Cephalothin

Base Information

• Chemical Name: Cephalothin
• CAS No.: 58-71-9
• Molecular Formula: C16H15N2NaO6S2
• Molecular Weight: 418.427
• Hs Code.: 29419000
• Mol file: 58-71-9.mol

Synonyms:5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,3-[(acetyloxy)methyl]-8-oxo-7-[(2-thienylacetyl)amino]-, monosodium salt,(6R-trans)-;Averon 1;Cefalothine sodium;Cemastin;Cephalothin sodium salt;Cephation;Ceporacin;Cepovenin;Coaxin;Keflin;Lilly 38253;Lospoven;Microtin;Seffin;Sodium(thienylacetamido)cephalosporanate;Sodium 3-acetoxymethyl-7b-(2-thienylacetamido)ceph-3-em-4-carboxylate;Sodium 7-(2-thienylacetamido)-3-acetoxymethyl-3-cephem-4-carboxylate;Sodium7-[2-(2-thienyl)acetamido]cephalosporanate;Sodium cefalotin;Sodiumcephalothin;Sodium cephalotin;Synclotin;Toricelocin;

Chemical Property of Cephalothin

Chemical Property:

• Appearance/Colour: Crystalline
• Melting Point: 240 °C
• Boiling Point: 757.2 °C at 760 mmHg
• Flash Point: 411.8 °C
• PSA: 169.38000
• LogP: -0.41360
• Storage Temp.: 2-8°C
• Solubility.: H2O: 50 mg/mL, clear, faintly yellow
• Water Solubility.: 158 mg/L

Purity/Quality:

99% ^*data from raw suppliers

Cephalothin Sodium ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Description: Cefalothin is a β-lactam cephalosporin antibiotic. It inhibits the growth of various Gram-positive and Gram-negative bacteria, including several strains of S. pyogenes, S. aureus, C. tetani, N. gonorrhoeae, Salmonella, and Shigella (MICs = 0.1-0.2, 0.312-0.625, 0.078, 1.25, 1.56-6.25, and 3.12-12.5 μg/ml, respectively). Cefalothin binds to E. coli penicillin-binding proteins (PBPs; IC50s = <0.25, 16, 37, and 1 μg/ml for PBP1a, 1bs, 2, and 3, respectively, in a radioligand binding assay), which interferes with bacterial morphogenesis. It exhibits antibacterial activity in mouse models of infection with S. pyogenes, D. pneumoniae, and S. aureus. Formulations containing cefalothin were previously used in the prophylaxis and treatment of bacterial infections.
• Uses: Cephalothin sodium salt is used to study the mechanism of liposome encapsulated antibiotics1, strategies for co-opting β-lactamases of Gram-negative bacteria for treatment of antibiotics2, and for immunology studies in relation to antibiotics.3 It is used to study the effect of expression, binding and inhibition of penicillin-binding proteins especially PBP6 on bacterial cell wall mucopeptide synthesis. Antibacterial;Bacterial transpeptidase inhibitor Cephalothin is a first-generation cephalosporin antibiotic used to study the mechanism of liposome encapsulated antibiotics,strategies for co-opting β-lactamases of Gram-negative bacteria for treatment of antibiotics,and for immunology studies in relation to antibiotics.It is used to study the effect of expression, binding and inhibition of penicillin-binding proteins especially PBP6 on bacterial cell wall mucopeptide synthesis.
• Therapeutic Function: Antibacterial
• Clinical Use: Cephalothin sodium (Keflin) occurs as a white to off-white,crystalline powder that is practically odorless. It is freelysoluble in water and insoluble in most organic solvents.Although it has been described as a broad-spectrum antibacterialcompound, it is not in the same class as the tetracyclines.Its spectrum of activity is broader than that ofpenicillin G and more similar to that of ampicillin. Unlikeampicillin, cephalothin is resistant to penicillinase producedby S. aureus and provides an alternative to the use ofpenicillinase-resistant penicillins for the treatment of infectionscaused by such strains.Cephalothin is absorbed poorly from the GI tract andmust be administered parenterally for systemic infections. It is relatively nontoxic and acid stable. It is excreted rapidlythrough the kidneys; about 60% is lost within 6 hours of administration.Pain at the site of intramuscular injection andthrombophlebitis following intravenous injection have beenreported. Hypersensitivity reactions have been observed,and there is some evidence of cross-sensitivity in patientsnoted previously to be penicillin sensitive.

Technology Process of Cephalothin

There total 3 articles about Cephalothin 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: 79.0%

→ sodium cephalothin (58-71-9)

Guidance literature:

Reference yield: 26.0%

cephalothin (153-61-7) → sodium cephalothin (58-71-9)

Guidance literature:

With sodium 2-ethylhexanoic acid; In acetone;

DOI:10.1016/S0040-4020(01)88547-1

Reference yield:

2-thienylacetic acid chloride (39098-97-0) + 7-Aminocephalosporanic acid (957-68-6) → sodium cephalothin (58-71-9)

Guidance literature:

With sodium hydrogencarbonate; sodium 2-ethylhexanoic acid; In water; acetone; at 0 - 5 ℃; for 0.5h;

upstream raw materials:

2-thienylacetic acid chloride

7-Aminocephalosporanic acid

cephalothin

Downstream raw materials:

(6R)-8-oxo-3-[1,2,3]thiadiazol-5-ylsulfanylmethyl-7t-(2-thiophen-2-yl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

(6R)-3-(4-benzhydryloxycarbonyl-[1,2,3]thiadiazol-5-ylsulfanylmethyl)-8-oxo-7t-(2-thiophen-2-yl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

7-β-thien-2-yl-acetamido-3-[(4-nitro-3-carboxyphenyl)-thio-methyl]-3-cephem-4-carboxylic acid

Desacetylcephalothin

Refernces

• 1、 Cowley,Humber,Laundon,et al.. "Synthesis of 3-functionalised cephalosporins by photoinitiated bromination. Transformations of 2,2,2-trichloroethyl 1S, 6R, 7R)-3-bromomethyl-7-formamidoceph-3-EM-4-carboxylate, 1-oxide". . p. 461 - 467. Retrieved 2007/10/02.