[(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(2H3)methoxyimino]acetamido]-3-[(Z)-2-(4-methyl-1,3-thiazol-5-yl)ethenyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carbonyloxy]methyl 2,2-dimethylpropanoate

• ChemBase ID: 163902
• Molecular Formular: C25H28N6O7S3
• Molecular Mass: 620.72082
• Monoisotopic Mass: 620.11816027
• SMILES: [C@H]1(C(=O)N2[C@@H]1SCC(=C2C(=O)OCOC(=O)C(C)(C)C)/C=C\c1scnc1C)NC(=O)/C(=N\OC)/c1csc(n1)N
• Canonical SMILES: CO/N=C(/c1csc(n1)N)\C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)OCOC(=O)C(C)(C)C)/C=C\c1scnc1C
• InChI: InChI=1S/C25H28N6O7S3/c1-12-15(41-10-27-12)7-6-13-8-39-21-17(29-19(32)16(30-36-5)14-9-40-24(26)28-14)20(33)31(21)18(13)22(34)37-11-38-23(35)25(2,3)4/h6-7,9-10,17,21H,8,11H2,1-5H3,(H2,26,28)(H,29,32)/b7-6-,30-16-/t17-,21-/m1/s1
• InChIKey: AFZFFLVORLEPPO-UVYJNCLZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(^2H₃)methoxyimino]acetamido]-3-[(Z)-2-(4-methyl-1,3-thiazol-5-yl)ethenyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carbonyloxy]methyl 2,2-dimethylpropanoate
• IUPAC Traditional name: [(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(^2H₃)methoxyimino]acetamido]-3-[(Z)-2-(4-methyl-1,3-thiazol-5-yl)ethenyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carbonyloxy]methyl 2,2-dimethylpropanoate
• Synonyms: (6R,7R)-7-[[(2Z)-(2-Amino-4-thiazolyl)(methoxy-d3)imino)acetyl]amino]-3-[(1Z)-2-(4-methyl-5-thiazolyl)ethenyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid Pivaloyloxymethyl Ester; Cefditoren-d3 Pivaloyloxymethyl Ester; Cefditorin-d3; ME 1207-d3; Meiact-d3; Spectracef-d3; Cefditoren Pivoxil-d3

Database IDs

• PubChem SID: 162258037
• PubChem CID: 71314603

CALCULATED PROPERTIES

• Acid pKa: 10.819918
• H Acceptors: 9
• H Donor: 2
• LogD (pH = 5.5): 2.7985902
• LogD (pH = 7.4): 2.8157759
• Log P: 2.8161485
• Molar Refractivity: 152.9045 cm^3
• Polarizability: 58.370113 Å^3
• Polar Surface Area: 175.4 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C242703

Labelled Cefditoren Pivoxil (C242700). An antibacterial. Third generation cephalosporin.

REFERENCES

• Sakagami, K., et al.: J. Antibiot., 43, 1047 (1990)
• Felmingham, D., Drugs Exp. Clin. Res., 20, 127 (1990)
• Iwai, N., et al.: Japan J. Antibiot., 47, 181 (1994)