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51454

Sigma-Aldrich

Methicillin sodium salt

≥95% (HPLC)

Synonym(s):

Sodium (2,6-dimethoxyphenyl)penicillin, Sodium methicillin

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About This Item

Empirical Formula (Hill Notation):
C17H19N2NaO6S
CAS Number:
Molecular Weight:
402.40
EC Number:
MDL number:
UNSPSC Code:
51283503
PubChem Substance ID:
NACRES:
NA.85

biological source

synthetic

Quality Level

Assay

≥95% (HPLC)

form

powder

color

white to off-white

antibiotic activity spectrum

Gram-positive bacteria

Mode of action

cell wall synthesis | interferes

storage temp.

2-8°C

SMILES string

[Na+].COc1cccc(OC)c1C(=O)N[C@H]2C3SC(C)(C)[C@@H](N3C2=O)C([O-])=O

InChI

1S/C17H20N2O6S.Na/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);/q;+1/p-1/t11-,12+,15-;/m1./s1

InChI key

MGFZNWDWOKASQZ-UMLIZJHQSA-M

Application

Methicillin is used to study bacterium susceptibility , methicillin-resistance in Staphylococcus aureus , and to inhibit cell-wall synthesis .

Biochem/physiol Actions

Methicillin inhibits cell wall synthesis. In Legionella pneumophila, methicillin causes the formation of membranous lesions through which cytoplasmic contents are lost .

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

Keep container tightly closed in a dry and well-ventilated place.Light sensitive

Pictograms

Health hazardExclamation mark

Signal Word

Danger

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Resp. Sens. 1 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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F G Rodgers et al.
Journal of medical microbiology, 31(1), 37-44 (1990-01-01)
The response of Legionella pneumophila to antibiotics that inhibit cell-wall, protein and DNA synthesis was examined by electronmicroscopy, MIC estimations and viable counts. Ampicillin, cefotaxime, methicillin, erythromycin, rifampicin and ciprofloxacin, each used separately at 20 times their respective MIC values
G L French et al.
The Journal of antimicrobial chemotherapy, 20(4), 599-608 (1987-10-01)
Four-hundred and seventy-six isolates of Staphylococcus aureus from patients in Hong Kong were tested for methicillin-resistance by agar dilution and disc diffusion methods, using heavy inocula. With Mueller-Hinton agar incubated at 30 degrees C for 24 h, 216 (MRSA) isolates
Ann L Bull et al.
Annals of surgery, 256(6), 1089-1092 (2012-07-25)
To compare risks for developing surgical site infection (SSI) due to Staphylococcus aureus when vancomycin is used for antibiotic prophylaxis with risks when a β-lactam antibiotic is administered for prophylaxis. Vancomycin is often used as surgical antibiotic prophylaxis for major
The absence of D-alanine from lipoteichoic acid and wall teichoic acid alters surface charge, enhances autolysis and increases susceptibility to methicillin in Bacillus subtilis.
Jorg Wecke, Kazimierz Madela, et al.
Microbiology, 143, 2953-2960 (1997)
Alex J McCarthy et al.
Veterinary dermatology, 23(4), 267-275 (2012-07-25)
Meticillin-resistant Staphylococcus aureus (MRSA) continues to pose a major threat to human health. In animals, MRSA has become established as a veterinary pathogen in pets and horses; in livestock, it presents a concern for public health as a reservoir that

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