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

• ChemBase ID: 104171
• Molecular Formular: C14H13N8NaO4S3
• Molecular Mass: 476.48899
• Monoisotopic Mass: 476.01195822
• SMILES: [Na+].O=C1N2C(=C(CS[C@@H]2[C@@H]1NC(=O)Cn1nnnc1)CSc1nnc(s1)C)C(=O)[O-]
• Canonical SMILES: O=C(N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)[O-])CSc1nnc(s1)C)Cn1cnnn1.[Na+]
• InChI: InChI=1S/C14H14N8O4S3.Na/c1-6-17-18-14(29-6)28-4-7-3-27-12-9(11(24)22(12)10(7)13(25)26)16-8(23)2-21-5-15-19-20-21;/h5,9,12H,2-4H2,1H3,(H,16,23)(H,25,26);/q;+1/p-1/t9-,12-;/m1./s1
• InChIKey: FLKYBGKDCCEQQM-WYUVZMMLSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (6R,7R)-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-7-[2-(1H-1,2,3,4-tetrazol-1-yl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• IUPAC Traditional name: sodium cefazolin(1-)
• Synonyms: Sodium Cephazolin; SKF-41558; Cefazolin Sodium Salt; (6R,7R)-3-[[(5-Methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-7-[(1H-tetrazol-1-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid Sodium Salt; Atirin; Azolin; Biazolina; Bor-Cefazol; Cefacidal; Cefamedin; Cefazina; Cefazoliin; Cefazolin Sodium; Cefazolin sodium salt; Acef; Cefazil; Kefzol; Totacef; Zolicef; CEFAZOLIN; 头孢唑啉 钠盐

Database IDs

• CAS Number: 27164-46-1
• EC Number: 248-278-4
• MDL Number: MFCD00056883
• Beilstein Number: 3585038
• PubChem SID: 24278318; 162091442
• PubChem CID: 23675322

CALCULATED PROPERTIES

• Acid pKa: 3.0265586
• H Acceptors: 9
• H Donor: 1
• LogD (pH = 5.5): -3.9590034
• LogD (pH = 7.4): -4.991068
• Log P: -1.5194101
• Molar Refractivity: 130.6933 cm^3
• Polarizability: 39.74596 Å^3
• Polar Surface Area: 158.92 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Ethanol; H2O: soluble50 mg/mL, clear, colorless; Methanol; Water
• Apperance: White to Off-White Solid
• Melting Point: 170-172°C (dec)

Safety Information

• Storage Condition: -20°C Freezer; 2-8°C
• RTECS: XI0390000
• 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
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (HPLC); 89.1-110.1%
• Salt Data: Na+
• Impurities: ≤16% water
• Empirical Formula (Hill Notation): C14H13N8NaO4S3
• Classification: Rare Derivatives of Natural Compounds

DETAILS

MP Biomedicals - 02154946

Sodium Salt

Sigma Aldrich - C5020

Biochem/physiol Actions
Used to study the effect of expression, binding and inhibition of penicillin-binding proteins, especially PBP2 and PBP4 on bacterial cell wall mucopeptide synthesis.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Toronto Research Chemicals - C242500

Semi-synthetic antibiotic derived from 7-amino-cephalosporanic acid. An antibacterial.

REFERENCES

• Kozatani, et al.: Chem. Pharm. Bull., 20, 1105 (1972)
• Birkhead, H.A., et al.: J. Infect. Dis., 128, 379 (1972)
• Zappala, A.E., et al.: Anal. Profiles Drug Subs., 4, 1 (1972)