1-{[(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(1-carboxy-1-methylethoxy)imino]acetamido]-2-carboxylato-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}(2H5)pyridin-1-ium

• ChemBase ID: 163933
• Molecular Formular: C22H22N6O7S2
• Molecular Mass: 546.57608
• Monoisotopic Mass: 546.09913907
• SMILES: [C@@H]12N(C(=C(CS1)C[n+]1ccccc1)C(=O)[O-])C(=O)[C@H]2NC(=O)/C(=N\OC(C)(C)C(=O)O)/c1nc(sc1)N
• Canonical SMILES: O=C1[C@@H](NC(=O)/C(=N\OC(C(=O)O)(C)C)/c2csc(n2)N)[C@@H]2N1C(=C(CS2)C[n+]1ccccc1)C(=O)[O-]
• InChI: InChI=1S/C22H22N6O7S2/c1-22(2,20(33)34)35-26-13(12-10-37-21(23)24-12)16(29)25-14-17(30)28-15(19(31)32)11(9-36-18(14)28)8-27-6-4-3-5-7-27/h3-7,10,14,18H,8-9H2,1-2H3,(H4-,23,24,25,29,31,32,33,34)/b26-13-/t14-,18-/m1/s1
• InChIKey: ORFOPKXBNMVMKC-DWVKKRMSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-{[(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(1-carboxy-1-methylethoxy)imino]acetamido]-2-carboxylato-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}(^2H₅)pyridin-1-ium
• IUPAC Traditional name: 1-{[(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(1-carboxy-1-methylethoxy)imino]acetamido]-2-carboxylato-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}(^2H₅)pyridin-1-ium
• Synonyms: 1-[[(6R,7R)-7-[[(2Z)-2-(2-Amino-4-thiazolyl)-2-[(1-carboxy-1-methylethoxy)imino]acetyl]amino]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]pyridine-d5; Biotum-d5; Ceftacidin-d5; Fortam-d5; Fortaz-d5; Fortum-d5; GR 20263-d5; Modacin-d5; Tazicef-d5; Tazidime-d5; Ceftazidime-d5 (90%)

Database IDs

• PubChem SID: 162258068
• PubChem CID: 71314619

CALCULATED PROPERTIES

• Acid pKa: 2.7689743
• H Acceptors: 10
• H Donor: 3
• LogD (pH = 5.5): -5.4758763
• LogD (pH = 7.4): -6.9236097
• Log P: -4.5463347
• Molar Refractivity: 143.8809 cm^3
• Polarizability: 50.415825 Å^3
• Polar Surface Area: 191.22 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White Solid
• Melting Point: >190°C (dec.)

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer, Under inert atmosphere

DETAILS

Toronto Research Chemicals - C244102

Third generation cephalosporin antibiotic. Antibacterial.

REFERENCES

• Brodie, A., et al.: Antimicrob. Agents Chemother., 17, 876 (1980)
• Richards, D.M., et al.: Drugs, 29, 105 (1980)
• Abounassif, M.A., et al.: Anal. Profiles Drug Subs., 19, 95 (1980)