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Cefazolin

Product Name
Cefazolin
CAS No.
25953-19-9
Chemical Name
Cefazolin
Synonyms
CEFAZOLIN ACID;cefazoline;cephazolin;Cafazolin;cephazoline;cez;Cefaprim;elzogram;CEFAZOLIN;cefamezin
CBNumber
CB3396249
Molecular Formula
C14H14N8O4S3
Formula Weight
454.51
MOL File
25953-19-9.mol
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Cefazolin Property

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)
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Safety

Hazard Codes 
Xn
Risk Statements 
20/21/22-36/37/38
Safety Statements 
26-36
WGK Germany 
3
HS Code 
2941906000
Hazardous Substances Data
25953-19-9(Hazardous Substances Data)
Toxicity
mouse,LD50,intramuscular,4gm/kg (4000mg/kg),Byoin Yakugaku. Hospital Pharmacology. Vol. 3, Pg. 220, 1978.
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H317May cause an allergic skin reaction

H334May cause allergy or asthma symptoms or breathing difficulties if inhaled

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P284Wear respiratory protection.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P342+P311IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
PHR1291
Product name
Cefazolin
Packaging
500mg
Price
$214
Updated
2024/03/01
Sigma-Aldrich
Product number
1097603
Product name
Cefazolin
Packaging
200mg
Price
$436
Updated
2024/03/01
Sigma-Aldrich
Product number
C0682800
Product name
Cefazolin
Purity
European Pharmacopoeia (EP) Reference Standard
Packaging
c0682800
Price
$153
Updated
2024/03/01
TRC
Product number
C242495
Product name
Cefazolin
Packaging
10g
Price
$415
Updated
2021/12/16
TRC
Product number
C242495
Product name
Cefazolin
Packaging
25g
Price
$825
Updated
2021/12/16
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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.

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).

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Cefazolin Suppliers

J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
94657
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Adamas Reagent, Ltd.
Tel
400-6009262 16621234537
Fax
021-64823266
Email
chenyj@titansci.com
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China
ProdList
14103
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Sichuan Kulinan Technology Co., Ltd
Tel
400-1166-196 18981987031
Fax
028-84555506 800101999
Email
cdhxsj@163.com
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China
ProdList
11707
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Sinopharm Chemical Reagent Co,Ltd.
Tel
86-21-63210123
Fax
86-21-63290778 86-21-63218885
Email
sj_scrc@sinopharm.com
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China
ProdList
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Spectrum Chemical Manufacturing Corp.
Tel
021-021-021-67601398-809-809-809 15221380277
Fax
021-57711696
Email
marketing_china@spectrumchemical.com
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China
ProdList
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Wuhan Fortuna Chemical Co., Ltd
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027-59207852 13308628970
Fax
QQ3130921841
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buy@fortunachem.com
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China
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2872
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Dalian Meilun Biotech Co., Ltd.
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0411-62910999 13889544652
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meilunui@163.com
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China
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S.Z. PhyStandard Bio-Tech. Co., Ltd.
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0755-83725681-603
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+86 755 28094224
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China
ProdList
4496
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Beijing HuaMeiHuLiBiological Chemical
Tel
010-56205725
Fax
010-65763397
Email
waley188@sohu.com
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China
ProdList
12335
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The future of Shanghai Industrial Co., Ltd.
Tel
021-61552785
Fax
021-55660885
Email
sales@shshiji.com
Country
China
ProdList
9545
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View Lastest Price from Cefazolin manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
Cefazolin 25953-19-9
Price
US $0.00/KG
Min. Order
1KG
Purity
98%min
Supply Ability
30tons/month
Release date
2023-01-18
Wuhan Han Sheng New Material Technology Co.,Ltd
Product
Cefazolin 25953-19-9
Price
US $0.00-0.00/g
Min. Order
100g
Purity
99%
Supply Ability
20 tons
Release date
2023-07-13
Hebei Zhanyao Biotechnology Co. Ltd
Product
Cefazolin 25953-19-9
Price
US $10.00/Kg/Bag
Min. Order
1Kg/Bag
Purity
99%
Supply Ability
20 Tons
Release date
2021-11-12

25953-19-9, CefazolinRelated Search:


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