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

• ChemBase ID: 163940
• Molecular Formular: C22H27N9O7S2
• Molecular Mass: 593.63588
• Monoisotopic Mass: 593.14748625
• SMILES: [C@H]1(C(=O)N2[C@@H]1SC=C(C2C(=O)OCOC(=O)C(C)(C)C)Cn1nnc(n1)C)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]1SC=C(C2C(=O)OCOC(=O)C(C)(C)C)Cn1nnc(n1)C
• InChI: InChI=1S/C22H27N9O7S2/c1-10-26-29-30(27-10)6-11-7-39-18-14(25-16(32)13(28-36-5)12-8-40-21(23)24-12)17(33)31(18)15(11)19(34)37-9-38-20(35)22(2,3)4/h7-8,14-15,18H,6,9H2,1-5H3,(H2,23,24)(H,25,32)/b28-13-/t14-,15?,18-/m1/s1
• InChIKey: OXSIJKGBMZQPQF-QWIQBTIHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-[(5-methyl-2H-1,2,3,4-tetrazol-2-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carbonyloxy]methyl 2,2-dimethylpropanoate
• IUPAC Traditional name: [(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-[(5-methyl-1,2,3,4-tetrazol-2-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carbonyloxy]methyl 2,2-dimethylpropanoate
• Synonyms: (6R,7R)-7-[[(2Z)-(2-Amino-4-thiazolyl)(methoxyimino)acetyl]amino]-3-[(5-methyl-2H-tetrazol-2-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic Acid (2,2-Dimethyl-1-oxopropoxy)methyl Ester; T 2588A; Δ2-Cefteram Pivoxil, 1:1 mixture with Cefteram Pivoxil (C244300)

Database IDs

• CAS Number: 104712-44-9
• PubChem SID: 162258075
• PubChem CID: 71314623

CALCULATED PROPERTIES

• Acid pKa: 10.744815
• H Acceptors: 11
• H Donor: 2
• LogD (pH = 5.5): 1.4278198
• LogD (pH = 7.4): 1.4430044
• Log P: 1.4433832
• Molar Refractivity: 152.9862 cm^3
• Polarizability: 54.1109 Å^3
• Polar Surface Area: 206.11 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 114-118°C

Safety Information

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

DETAILS

Toronto Research Chemicals - C244310

A a minor metabolite of Cefteram Pivoxil, a third-generation oral cephalosporin.

REFERENCES

• Saab, A.N., et al.: J. Pharm. Sci., 79, 802 (1990)