Cefazolin
Chemical Properties of Cefazolin
Cefazolin, also known by its chemical name \( C_{14}H_{14}N_{8}O_{4}S_{3} \), is a first-generation cephalosporin antibiotic with a broad spectrum of activity against bacteria. It is a semi-synthetic compound designed for parenteral administration, meaning it is not absorbed from the gastrointestinal tract and must be administered by injection[3].
Molecular Structure and Physical Properties
Cefazolin has a molecular weight of 454.03 Da and a topological polar surface area of 234.93 Ų. It is characterized by its rotatable bonds, which number eight, and it has an XLogP value of 0.28, indicating its partition coefficient between octanol and water. The compound has one of Lipinski's rules broken, which is a set of criteria for determining the drug-likeness of a compound[5].
The compound is a white to yellowish-white, odorless crystalline powder with a bitter, salty taste. It is easily soluble in water and crystallizes in alpha, beta, and gamma forms[6].
Pharmacokinetics
Cefazolin achieves high serum levels and is excreted quickly via the urine. After intramuscular injection, peak serum concentrations are attained within 1-2 hours. The drug is not metabolized and is excreted unchanged in the urine, with approximately 60% of the drug excreted within the first six hours, increasing to 70%-80% within 24 hours. The serum half-life of cefazolin is approximately 1.8 hours following intravenous administration and approximately 2.0 hours following intramuscular administration. It has a plasma protein binding rate of 74-86%[3][4].
Mechanism of Action
Cefazolin exerts its bactericidal action by inhibiting bacterial cell wall synthesis. It binds to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, thereby inhibiting the third and last stage of bacterial cell wall synthesis. This action leads to cell lysis, which is mediated by bacterial cell wall autolytic enzymes such as autolysins[3].
Clinical Use
Cefazolin is mainly used for the treatment of bacterial infections of the skin, bones, joints, stomach, blood, heart valves, and urinary tract. It is listed on the WHO Essential Medicines List, indicating its importance in a basic health system[5].
Chemical Identifiers
The compound has several synonyms, including Ancef®, cephazolin, CEZ, Kefzol®, and SK&F-41558. Its IUPAC name is \( (6R,7R)-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanylmethyl]-8-oxo-7-[[2-(tetrazol-1-yl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid \)[5].
Safety and Toxicity
Information on the toxicity of cefazolin is not provided in the search results, but as with all medications, it should be used under the guidance of a healthcare provider to avoid adverse effects and interactions with other drugs[3].
In summary, cefazolin is a well-characterized antibiotic with specific chemical and pharmacokinetic properties that make it effective against a range of bacterial infections. It is a critical drug in the treatment of various infections and is included in the list of essential medicines due to its importance in healthcare[3][5].
Citations:
[1] https://pubchem.ncbi.nlm.nih.gov/compound/Cefazolin
[2] https://pubchem.ncbi.nlm.nih.gov/compound/33255
[3] https://go.drugbank.com/drugs/DB01327
[4] https://www.sciencedirect.com/topics/chemistry/cefazolin
[5] https://www.guidetopharmacology.org/GRAC/LigandDisplayForward?ligandId=10935
[6] https://www.drugfuture.com/chemdata/cefazolin.html
[7] https://www.ebi.ac.uk/chebi/searchId.do?chebiId=474053
[8] http://www.chemspider.com/Chemical-Structure.30723.html