sodium (6R,7R)-7-[(2R)-2-(formyloxy)-2-phenylacetamido]-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: 104170
• Molecular Formular: C19H17N6NaO6S2
• Molecular Mass: 512.49465
• Monoisotopic Mass: 512.05486858
• SMILES: [Na+].O=C1N2C(=C(CS[C@@H]2[C@@H]1NC(=O)[C@H](OC=O)c1ccccc1)CSc1nnnn1C)C(=O)[O-]
• Canonical SMILES: O=CO[C@@H](C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)[O-])CSc1nnnn1C)c1ccccc1.[Na+]
• InChI: InChI=1S/C19H18N6O6S2.Na/c1-24-19(21-22-23-24)33-8-11-7-32-17-12(16(28)25(17)13(11)18(29)30)20-15(27)14(31-9-26)10-5-3-2-4-6-10;/h2-6,9,12,14,17H,7-8H2,1H3,(H,20,27)(H,29,30);/q;+1/p-1/t12-,14-,17-;/m1./s1
• InChIKey: ICZOIXFFVKYXOM-YCLOEFEOSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (6R,7R)-7-[(2R)-2-(formyloxy)-2-phenylacetamido]-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 (6R,7R)-7-[(2R)-2-(formyloxy)-2-phenylacetamido]-3-{[(1-methyl-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• Synonyms: (6R,7R)-7-[[(2R)-2-(Formyloxy)-2-phenylacetyl]amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid Sodium Salt; Bergacef; Cedol; Cefam; Cefamandole Formate Sodium; Cefiran; Cemado; Cemandil; Cephamandole Nafate; Fado; Kefadol; Kefandol; Lampomandol; Mandokef; Mandol; Mandolsan; Neocefal; O-Formylcefamandole Sodium; Pavecef; NSC 299588; CEFAMANDOLE NAFATE; Cefamandole formate sodium salt; Cefamandole nafate

Database IDs

• CAS Number: 42540-40-9
• EC Number: 255-877-4
• MDL Number: MFCD00864877
• PubChem SID: 24892951; 162092446
• PubChem CID: 23665731

CALCULATED PROPERTIES

• Acid pKa: 3.299581
• H Acceptors: 8
• H Donor: 1
• LogD (pH = 5.5): -1.7637454
• LogD (pH = 7.4): -3.0067348
• Log P: 0.41951233
• Molar Refractivity: 142.1436 cm^3
• Polarizability: 45.281013 Å^3
• Polar Surface Area: 159.44 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid
• Melting Point: 190-193°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere
• RTECS: XI0380000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• 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
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Product Information

• Purity: ~95%
• Linear Formula: C19H17N6O6S2Na

DETAILS

MP Biomedicals - 02154945

(cefamandole formate sodium salt) Contains approx. 5% sodium carbonate.

Sigma Aldrich - C7270

Physical form
sodium carbonate: approx. 5%
Application
Cefamandole is used to study the effects of expression and inhibition of PBP 2A and other penicillin-binding proteins (PDPs) on bacterial cell wall mucopeptide synthesis.
Biochem/physiol Actions
Cefamandole nafate inhibits bacterial cell wall synthesis by inhibiting PBP 2A and other penicillin-binding proteins. Cefamandole nafate has been shown to be rapidly converted to cefamandolein bacteriological media 1.

Toronto Research Chemicals - C237505

Antibacterial.

REFERENCES

• Taha, M., et al.: Bioorg. Med. Chem., 16, 1218 (2008)
• Gohil, V., et al.: Nat. Biotechnol., 28, 249 (2008)