sodium (6R,7R)-3-[(acetyloxy)methyl]-7-[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: 104172
• Molecular Formular: C16H16N5NaO7S2
• Molecular Mass: 477.44731
• Monoisotopic Mass: 477.03888416
• SMILES: O=C1N2C(=C(CS[C@@H]2[C@@H]1NC(=O)/C(=N/OC)/c1nc(sc1)N)COC(=O)C)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-AAUIGXPGSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (6R,7R)-3-[(acetyloxy)methyl]-7-[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; sodium (6R,7R)-3-[(acetyloxy)methyl]-7-[(2E)-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 (6R,7R)-3-[(acetyloxy)methyl]-7-[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; sodium (6R,7R)-3-[(acetyloxy)methyl]-7-[(2E)-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
• Synonyms: Cefotaxim sodium salt; Cefotaxime sodium salt; sodium (6R,7R)-3-[(acetyloxy)methyl]-7-[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; Cefotaxime sodium; (6R-(6-a,7-b(Z)))-3-((Acetyloxy) methyl)-7-(((2-amino-4-thiazolyl) (methoxyimio) acetyl) amino)-8-oxo-5-thia-1-azabicyclo (4,2,0) oct-2-ene-2-carboxylic acid, sodium salt; CEFOTAXIME; Cefotaxim sodium salt 钠盐; Cefotaxime sodium salt 钠盐

Database IDs

• CAS Number: 64485-93-4
• EC Number: 264-915-9
• MDL Number: MFCD00036878; MFCD00079073
• Beilstein Number: 5711411
• PubChem SID: 162093058
• PubChem CID: 23672566

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: soluble50 mg/mL, clear, light yellow
• Hydrophobicity(logP): -2.777

Safety Information

• Storage Condition: 2-8°C
• 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

• Purity: ≥98.0% (TLC); 95%
• Impurities: ≤5% water
• Empirical Formula (Hill Notation): C16H16N5NaO7S2

DETAILS

MP Biomedicals - 02154947

Sodium Salt Purity: 95% A cephalosporin. Acts by interference of synthesis of peptidoglycan of the bacterial cell wall.

Sigma Aldrich - 22128

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.