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

• ChemBase ID: 153576
• Molecular Formular: C16H17KN2O5S
• Molecular Mass: 388.47988
• Monoisotopic Mass: 388.04952433
• SMILES: CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)COc1ccccc1)C(=O)[O-])C.[K+]
• Canonical SMILES: O=C(N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)[O-])(C)C)COc1ccccc1.[K+]
• InChI: InChI=1S/C16H18N2O5S.K/c1-16(2)12(15(21)22)18-13(20)11(14(18)24-16)17-10(19)8-23-9-6-4-3-5-7-9;/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22);/q;+1/p-1/t11-,12+,14-;/m1./s1
• InChIKey: HCTVWSOKIJULET-LQDWTQKMSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: potassium (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenoxyacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• IUPAC Traditional name: potassium phenoxymethylpenicillin(1-)
• Synonyms: Phenoxymethylpenicillinic acid potassium salt; Phenoxymethylpenicillin potassium salt; Phenoxymethylpenicillinic acid potassium salt; Penicillin V potassium salt; Penicillin V potassium salt; (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-[(2-phenoxyacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid Potassium; 6-(Phenoxyacetamido)penicillanic Acid Potassium; Antibiocin; Calciopen K; Cilacil; Fenoxypen; Vepicombin; Penicillin V Potassium Salt; 苯氧甲基青霉素 钾盐; 青霉素 V 钾盐; 青霉素 V 钾盐

Database IDs

• CAS Number: 132-98-9
• EC Number: 205-086-5
• MDL Number: MFCD00051771
• Beilstein Number: 3899451
• PubChem SID: 162247715; 24870330; 24898194; 24898501
• PubChem CID: 23676814

CALCULATED PROPERTIES

• Acid pKa: 3.390268
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): -1.3336357
• LogD (pH = 7.4): -2.6421306
• Log P: 0.7632417
• Molar Refractivity: 96.6051 cm^3
• Polarizability: 33.95466 Å^3
• Polar Surface Area: 98.77 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: powder; White Solid
• Melting Point: 234-238°C (dec)

Safety Information

• Storage Condition: -20°C Freezer
• RTECS: XH9275000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-42/43
• Safety Statements: 22-26-36/37-45
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H302-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

• Grade: VETRANAL™, analytical standard
• Potency: ≥1460 units per mg
• Activity: ~1,500 U/mg
• Suitability: suitable for 1694 per US EPA; suitable for cell culture
• Product Line: BioReagent
• Linear Formula: C16H17N2O5SK
• Empirical Formula (Hill Notation): C16H17N2O5SK

DETAILS

Sigma Aldrich - P1382

Application
Phenoxymethylpenicillinic acid, also known as Penicillin V, is narrow spectrum antibiotic used to treat mild to moderate infections caused by susceptible bacteria. It is a natural penicillin antibiotic that is administered orally. Penicillin V is a penicillin β-lactam antibiotic used in the treatment of bacterial infections caused by susceptible, usually gram-positive, organisms. It is commonly used in cell culture in combination with streptomcyin and other antibiotics. It is used to study penicillin-binding protein 21, molecular cloning of the Bacillus sphaericus penicillin V amidase gene2, and gastrointestinal persistence and bile tolerance of Listeria monocytogenes3.
Biochem/physiol Actions
Phenoxymethylpenicillinic acid binds to specific penicillin-binding proteins (PBPs) and inhibits the synthesis of bacterial cell walls by preventing cell wall peptidoglycan chain cross-linking. This causes cell lysis, which is mediated by autolytic enzymes such as autolysins. Phenoxymethylpenicillnic acid may interfere with autolysin inhibitors.
Phenoxymethylpenicillinic acid inhibits the synthesis of bacterial cell walls by preventing cell wall peptidoglycan chain cross-linking. It is commonly used in cell culture in combination with streptomcyin and other antibiotics.

Sigma Aldrich - P4807

Biochem/physiol Actions
Penicillin V inhibits the synthesis of bacterial cell walls by blocking cell wall peptidoglycan chain cross-linking. Used in cell culture in combination with streptomcyin and other antibiotics.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - 46616

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - P223500

Antibacterial.

REFERENCES

• Goldenthal, E.I., et al.: Toxicol. Appl. Pharmacol., 18, 185 (1971)
• Dunham, J.M., et al.: Anal. Profiles Drug Subs., 1, 249 (1971)