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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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Yukio Kato et al.
Drug metabolism and disposition: the biological fate of chemicals, 36(6), 1088-1096 (2008-03-15)
In the present study, we attempted to identify the membrane permeation process(es) primarily involved in the molecular-weight-dependent biliary excretion of beta-lactam antibiotics. A search of the literature indicated that the molecular weight threshold operates mainly in the transport process across
Chang-I Ho et al.
Journal of the Chinese Medical Association : JCMA, 71(12), 643-645 (2008-12-31)
A 73-year-old woman with leukemia presented with urinary tract infection, splenic abscess, and a renal mass. Both urine culture and pus culture of the splenic abscess yielded Klebsiella pneumoniae. Percutaneous biopsy of the renal mass confirmed the diagnosis of xanthogranulomatous
Minako Kobayashi et al.
Surgery today, 40(4), 326-333 (2010-03-27)
To evaluate the effectiveness of our surgical site infection (SSI) preventive strategies for rectal cancer patients. We compared the incidences and risk factors for SSI before (1990-1999) and after the implementation of our SSI prevention policies (2002-2006). A total of
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
Asako Doi et al.
International journal of infectious diseases : IJID : official publication of the International Society for Infectious Diseases, 17(3), e159-e163 (2012-11-13)
Urinary tract infections (UTIs) caused by extended-spectrum beta-lactamase (ESBL)-producing Enterobacteriaceae are on the increase. Although cefmetazole is stable in vitro against the hydrolyzing activity of ESBLs, no clinical study has ever evaluated its role in infections caused by these organisms.
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