Cefalotin

Chemical compound

Pharmaceutical compound

Cefalotin
Clinical data

AHFS/Drugs.com	International Drug Names
MedlinePlus	a682860
Pregnancy category	AU: A
Routes of administration	Intravenous
ATC code	J01DB03 (WHO )
Legal status
Legal status	AU: S4 (Prescription only) UK: POM (Prescription only)
Pharmacokinetic data
Bioavailability	n/a
Protein binding	65 to 80%
Metabolism	Hepatic
Elimination half-life	30 minutes to 1 hour
Excretion	Renal
Identifiers
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
CAS Number	153-61-7 ^checkY
PubChem CID	6024
DrugBank	DB00456 ^checkY
ChemSpider	5802 ^checkY
UNII	R72LW146E6
KEGG	D07635 ^checkY
ChEBI	CHEBI:124991 ^checkY
ChEMBL	ChEMBL617 ^checkY
CompTox Dashboard (EPA)	DTXSID4022783 Edit this at Wikidata
ECHA InfoCard	100.005.288 Edit this at Wikidata
Chemical and physical data
Formula	C₁₆H₁₆N₂O₆S₂
Molar mass	396.43 g·mol⁻¹
3D model (JSmol)	Interactive image
Melting point	160 to 160.5 °C (320.0 to 320.9 °F)
SMILES O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)Cc3sccc3)COC(=O)C)C(=O)O
InChI InChI=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^checkY Key:XIURVHNZVLADCM-IUODEOHRSA-N^checkY
(verify)

Cefalotin (INN) /ˌsɛfəˈloʊtɪn/ or cephalothin (USAN) /ˌsɛfəˈloʊθɪn/ is a first-generation cephalosporin antibiotic with broad spectrum antibiotic activity.^[1]^[2] It was the first cephalosporin marketed (1964) and continues to be widely used.^[3] 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.^[2]

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.^[4]

The compound is a derivative of thiophene-2-acetic acid.^[5]

References

[edit ]

^ Hameed TK, Robinson JL (July 2002). "Review of the use of cephalosporins in children with anaphylactic reactions from penicillins". The Canadian Journal of Infectious Diseases. 13 (4): 253–8. doi:10.1155/2002/712594 . PMC 2094874 . PMID 18159398.
^ ^a ^b "Cefalotin - an overview | ScienceDirect Topics". www.sciencedirect.com. Retrieved 2024年01月26日.
^ Greenwood D (21 February 2008). Antimicrobial Drugs: Chronicle of a Twentieth Century Medical Triumph. OUP Oxford. pp. 128–. ISBN 978-0-19-953484-5.
^ International Drug Names : Cefalotin
^ Swanston, Jonathan (2006). "Thiophene". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a26_793.pub2. ISBN 3527306730..

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Antibacterials active on the cell wall and envelope (J01C-J01D)

β-lactams
(inhibit synthesis
of peptidoglycan
layer of bacterial
cell wall by binding
to and inhibiting
PBPs, a group of
D-alanyl-D-alanine
transpeptidases)

Penicillins (Penams)

Narrow
spectrum

β-lactamase sensitive (1st generation)	Benzylpenicillin (G) ^# Benzathine benzylpenicillin ^# Procaine benzylpenicillin ^# Phenoxymethylpenicillin (V) ^# Propicillin ^‡ Pheneticillin ^‡ Azidocillin ^‡ Clometocillin ^‡ Penamecillin ^‡
β-lactamase resistant (2nd generation)	Cloxacillin ^# (Dicloxacillin Flucloxacillin) Oxacillin Nafcillin Methicillin ^‡

Extended
spectrum

Aminopenicillins (3rd generation)	Amoxicillin ^# Ampicillin ^# (Pivampicillin Hetacillin ^‡ Bacampicillin ^‡ Lenampicillin Metampicillin ^‡ Talampicillin ^‡) Epicillin ^‡
Carboxypenicillins (4th generation)	Ticarcillin Carbenicillin ^‡ / Carindacillin ^‡ Temocillin ^‡
Ureidopenicillins (4th generation)	Piperacillin Azlocillin ^‡ Mezlocillin ^‡
Other	Mecillinam (Pivmecillinam) Sulbenicillin ^‡

Carbapenems / Penems

Cephems
Cephalosporins
Cephamycins
Carbacephems

1st generation	Cefazolin ^# Cefalexin ^# Cefadroxil Cefapirin Cefazedone ^‡ Cefazaflur ^‡ Cefradine ^‡ Cefroxadine ^‡ Ceftezole ^‡ Cefaloglycin ^‡ Cefacetrile ^‡ Cefalonium ^‡ Cefaloridine ^‡ Cefalotin Cefatrizine ^‡
2nd generation	Cefaclor Cefprozil Cefuroxime Cefuroxime axetil Cefamandole ^‡ Cefonicid ^‡ Ceforanide ^‡ Cefuzonam ^‡ Cephamycin (Cefoxitin Cefotetan Cefminox ^‡ Cefbuperazone ^‡ Cefmetazole ^‡) Carbacephem (Loracarbef ^‡)
3rd generation	Cefixime ^# Ceftriaxone ^# Cefotaxime ^# Antipseudomonal (Ceftazidime ^# Cefoperazone) Cefdinir Cefcapene Cefdaloxime Ceftizoxime Cefmenoxime Cefpiramide Cefpodoxime Ceftibuten Cefditoren Cefotiam ^‡ Cefetamet ^‡ Cefodizime ^‡ Cefpimizole ^‡ Cefsulodin ^‡ Cefteram ^‡ Ceftiolene ^‡ Oxacephem (Flomoxef Latamoxef ^‡)
4th generation	Cefepime Cefozopran ^‡ Cefpirome Cefquinome ^‡
5th generation	Ceftaroline fosamil Ceftolozane Ceftobiprole
Siderophore	Cefiderocol ^#
Veterinary	Ceftiofur Cefquinome Cefovecin

Monobactams

β-lactamase inhibitors

Combinations

Polypeptides

Lipopeptides	Insert into bacterial cell wall causing perforation and depolarization: Daptomycin Surfactin
Other	Inhibits PG elongation and crosslinking: Ramoplanin ^§

Intracellular

Inhibit PG subunit synthesis and transport: NAM synthesis inhibition (Fosfomycin)
DADAL/AR inhibitors (Cycloserine)
bactoprenol inhibitors (Bacitracin)

Other

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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