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Revision as of 20:38, 10 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'DrugBank').← Previous edit Latest revision as of 15:05, 13 March 2023 edit undoAnomieBOT (talk | contribs)Bots6,570,843 editsm Dating maintenance tags: {{Cn}} 
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{{Short description|Chemical compound}}
{{Drugbox {{Drugbox
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 443508168 | verifiedrevid = 460022704
| IUPAC_name = | IUPAC_name =
| image = Cefapirin.svg | image = Cefapirin.svg

<!--Clinical data--> <!--Clinical data-->
| tradename = | tradename =
| Drugs.com = {{drugs.com|international|cefapirin}} | Drugs.com = {{drugs.com|international|cefapirin}}
| MedlinePlus = a601206 | MedlinePlus = a601206
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = B | pregnancy_US = B
| pregnancy_category = | pregnancy_category =
| legal_AU = <!-- Unscheduled / S2 / S4 / S8 --> | legal_AU = <!-- Unscheduled / S2 / S4 / S8 -->
| legal_UK = <!-- GSL / P / POM / CD --> | legal_UK = <!-- GSL / P / POM / CD -->
| legal_US = Rx-only | legal_US = Rx-only
| legal_status = | legal_status =
| routes_of_administration = ], ] | routes_of_administration = ], ]

<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
| bioavailability = | bioavailability =
| protein_bound = | protein_bound =
| metabolism = | metabolism =
| elimination_half-life = | elimination_half-life =
| excretion = | excretion =

<!--Identifiers--> <!--Identifiers-->
| CASNo_Ref = {{cascite|correct|CAS}} | CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 21593-23-7 | CAS_number = 21593-23-7
| ATC_prefix = J01 | ATC_prefix = J01
| ATC_suffix = DB08 | ATC_suffix = DB08
| ATC_supplemental = {{ATCvet|J51|DA30}} | ATC_supplemental = {{ATCvet|G51|AA05}} {{ATCvet|J51|DB08}}
| PubChem = 30699 | PubChem = 30699
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
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| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1599 | ChEMBL = 1599

<!--Chemical data--> <!--Chemical data-->
| C=17 | H=17 | N=3 | O=6 | S=2 | C=17 | H=17 | N=3 | O=6 | S=2
| molecular_weight = 423.466 g/mol
| smiles = O=C2N1/C(=C(\CS12NC(=O)CSc3ccncc3)COC(=O)C)C(=O)O | smiles = O=C2N1/C(=C(\CS12NC(=O)CSc3ccncc3)COC(=O)C)C(=O)O
| InChI = 1/C17H17N3O6S2/c1-9(21)26-6-10-7-28-16-13(15(23)20(16)14(10)17(24)25)19-12(22)8-27-11-2-4-18-5-3-11/h2-5,13,16H,6-8H2,1H3,(H,19,22)(H,24,25)/t13-,16-/m1/s1
| InChIKey = UQLLWWBDSUHNEB-CZUORRHYBF
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C17H17N3O6S2/c1-9(21)26-6-10-7-28-16-13(15(23)20(16)14(10)17(24)25)19-12(22)8-27-11-2-4-18-5-3-11/h2-5,13,16H,6-8H2,1H3,(H,19,22)(H,24,25)/t13-,16-/m1/s1 | StdInChI = 1S/C17H17N3O6S2/c1-9(21)26-6-10-7-28-16-13(15(23)20(16)14(10)17(24)25)19-12(22)8-27-11-2-4-18-5-3-11/h2-5,13,16H,6-8H2,1H3,(H,19,22)(H,24,25)/t13-,16-/m1/s1
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| StdInChIKey = UQLLWWBDSUHNEB-CZUORRHYSA-N | StdInChIKey = UQLLWWBDSUHNEB-CZUORRHYSA-N
}} }}
'''Cefapirin''' (], also spelled '''cephapirin''') is an injectable, first-generation ] ]. It is marketed under the trade name '''Cefadyl'''. Production for use in humans has been discontinued in the United States.<ref>http://www.accessdata.fda.gov/scripts/cder/drugsatfda/index.cfm?fuseaction=Search.Overview&DrugName=CEFADYL</ref> '''Cefapirin''' (], also spelled '''cephapirin''') is an injectable, first-generation ] ]. It is marketed under the trade name Cefadyl. Production for use in humans has been discontinued in the United States.<ref>{{cite web | title = CEFADYL | url = http://www.accessdata.fda.gov/scripts/cder/drugsatfda/index.cfm?fuseaction=Search.Overview&DrugName=CEFADYL | publisher = U.S. Food and Drug Administration }}</ref>


It also has a role in ] as '''Metricure''', an intrauterine preparation and combined with ] in '''Mastiplan''', an intramammary preparation. Both are licenced in ]. It also has a role in ] as Metricure, an intrauterine preparation, and combined with ] in Mastiplan, an intramammary preparation. Both are licensed in ].{{cn|date=March 2023}}


==References== ==Synthesis==
]
In one of the syntheses, ] (]) is reacted with bromoacetyl chloride to give the amide. The halo group is then displaced by 4-thiopyridine.<ref name=Crast/>

== References ==
{{reflist}} {{reflist}}


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{{antibiotic-stub}} {{antibiotic-stub}}

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