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

• ChemBase ID: 163907
• Molecular Formular: C20H26ClN5O7S2
• Molecular Mass: 548.03274
• Monoisotopic Mass: 547.09621788
• SMILES: S1[C@H]2N(C(=C(C1)C)C(=O)OCOC(=O)C(C)(C)C)C(=O)[C@H]2NC(=O)/C(=N\OC)/c1csc(n1)N.Cl
• 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.Cl
• InChI: InChI=1S/C20H25N5O7S2.ClH/c1-9-6-33-16-12(23-14(26)11(24-30-5)10-7-34-19(21)22-10)15(27)25(16)13(9)17(28)31-8-32-18(29)20(2,3)4;/h7,12,16H,6,8H2,1-5H3,(H2,21,22)(H,23,26);1H/b24-11-;/t12-,16-;/m1./s1
• InChIKey: XAAOHMIKXULDKJ-IZXJIOGHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carbonyloxy]methyl 2,2-dimethylpropanoate hydrochloride
• IUPAC Traditional name: [(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carbonyloxy]methyl 2,2-dimethylpropanoate hydrochloride
• Synonyms: (6R,7R)-7-[[(2Z)-2-(2-Amino-4-thiazolyl)-2-(methoxyimino)acetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid (2,2-Dimethyl-1-oxopropoxy)methyl Ester; Cefetamet (Pivaloyloxy)methyl Ester; Ceftamet Pivoxil; Cefyl; Ro 15-8075; Cefetamet Pivoxil

Database IDs

• CAS Number: 65243-33-6
• PubChem SID: 162258042
• PubChem CID: 5489410

CALCULATED PROPERTIES

• Acid pKa: 10.942633
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): 2.131545
• LogD (pH = 7.4): 2.14948
• Log P: 2.1498265
• Molar Refractivity: 122.9069 cm^3
• Polarizability: 47.570835 Å^3
• Polar Surface Area: 162.51 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Pale Yellow Solid
• Melting Point: 158-160°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - C242780

Third generation cephalosporin antibiotics. Antibacterial.

REFERENCES

• Thomas, M.G., et al.: Antimicrob. Agents Chemother., 29, 945 (1986)
• Seiler, J., et al.: Toxicol. Lett., 131, 105 (1986)
• Escher, B., et al.: Environ. Sci. Technol., 39, 3090 (1986)