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}pyridin-1-ium

• ChemBase ID: 321
• Molecular Formular: C22H22N6O7S2
• Molecular Mass: 546.57608
• Monoisotopic Mass: 546.09913907
• SMILES: S1[C@H]2N(C(=O)[C@H]2NC(=O)/C(=N\OC(C)(C)C(=O)O)/c2nc(sc2)N)C(=C(C1)C[n+]1ccccc1)C(=O)[O-]
• 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}pyridin-1-ium
• IUPAC Traditional name: fortum; ceftazidime
• Brand Name: Ceftazidima [INN-Spanish]; Ceftazidime Sodium In Plastic Container; Ceftazidime pentahydrate; Ceftazidimum [INN-Latin]; Ceptaz; Fortaz; Fortaz In Plastic Container; Pentacef; Tazicef; Tazidime; Tazidime In Plastic Container
• Synonyms: Ceftazidime; 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]pyridinium Inner Salt Pentahydrate; Biotum; Ceftacidin; Fortam; Fortaz; Fortum; GR 20263; Modacin; Tazicef; Tazidime; Ceftazidime Pentahydrate(Contain 1 equivalent of Na2CO3 as stabilizer)

Database IDs

• CAS Number: 78439-06-2
• PubChem SID: 160963784; 46506143
• PubChem CID: 5481173

CALCULATED PROPERTIES

JChem

• 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: 50.377937 Å^3
• Polar Surface Area: 191.22 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -1.21
• LOG S: -5.02
• Solubility (Water): 5.73e-03 g/l

PROPERTIES

Physical Property

• Solubility: 396 mg/L; DMSO; Methanol; water
• Apperance: White Solid
• Melting Point: >150°C (dec.)
• Hydrophobicity(logP): -1.60

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

DrugBank - DB00438

• Drug Groups: approved
• Description: Semisynthetic, broad-spectrum antibacterial derived from cephaloridine and used especially for Pseudomonas and other gram-negative infections in debilitated patients. [PubChem]
• Indication: For the treatment of patients with infections caused by susceptible strains of organisms in the following diseases: lower respiratory tract infections,skin and skin structure infections, urinary tract infections, bacterial septicemia, bone and joint infections, gynecologic infections, intra abdominal infections (including peritonitis), and central nervous system infections (including meningitis).
• Pharmacology: Ceftazidime is a semisynthetic, broad-spectrum, beta-lactam antibiotic for parenteral administration. Ceftazidime is bactericidal in action exerting its effect by inhibition of enzymes responsible for cell-wall synthesis, primarily penicillin binding protein 3 (PBP3). A wide range of gram-negative organisms is susceptible to ceftazidime in vitro, including strains resistant to gentamicin and other aminoglycosides. In addition, ceftazidime has been shown to be active against gram-positive organisms. It is highly stable to most clinically important beta-lactamases, plasmid or chromosomal, which are produced by both gram-negative and gram-positive organisms and, consequently, is active against many strains resistant to ampicillin and other cephalosporins. Ceftazidime has activity against the gram-negative organisms Pseudomonas and Enterobacteriaceae. Its activity against Pseudomonas is a distinguishing feature of ceftazidime among the cephalosporins.
• Toxicity: Ceftazidime overdosage has occurred in patients with renal failure. Reactions have included seizure activity, encephalopathy, asterixis, neuromuscular excitability, and coma.
• Affected Organisms: Enteric bacteria and other eubacteria
• Absorption: The absorption of ceftazidime is directly proportional to the size of the dose.
• Half Life: Half-life, following IV administration, is approximately 1.9-hours. Since ceftazidime is eliminated almost solely by the kidneys, its serum half-life is significantly prolonged in patients with impaired renal function.
• Protein Binding: < 10%
• Elimination: The elimination of ceftazidime by the kidneys resulted in high therapeutic concentrations in the urine.
• Clearance: * 115 mL/min
• External Links: Wikipedia; RxList; Drugs.com

Toronto Research Chemicals - C244100

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)