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Cefazolin

Cefazolin Structure
CAS No.
25953-19-9
Chemical Name:
Cefazolin
Synonyms
CEFAZOLIN ACID;cefazoline;cephazolin;Cafazolin;cephazoline;cez;Cefaprim;elzogram;cefamezin;CEFAZOLIN
CBNumber:
CB3396249
Molecular Formula:
C14H14N8O4S3
Molecular Weight:
454.51
MOL File:
25953-19-9.mol
MSDS File:
SDS
Modify Date:
2024/7/2 8:55:06

Cefazolin Properties

Melting point 198-200 C
Density 2.01±0.1 g/cm3(Predicted)
storage temp. Hygroscopic, -20°C Freezer, Under inert atmosphere
solubility DMSO (Slightly), Methanol (Very Slightly, Heated)
pka pKa 2.15 (Uncertain)
form Solid
color White to Off-White
Stability Hygroscopic
CAS DataBase Reference 25953-19-9(CAS DataBase Reference)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS08
Signal word  Danger
Hazard statements  H317-H334
Precautionary statements  P261-P280-P284-P304+P340-P342+P311
Hazard Codes  Xn
Risk Statements  20/21/22-36/37/38
Safety Statements  26-36
WGK Germany  3
HS Code  2941906000
Toxicity mouse,LD50,intramuscular,4gm/kg (4000mg/kg),Byoin Yakugaku. Hospital Pharmacology. Vol. 3, Pg. 220, 1978.

Cefazolin price More Price(1)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) PHR1291 Cefazolin Pharmaceutical Secondary Standard; Certified Reference Material 25953-19-9 500MG ₹18759.73 2022-06-14 Buy
Product number Packaging Price Buy
PHR1291 500MG ₹18759.73 Buy

Cefazolin Chemical Properties,Uses,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

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Uses

Cefazolin is an antibacterial compound derived from 7-amino-cephalosporanic acid.

Definition

ChEBI: A cephalosporin compound having [(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl and (1H-tetrazol-1-ylacetyl)amino side-groups.

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.

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Cefazolin Spectrum

CEFAZOLIN (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 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 cephamezine Cephazolin,sodium salt Cefazoline sodium sterile IP/Bp 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 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) (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 Cefazolin Acid L 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 Cefazolin AcidQ: What is Cefazolin Acid Q: What is the CAS Number of Cefazolin Acid Q: What is the storage condition of Cefazolin Acid Q: What are the applications of Cefazolin Acid Cefazolin (C0682800) Cefazolin vial 1 g Cefazolin (1097603) (6R,7R)-7-(2-(1H-Tetrazol-1-yl)acetamido)-3-(((5-methyl-1,3,4-thiadiazol-2-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid CEFAZOLIN ACID cefazoline cephazolin cephazoline Cafazolin 25953-19-9 8821-53-3 C14H14N8O4S3