sodium (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

• ChemBase ID: 102198
• Molecular Formular: C16H17N2NaO4S
• Molecular Mass: 356.37195
• Monoisotopic Mass: 356.08067232
• SMILES: [Na+].O=C([O-])[C@@H]1N2C(=O)[C@@H](NC(=O)Cc3ccccc3)[C@H]2SC1(C)C
• Canonical SMILES: O=C(Cc1ccccc1)N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)[O-])(C)C.[Na+]
• InChI: InChI=1S/C16H18N2O4S.Na/c1-16(2)12(15(21)22)18-13(20)11(14(18)23-16)17-10(19)8-9-6-4-3-5-7-9;/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22);/q;+1/p-1/t11-,12+,14-;/m1./s1
• InChIKey: FCPVYOBCFFNJFS-LQDWTQKMSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• IUPAC Traditional name: sodium benzylpenicillin(1-)
• Synonyms: Penicillin G sodium salt; Benzylpenicillin; PENICILLIN G SODIUM SALT U.S.P.; Benzylpenicillin sodium salt; PENICILLIN G SODIUM SALT; Benzylpenicillin sodium salt 钠盐; Penicillin G sodium salt 钠盐

Database IDs

• CAS Number: 69-57-8
• EC Number: 200-710-2
• MDL Number: MFCD00069666
• Beilstein Number: 3834217
• PubChem SID: 24899068; 24898384; 162089932
• PubChem CID: 23668834

CALCULATED PROPERTIES

• Acid pKa: 3.5292811
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.8828292
• LogD (pH = 7.4): -2.2857618
• Log P: 1.080678
• Molar Refractivity: 95.3649 cm^3
• Polarizability: 33.23371 Å^3
• Polar Surface Area: 89.54 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble100 mg/mL (Solutions should be filter sterilized and stored at 2-8°C for 1 week or at -20°C for extended periods. Solutions are stable at 37°C for 3 days.)
• Apperance: powder

Safety Information

• Storage Condition: 2-8°C; 2-8°C, Protect from light
• RTECS: XH9800000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 2
• Risk Statements: 42/43
• Safety Statements: 22-36/37-45
• 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

Product Information

• Grade: USP
• Potency: ≥1477 units per mg
• Suitability: suitable for cell culture

DETAILS

MP Biomedicals - 02156065

Sodium Salt
Approx. 1650 units per mg.

MP Biomedicals - 02100548

Sodium Salt
(Not less than 1,500 units per mg)
Meets or exceeds U.S.P. specifications

Sigma Aldrich - PENNA

Biochem/physiol Actions
Mode of Action: Inhibits bacterial cell wall synthesis.Antimicrobial spectrum: Gram-positive bacteria.
Penicillin G is active against gram-positive and gram-negative aerobic and anaerobic bacteria. Penicillin G inhibits cell wall synthesis by binding to penicillin binding proteins (PBPs), which inhibits peptidoglycan chain cross-linking. Penicillin G is stable against hydrolysis by β-lactamases, such as penicillinases and cephalosporinases.
Application
Penicillin G is narrow spectrum antibiotic. It is the drug of choice for Streptococcus pneumoniae, groups A, B, C and G streptococci, nonenterococcal group D streptococci, viridans group streptococci, and non-penicillinase producing staphylococcus. Penicillin G sodium salt is used to study the diagnostic and therapeutic implications of gentamicin-resistant Enterococcus faecalis sequence type 6 with reduced penicillin susceptibility 1. It is used in cell culture alone as well as in combination with streptomcyin and other antibiotics2.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - P3032

Biochem/physiol Actions
Mode of Action: Inhibits bacterial cell wall synthesis.Antimicrobial spectrum: Gram-positive bacteria.
Reconstitution
Recommended for use in cell culture media at 100,000 units/L. Solutions should be filter sterilized and stored at 2-8 °C for up to 1 week, -20 °C for extended periods. Solutions are stable at 37 °C for 3 days.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information