132-92-3 Usage
Description
Sodium 6-(2,6-dimethoxybenzamido)penicillanate, also known as Methicillin, is a semisynthetic penicillin antibiotic derived from the penicillin group. It possesses antimicrobial properties and is particularly effective against Gram-positive bacteria, especially Staphylococcus aureus. Methicillin works by inhibiting bacterial cell wall synthesis, targeting penicillin-binding proteins (PBPs) that catalyze the formation of a pentaglycine crosslink between alanine and lysine residues, which provides additional strength to the cell wall. The absence of this crosslink compromises the cell wall's integrity, leading to cell lysis and death. Methicillin Sodium Salt is inactivated by gastric acid, so it is administered through other means where gastric acid is not present, such as in vitro cell cultures.
Uses
Used in Antimicrobial Applications:
Sodium 6-(2,6-dimethoxybenzamido)penicillanate is used as an antimicrobial agent for targeting the cell wall of Gram-positive organisms, particularly Staphylococcus aureus. It inhibits cell-wall synthesis, leading to cell lysis and death.
Used in Bacterium Susceptibility Studies:
Sodium 6-(2,6-dimethoxybenzamido)penicillanate is used as a research tool for studying methicillin-resistance in S. aureus, helping to understand the mechanisms of resistance and develop new strategies to combat it.
Used in Pharmaceutical Industry:
Sodium 6-(2,6-dimethoxybenzamido)penicillanate is used as an active pharmaceutical ingredient in the development of antibiotics, specifically for treating infections caused by methicillin-sensitive Staphylococcus aureus and other Gram-positive bacteria.
Used in Research and Development:
Sodium 6-(2,6-dimethoxybenzamido)penicillanate is used as a research compound for investigating the mechanisms of action, resistance, and potential applications in the development of new antimicrobial agents.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 132-92-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,3 and 2 respectively; the second part has 2 digits, 9 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 132-92:
(5*1)+(4*3)+(3*2)+(2*9)+(1*2)=43
43 % 10 = 3
So 132-92-3 is a valid CAS Registry Number.
InChI:InChI=1/C17H20N2O6S.Na.H2O/c1-17(2)12(16(22)23)19-14(21)11(15(19)26-17)18-13(20)10-8(24-3)6-5-7-9(10)25-4;;/h5-7,11-12,15H,1-4H3,(H,18,20)(H,22,23);;1H2/q;+1;/p-1/t11-,12+,15-;;/m1../s1