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-2-en-3-yl]methyl}-1-methylpyrrolidin-1-ium hydrate

• ChemBase ID: 163904
• Molecular Formular: C19H26N6O6S2
• Molecular Mass: 498.57634
• Monoisotopic Mass: 498.13552458
• 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.O
• Canonical SMILES: CO/N=C(/c1csc(n1)N)\C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)[O-])C[N+]1(C)CCCC1.O
• InChI: InChI=1S/C19H24N6O5S2.H2O/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;/h9,13,17H,3-8H2,1-2H3,(H3-,20,21,22,26,28,29);1H2/b23-12-;/t13-,17-;/m1./s1
• InChIKey: AYEVWJLUTMOIKX-LSGRDSQZSA-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-2-en-3-yl]methyl}-1-methylpyrrolidin-1-ium hydrate
• IUPAC Traditional name: cefepime hydrate
• Synonyms: 1-[[(6R,7R)-7-[[(2Z)-(2-Amino-4-thiazolyl)(methoxyimino)acetyl]amino]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-1-methylpyrrolidinium Inner Salt Dihydrochloride Monohydrate; Axepim; Cepimex; Maxipime; Cefepime Dihydrochloride Monohydrate

Database IDs

• CAS Number: 123171-59-5
• PubChem SID: 162258039
• PubChem CID: 71314605

CALCULATED PROPERTIES

• Acid pKa: 3.2528262
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): -3.4631
• LogD (pH = 7.4): -3.4483533
• Log P: -3.8011866
• Molar Refractivity: 141.9753 cm^3
• Polarizability: 45.275974 Å^3
• Polar Surface Area: 150.04 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White to Off-White Solid
• Melting Point: >175°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - C242750

Semisynthetic, fourth generation cephalosporin antibiotic. Antibacterial.

REFERENCES

• Khan, N.J., et al.: Antimicrob. Agents Chemother., 26, 585 (1984)
• Naito, T., et al.: J. Antibiot., 39, 1092 (1984)
• Okamoto, M.P., et al.: Clin. Pharmacokinet., 25, 88 (1984)