sodium (6R,7S)-7-{2-[(cyanomethyl)sulfanyl]acetamido}-7-methoxy-3-{[(1-methyl-1H-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

• ChemBase ID: 155518
• Molecular Formular: C15H16N7NaO5S3
• Molecular Mass: 493.51621
• Monoisotopic Mass: 493.02727393
• SMILES: Cn1c(nnn1)SCC1=C(N2[C@@H]([C@@](C2=O)(NC(=O)CSCC#N)OC)SC1)C(=O)[O-].[Na+]
• Canonical SMILES: N#CCSCC(=O)N[C@]1(OC)C(=O)N2[C@@H]1SCC(=C2C(=O)[O-])CSc1nnnn1C.[Na+]
• InChI: 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
• InChIKey: BITQGIOJQWZUPL-PBCQUBLHSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (6R,7S)-7-{2-[(cyanomethyl)sulfanyl]acetamido}-7-methoxy-3-{[(1-methyl-1H-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• IUPAC Traditional name: sodium cefmetazole(1-)
• Synonyms: Cefmetazole sodium salt

Database IDs

• CAS Number: 56796-39-5
• MDL Number: MFCD00214260
• PubChem SID: 24278328; 162249656
• PubChem CID: 23666711

CALCULATED PROPERTIES

• Acid pKa: 3.3825634
• H Acceptors: 9
• H Donor: 1
• LogD (pH = 5.5): -2.7527611
• LogD (pH = 7.4): -4.0735326
• Log P: -0.6482912
• Molar Refractivity: 135.4078 cm^3
• Polarizability: 42.302906 Å^3
• Polar Surface Area: 166.16 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 2
• Risk Statements: 36/37/38-42/43
• Safety Statements: 26-36
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H315-H317-H319-H334-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338-P342 + P311
• Storage Temperature: 2-8°C

Product Information

• Shelf Life: (limited shelf life, expiry date on the label)
• Linear Formula: C15H16N7O5S3Na

DETAILS

Sigma Aldrich - C6048

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 .
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.
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.