sodium (6R,7R)-7-[(2R)-2-hydroxy-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: 131111
• Molecular Formular: C18H17N6NaO5S2
• Molecular Mass: 484.48455
• Monoisotopic Mass: 484.05995396
• SMILES: Cn1c(nnn1)SCC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)[C@@H](c2ccccc2)O)SC1)C(=O)[O-].[Na+]
• Canonical SMILES: O[C@@H](C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)[O-])CSc1nnnn1C)c1ccccc1.[Na+]
• InChI: InChI=1S/C18H18N6O5S2.Na/c1-23-18(20-21-22-23)31-8-10-7-30-16-11(15(27)24(16)12(10)17(28)29)19-14(26)13(25)9-5-3-2-4-6-9;/h2-6,11,13,16,25H,7-8H2,1H3,(H,19,26)(H,28,29);/q;+1/p-1/t11-,13-,16-;/m1./s1
• InChIKey: OJMNTWPPFNMOCJ-CFOLLTDRSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (6R,7R)-7-[(2R)-2-hydroxy-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 cefamandole(1-)
• Synonyms: (6R,7R)-7-[[(2R)-2-Hydroxy-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; Sodium Cefamandole; Cefamandole Sodium Salt; Cefamandole sodium salt

Database IDs

• CAS Number: 30034-03-8
• EC Number: 250-009-0
• MDL Number: MFCD07793339
• PubChem SID: 24892939; 162225389
• PubChem CID: 23672568

CALCULATED PROPERTIES

• Acid pKa: 3.3241954
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): -2.132789
• LogD (pH = 7.4): -3.3938322
• Log P: 0.027085615
• Molar Refractivity: 137.4826 cm^3
• Polarizability: 43.246162 Å^3
• Polar Surface Area: 153.37 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: White to Off-White Solid
• Melting Point: >160°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer
• 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

DETAILS

Sigma Aldrich - C7145

Application
Cefamandole is used to study antibiotic resistance, the effects of expression and inhibition of penicillin-binding proteins, and the cooperation of antibiotics with host defence mechanisms 1,2.
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, a cephalosporin antibiotic, disrupts the synthesis of the peptidoglycan layer of bacterial cell walls. As Cefamandole is broken down in the body, it releases free N-methylthiotetrazole, which can cause hypoprothrombinemia 3.

Toronto Research Chemicals - C237500

Broad-spectrum semi-synthetic cephalosporin antibiotic.

REFERENCES

• Wick, W.E., et al.: Antimicrob. Agents Chemother., 1, 221 (1972)
• Russel, A.D, et al.: J. Antimicrob. Chemother., 1, 97 (1972)
• Bishara, R.H., et al.: Anal. Profiles Drug Subs., 9, 125 (1972)