1-{[(6R,7R)-7-[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 pentahydrate

• ChemBase ID: 155510
• Molecular Formular: C22H32N6O12S2
• Molecular Mass: 636.65248
• Monoisotopic Mass: 636.15196249
• SMILES: CC(C)(C(=O)O)O/N=C(\c1csc(n1)N)/C(=O)N[C@H]1[C@@H]2N(C1=O)C(=C(CS2)C[n+]1ccccc1)C(=O)[O-].O.O.O.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-].O.O.O.O.O
• InChI: InChI=1S/C22H22N6O7S2.5H2O/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);5*1H2/t14-,18-;;;;;/m1...../s1
• InChIKey: NMVPEQXCMGEDNH-OKDPUKRASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-{[(6R,7R)-7-[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 pentahydrate
• IUPAC Traditional name: ceftazidime pentahydrate
• Synonyms: 1-[[(6R,7R)-7-[[(2Z)-(2-amino-4-thiazolyl)[(1-carboxy-1-methylethoxy)imino]acetyl]amino]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]pyridinum; Ceftazidime hydrate

Database IDs

• MDL Number: MFCD00153936
• PubChem SID: 24892644; 162249648
• PubChem CID: 5362051

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

PROPERTIES

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 42/43
• Safety Statements: 22-36/37-45
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H317-H319-H334
• GHS Precautionary statements: P261-P280-P305 + P351 + P338-P342 + P311
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: 90.0-105.0%
• Contains: 10% sodium carbonate as stabilizer
• Empirical Formula (Hill Notation): C22H22N6O7S2 · xH2O

DETAILS

Sigma Aldrich - C3809

Frequently Asked Questions
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General description
Broad spectrum antibiotic; third generation cephalosporin
Application
Ceftazidime hydrate is used to study the effect of expression, binding and inhibition of penicillin-binding proteins especially PBP3 on bacterial cell wall mucopeptide synthesis. It is also used in bacterial susceptibility studies 1 and to select mutant colonies of interest 2.
Biochem/physiol Actions
Cephalosporins, such as ceftazidime , disrupt the synthesis of the peptidoglycan layer of bacterial cell walls.