(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• ChemBase ID: 1166
• Molecular Formular: C13H13N5O5S2
• Molecular Mass: 383.40282
• Monoisotopic Mass: 383.03581054
• SMILES: S1[C@H]2N(C(=O)[C@H]2NC(=O)/C(=N\OC)/c2nc(sc2)N)C(=CC1)C(=O)O
• Canonical SMILES: CO/N=C(/c1csc(n1)N)\C(=O)N[C@H]1[C@H]2SCC=C(N2C1=O)C(=O)O
• InChI: InChI=1S/C13H13N5O5S2/c1-23-17-7(5-4-25-13(14)15-5)9(19)16-8-10(20)18-6(12(21)22)2-3-24-11(8)18/h2,4,8,11H,3H2,1H3,(H2,14,15)(H,16,19)(H,21,22)/b17-7-/t8-,11-/m1/s1
• InChIKey: NNULBSISHYWZJU-LLKWHZGFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: ceftizoxime
• Brand Name: Cefizox; Cefizox in plastic container; Ceftix; Epocelin; Eposerin
• Synonyms: Ceftizoxima [inn-spanish]; Ceftizoximum [inn-latin]; Ceftizoxime

Database IDs

• CAS Number: 68401-81-0
• PubChem SID: 46505647; 160964629
• PubChem CID: 6533629

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.7960377
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -2.4313903
• LogD (pH = 7.4): -3.582094
• Log P: -0.84618473
• Molar Refractivity: 89.9001 cm^3
• Polarizability: 33.71099 Å^3
• Polar Surface Area: 147.21 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.4
• LOG S: -3.22
• Solubility (Water): 2.29e-01 g/l

DETAILS

DrugBank - DB01332

• Drug Groups: approved
• Description: A semisynthetic cephalosporin antibiotic which can be administered intravenously or by suppository. The drug is highly resistant to a broad spectrum of beta-lactamases and is active against a wide range of both aerobic and anaerobic gram-positive and gram-negative organisms. It has few side effects and is reported to be safe and effective in aged patients and in patients with hematologic disorders. [PubChem]
• Indication: For the treatment of infections due to susceptible strains of microorganisms.
• Pharmacology: Ceftizoxime is highly resistant to a broad spectrum of beta-lactamases and is active against a wide range of both aerobic and anaerobic gram-positive and gram-negative organisms. It has few side effects and is reported to be safe and effective in aged patients and in patients with hematologic disorders.
• Affected Organisms: Enteric bacteria and other eubacteria
• Biotransformation: Ceftizoxime is not metabolized, and is excreted virtually unchanged by the kidneys in 24 hours.
• Protein Binding: 30% protein bound
• Elimination: Ceftizoxime is not metabolized, and is excreted virtually unchanged by the kidneys in 24 hours.
• External Links: Wikipedia; RxList; Drugs.com