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C6048

Sigma-Aldrich

Cefmetazole sodium salt

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About This Item

Linear Formula:
C15H16N7O5S3Na
CAS Number:
56796-39-5
Molecular Weight:
493.52
MDL number:
MFCD00214260
UNSPSC Code:
51282205
PubChem Substance ID:
24278328
NACRES:
NA.85

form

powder

shelf life

limited shelf life, expiry date on the label

solubility

H2O: 50 mg/mL

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

Mode of action

cell wall synthesis | interferes

storage temp.

2-8°C

SMILES string

[Na+].[H][C@]12SCC(CSc3nnnn3C)=C(N1C(=O)[C@]2(NC(=O)CSCC#N)OC)C([O-])=O

InChI

1S/C15H17N7O5S3.Na/c1-21-14(18-19-20-21)30-6-8-5-29-13-15(27-2,17-9(23)7-28-4-3-16)12(26)22(13)10(8)11(24)25;/h13H,4-7H2,1-2H3,(H,17,23)(H,24,25);/q;+1/p-1/t13-,15+;/m1./s1

InChI key

BITQGIOJQWZUPL-PBCQUBLHSA-M

General description

Chemical structure: ß-lactam

Application

Cefmetazole is used to study the effect of expression, binding, and inhibition of penicillin-binding proteins (PDPs) other than PBP2 on bacterial cell wall mucopeptide synthesis. Cefmetazole is used to study protein mediated transport of antibiotics.

Biochem/physiol Actions

Cefmetazole disrupts the synthesis of the peptidoglycan layer of bacterial cell walls which is responsible for cell wall structural integrity. Peptidoglycan synthesis is facilitated by transpeptidases known as penicillin-binding proteins (PBPs). PBPs bind to the D-Ala-D-Ala at the end of muropeptides (peptidoglycan precursors) to crosslink the peptidoglycan. Cefmetazole mimics the D-Ala-D-Ala site, thereby competitively inhibiting PBP crosslinking of peptidoglycan. It is effective against both Gram-positive and Gram-negative bacteria.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

Keep container tightly closed in a dry and well-ventilated place. Hygroscopic Handle and store under inert gas.

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

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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Shin Fujita et al.
Archives of surgery (Chicago, Ill. : 1960), 142(7), 657-661 (2007-07-20)
Use of prophylactic antibiotics in elective colorectal surgery is essential. Although single-dose prophylactic antibiotics are recommended, the efficacy of single-dose cephalosporin without metronidazole and oral antibiotics is not fully proven. We conducted a multicenter, randomized trial of a single dose
Masato Tomita et al.
Modern rheumatology, 17(5), 409-412 (2007-10-12)
Infection is one of the most serious complications after artificial arthroplasty. In order to establish the effective prevention for after operative infection, we measured the serum and bone marrow blood cefmetazole (CMZ) concentration time dependently (1 g CMZ, one shot).
Hirotoshi Okumura et al.
Toxicological sciences : an official journal of the Society of Toxicology, 97(2), 533-538 (2007-03-08)
The liver of a chimeric urokinase-type plasminogen activator (uPA)(+/+)/severe combined immunodeficient (SCID) mouse line recently established in Japan could be replaced by more than 80% with human hepatocytes. We previously reported that the chimeric mice with humanized liver could be
Junzo Shimizu et al.
Surgery today, 40(10), 954-957 (2010-09-28)
Postoperative antimicrobial therapy is generally administered as standard prophylaxis against postoperative infection, despite a lack of sufficient evidence for its usefulness. This study was a phase II study to evaluate the necessity of postoperative antibiotic prophylaxis in patients undergoing a
Xing-Yi Zhang et al.
Zhonghua nei ke za zhi, 50(4), 295-298 (2011-05-24)
To evaluate the efficacy and safety of intravenous cefmetazole in the treatment of patients with aspiration pneumonia. A multicenter, prospective and open-labeled trial was conducted. A total of 1522 patients were enrolled at the beginning, and only 1324 were evaluated
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