Cefalotin: Difference between revisions

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{{Drugbox

| verifiedrevid = ~~443507991~~

| verifiedrevid = 460022605

| 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

| image = Cefalotin.svg

| width = 300

| tradename =

| Drugs.com = {{drugs.com|international|cefalotin}}

| MedlinePlus = a682860

| pregnancy_US = B

| pregnancy_AU = A

| legal_AU = S4

| legal_UK = POM

| routes_of_administration = [[Intravenous therapy|IV]]

| routes_of_administration = [[Intravenous therapy|Intravenous]]

| bioavailability = n/a

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| elimination_half-life = 30 minutes to 1 hour

| excretion = [[Kidney|Renal]]

| ~~CASNo_Ref~~ = {{cascite|correct|~~CAS~~}}

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 153-61-7

| ATC_prefix = J01

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| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 617

| C=16 | H=16 | N=2 | O=6 | S=2

| molecular_weight = 396.44 g/mol

| smiles = O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)Cc3sccc3)COC(=O)C)C(=O)O

| 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

| InChIKey = XIURVHNZVLADCM-IUODEOHRBQ

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = XIURVHNZVLADCM-IUODEOHRSA-N

| melting_point = 160

| melting_high = 160.5

}}

'''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]]).

'''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" />

==See also==

*[[Cephalosporin]]

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>

*[[Cefalexin]]

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>

== References ==

[[Category:Cephalosporin antibiotics]]

[[Category:Eli Lilly and Company]]

[[Category:Drugs developed by Eli Lilly and Company]]

[[Category:~~Thiazoles~~]]

[[Category:Thiophenes]]

[[Category:Acetate esters]]

[[es:Cefalotina]]

[[fr:Céfalotine]]

[[it:Cefalotina]]

[[pt:Cefalotina]]

[[th:เซฟาโลติน]]