| Revision as of 12:07, 17 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 456981376 of page Faropenem for the Chem/Drugbox validation project (updated: 'CAS_number'). |
Latest revision as of 06:38, 3 January 2024 edit Maxim Masiutin (talk | contribs)Extended confirmed users, IP block exemptions, Pending changes reviewers30,619 edits Add: s2cid. Added the cs1 style template to denot "vanc" because references contain "vauthors". |
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{{Short description|Chemical compound}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Drugbox |
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{{cs1 config|name-list-style=vanc}}{{Drugbox |
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| Verifiedfields = changed |
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| Verifiedfields = changed |
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| Watchedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 399927936 |
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| verifiedrevid = 461099067 |
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| IUPAC_name = |
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| IUPAC_name = |
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| image = Faropenem.svg |
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| image = Faropenem.svg |
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| bioavailability = |
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| bioavailability = |
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| protein_bound = |
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| protein_bound = |
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| metabolism = |
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| metabolism = |
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⚫ |
| excretion = |
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| elimination_half-life = |
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| ⚫ |
| excretion = |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number_Ref = {{cascite|changed|??}} |
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| CAS_number = <!-- blanked - oldvalue: 106560-14-9 --> |
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| CAS_number = 106560-14-9 |
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| ATC_prefix = none |
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| ATC_prefix = J01 |
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| ATC_suffix = |
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| ATC_suffix = DI03 |
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| PubChem = 65894 |
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| PubChem = 65894 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 59303 |
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| ChemSpiderID = 59303 |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = F52Y83BGH3 |
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| UNII = F52Y83BGH3 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 51257 |
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| ChEBI = 51257 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 556262 |
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| ChEMBL = 556262 |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=12 | H=15 | N=1 | O=5 | S=1 |
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| C=12 | H=15 | N=1 | O=5 | S=1 |
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| molecular_weight = 285.317 g/mol |
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| smiles = O=C2N1/C(=C(\S12(O)C)3OCCC3)C(=O)O |
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| smiles = O=C2N1/C(=C(\S12(O)C)3OCCC3)C(=O)O |
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| 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 |
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| InChIKey = HGGAKXAHAYOLDJ-FHZUQPTBBM |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| 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 |
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| 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 |
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| StdInChIKey = HGGAKXAHAYOLDJ-FHZUQPTBSA-N |
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| StdInChIKey = HGGAKXAHAYOLDJ-FHZUQPTBSA-N |
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}} |
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}} |
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'''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> |
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==Forms== |
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Faropenem was developed by ], which markets it in two forms. |
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* The sodium salt '''faropenem sodium''', available under the trade name '''Farom''', has been marketed in Japan since 1997. ({{PubChem|636379}}) |
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* 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> |
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<!-- 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}} --> |
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==Clinical use== |
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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}} |
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* acute bacterial sinusitis |
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* community-acquired pneumonia |
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* acute exacerbations of chronic bronchitis |
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* uncomplicated skin and skin structure infections |
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* urinary tract infections |
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==History== |
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<!-- FDA rejects Replidyne’s faropenem |
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Louisville firm drug rejected; considered “nonapprovable’ |
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10/24/06 --> |
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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}} |
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In India it is available as Farokaa 200/300 ER and marketed by Troikaa Pharmaceuticals Ltd. |
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==References== |
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{{reflist}} |
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==External links== |
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* |
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{{CephalosporinAntiBiotics}} |
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] |
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] |