sodium (6R,7R)-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-7-{2-[(1-15N)-1H-1,2,3,4-tetrazol-1-yl](1,2-13C2)acetamido}-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

• ChemBase ID: 163889
• Molecular Formular: C14H13N8NaO4S3
• Molecular Mass: 479.46770857
• Monoisotopic Mass: 479.01570279
• SMILES: S1[C@H]2N(C(=C(C1)CSc1nnc(s1)C)C(=O)[O-])C(=O)[C@H]2N[13C](=O)[13CH2][15n]1nnnc1.[Na+]
• Canonical SMILES: O=[13C](N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)[O-])CSc1nnc(s1)C)[13CH2][15n]1cnnn1.[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/i2+1,8+1,21+1
• InChIKey: FLKYBGKDCCEQQM-HZAGCXHJSA-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-[(1-^1^5N)-1H-1,2,3,4-tetrazol-1-yl](1,2-^1^3C₂)acetamido}-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• IUPAC Traditional name: sodium (6R,7R)-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-7-{2-[(1-^1^5N)-1,2,3,4-tetrazol-1-yl](1,2-^1^3C₂)acetamido}-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• Synonyms: (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-13C2,15N Sodium Salt; Atirin-13C2,15N; Azolin-13C2,15N; Biazolina-13C2,15N; Bor-Cefazol-13C2,15N; Cefacidal-13C2,15N; Cefamedin-13C2,15N; Cefazil-13C2,15N; Cefazina-13C2,15N; Cefazoliin-13C2,15N; Sodium Cephazolin-13C2,15N; Totacef-13C2,15N; Zolicef-13C2,15N; SKF-41558-13C2,15N; Cefazolin-13C2,15N Sodium Salt

Database IDs

• PubChem SID: 162258024
• PubChem CID: 71314594

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

DETAILS

Toronto Research Chemicals - C242502

Labelled Cefazolin (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)