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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:
132-92-3
Molecular Weight:
402.40
EC Number:
205-083-9
MDL number:
MFCD07787409
UNSPSC Code:
51283503
PubChem Substance ID:
329757690
NACRES:
NA.85

biological source

synthetic

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
GHS08,GHS07

Signal Word

Danger

Hazard Statements

H315,H317,H319,H334,H335

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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
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
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
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
View All Related Papers

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