sodium (6R,7R)-3-[(acetyloxy)methyl]-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-carboxylate

• ChemBase ID: 133418
• Molecular Formular: C16H16N5NaO7S2
• Molecular Mass: 477.44731
• Monoisotopic Mass: 477.03888416
• SMILES: CC(=O)OCC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)/C(=N\OC)/c2csc(n2)N)SC1)C(=O)[O-].[Na+]
• Canonical SMILES: CO/N=C(/c1csc(n1)N)\C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)[O-])COC(=O)C.[Na+]
• InChI: InChI=1S/C16H17N5O7S2.Na/c1-6(22)28-3-7-4-29-14-10(13(24)21(14)11(7)15(25)26)19-12(23)9(20-27-2)8-5-30-16(17)18-8;/h5,10,14H,3-4H2,1-2H3,(H2,17,18)(H,19,23)(H,25,26);/q;+1/p-1/b20-9-;/t10-,14-;/m1./s1
• InChIKey: AZZMGZXNTDTSME-JUZDKLSSSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (6R,7R)-3-[(acetyloxy)methyl]-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-carboxylate
• IUPAC Traditional name: sodium cefotaxime(1-)
• Synonyms: Cefotaxime sodium salt; (6R,7R)-3-[(Acetyloxy)methyl]-7-[[(2Z)-2-(2-amino-4-thiazolyl)-2-(methoxyimino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid Sodium Salt; Cefotax; HR 756; Pretor; Tolycar; Cefotaxime Sodium; Cefotaxim sodium salt 钠盐; Cefotaxime sodium salt 钠盐

Database IDs

• CAS Number: 64485-93-4
• EC Number: 264-915-9
• MDL Number: MFCD00079073
• Beilstein Number: 5711411
• PubChem SID: 162227695; 24278336; 24892923
• PubChem CID: 10695961

CALCULATED PROPERTIES

• Acid pKa: 3.1773155
• H Acceptors: 9
• H Donor: 2
• LogD (pH = 5.5): -2.9842594
• LogD (pH = 7.4): -4.1677856
• Log P: -1.9052299
• Molar Refractivity: 115.9454 cm^3
• Polarizability: 39.9619 Å^3
• Polar Surface Area: 176.34 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble (aqueous solutions of pH 4.3-6.2 are stable up to 3 weeks at 2-8 °C.); Methanol; Water
• Apperance: White Solid; white to yellow powder
• Melting Point: > 165°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere
• RTECS: XI0250000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 2
• Risk Statements: 42/43
• Safety Statements: 22-36/37
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H317-H334
• GHS Precautionary statements: P261-P280-P342 + P311
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Potency: 916-964 μg per mg
• Suitability: plant cell culture tested; suitable for 1694 per US EPA

DETAILS

Sigma Aldrich - C7039

Other Notes
Broad spectrum third generation cephalosporin antibiotic.
Biochem/physiol Actions
Cefotaxim inhibits bacterial cell wall synthesis by binding to penicillin-binding proteins (PBPs) which inhibits the final transpeptidation step of peptidoglycan synthesis in bacterial cell walls. As a result, bacteria lyse due to cell wall autolytic enzymes.
Cefotaxime, a cephalosporin antibiotic, is active against both gram-negative and gram-positive bacteria. In addition, cefotaxime blocks the division of cyanobacteria and lower plant organelles/plastids such as the photosynthetic organelles of Glaucophytes and chloroplasts of bryophytes.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - C7912

Biochem/physiol Actions
Used to study the effect of expression, binding and inhibition of penicillin-binding proteins especially PBP2 on bacterial cell wall mucopeptide synthesis.
Cefotaxim inhibits bacterial cell wall synthesis by binding to penicillin-binding proteins (PBPs) which inhibits the final transpeptidation step of peptidoglycan synthesis in bacterial cell walls. As a result, bacteria lyse due to cell wall autolytic enzymes.
Other Notes
Broad spectrum third generation cephalosporin antibiotic.
Application
Cefotaxim is a broad spectrum third generation cephalosporin antibiotic that is used to study the effect of expression, binding and inhibition of penicillin-binding proteins especially PBP2 on bacterial cell wall mucopeptide synthesis. It has been used to find new residues involved in cefotaxime hydrolysis in CTX-M β-lactamases1, to study antibiotic-susceptible and -resistant Streptococcus pneumoniae infections 2, and to study pneumococcal pneumonia and the pharmokinetics of various treatments3.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Toronto Research Chemicals - C242950

Broad spectrum third generation cephalosporin antibiotic. The name Cefotaxime applies to the isomer having a syn-methoxy imino group.

REFERENCES

• Wise, R., et al.: Antimicrob. Agents Chemother., 14, 807 (1978)
• Muhtadi, F.J., et al.: Anal. Profiles Drug Subs., 11, 139 (1978)