Cefazolin
- 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
- MDL Number:
- MFCD00243010
- MOL File:
- 25953-19-9.mol
- MSDS File:
- SDS
| 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) |
| FDA UNII | IHS69L0Y4T |
| ATC code | J01DB04 |
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(9)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | PHR1291 | Cefazolin | 25953-19-9 | 500mg | $214 | 2024-03-01 | Buy |
| Sigma-Aldrich | 1097603 | Cefazolin | 25953-19-9 | 200mg | $436 | 2024-03-01 | Buy |
| Sigma-Aldrich | C0682800 | Cefazolin European Pharmacopoeia (EP) Reference Standard | 25953-19-9 | c0682800 | $153 | 2024-03-01 | Buy |
| TRC | C242495 | Cefazolin | 25953-19-9 | 10g | $415 | 2021-12-16 | Buy |
| TRC | C242495 | Cefazolin | 25953-19-9 | 25g | $825 | 2021-12-16 | 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
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.
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
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Preparation Products
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Henan Tianfu Chemical Co.,Ltd. | +86-0371-55170693 +86-19937530512 | info@tianfuchem.com | China | 21634 | 55 |
| Xiamen AmoyChem Co., Ltd | +86-86-5926051114 +8618959220845 | sales@amoychem.com | China | 6383 | 58 |
| HubeiwidelychemicaltechnologyCo.,Ltd | 18627774460 | faith@widelychemical.com | CHINA | 742 | 58 |
| Hubei xin bonus chemical co. LTD | 86-13657291602 | linda@hubeijusheng.com | CHINA | 22963 | 58 |
| CONIER CHEM AND PHARMA LIMITED | +8618523575427 | sales@conier.com | China | 49374 | 58 |
| career henan chemical co | +86-0371-86658258 +8613203830695 | factory@coreychem.com | China | 29811 | 58 |
| Antai Fine Chemical Technology Co.,Limited | 18503026267 | info@antaichem.com | CHINA | 9636 | 58 |
| SIMAGCHEM CORP | +86-13806087780 | sale@simagchem.com | China | 17365 | 58 |
| TargetMol Chemicals Inc. | +1-781-999-5354 +1-00000000000 | marketing@targetmol.com | United States | 32165 | 58 |
| Hubei Ipure Biology Co., Ltd | +8613367258412 | ada@ipurechemical.com | China | 10319 | 58 |
View Lastest Price from Cefazolin manufacturers
| Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
|---|---|---|---|---|---|---|---|---|
 |
2024-11-22 | Cefazolin
25953-19-9
|
US $0.00 / KG | 1KG | 98%min | 30tons/month | WUHAN FORTUNA CHEMICAL CO., LTD | |
 |
2024-11-19 | Cefazolin
25953-19-9
|
US $48.00 / mg | 100% | 10g | TargetMol Chemicals Inc. | ||
 |
2023-09-14 | Cefazolin
25953-19-9
|
US $0.00-0.00 / g | 100g | 99% | 20 tons | Wuhan Han Sheng New Material Technology Co.，Ltd |
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