1-{[(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-2-carboxylato-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-en-3-yl]methyl}-1-methylpyrrolidin-1-ium; ethoxyethane

• ChemBase ID: 163903
• Molecular Formular: C23H34N6O6S2
• Molecular Mass: 554.68266
• Monoisotopic Mass: 554.19812484
• SMILES: S1[C@H]2N(C(C(=C1)C[N+]1(CCCC1)C)C(=O)[O-])C(=O)[C@H]2NC(=O)/C(=N\OC)/c1csc(n1)N.CCOCC
• Canonical SMILES: CO/N=C(/c1csc(n1)N)\C(=O)N[C@@H]1C(=O)N2[C@@H]1SC=C(C2C(=O)[O-])C[N+]1(C)CCCC1.CCOCC
• InChI: InChI=1S/C19H24N6O5S2.C4H10O/c1-25(5-3-4-6-25)7-10-8-31-17-13(16(27)24(17)14(10)18(28)29)22-15(26)12(23-30-2)11-9-32-19(20)21-11;1-3-5-4-2/h8-9,13-14,17H,3-7H2,1-2H3,(H3-,20,21,22,26,28,29);3-4H2,1-2H3/b23-12-;/t13-,14?,17-;/m1./s1
• InChIKey: DBCVQAGQPYVVDA-XVKMNWMGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-{[(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-2-carboxylato-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-en-3-yl]methyl}-1-methylpyrrolidin-1-ium; ethoxyethane
• IUPAC Traditional name: 1-{[(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-2-carboxylato-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-en-3-yl]methyl}-1-methylpyrrolidin-1-ium; diethyl ether
• Synonyms: 1-[[(6R,7R)-7-[[(2Z)-2-(2-Amino-4-thiazolyl)-2-(methoxyimino)acetyl]amino]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-en-3-yl]methyl]-1-methylpyrrolidinium Inner Salt Etherate; Δ2-Cefepime Etherate

Database IDs

• CAS Number: 88040-25-9
• PubChem SID: 162258038
• PubChem CID: 71314604

CALCULATED PROPERTIES

• Acid pKa: 3.0100222
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): -3.5538924
• LogD (pH = 7.4): -3.5405455
• Log P: -3.85784
• Molar Refractivity: 140.6917 cm^3
• Polarizability: 45.2824 Å^3
• Polar Surface Area: 150.04 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Brown Solid
• Melting Point: >151°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - C242740

The Δ2-isomer of Cefepime (C242750), a new series of cephalosporins.

REFERENCES

• Naito, T., et al.: J. Antibiot., 39, 1092 (1986)