Cefazolin sodium salt

Base Information

• Chemical Name: Cefazolin sodium salt
• CAS No.: 27164-46-1
• Molecular Formula: C14H14N8O4S3. Na
• Molecular Weight: 476.496
• Hs Code.: 29349990
• Mol file: 27164-46-1.mol

Synonyms:5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid,3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-7-[(1H-tetrazol-1-ylacetyl)amino]-,monosodium salt, (6R,7R)- (9CI);5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid, 3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-7-[2-(1H-tetrazol-1-yl)acetamido]-,monosodium salt (8CI);3-[[(5-Methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-7-[2-(1H-tetrazol-1-yl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid sodium salt;Acef;Ancef;Atirin;Biazolina;Bor-Cefazol;Cefacidal;Cefazil;Cefazoliin;Cefazolin sodium;Cefazoline sodium;Cephazolin sodium;Cephazolin sodiumsalt;Firmacef;Gramaxin;Kefzol;Lampocef;Liviclina;Monosodium cafazolin;Reflin;SKF 41558;Sodium cefazolin;Sodium cephazolin;Totacef;Zolicef;Cefazolin sodium salt;

Chemical Property of Cefazolin sodium salt

Chemical Property:

• Appearance/Colour: White to off-white powder
• Melting Point: 190 °C
• Refractive Index: 20 ° (C=10, H2O)
• PSA: 237.76000
• LogP: -1.64200
• Storage Temp.: 2-8°C
• Sensitive.: Light Sensitive
• Solubility.: H2O: 50 mg/mL, clear, colorless
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 7
• Exact Mass: 477.01978376
• Heavy Atom Count: 30
• Complexity: 740

Purity/Quality:

99% ^*data from raw suppliers

Cefazolin Sodium ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi, Xn
• Hazard Codes: Xn,Xi
• Statements: 42/43-36/37/38-20/21/22
• Safety Statements: 22-36/37-36-26

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.[Na]
• Isomeric SMILES: CC1=NN=C(S1)SCC2=C(N3[C@@H]([C@@H](C3=O)NC(=O)CN4C=NN=N4)SC2)C(=O)O.[Na]
• Uses: Semi-synthetic antibiotic derived from 7-amino-cepphalosporanic acid. An antibacterial enzyme inhibitor, Gaucher's disease therapy Semi-synthetic antibiotic derived from 7-amino-cephalosporanic acid. An antibacterial.
• Therapeutic Function: Antibacterial
• Clinical Use: Cefazolin (Ancef, Kefzol) is one of a series of semisyntheticcephalosporins in which the C-3 acetoxy function has beenreplaced by a thiol-containing heterocycle—here, 5-methyl-2-thio-1,3,4-thiadiazole. It also contains the somewhatunusual tetrazolylacetyl acylating group. Cefazolin wasreleased in 1973 as a water-soluble sodium salt. It is activeonly by parenteral administration.Cefazolin provides higher serum levels, slower renalclearance, and a longer half-life than other first-generationcephalosporins. It is approximately 75% protein bound inplasma, a higher value than for most other cephalosporins.Early in vitro and clinical studies suggest that cefazolin ismore active against Gram-negative bacilli but less activeagainst Gram-positive cocci than either cephalothin orcephaloridine. Occurrence rates of thrombophlebitis followingintravenous injection and pain at the site of intramuscularinjection appear to be the lowest of the parenteralcephalosporins.

Technology Process of Cefazolin sodium salt

There total 5 articles about Cefazolin sodium salt 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: 93.5%

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

Guidance literature:

cefazolin; With pyrographite; In water; acetone; at 35 ℃; for 0.5h;

With sodium hydrogencarbonate; In water; acetone; at 30 - 35 ℃; for 5h; Reagent/catalyst;

Reference yield: 15.9%

→ cefazolin sodium (27164-46-1)

Guidance literature:

Reference yield:

7-Aminocephalosporanic acid (957-68-6) → cefazolin sodium (27164-46-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: boron trifluoride dimethyl carbonate complex; hydrogenchloride / N,N-dimethyl-formamide / 0.17 h / 35 - 40 °C

1.2: 1.33 h / 25 - 35 °C / pH 2 - 3

2.1: N,N,N',N'-tetramethylguanidine / dichloromethane / 0.5 h / -30 °C

3.1: sodium hydroxide / acetonitrile; water / -10 - -5 °C / pH 7 / Large scale

With hydrogenchloride; boron trifluoride dimethyl carbonate complex; sodium hydroxide; N,N,N',N'-tetramethylguanidine; In dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

upstream raw materials:

cefazolin

7-Aminocephalosporanic acid

(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

Downstream raw materials:

2-mercapto-5-methyl-1,3,4-thiadiazole

cefazolin

delta-3 methyl ester of cefazolin

Refernces

• 1、 -. "Preparation method of cefazolin sodium with previous research quality and medicine preparation of cefazolin sodium". Paragraph 0029-0030. . Retrieved 2017/02/23.
• 2、 -. "Cefazolin Sodium Pentahydrate Crystal and Its Molecular Assembly Preparation Method". Page/Page column 2-3. . Retrieved 2009/12/23.