cefalotin

{{short description|Chemical compound}}

{{cs1 config|name-list-style=vanc|display-authors=6}}

{{Drugbox

| verifiedrevid = 460022605

| IUPAC_name = (6R,7R)-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

| bioavailability = n/a

| protein_bound = 65 to 80%

| metabolism = Hepatic

| elimination_half-life = 30 minutes to 1 hour

| excretion = Renal

| 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

| 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.{{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 }}{{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 }} It was the first cephalosporin marketed (1964) and continues to be widely used.{{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–}} 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.

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.{{drugs.com|international|cefalotin}}: Cefalotin

The compound is a derivative of thiophene-2-acetic acid.{{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 }}.