سفالوتین

Also known as cefalotin sodium, Keflin®, CET, 7-(2'-thienylacetamido)cephalosporanic acid, Cefalotin, Cephalothin, 7-(Thiophene-2-acetamido)cephalosporin, Cefalotina

Cefalotin (INN) or cephalothin (USAN) is a first-generation cephalosporin antibiotic with broad spectrum antibiotic activity. It was the first cephalosporin marketed (1964) and continues to be widely used. 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.

Chemical data

Formula: C16H16N2O6S2
Molecular weight: 396.4 g/mol
IUPAC name: (6R,7R)-3-(acetyloxymethyl)-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
SMILES: CC(=O)OCC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)CC3=CC=CS3)SC1)C(=O)O
InChIKey: XIURVHNZVLADCM-IUODEOHRSA-N
XLogP: -0.4
Polar surface area: 167 Å²
H-bond donors: 2
H-bond acceptors: 8
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 1974
Admin. routes: parenteral
Indications: bacterial disease

via ChEMBL · EBI

Research

4,740 papers

Review for Analytical Methods for the Determination of Sodium Cephalothin.Critical reviews in analytical chemistry · 2019
[Cephaloridine--cephalothin].Tidsskrift for den Norske laegeforening : tidsskrift for praktisk medicin, ny raekke · 1965
Cephalothin, gentamicin, colistin hazards.JAMA · 1973
Cephalothin (Keflin).The Medical letter on drugs and therapeutics · 1965
Letter: Cephalothin-induced granulocytopenia.Annals of internal medicine · 1975

via PubMed

Wikidata facts

Subclass of: chemical compound
Mass: 396.045
Has use: medication

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chemical formula: C₁₆H₁₆N₂O₆S₂
subject has role: bactericide
canonical SMILES: CC(=O)OCC1=C(N2C(C(C2=O)NC(=O)CC3=CC=CS3)SC1)C(=O)O
isomeric SMILES: CC(=O)OCC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)CC3=CC=CS3)SC1)C(=O)O
medical condition treated: staphylococcal infection
defined daily dose: 4
MCN code: 3004.20.51
Commons category: Cefalotin

Sources (5)

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