sodium (6R,7R)-3-[(acetyloxy)methyl]-8-oxo-7-[2-(thiophen-2-yl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

• ChemBase ID: 105794
• Molecular Formular: C16H15N2NaO6S2
• Molecular Mass: 418.41987
• Monoisotopic Mass: 418.02692249
• SMILES: [Na+].O=C1N2C(=C(CS[C@@H]2[C@@H]1NC(=O)Cc1sccc1)COC(=O)C)C(=O)[O-]
• Canonical SMILES: CC(=O)OCC1=C(C(=O)[O-])N2[C@H](SC1)[C@@H](C2=O)NC(=O)Cc1cccs1.[Na+]
• InChI: InChI=1S/C16H16N2O6S2.Na/c1-8(19)24-6-9-7-26-15-12(14(21)18(15)13(9)16(22)23)17-11(20)5-10-3-2-4-25-10;/h2-4,12,15H,5-7H2,1H3,(H,17,20)(H,22,23);/q;+1/p-1/t12-,15-;/m1./s1
• InChIKey: VUFGUVLLDPOSBC-XRZFDKQNSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (6R,7R)-3-[(acetyloxy)methyl]-8-oxo-7-[2-(thiophen-2-yl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• IUPAC Traditional name: sodium cefalotin(1-)
• Synonyms: (6R,7R)-3-[(Acetyloxy)methyl]-8-oxo-7-[[2-(2-thienyl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; 7-(2-Thienylacetamido)cephalosporanic Acid; 7-(Thiophene-2-acetamido)cephalosporin; 7-[2-(2-Thienyl)acetylamido]cephalosporanic Acid; CT; Cefalotin; Cephalotin; Cephalothin; 7-(2-Thienylacetamido)cephalosporanic acid sodium salt; Cephalotin sodium salt; Cephalothin sodium salt; 7-[2-Thienylacetamido]-cephalosporanic acid; CEPHALOTHIN SODIUM SALT

Database IDs

• CAS Number: 58-71-9
• EC Number: 200-394-6
• MDL Number: MFCD00072025
• Beilstein Number: 4120706
• PubChem SID: 162094211; 24278314; 24892330
• PubChem CID: 23675321

CALCULATED PROPERTIES

• Acid pKa: 3.625907
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): -1.8540871
• LogD (pH = 7.4): -3.3175669
• Log P: 0.016272906
• Molar Refractivity: 104.6311 cm^3
• Polarizability: 36.26567 Å^3
• Polar Surface Area: 115.84 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble50 mg/mL, clear, faintly yellow
• Melting Point: 204-205

Safety Information

• Storage Condition: 0°C
• RTECS: XI0388300
• 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: ≥99.0% (TLC); 96.0-101.0%
• Salt Data: Na+
• Suitability: suitable for cell culture
• Empirical Formula (Hill Notation): C16H15N2NaO6S2
• Classification: Derivatives & analogs of Natural Compounds

DETAILS

MP Biomedicals - 02194155

Sodium Salt

Sigma Aldrich - C4520

Biochem/physiol Actions
Cephalothin is a first-generation cephalosporin antibiotic that disrupts the synthesis of the peptidoglycan layer of bacterial cell walls. It is effective against gram-positive and gram-negative bacteria. Mode of Resistance: Cephalosporinase production.
Mode of Action: Inhibits cell wall synthesis.Antimicrobial spectrum: Gram-positive cocci.Mode of Resistance: Cephalosporinase production.
Other Notes
First generation cephalosporin antibiotic.
Application
Cephalothis is used to study the mechanism of liposome encapsulated antibiotics 1, strategies for co-opting β-lactamases of Gram-negative bacteria for treatment of antibiotics 2, and for immunology studies in relation to antibiotics 3. It is used to study the effect of expression, binding and inhibition of penicillin-binding proteins especially PBP6 on bacterial cell wall mucopeptide synthesis.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - C3050

Biochem/physiol Actions
Mode of Action: Inhibits cell wall synthesis.Antimicrobial spectrum: Gram-positive cocci.Mode of Resistance: Cephalosporinase production.
Mode of Action: Inhibits cell wall synthesis.Antimicrobial spectrum: Gram-positive cocci.Mode of Resistance: Cephalosporinase production.
Other Notes
First generation cephalosporin antibiotic.
General description
Cephalotin is a first generation cephalosporin antibiotic.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - 22241

Biochem/physiol Actions
Mode of Action: Inhibits cell wall synthesis.Antimicrobial spectrum: Gram-positive cocci.Mode of Resistance: Cephalosporinase production.
Other Notes
First generation cephalosporin antibiotic.

Toronto Research Chemicals - C261150

A first generation cephalosporin antibiotic with a wide range antibacterial activity. It is effective against gram-positive and gram-negative bacteria, and has been tested in respiratory disease and neuromuscular junction studies.

REFERENCES

• Shibata, K., et al.: J. Antibiot., 50, 135 (1997)
• Farra, A., et al.: Int. J. Antimicrob. Agents., 31, 427 (1997)
• Pichardo, C., et al.: Eur. J. Clin. Microbiol. Infect. Dis., 30, 289 (1997)