sodium (6R,7R)-7-[(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-(4-hydroxyphenyl)acetamido]-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: 106176
• Molecular Formular: C25H26N9NaO8S2
• Molecular Mass: 667.64921
• Monoisotopic Mass: 667.12434512
• SMILES: [Na+].O=C1N2C(=C(CS[C@@H]2[C@@H]1NC(=O)[C@@H](c1ccc(O)cc1)NC(=O)N1C(=O)C(=O)N(CC)CC1)CSc1nnnn1C)C(=O)[O-]
• Canonical SMILES: CCN1CCN(C(=O)C1=O)C(=O)N[C@H](c1ccc(cc1)O)C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)[O-])CSc1nnnn1C.[Na+]
• InChI: InChI=1S/C25H27N9O8S2.Na/c1-3-32-8-9-33(21(39)20(32)38)24(42)27-15(12-4-6-14(35)7-5-12)18(36)26-16-19(37)34-17(23(40)41)13(10-43-22(16)34)11-44-25-28-29-30-31(25)2;/h4-7,15-16,22,35H,3,8-11H2,1-2H3,(H,26,36)(H,27,42)(H,40,41);/q;+1/p-1/t15-,16-,22-;/m1./s1
• InChIKey: NCFTXMQPRQZFMZ-WERGMSTESA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (6R,7R)-7-[(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-(4-hydroxyphenyl)acetamido]-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-(4-ethyl-2,3-dioxopiperazine-1-carbonylamino)-2-(4-hydroxyphenyl)acetamido]-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: Cefoperazone sodium salt; (6R,7R)-7-[[(2R)-2-[[(4-Ethyl-2,3-dioxo-1-piperazinyl)carbonyl]amino]-2-(4-hydroxyphenyl)acetyl]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; Bioperazone; CP 52640-2; Cefazone; Cefobine; Cefobis; Cefogram; Cefomycin; T 1551; Tomabef; Cefoperazone Sodium Salt; CEFOPERAZONE SODIUM SALT U.S.P.; 头孢哌酮 钠盐

Database IDs

• CAS Number: 62893-20-3
• EC Number: 263-751-5
• MDL Number: MFCD07793331
• Beilstein Number: 4902135
• PubChem SID: 24892686; 162094238
• PubChem CID: 23663974

CALCULATED PROPERTIES

• Acid pKa: 3.3837204
• H Acceptors: 11
• H Donor: 3
• LogD (pH = 5.5): -3.0036721
• LogD (pH = 7.4): -4.3111243
• Log P: -0.9004894
• Molar Refractivity: 179.8942 cm^3
• Polarizability: 59.20946 Å^3
• Polar Surface Area: 223.09 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble50 mg/mL, clear, faintly yellow; Water
• Apperance: White to Off-White Solid
• Melting Point: 200-202°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere
• RTECS: XI0374000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 2
• Risk Statements: 42/43
• Safety Statements: 22-36/37
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H317-H334
• GHS Precautionary statements: P261-P280-P342 + P311
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥90% (HPLC); 870-1015 μg/mg (anhydrous basis)
• Grade: USP
• Impurities: ≤5% water
• Empirical Formula (Hill Notation): C25H26N9NaO8S2

DETAILS

Sigma Aldrich - C4292

Application
Cefoperazone is used to study drug-protein binding 1,2, expression and inhibition of penicillin-binding proteins (PBPs) during cell wall synthesis.
Cefoperazone is used to study the effect of expression, binding, and inhibition of penicillin-binding proteins (PBPs) other than PBP2 on bacterial cell wall mucopeptide synthesis.
Biochem/physiol Actions
Cefoperazone exerts its bactericidal effect by inhibiting the bacterial cell wall synthesis. Cefoperazone has a dual excretory pattern, primarily via the biliary system and secondarily via the kidney 2.

Toronto Research Chemicals - C242900

Broad spectrum third generation cephalosporin antibiotic. An antibacterial.

REFERENCES

• Borobio, M.V., et al.: Antimicrob. Agents Chemother., 17, 129 (1980)
• Brogden, R.N., et al.: Drugs, 22, 423 (1980)