Cefalotin: Difference between revisions
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Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'DrugBank'). |
Akhil 0950 (talk | contribs) Add cefadroxil as another commonly-used first-generation cephalosporin |
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{{short description|Chemical compound}} |
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{{Unreferenced stub|auto=yes|date=December 2009}} |
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{{Drugbox |
{{Drugbox |
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| verifiedrevid = |
| verifiedrevid = 460022605 |
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| IUPAC_name = (6''R'',7''R'')-3-[(acetoxy)methyl]-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid |
| IUPAC_name = (6''R'',7''R'')-3-[(acetoxy)methyl]-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid |
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| image = Cefalotin.svg |
| image = Cefalotin.svg |
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| width = 300 |
| width = 300 |
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<!--Clinical data--> |
<!--Clinical data--> |
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| tradename = |
| tradename = |
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| Drugs.com = {{drugs.com|international|cefalotin}} |
| Drugs.com = {{drugs.com|international|cefalotin}} |
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| MedlinePlus = a682860 |
| MedlinePlus = a682860 |
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| pregnancy_US = B |
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| pregnancy_AU = A |
| pregnancy_AU = A |
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| legal_AU = S4 |
| legal_AU = S4 |
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| legal_UK = POM |
| legal_UK = POM |
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| routes_of_administration = [[Intravenous therapy| |
| routes_of_administration = [[Intravenous therapy|Intravenous]] |
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<!--Pharmacokinetic data--> |
<!--Pharmacokinetic data--> |
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| bioavailability = n/a |
| bioavailability = n/a |
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| elimination_half-life = 30 minutes to 1 hour |
| elimination_half-life = 30 minutes to 1 hour |
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| excretion = [[Kidney|Renal]] |
| excretion = [[Kidney|Renal]] |
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<!--Identifiers--> |
<!--Identifiers--> |
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| |
| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 153-61-7 |
| CAS_number = 153-61-7 |
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| ATC_prefix = J01 |
| ATC_prefix = J01 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 617 |
| ChEMBL = 617 |
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<!--Chemical data--> |
<!--Chemical data--> |
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| C=16 | H=16 | N=2 | O=6 | S=2 |
| C=16 | H=16 | N=2 | O=6 | S=2 |
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| molecular_weight = 396.44 g/mol |
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| smiles = O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)Cc3sccc3)COC(=O)C)C(=O)O |
| smiles = O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)Cc3sccc3)COC(=O)C)C(=O)O |
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| InChI = 1/C16H16N2O6S2/c1-8(19)24-6-9-7-26-15-12(14(21)18(15)13(9)16(22)23)17-11(20)5-10-3-2-4-25-10/h2-4,12,15H,5-7H2,1H3,(H,17,20)(H,22,23)/t12-,15-/m1/s1 |
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| InChIKey = XIURVHNZVLADCM-IUODEOHRBQ |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C16H16N2O6S2/c1-8(19)24-6-9-7-26-15-12(14(21)18(15)13(9)16(22)23)17-11(20)5-10-3-2-4-25-10/h2-4,12,15H,5-7H2,1H3,(H,17,20)(H,22,23)/t12-,15-/m1/s1 |
| StdInChI = 1S/C16H16N2O6S2/c1-8(19)24-6-9-7-26-15-12(14(21)18(15)13(9)16(22)23)17-11(20)5-10-3-2-4-25-10/h2-4,12,15H,5-7H2,1H3,(H,17,20)(H,22,23)/t12-,15-/m1/s1 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = XIURVHNZVLADCM-IUODEOHRSA-N |
| StdInChIKey = XIURVHNZVLADCM-IUODEOHRSA-N |
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| melting_point = 160 |
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| melting_high = 160.5 |
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}} |
}} |
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'''Cefalotin''' ([[International Nonproprietary Name|INN]]) ({{IPAc-en|icon|ˌ|s|ɛ|f|ə|ˈ|l|oʊ|t|ɨ|n}}) or '''cephalothin''' ([[United States Adopted Name|USAN]]) ({{IPAc-en|icon|ˌ|s|ɛ|f|ə|ˈ|l|oʊ|θ|ɨ|n}}) is a first-generation [[cephalosporin]] [[antibiotic]]. It was the first cephalosporin marketed and continues to be widely used. It is an [[intravenous]]ly administered agent with a similar antimicrobial spectrum to [[cefazolin]] and the oral agent [[cefalexin]]. '''Cefalotin sodium''' is commonly marketed under the trade name '''Keflin''' ([[Eli Lilly and Company|Lilly]]). |
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'''Cefalotin''' ([[International Nonproprietary Name|INN]]) {{IPAc-en|ˌ|s|ɛ|f|ə|ˈ|l|oʊ|t|ᵻ|n}} or '''cephalothin''' ([[United States Adopted Name|USAN]]) {{IPAc-en|ˌ|s|ɛ|f|ə|ˈ|l|oʊ|θ|ᵻ|n}} is a first-generation [[cephalosporin]] [[antibiotic]] with broad spectrum antibiotic activity.<ref>{{cite journal | vauthors = Hameed TK, Robinson JL | title = Review of the use of cephalosporins in children with anaphylactic reactions from penicillins | journal = The Canadian Journal of Infectious Diseases | volume = 13 | issue = 4 | pages = 253–8 | date = July 2002 | pmid = 18159398 | pmc = 2094874 | doi = 10.1155/2002/712594 | doi-access = free }}</ref><ref name=":0">{{Cite web |title=Cefalotin - an overview {{!}} ScienceDirect Topics |url=https://www.sciencedirect.com/topics/biochemistry-genetics-and-molecular-biology/cefalotin |access-date=2024-01-26 |website=www.sciencedirect.com}}</ref> It was the first cephalosporin marketed (1964) and continues to be widely used.<ref name="Greenwood2008">{{cite book| first = David | last = Greenwood | name-list-style = vanc |title=Antimicrobial Drugs: Chronicle of a Twentieth Century Medical Triumph|url=https://books.google.com/books?id=i4_FZHmzjzwC&pg=PA128|date=21 February 2008|publisher=OUP Oxford|isbn=978-0-19-953484-5|pages=128–}}</ref> Cefalotin is used for bacterial infections of the respiratory tract, urinary tract, skin, soft tissues, bones and joints, sepsis, peritonitis, osteomyelitis, mastitis, infected wounds, and post-operational infections.<ref name=":0" /> |
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==See also== |
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*[[Cephalosporin]] |
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It is an [[intravenous]]ly administered agent with a similar antimicrobial spectrum to [[cefazolin]] and the oral agents [[cefalexin]] and [[cefadroxil]]. '''Cefalotin sodium''' is marketed as '''Keflin''' ([[Eli Lilly and Company|Lilly]]) and under other trade names.<ref>{{drugs.com|international|cefalotin}}: Cefalotin</ref> |
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*[[Cefalexin]] |
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The compound is a derivative of [[thiophene-2-acetic acid]].<ref name="Ullmann">{{cite book| first = Jonathan | last = Swanston |chapter = Thiophene | title = Ullmann's Encyclopedia of Industrial Chemistry | publisher = Wiley-VCH | location = Weinheim | date = 2006 | doi = 10.1002/14356007.a26_793.pub2| isbn = 3527306730 }}.</ref> |
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== References == |
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{{reflist}} |
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{{CephalosporinAntiBiotics}} |
{{CephalosporinAntiBiotics}} |
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[[Category:Cephalosporin antibiotics]] |
[[Category:Cephalosporin antibiotics]] |
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[[Category:Eli Lilly and Company]] |
[[Category:Drugs developed by Eli Lilly and Company]] |
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[[Category: |
[[Category:Thiophenes]] |
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[[Category:Acetate esters]] |
[[Category:Acetate esters]] |
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{{Antibiotic-stub}} |
{{Antibiotic-stub}} |
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[[es:Cefalotina]] |
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[[fr:Céfalotine]] |
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[[it:Cefalotina]] |
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[[pt:Cefalotina]] |
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[[th:เซฟาโลติน]] |