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Methicillin Sodium Salt

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Methicillin Sodium Salt Basic information

Product Name:
Methicillin Sodium Salt
Synonyms:
  • Methicillin sodium salt
  • Sodium (2,6-dimethoxyphenyl)penicillin, Sodium methicillin
  • (2S,5R,6R)-6-[(2,6-Dimethoxybenzoyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid sodium salt
  • 6α-[(2,6-Dimethoxybenzoyl)amino]penicillanic acid sodium salt
  • Sodium (2,6-dimethoxyphenyl)penicillin
  • Sodium methicillin
  • Meticillin sodium salt
  • meticillin sodium
CAS:
132-92-3
MF:
C17H19N2NaO6S
MW:
402.39733
EINECS:
205-083-9
Product Categories:
  • Chiral Reagents
  • Heterocycles
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Sulfur & Selenium Compounds
  • STAPHCILLIN
Mol File:
132-92-3.mol
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Methicillin Sodium Salt Chemical Properties

Melting point:
196-197℃
Boiling point:
640℃
Flash point:
>110°(230°F)
storage temp. 
2-8°C
solubility 
DMSO (Slightly), Methanol (Slightly), Water (Slightly)
form 
powder
color 
white to off-white
Water Solubility 
Slightly soluble in acetone. Soluble in ethanol or water
Sensitive 
Light Sensitive
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Safety Information

Hazard Codes 
Xn
Risk Statements 
36/37/38-42/43
Safety Statements 
26-36
WGK Germany 
2
RTECS 
XH8950000
Toxicity
LD50 oral in mouse: > 4gm/kg
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Methicillin Sodium Salt Usage And Synthesis

Description

Methicillin is a semisynthetic penicillin antibiotic that can inhibit bacterial cell wall synthesis. It can be used to study methicillin-resistance in S. aureus.

Uses

Semi-synthetic antibiotic related to Penicillin. Antimicrobial.

Uses

antibacterial

Uses

Targets primarily the cell wall of Gram-positive organisms especially Staphylococcus aureus. Methicillin is used to study bacterium susceptibility, and to inhibit cell-wall synthesis. PBP's are enzymes which catalyze a pentaglycine crosslink between alanine and lysine residues providing additional strength to the cell wall. Without a pentaglycine crosslink, the integrity of the cell wall is severely compromised and ultimately leads to cell lysis and death. Methicillin Sodium Salt is inactivated by gastric acid so it is given to cells by other means in which gastric acid is not present in vitro.

Definition

ChEBI: Methicillin sodium is an organic sodium salt. It contains a methicillin(1-).

brand name

Staphcillin (Apothecon).

Clinical Use

During 1960, methicillin sodium, 2,6-dimethoxyphenylpenicillinsodium (Staphcillin), the second penicillin produced asa result of the research that developed synthetic analogs, wasintroduced for medicinal use.
Methicillin sodium is particularly resistant to inactivationby the penicillinase found in staphylococci and somewhatmore resistant than penicillin G to penicillinase fromBacillus cereus.

in vitro

similar to other β-lactam antibiotics, meticillin acts via inhibiting the synthesis of bacterial cell walls. meticillin can block the cross-linkage between the linear peptidoglycan polymer chains by binding to and competitively inhibiting the transpeptidase enzyme or penicillin-binding proteins [1].

in vivo

in a previous animal study, the treatment with methicillin or gentamicin or both was started 3 days after infection to a experimental mouse model of foreign body infection. results found that the treatment showed a significant effect, demonstrated as reduction of bacteria on the foreign body, for all three regimens with a reduction of up to 2 log units, but there was no synergism. however, the actual efficacy of the treatment was poor, though the local methicillin concentrations was greater than the mic for at least 72 h [2].

References

[1] https://en. wikipedia.org/wiki/meticillin
[2] espersen f, frimodt-m ller n, corneliussen l, riber u, rosdahl vt, skinh j p. effect of treatment with methicillin and gentamicin in a new experimental mouse model of foreign body infection. antimicrob agents chemother. 1994 sep;38(9):2047-53.

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