Cefazolin

Base Information

• Chemical Name: Cefazolin
• CAS No.: 25953-19-9
• Molecular Formula: C14H14N8O4S3
• Molecular Weight: 454.514
• Hs Code.: 2941906000
• European Community (EC) Number: 247-362-8
• UNII: IHS69L0Y4T
• DSSTox Substance ID: DTXSID2022753
• Nikkaji Number: J17.146H
• Wikipedia: Cefazolin
• Wikidata: Q415739
• NCI Thesaurus Code: C28913
• RXCUI: 2180
• Pharos Ligand ID: 8KFPHHX5955R
• Metabolomics Workbench ID: 43496
• ChEMBL ID: CHEMBL1435
• Mol file: 25953-19-9.mol

Synonyms:Ancef;Cefamedin;Cefamezine;Cefazolin;Cefazolin Sodium;Cephamezine;Cephazolin;Cephazolin Sodium;Cephazolin, Sodium;Gramaxin;Kefzol;Sodium Cephazolin;Sodium, Cefazolin;Sodium, Cephazolin;Totacef

Chemical Property of Cefazolin

Chemical Property:

• Appearance/Colour: needle-like crystals
• Melting Point: 198-200 °C
• Refractive Index: 1.961
• PKA: pKa 2.15 (Uncertain)
• PSA: 234.93000
• Density: 2.01 g/cm³
• LogP: -0.30730
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Very Slightly, Heated)
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 7
• Exact Mass: 454.03001448
• Heavy Atom Count: 29
• Complexity: 740

Purity/Quality:

99% ^*data from raw suppliers

Cefazolin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=NN=C(S1)SCC2=C(N3C(C(C3=O)NC(=O)CN4C=NN=N4)SC2)C(=O)O
• Isomeric SMILES: CC1=NN=C(S1)SCC2=C(N3[C@@H]([C@@H](C3=O)NC(=O)CN4C=NN=N4)SC2)C(=O)O
• Recent ClinicalTrials: DOTS: Dalbavancin as an Option for Treatment of Staphylococcus Aureus Bacteremia
• Recent EU Clinical Trials: A Multicenter, Open-Label, Evaluator-Blinded, Randomized Study to Evaluate the Safety and Tolerability of Single-Dose IV Oritavancin Versus Standard of Care for the Treatment of Pediatric Subjects with Acute Bacterial Skin And Skin Structure Infections
• Recent NIPH Clinical Trials: Randomized clinical trial of antibiotic prophylaxis versus no intervention in muscle biopsy
• 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.
• Uses: Cefazolin is an antibacterial compound derived from 7-amino-cephalosporanic acid. Antibacterial (systemic).
• Therapeutic Function: Antibacterial
• 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.

Technology Process of Cefazolin

There total 15 articles about Cefazolin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

C8H12N4O3 (43194-95-2) + 7-amino-3-<(5-methyl-1,3,4-thiadiazol-2-yl)thiomethyl>-Δ3-cephem-4-carboxylic acid hydrochloride (98493-37-9,102417-70-9) → cefazolin (25953-19-9)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In dichloromethane; at -10 - -5 ℃; for 1h;

DOI:10.1016/S0040-4020(01)96757-2

Reference yield: 79.0%

cefazolin sodium (27164-46-1) → cefazolin (25953-19-9)

Guidance literature:

With hydrogenchloride; In water;

Reference yield: 78.0%

(6R,7R)-7-amino-3-(5-methyl-1,3,4-thiadiazol-2-ylthiomethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (30246-33-4) + (1H-tetrazol-1-yl)-2-acetic acid methyl ester (55633-19-7) → cefazolin (25953-19-9)

Guidance literature:

With phosphate buffer; PGA Coli A; at 4 ℃; pH 7.5;

DOI:10.1021/jo971166u

upstream raw materials:

C₈H₁₂N₄O₃

7-amino-3-<(5-methyl-1,3,4-thiadiazol-2-yl)thiomethyl>-Δ³-cephem-4-carboxylic acid hydrochloride

delta-3 methyl ester of cefazolin

7-((tetrazol-1'-yl)acetylamino)-3-acetyloxymethyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Downstream raw materials:

delta-3 methyl ester of cefazolin

Δ2-cefazolin diphenylmethyl ester

Δ3-cefazolin diphenylmethyl ester

cefazolin sodium

Refernces

• 1、 Bonomi, Paolo,Bavaro, Teodora,Serra, Immacolata,Tagliani, Auro,Terreni, Marco,Ubiali, Daniela. "Modulation of the microenvironment surrounding the active site of penicillin g acylase immobilized on acrylic carriers improves the enzymatic synthesis of cephalosporins". . p. 14349 - 14365. Retrieved 2013.
• 2、 -. "Preparation method of cefazolin sodium with previous research quality and medicine preparation of cefazolin sodium". . . Retrieved 2017/02/23.