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

• ChemBase ID: 163927
• Molecular Formular: C15H17N5O6S2
• Molecular Mass: 427.45538
• Monoisotopic Mass: 427.06202529
• SMILES: S1[C@H]2N(C(=C(C1)COC)C(=O)O)C(=O)[C@H]2NC(=O)/C(=N\OC)/c1nc(sc1)N
• Canonical SMILES: CO/N=C(/c1csc(n1)N)\C(=O)N[C@H]1[C@H]2SCC(=C(N2C1=O)C(=O)O)COC
• InChI: InChI=1S/C15H17N5O6S2/c1-25-3-6-4-27-13-9(12(22)20(13)10(6)14(23)24)18-11(21)8(19-26-2)7-5-28-15(16)17-7/h5,9,13H,3-4H2,1-2H3,(H2,16,17)(H,18,21)(H,23,24)/b19-8-/t9-,13-/m1/s1
• InChIKey: WYUSVOMTXWRGEK-HBWVYFAYSA-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-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: (6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(^2H₃)methoxyimino]acetamido]-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• Synonyms: (6R,7R)-7-[[(2Z)-2-(2-Amino-4-thiazolyl)-2-(methoxyimino-d3)acetyl]amino]-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; Cefpodoxime-d3; R 3763-d3; Cefpodoxime-d3 Acid

Database IDs

• PubChem SID: 162258062
• PubChem CID: 46780202

CALCULATED PROPERTIES

• Acid pKa: 3.217438
• H Acceptors: 9
• H Donor: 3
• LogD (pH = 5.5): -2.7401698
• LogD (pH = 7.4): -3.9569473
• Log P: -1.6657981
• Molar Refractivity: 100.708 cm^3
• Polarizability: 38.09913 Å^3
• Polar Surface Area: 156.44 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: White to Off-White Solid
• Melting Point: >235°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - C243852

A labelled metabolite of Cefpodoxime Proxetil (C243860). An antibacterial.

REFERENCES

• Fujimoto, K., et al.: J. Antibiot., 40, 370 (1987)
• Utsui, Y., et al.: Antimicrob. Agents Chemother., 31, 1085 (1987)