004 Feb	15077995
The glycopeptide vancomycin does not enhance toll-like receptor 2 (TLR2) activation by Streptococcus pneumoniae.	2004 Jul	15190028
Bacterial resistance to antimicrobials in urinary isolates.	2004 Sep	15364302
In vitro investigation of the indirect pathogenicity of beta-lactamase-producing microorganisms in the nasopharyngeal microflora.	2005 Apr	15763284
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	16258826
Faropenem: review of a new oral penem.	2007 Apr	17402834
Efficacy and safety of faropenem in eradication therapy of Helicobacter pylori.	2007 Dec	18001403
In vitro activities of faropenem, ertapenem, imipenem and meropenem against Borrelia burgdorferi s.l.	2007 Jul	17512703
[Efficacy and safety of faropenem in pediatric patients with bacterial infectious diseases].	2008 Dec	19288854
Multidrug-resistant Gram-negative bacterial infections: the emerging threat and potential novel treatment options.	2008 Feb	18246520
Determination of faropenem in human plasma and urine by liquid chromatography-tandem mass spectrometry.	2008 Jan	17604362
Emerging therapies for the treatment of Helicobacter pylori infections.	2008 Nov	18845620
The determinants of the antibiotic resistance process.	2009	21694883
A case of multidrug-resistant Salmonella enterica serovar Typhi treated with a bench to bedside approach.	2009 Feb 28	19259362
Quinolone and cephalosporin resistance in enteric Fever.	2010 Sep	20927288
In vitro and in vivo efficacy of β-lactams against replicating and slowly growing/nonreplicating Mycobacterium tuberculosis.	2013 Jun	23507276

Patents

Sample Use Guides

In Vivo Use Guide

150 - 300 mg three times a day

Route of Administration: Oral

In Vitro Use Guide

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 GMT 2023` Edited by `admin` on `Fri Dec 15 19:12:48 GMT 2023`
Record UNII	7O46G914RQ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FAROPENEM SODIUM

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

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