(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-[(E)-2-{[5,6-dioxo-4-(2-oxoethyl)-1,4,5,6-tetrahydro-1,2,4-triazin-3-yl]sulfanyl}ethenyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• ChemBase ID: 163943
• Molecular Formular: C20H18N8O8S3
• Molecular Mass: 594.60072
• Monoisotopic Mass: 594.04097258
• SMILES: [C@H]1(C(=O)N2[C@@H]1SCC(=C2C(=O)O)/C=C/Sc1n(c(=O)c(=O)[nH]n1)CC=O)NC(=O)/C(=N\OC)/c1nc(sc1)N
• Canonical SMILES: O=CCn1c(S/C=C/C2=C(C(=O)O)N3[C@H](SC2)[C@@H](C3=O)NC(=O)/C(=N\OC)/c2csc(n2)N)n[nH]c(=O)c1=O
• InChI: InChI=1S/C20H18N8O8S3/c1-36-26-10(9-7-39-19(21)22-9)13(30)23-11-15(32)28-12(18(34)35)8(6-38-17(11)28)2-5-37-20-25-24-14(31)16(33)27(20)3-4-29/h2,4-5,7,11,17H,3,6H2,1H3,(H2,21,22)(H,23,30)(H,24,31)(H,34,35)/b5-2+,26-10-/t11-,17-/m1/s1
• InChIKey: WJXAHFZIHLTPFR-JLRJEBFFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-[(E)-2-{[5,6-dioxo-4-(2-oxoethyl)-1,4,5,6-tetrahydro-1,2,4-triazin-3-yl]sulfanyl}ethenyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: ceftiolene
• Synonyms: (6R,7R)-7-[[(2Z)-(2-Amino-4-thiazolyl)(methoxyimino)acetyl]amino]-8-oxo-3-[(1E)-2-[[1,4,5,6-tetrahydro-5,6-dioxo-4-(2-oxoethyl)-1,2,4-triazin-3-yl]thio]ethenyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; Cefathiolene; Cefatiolene; RP 42980; [6R-[3(E),6α,7β(Z)]]-7-[[(2-Amino-4-thiazolyl)(methoxyimino)acetyl]amino]-8-oxo-3-[2-[[1,4,5,6-tetrahydro-5,6-dioxo-4-(2-oxoethyl)-1,2,4-triazin-3-yl]thio]ethenyl]-5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; Ceftiolene

Database IDs

• CAS Number: 77360-52-2
• PubChem SID: 162258078
• PubChem CID: 6537430

CALCULATED PROPERTIES

• Acid pKa: 3.2393026
• H Acceptors: 12
• H Donor: 4
• LogD (pH = 5.5): -3.5211868
• LogD (pH = 7.4): -5.453847
• Log P: -2.404968
• Molar Refractivity: 138.8658 cm^3
• Polarizability: 52.129494 Å^3
• Polar Surface Area: 226.05 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C244750

A third-generation cephalosporin; β-lactam antibiotic.

REFERENCES

• Williamson, R. et al.: J. Antimicrob. Chemother., 14, 581 (1984)
• Duval, J. et al.: Pathol. Biol., 31, 357 (1984)