{{short description|Chemical compound}} {{cs1 config|name-list-style=vanc|display-authors=6}} {{Drugbox | 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 | image_class = skin-invert-image | width = 300 <!--Clinical data--> | 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 <!--Pharmacokinetic data--> | bioavailability = n/a | protein_bound = 65 to 80% | metabolism = Hepatic | elimination_half-life = 30 minutes to 1 hour | excretion = Renal <!--Identifiers--> | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 153-61-7 | ATC_prefix = J01 | ATC_suffix = DB03 | PubChem = 6024 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB00456 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 5802 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = R72LW146E6 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = D07635 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 124991 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 617 <!--Chemical data--> | C=16 | H=16 | N=2 | O=6 | S=2 | smiles = O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)Cc3sccc3)COC(=O)C)C(=O)O | 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''' (INN) {{IPAc-en|ˌ|s|ɛ|f|ə|ˈ|l|oʊ|t|ᵻ|n}} or '''cephalothin''' (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="Vardanyan_2006">{{cite book |doi=10.1016/B978-044452166-8/50032-7 |chapter=Antibiotics |title=Synthesis of Essential Drugs |date=2006 | vauthors = Vardanyan R, Hruby V |pages=425–498 |isbn=978-0-444-52166-8 }}</ref> It was the first cephalosporin marketed (1964) and continues to be widely used.<ref name="Greenwood2008">{{cite book| vauthors = Greenwood D |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="Vardanyan_2006" />
It is an intravenously administered agent with a similar antimicrobial spectrum to cefazolin and the oral agents cefalexin and cefadroxil. '''Cefalotin sodium''' is marketed as '''Keflin''' (Lilly) and under other trade names.<ref>{{drugs.com|international|cefalotin}}: Cefalotin</ref>
The compound is a derivative of thiophene-2-acetic acid.<ref name="Ullmann">{{cite book| vauthors = Swanston J |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 == {{reflist}}
{{CephalosporinAntiBiotics}}
Category:Cephalosporin antibiotics Category:Drugs developed by Eli Lilly and Company Category:Thiophenes Category:Acetate esters