Faropenem

Faropenem
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Oral
ATC code
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC12H15NO5S
Molar mass285.31 g·mol−1
3D model (JSmol)
SMILES
  • O=C2N1/C(=C(\S[C@@H]1[C@H]2[C@H](O)C)[C@@H]3OCCC3)C(=O)O
InChI
  • 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 checkY
  • Key:HGGAKXAHAYOLDJ-FHZUQPTBSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Faropenem is an orally active beta-lactam antibiotic belonging to the penem group.[1] It is resistant to some forms of extended-spectrum beta-lactamase.[2] It is available for oral use.[3]

Forms

Faropenem was developed by Daiichi Asubio Pharma, which markets it in two forms.

  • The sodium salt faropenem sodium, available under the trade name Farom, has been marketed in Japan since 1997. (CID 636379 from PubChem)
  • The prodrug form faropenem medoxomil[4] (also known as faropenem daloxate) has been licensed from Daiichi Asubio Pharma by Replidyne, which plans to market it in conjunction with Forest Pharmaceuticals. The trade name proposed for the product was Orapem, but company officials recently announced this name was rejected by the FDA.[5]


Clinical use

As of 8 September 2015, Faropenem has yet to receive marketing approval in the United States, and was submitted for consideration by the United States Food and Drug Administration (FDA) on 20 December 2005. The new drug application dossier submitted included these proposed indications:

  • acute bacterial sinusitis
  • community-acquired pneumonia
  • acute exacerbations of chronic bronchitis
  • uncomplicated skin and skin structure infections
  • urinary tract infections

History

The FDA refused to approve faropenem, an antibiotic manufactured by Louisville-based Replidyne. The FDA said the drug was “nonapprovable”, but did not refer to specific safety concerns about the product. The company will have to conduct new studies and clinical trials, lasting an estimated two more years, to prove the drug treats community-acquired pneumonia, bacterial sinusitis, chronic bronchitis, and skin infections.

In India it is available as Farobact 200/300ER CIPLA.

References

  1. ↑ Critchley IA, Brown SD, Traczewski MM, Tillotson GS, Janjic N (December 2007). "National and regional assessment of antimicrobial resistance among community-acquired respiratory tract pathogens identified in a 2005-2006 U.S. Faropenem surveillance study". Antimicrob. Agents Chemother. 51 (12): 4382–9. doi:10.1128/AAC.00971-07. PMC 2168020. PMID 17908940.
  2. ↑ Mushtaq S, Hope R, Warner M, Livermore DM (May 2007). "Activity of faropenem against cephalosporin-resistant Enterobacteriaceae". J. Antimicrob. Chemother. 59 (5): 1025–30. doi:10.1093/jac/dkm063. PMID 17353220.
  3. ↑ Milazzo I, Blandino G, Caccamo F, Musumeci R, Nicoletti G, Speciale A (March 2003). "Faropenem, a new oral penem: antibacterial activity against selected anaerobic and fastidious periodontal isolates". J. Antimicrob. Chemother. 51 (3): 721–5. doi:10.1093/jac/dkg120. PMID 12615878.
  4. ↑ Gettig JP, Crank CW, Philbrick AH (January 2008). "Faropenem medoxomil". Ann Pharmacother. 42 (1): 80–90. doi:10.1345/aph.1G232. PMID 18094341. Archived from the original on 2013-02-03.
  5. ↑ (Q1 06 Investor Conf Call)(CID 6918218 from PubChem)
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