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Cephalothin

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Cephalothin Basic information

Product Name:
Cephalothin
Synonyms:
  • SodiuM (6R,7R)-3-(acetoxyMethyl)-8-oxo-7-(2-(thiophen-2-yl)acetaMido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
  • Cephalotin sodium salt, Antibiotic for Culture Media Use Only
  • monosodium (6r,7r)-3-acetoxymethyl-8-oxo-7-[2-(thiophen-2-yl)acetylamido]-5-thia-1-azabicyclo[4.2.0.]oct-2-ene-2-carboxylate
  • synclotin
  • Sodium cephalothin
  • 7-(2-(2-thienyl)acetamido)-,acetate,monosodiumsalt
  • cefalothinesodium
  • cefalotinasodica
CAS:
58-71-9
MF:
C16H15N2NaO6S2
MW:
418.42
EINECS:
200-394-6
Product Categories:
  • Amines
  • Chiral Reagents
  • Heterocycles
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Pharmaceutical intermediate
  • antibiotic
Mol File:
58-71-9.mol
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Cephalothin Chemical Properties

Melting point:
240°C
alpha 
D +135° (c = 1.0 in water)
storage temp. 
2-8°C
solubility 
H2O: 50 mg/mL, clear, faintly yellow
form 
neat
Water Solubility 
158 mg/L
Merck 
13,1994
BRN 
4120706
CAS DataBase Reference
58-71-9(CAS DataBase Reference)
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Safety Information

Hazard Codes 
Xn,Xi
Risk Statements 
42/43
Safety Statements 
22-36/37
WGK Germany 
2
RTECS 
XI0388300
HS Code 
29419000
Toxicity
LD50 in mice, rats (mg/kg): >20000, >10000 orally; 5670, 7716 i.p. (Kuramoto)

MSDS

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Cephalothin Usage And Synthesis

Chemical Properties

Crystalline

Originator

Keflin,Lilly,US,1964

Uses

Antibacterial;Bacterial transpeptidase inhibitor

Uses

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.

Manufacturing Process

7-(2'-Thienylacetamido)cephalosporanic acid sodium salt may be produced from 2-thienylacetyl chloride, obtainable by treatment of 2-thienylacetic acid [Ernst, Berichte, 19 (1886) 3281] with thionyl chloride in a conventional manner. The 2-thienylacetyl chloride is then reacted with 7- aminocephalosporanic acid and then converted to the sodium salt using sodium hydroxide.

brand name

Keflin (Lilly); Seffin (GlaxoSmithKline).

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.

Cephalothin Preparation Products And Raw materials

Preparation Products

Raw materials

CephalothinSupplier

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