| Revision as of 13:57, 23 October 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{drugbox}} (changes to verified and watched fields - updated 'KEGG_Ref', 'CAS_number_Ref') per Chem/Drugbox validation (report errors or bugs)← Previous edit | Latest revision as of 06:38, 3 January 2024 edit undoMaxim Masiutin (talk | contribs)Extended confirmed users, IP block exemptions, Pending changes reviewers31,058 edits Add: s2cid. Added the cs1 style template to denot "vanc" because references contain "vauthors". | ||
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| {{Short description|Chemical compound}} | |||
| {{Drugbox | |||
| {{cs1 config|name-list-style=vanc}}{{Drugbox | |||
| | Verifiedfields = changed | | Verifiedfields = changed | ||
| | Watchedfields = changed | | Watchedfields = changed | ||
| | verifiedrevid = |
| verifiedrevid = 461099067 | ||
| | IUPAC_name = | | IUPAC_name = | ||
| | image = Faropenem.svg | | image = Faropenem.svg | ||
| Line 22: | Line 23: | ||
| | bioavailability = | | bioavailability = | ||
| | protein_bound = | | protein_bound = | ||
| | metabolism = |
| metabolism = | ||
| ⚫ | | excretion = | ||
| | elimination_half-life = | |||
| ⚫ | | excretion = |
||
| <!--Identifiers--> | <!--Identifiers--> | ||
| | CAS_number_Ref = {{cascite| |
| CAS_number_Ref = {{cascite|changed|??}} | ||
| | CAS_number = 106560-14-9 | | CAS_number = 106560-14-9 | ||
| | ATC_prefix = |
| ATC_prefix = J01 | ||
| | ATC_suffix = |
| ATC_suffix = DI03 | ||
| | PubChem = 65894 | | PubChem = 65894 | ||
| | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | ||
| Line 36: | Line 36: | ||
| | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ||
| | ChemSpiderID = 59303 | | ChemSpiderID = 59303 | ||
| | UNII_Ref = {{fdacite| |
| UNII_Ref = {{fdacite|correct|FDA}} | ||
| | UNII = F52Y83BGH3 | | UNII = F52Y83BGH3 | ||
| | ChEBI_Ref = {{ebicite| |
| ChEBI_Ref = {{ebicite|correct|EBI}} | ||
| | ChEBI = 51257 | | ChEBI = 51257 | ||
| | ChEMBL_Ref = {{ebicite| |
| ChEMBL_Ref = {{ebicite|correct|EBI}} | ||
| | ChEMBL = 556262 | | ChEMBL = 556262 | ||
| <!--Chemical data--> | <!--Chemical data--> | ||
| | C=12 | H=15 | N=1 | O=5 | S=1 | | C=12 | H=15 | N=1 | O=5 | S=1 | ||
| | molecular_weight = 285.317 g/mol | |||
| | smiles = O=C2N1/C(=C(\S12(O)C)3OCCC3)C(=O)O | | smiles = O=C2N1/C(=C(\S12(O)C)3OCCC3)C(=O)O | ||
| | InChI = 1/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 | |||
| | InChIKey = HGGAKXAHAYOLDJ-FHZUQPTBBM | |||
| | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | ||
| | StdInChI = 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 | | StdInChI = 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 | ||
| Line 54: | Line 51: | ||
| | StdInChIKey = HGGAKXAHAYOLDJ-FHZUQPTBSA-N | | StdInChIKey = HGGAKXAHAYOLDJ-FHZUQPTBSA-N | ||
| }} | }} | ||
| '''Faropenem''' is an orally |
'''Faropenem''' is an orally active ] belonging to the ] group.<ref name="pmid17908940">{{cite journal |vauthors=Critchley IA, Brown SD, Traczewski MM, Tillotson GS, Janjic N |title=National and regional assessment of antimicrobial resistance among community-acquired respiratory tract pathogens identified in a 2005-2006 U.S. Faropenem surveillance study |journal=Antimicrob. Agents Chemother. |volume=51 |issue=12 |pages=4382–9 |date=December 2007 |pmid=17908940 |pmc=2168020 |doi=10.1128/AAC.00971-07 |url=}}</ref> It is resistant to some forms of extended-spectrum ].<ref name="pmid17353220">{{cite journal |vauthors=Mushtaq S, Hope R, Warner M, Livermore DM |title=Activity of faropenem against cephalosporin-resistant Enterobacteriaceae |journal=J. Antimicrob. Chemother. |volume=59 |issue=5 |pages=1025–30 |date=May 2007 |pmid=17353220 |doi=10.1093/jac/dkm063 |doi-access=free }}</ref> It is available for oral use.<ref name="pmid12615878">{{cite journal |vauthors=Milazzo I, Blandino G, Caccamo F, Musumeci R, Nicoletti G, Speciale A |title=Faropenem, a new oral penem: antibacterial activity against selected anaerobic and fastidious periodontal isolates |journal=J. Antimicrob. Chemother. |volume=51 |issue=3 |pages=721–5 |date=March 2003 |pmid=12615878 |doi= 10.1093/jac/dkg120|doi-access=free }}</ref> | ||
| It is resistant to some forms of extended-spectrum ].<ref name="pmid17353220">{{cite journal |author=Mushtaq S, Hope R, Warner M, Livermore DM |title=Activity of faropenem against cephalosporin-resistant Enterobacteriaceae |journal=J. Antimicrob. Chemother. |volume=59 |issue=5 |pages=1025–30 |year=2007 |month=May |pmid=17353220 |doi=10.1093/jac/dkm063 |url=http://jac.oxfordjournals.org/cgi/pmidlookup?view=long&pmid=17353220}}</ref> | |||
| It is orally available.<ref name="pmid12615878">{{cite journal |author=Milazzo I, Blandino G, Caccamo F, Musumeci R, Nicoletti G, Speciale A |title=Faropenem, a new oral penem: antibacterial activity against selected anaerobic and fastidious periodontal isolates |journal=J. Antimicrob. Chemother. |volume=51 |issue=3 |pages=721–5 |year=2003 |month=March |pmid=12615878 |doi= 10.1093/jac/dkg120|url=http://jac.oxfordjournals.org/cgi/pmidlookup?view=long&pmid=12615878}}</ref> | |||
| ==Forms== | ==Forms== | ||
| Faropenem was developed by ], which markets it in two forms. | Faropenem was developed by ], which markets it in two forms. | ||
| * The sodium salt '''faropenem sodium''', available under the trade name '''Farom''', has been marketed in Japan since |
* The sodium salt '''faropenem sodium''', available under the trade name '''Farom''', has been marketed in Japan since 1997. ({{PubChem|636379}}) | ||
| ⚫ | * The prodrug form '''faropenem medoxomil'''<ref name="pmid18094341">{{cite journal |vauthors=Gettig JP, Crank CW, Philbrick AH |title=Faropenem medoxomil |journal=Ann Pharmacother |volume=42 |issue=1 |pages=80–90 |date=January 2008 |pmid=18094341 |doi=10.1345/aph.1G232 |s2cid=28859560 |url=http://www.theannals.com/cgi/pmidlookup?view=long&pmid=18094341 |archive-url=https://archive.today/20130203200812/http://www.theannals.com/cgi/pmidlookup?view=long&pmid=18094341 |url-status=dead |archive-date=2013-02-03 }}</ref> (also known as '''faropenem daloxate''') has been licensed from Daiichi Asubio Pharma by ], 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.<ref>(Q1 06 Investor Conf Call)({{PubChem|6918218}})</ref> | ||
| ⚫ | * The prodrug form '''faropenem medoxomil'''<ref name="pmid18094341">{{cite journal | |
||
| The company also stated their hope to have the product available for commercial sale months before the 2007 influenza season.{{Fact|date=December 2008}} | <!-- out of date The company also stated their hope to have the product available for commercial sale months before the 2007 influenza season.{{Fact|date=December 2008}} --> | ||
| ==Clinical use== | ==Clinical use== | ||
| Faropenem has yet to receive marketing approval in the United States, and was submitted for consideration by the United States ] (FDA) on 20 December 2005. The new drug application |
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 ] (FDA) on 20 December 2005. The new drug application dossier submitted included these proposed indications:{{cn|date=March 2023}} | ||
| * acute bacterial sinusitis | * acute bacterial sinusitis | ||
| * community |
* community-acquired pneumonia | ||
| * acute exacerbations of chronic bronchitis | * acute exacerbations of chronic bronchitis | ||
| * uncomplicated skin and skin structure infections |
* uncomplicated skin and skin structure infections | ||
| * urinary tract infections | |||
| ==History== | ==History== | ||
| FDA rejects Replidyne’s faropenem | <!-- FDA rejects Replidyne’s faropenem | ||
| Louisville firm drug rejected; considered “nonapprovable’ | Louisville firm drug rejected; considered “nonapprovable’ | ||
| 10/24/06 | 10/24/06 --> | ||
| The |
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.{{Citation needed|date=June 2015}} | ||
| In India it is available as Farokaa 200/300 ER and marketed by Troikaa Pharmaceuticals Ltd. | |||
| 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. | |||
| ==References== | ==References== | ||
| Line 87: | Line 80: | ||
| ==External links== | ==External links== | ||
| * | * | ||
| * | |||
| {{CephalosporinAntiBiotics}} | {{CephalosporinAntiBiotics}} | ||
Latest revision as of 06:38, 3 January 2024
Chemical compound Pharmaceutical compound | |
| Clinical data | |
|---|---|
| AHFS/Drugs.com | International Drug Names |
| Routes of administration | Oral |
| ATC code | |
| Identifiers | |
| CAS Number | |
| PubChem CID | |
| ChemSpider | |
| UNII | |
| ChEBI | |
| ChEMBL | |
| CompTox Dashboard (EPA) | |
| Chemical and physical data | |
| Formula | C12H15NO5S |
| Molar mass | 285.31 g·mol |
| 3D model (JSmol) | |
SMILES
| |
InChI
| |
| (what is this?) (verify) | |
Faropenem is an orally active beta-lactam antibiotic belonging to the penem group. It is resistant to some forms of extended-spectrum beta-lactamase. It is available for oral use.
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 (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.
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 Farokaa 200/300 ER and marketed by Troikaa Pharmaceuticals Ltd.
References
- 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.
- 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.
- 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.
- Gettig JP, Crank CW, Philbrick AH (January 2008). "Faropenem medoxomil". Ann Pharmacother. 42 (1): 80–90. doi:10.1345/aph.1G232. PMID 18094341. S2CID 28859560. Archived from the original on 2013-02-03.
- (Q1 06 Investor Conf Call)(CID 6918218 from PubChem)