(6R,7R)-7-[2-(3,5-dichloro-4-oxo-1,4-dihydropyridin-1-yl)acetamido]-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• ChemBase ID: 163871
• Molecular Formular: C18H15Cl2N5O5S3
• Molecular Mass: 548.4432
• Monoisotopic Mass: 546.96123697
• SMILES: S1[C@H]2N(C(=C(C1)CSc1nnc(s1)C)C(=O)O)C(=O)[C@H]2NC(=O)Cn1cc(c(=O)c(c1)Cl)Cl
• Canonical SMILES: Cc1nnc(s1)SCC1=C(C(=O)O)N2[C@H](SC1)[C@@H](C2=O)NC(=O)Cn1cc(Cl)c(=O)c(c1)Cl
• InChI: InChI=1S/C18H15Cl2N5O5S3/c1-7-22-23-18(33-7)32-6-8-5-31-16-12(15(28)25(16)13(8)17(29)30)21-11(26)4-24-2-9(19)14(27)10(20)3-24/h2-3,12,16H,4-6H2,1H3,(H,21,26)(H,29,30)/t12-,16-/m1/s1
• InChIKey: VTLCNEGVSVJLDN-MLGOLLRUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-7-[2-(3,5-dichloro-4-oxo-1,4-dihydropyridin-1-yl)acetamido]-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: cefazedone
• Synonyms: (6R,7R)-7-[[2-(3,5-Dichloro-4-oxo-1(4H)-pyridinyl)acetyl]amino]-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; (6R-trans)-Cefazedone; Refosporen; Cefazedone

Database IDs

• CAS Number: 56187-47-4
• PubChem SID: 162258006
• PubChem CID: 71736

CALCULATED PROPERTIES

• Acid pKa: 3.1909127
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): -1.1804726
• LogD (pH = 7.4): -2.3414257
• Log P: 1.1062491
• Molar Refractivity: 128.8153 cm^3
• Polarizability: 48.121178 Å^3
• Polar Surface Area: 132.8 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C241500

Semi-synthetic cephalosporin antibiotic. Antibacterial.

REFERENCES

• Vander Stichele, R., et al.: Br. J. Clin. Pharmacol., 58, 419 (2004)
• Goossens, H., et al.: Lancet, 365, 579 (2004)
• Ferech, M., et al.: J. Antimicrob. Chemother., 58, 401 (2004)