[(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-2-ene-2-carbonyloxy]methyl 2,2-dimethylpropanoate

• ChemBase ID: 163939
• Molecular Formular: C22H27N9O7S2
• Molecular Mass: 593.63588
• Monoisotopic Mass: 593.14748625
• SMILES: [C@H]1(C(=O)N2[C@@H]1SCC(=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]1SCC(=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/h8,14,18H,6-7,9H2,1-5H3,(H2,23,24)(H,25,32)/b28-13-/t14-,18-/m1/s1
• InChIKey: UIYAXIPXULMHAI-JLGRZTKVSA-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-2-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-2-ene-2-carbonyloxy]methyl 2,2-dimethylpropanoate
• Synonyms: Antibiotic T 2588; Ro 19-5248; T 2588; Tomiron; Tomiron 100; Cefteram Pivoxil; (6R,7R)-7-[[(2Z)-2-(2-Amino-4-thiazolyl)-2-(methoxyimino)acetyl]amino]-3-[(5-methyl-2H-tetrazol-2-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid (2,2-Dimethyl-1-oxopropoxy)methyl Ester

Database IDs

• CAS Number: 82547-81-7
• PubChem SID: 162258074
• PubChem CID: 5362114

CALCULATED PROPERTIES

• Acid pKa: 10.731049
• H Acceptors: 11
• H Donor: 2
• LogD (pH = 5.5): 1.7361666
• LogD (pH = 7.4): 1.7515875
• Log P: 1.751976
• Molar Refractivity: 154.2698 cm^3
• Polarizability: 54.10525 Å^3
• Polar Surface Area: 206.11 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 125-128°C

Safety Information

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

DETAILS

Toronto Research Chemicals - C244300

Third generation, orally active cephalosporin antibiotic. Antibacterial.

REFERENCES

• Wise, R., et al.: Antimicrob. Agents Chemother., 29, 1067 (1986)
• Hirai, S., et al.: Jpn. J. Antibiot., 39, 958 (1986)
• Lentz, K., et al.: Int. J. Pharm., 200, 41 (1986)
• Takagi, T., et al.: Mol. Pharmaceutics, 3, 631 (1986)
• Gu, C., et al.: Pharm. Res.,