[(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)pent-2-enamido]-3-[(carbamoyloxy)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carbonyloxy]methyl 2,2-bis(2H3)methyl(2H3)propanoate

• ChemBase ID: 163895
• Molecular Formular: C23H29N5O8S2
• Molecular Mass: 567.63506
• Monoisotopic Mass: 567.14575491
• SMILES: [C@@H]12N(C(=C(CS1)COC(=O)N)C(=O)OCOC(=O)C(C)(C)C)C(=O)[C@H]2NC(=O)/C(=C\CC)/c1csc(n1)N
• Canonical SMILES: CC/C=C(/c1csc(n1)N)\C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)OCOC(=O)C(C)(C)C)COC(=O)N
• InChI: InChI=1S/C23H29N5O8S2/c1-5-6-12(13-9-38-21(24)26-13)16(29)27-14-17(30)28-15(11(7-34-22(25)33)8-37-18(14)28)19(31)35-10-36-20(32)23(2,3)4/h6,9,14,18H,5,7-8,10H2,1-4H3,(H2,24,26)(H2,25,33)(H,27,29)/b12-6-/t14-,18-/m1/s1
• InChIKey: WVPAABNYMHNFJG-QDVBXLKVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)pent-2-enamido]-3-[(carbamoyloxy)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carbonyloxy]methyl 2,2-bis(^2H₃)methyl(^2H₃)propanoate
• IUPAC Traditional name: [(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)pent-2-enamido]-3-[(carbamoyloxy)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carbonyloxy]methyl 2,2-bis(^2H₃)methyl(^2H₃)propanoate
• Synonyms: (6R,7R)-3-[[(Aminocarbonyl)oxy]methyl]-7-[[(2Z)-2-(2-amino-4-thiazolyl)-1-oxo-2-pentenyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid, (2,2-Dimethyl-1-oxopropoxy)methyl Ester-d9; S-1108-d9; Fumax-d9; Cefcapene Pivoxil-d9

Database IDs

• PubChem SID: 162258030
• PubChem CID: 45038587

CALCULATED PROPERTIES

• Acid pKa: 11.478216
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): 2.1207798
• LogD (pH = 7.4): 2.1307843
• Log P: 2.130946
• Molar Refractivity: 137.9681 cm^3
• Polarizability: 53.406208 Å^3
• Polar Surface Area: 193.24 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C242552

Antibacterial. Orally absorbed cephalosporin; ester prodrug of the active free acid metabolite, cefcapene.

REFERENCES

• Neu, H.C., et al.: Antimicrob.Agents Chemother., 36, 1336 (1992)
• Ishikura, K., et al.: J. Antibiot., 47, 466 (1992)