ChemicalBook > CAS DataBase List > Cefazolin

Cefazolin

Cefazolin Structure
Cefazolin
  • CAS No.25953-19-9
  • Chemical Name:Cefazolin
  • CBNumber:CB3396249
  • Molecular Formula:C14H14N8O4S3
  • Formula Weight:454.51
  • MOL File:25953-19-9.mol
Cefazolin Property
Safety
Hazard and Precautionary Statements (GHS)
  • Symbol(GHS)
  • Signal wordDanger
  • Hazard statements H317-H334
  • Precautionary statements P261-P280-P284-P304+P340-P342+P311
Cefazolin Price More Price(10)
  • Brand: Sigma-Aldrich
  • Product number: PHR1291
  • Product name : Cefazolin
  • Purity: 
  • Packaging: 500mg
  • Price: $160
  • Updated: 2021/12/16
  • Buy: Buy
  • Brand: Sigma-Aldrich
  • Product number: 1097603
  • Product name : Cefazolin
  • Purity: 
  • Packaging: 200mg
  • Price: $366
  • Updated: 2021/12/16
  • Buy: Buy
  • Brand: Sigma-Aldrich
  • Product number: C0682800
  • Product name : Cefazolin
  • Purity: European Pharmacopoeia (EP) Reference Standard
  • Packaging: 
  • Price: $190
  • Updated: 2021/12/16
  • Buy: Buy
  • Brand: TRC
  • Product number: C242495
  • Product name : Cefazolin
  • Purity: 
  • Packaging: 10g
  • Price: $415
  • Updated: 2021/12/16
  • Buy: Buy
  • Brand: TRC
  • Product number: C242495
  • Product name : Cefazolin
  • Purity: 
  • Packaging: 25g
  • Price: $825
  • Updated: 2021/12/16
  • Buy: Buy

Cefazolin Chemical Properties,Usage,Production

  • Description Cefazolin has the natural acetyl side chain at C-3 replaced by a thio-linked thiadiazole ring. Although this group is an activating leaving group, the moiety is not subject to the inactivating host hydrolysis reaction that characterizes cephapirin. At C-7, it possesses a tetrazoylmethylene unit. Cefazolin is less irritating on injection than its cohort in this generation of drugs and has a longer half-life than cephapirin. Its dosing should be reduced in the presence of renal impairment. It is comparatively unstable and should be protected from heat and light.
  • Chemical Properties needles
  • Originator Cefamedin,Fujisawa,Japan,1971
  • Uses Cefazolin is an antibacterial compound derived from 7-amino-cephalosporanic acid.
  • Uses Antibacterial (systemic).
  • Definition ChEBI: A cephalosporin compound having [(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl and (1H-tetrazol-1-ylacetyl)amino side-groups.
  • Manufacturing Process 7-Aminocephalosporanic acid is converted to its sodium salt and acylated with 1H-tetrazole-1-acetyl chloride. The acetoxy group is then displaced by reaction with 5-methyl-1,3,4-thiadiazole-2-thiol in buffer solution. The product acid is converted to the sodium salt by NaHCO3.
  • Therapeutic Function Antibacterial
  • Antimicrobial activity Enterobacter, Klebsiella, Providencia, Serratia spp. and Pr. vulgaris are all resistant. B. fragilis is resistant, but other anaerobes are susceptible.
  • Pharmacokinetics Distribution
    The volume of distribution is the smallest of the cephalosporins in group 1, perhaps an indication of relative confinement to the plasma space. It crosses inflamed synovial membranes, but the levels achieved are well below those of the simultaneous serum levels and entry to the CSF is poor. In patients receiving 10 mg/kg by intravenous bolus, mean concentrations in cancellous bone were 3.0 mg/kg when the mean serum concentration was 33 mg/L, giving a bone:serum ratio of 0.09. Some crosses the placenta, but the concentrations found in the fetus and membranes are low.
    Metabolism and excretion
    It is not metabolized. Around 60% of the dose is excreted in the urine within the first 6 h, producing concentrations in excess of 1 g/L. Excretion is depressed by probenecid. The renal clearance is around 65 mL/min and declines in renal failure, when the half-life may rise to 40 h, although levels in the urine sufficient to inhibit most urinary pathogens are still found. It is moderately well removed by hemodialysis and less well by peritoneal dialysis.
    Levels sufficient to inhibit a number of enteric organisms likely to infect the biliary tract are found in T-tube bile (17–31 mg/L after a 1 g intravenous dose), but this is principally due to the high serum levels of the drug and the total amounts excreted via the bile are small.
  • Clinical Use Cefazolin has been widely used in surgical prophylaxis, especially in biliary tract (because of the moderately high concentrations achieved in bile), orthopedic, cardiac and gynecological surgery.
  • Side effects Side effects are those common to other cephalosporins ,including rare bleeding disorders and encephalopathy in patients in whom impaired excretion or direct instillation leads to very high CSF levels. Neutropenia has been described and hypoprothrombinemic bleeding has been attributed to the side chain.
  • Chemical Synthesis Cefazolin, (6R-trans)-3[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo- 7-[(1H-tetrazol-1-ylacetyl)amino]-5-thia-1-azabycyclo[4.2.0]oct-2-en-2-carboxylic acid (32.1.2.7), is synthesized by reacting 7-aminocephalosporanic acid with a mixed anhydride (32.1.2.6), which is the result of a reaction of tetrazolylacetic acid with pivalic (trimethylacetic) acid chloride. Further reaction with 2-mercapto-5-methyl-1,3,4-thiadiazole results in a substitution of the 3-acetoxy group with a mercaptothiadiazol group, giving cefazolin (32.1.2.7).

Cefazolin Preparation Products And Raw materials
Raw materials
Preparation Products
Global(158)Suppliers
  • Supplier:
    Henan Tianfu Chemical Co.,Ltd.
  • Tel:0371-55170693
  • Fax:0371-55170693
  • Email:info@tianfuchem.com
  • Country:China
  • ProdList:22607
  • Advantage:55
  • Supplier:
    Xiamen AmoyChem Co., Ltd
  • Tel:+86 592-605 1114
  • Fax:
  • Email:sales@amoychem.com
  • Country:CHINA
  • ProdList:6369
  • Advantage:58
  • Supplier:
    BOC Sciences
  • Tel:1-631-485-4226
  • Fax:1-631-614-7828
  • Email:inquiry@bocsci.com
  • Country:United States
  • ProdList:19752
  • Advantage:58
  • Supplier:
    career henan chemical co
  • Tel:15093356674 0371-55982848
  • Fax:0086-371-86658258
  • Email:factory@coreychem.com
  • Country:CHINA
  • ProdList:29864
  • Advantage:58
  • Supplier:
    Jinan Honest Pharm Co., Ltd
  • Tel:+86-15318812076
  • Fax:
  • Email:sale@jnhonestpharm.com; honestpharm@163.com;
  • Country:CHINA
  • ProdList:290
  • Advantage:58
25953-19-9, CefazolinRelated Search:
  • CEFAZOLIN
  • CEFAZOLIN ACID
  • (6r-trans)-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-7-[[(1h-tetr
  • 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylicacid,3-(((5-methyl-1,3,4-thia
  • (6R,7R)-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-7-[[1-oxo-2-(1-tetrazolyl)ethyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  • 7-(1-(1h-)-tetrazolylacetamido)-3-[2-(5-methyl-1,3,4-thiadiazolyl)thiomethyl]d
  • azol-1-yl)acetyl]-amino]-5-thia-1-azabicylo
  • cefamezin
  • CefazoilnV
  • cefazoline
  • cephamezine
  • cephazolin
  • cephazoline
  • Cephazolin,sodium salt
  • Cefazoline sodium sterile IP/Bp
  • Cafazolin
  • CEFAZOLIN,USP
  • 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-7-[(1H-tetrazol-1-ylacetyl)amino]-, (6R,7R)-
  • 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-7-[(1H-tetrazol-1-ylacetyl)amino]-, (6R-trans)-
  • 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-7-[2-(1H-tetrazol-1-yl)acetamido]- (8CI)
  • 7-(1-(1H)-Tetrazolylacetamido)-3-[2-(5-methyl-1,3,4-thiadiazolyl)thiomethyl]-D3-cephem-4-carboxylic acid
  • 7-(1H-Tetrazol-1-ylacetamido)-3-(5-methyl-1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid
  • Cefaprim
  • Cefazolin Acid L
  • cez
  • diazol-2-yl)thio)methyl)-8-oxo-7-((1h-tetra
  • diazol-2-yl)thio)methyl)-8-oxo-7-(2-(1h-t-
  • diazol-2-yl)thio)methyl)-8-oxo-7-(2-(1h-tetrazol-1-yl)acetamido)-
  • elta3-cephem-4-carboxylicacid
  • elzogram
  • (6R)-3-[[(5-Methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-7α-[[2-(1H-tetrazol-1-yl)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  • (6R,7R)-3-[[(5-Methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-7-[2-(1H-tetrazol-1-yl)acetylamino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  • 7-[1-(1H)-tetrazolylacetoamido]-3-[2-(5-methyl-1,3,4-thiadiazolyl)-thiomethyl]-.DELTA.-3-cephem-4-carboxylic acid
  • Cefazolin (400 mg)
  • CeftazidinMe
  • (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
  • Cefazolin (200 mg)
  • Cefazolin CRS
  • 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-7-[[2-(1H-tetrazol-1-yl)acetyl]amino]-, (6R,7R)-
  • Cefazolin USP/EP/BP
  • Cefazolin Sodium Impurity L
  • 25953-19-9
  • C14H14N8O4S3