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

• ChemBase ID: 102196
• Molecular Formular: C16H17KN2O4S
• Molecular Mass: 372.48048
• Monoisotopic Mass: 372.05460971
• SMILES: [K+].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.[K+]
• InChI: InChI=1S/C16H18N2O4S.K/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: IYNDLOXRXUOGIU-LQDWTQKMSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: potassium (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• IUPAC Traditional name: potassium benzylpenicillin(1-)
• Synonyms: (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid Potassium Salt; Penicillin G Potassium Salt; Benzylpenicillin Potassium; Cosmopen; Cristapen; Crytapen; Eskacillin; Falapen; Forpen; Hipercilina; Hyasorb; Hylenta; M-Cillin; Monopen; NSC 131815; Notaral; Pentid; Pentids; Potassium 6-(Phenylacetamido)penicillanate; Potassium Benzylpenicillin; Potassium Benzylpenicillinate; Potassium Penicillin G; Scotcil; Tabilin; Benzyl Penicillinate Potassium Salt; Benzylpenicillin potassium salt; PENICILLIN G POTASSIUM SALT; Benzylpenicillin; Penicillin G potassium salt; 苄青霉素 钾盐; 青霉素 G 钾盐

Database IDs

• CAS Number: 113-98-4
• EC Number: 204-038-0
• MDL Number: MFCD00036193
• Beilstein Number: 3832841
• PubChem SID: 24870324; 162088610; 24899067; 24898878; 24898970
• PubChem CID: 23664709
• E Number: E705

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; Water
• Apperance: Off-White Solid; powder
• Melting Point: 214-217; 246-248°C (dec.)
• Optical Rotation: [α]20/D +290±5°, c = 2% in H2O
• Absorption Wavelength: λ: 264 nm Amax: ≤0.850; λ: 280 nm Amax: ≤0.100

Safety Information

• Storage Condition: 2-8°C; Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• RTECS: XH9700000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 2
• Risk Statements: 42/43
• Safety Statements: 36/37
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H317
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (HPLC)
• Grade: VETRANAL™, analytical standard
• Potency: 1440-1680 units per mg
• Suitability: meets USP testing specifications; suitable for 1694 per US EPA; suitable for cell culture
• Shelf Life: (limited shelf life, expiry date on the label)
• λ: 0.2 % in H2O
• Empirical Formula (Hill Notation): C16H17KN2O4S

DETAILS

MP Biomedicals - 02194536

Cell Culture Reagent
Potassium salt
Approx. 1,500-1,700 units/mg

MP Biomedicals - 02100543

Potassium Salt
Activity: ~1,500-1,700 units/mg

Sigma Aldrich - P7794

Application
Recommended for use in cell culture applications 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.
Biochem/physiol Actions
Mode of Action: Inhibits bacterial cell wall synthesis.Antimicrobial spectrum: Gram-positive bacteria
Mode of Action: Use to inhibit the synthesis of bacterial cell walls by inhibition of the cell wall peptidoglycan chain cross-lining. Antimicrobial spectrum: Gram-positive bacteria
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - PENK

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-lining. Penicillin G is stable against hydrolysis by β-lactamases, such as penicillinases and cephalosporinases.
Application
Penicillin G is a 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 potassium salt is used to study murosomes of staphylococci1 and the penicillin-induced lysis of Streptococcus mutans2.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - 46609

Biochem/physiol Actions
Mode of Action: Inhibits bacterial cell wall synthesis.Antimicrobial spectrum: Gram-positive bacteria
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 13750

Biochem/physiol Actions
Mode of Action: Inhibits bacterial cell wall synthesis.Antimicrobial spectrum: Gram-positive bacteria

Sigma Aldrich - P8721

Application
Use in cell culture in combination with streptomcyin and other antibiotics.
Biochem/physiol Actions
Inhibits the synthesis of bacterial cell walls by inhibition of the cell wall peptidoglycan chain cross-lining. Antimicrobial spectrum: Gram-positive bacteria
Mode of Action: Inhibits bacterial cell wall synthesis.Antimicrobial spectrum: Gram-positive bacteria
Reconstitution
溶液应过滤杀菌，在 2-8°C 下最长可储存一周，在 -20°C 下可长期储存。溶液在 37°C 下可稳定 3 天。

Toronto Research Chemicals - B288601

An antibiotic substance produced by Penicillium sp. Antibacterial.

REFERENCES

• Chain, E., et al.: Lancet, 2, 226 (1929)
• Fleming, A., et al.: Br. J. Exp. Pathol., 10, 226 (1929)
• Clutterbuck, P.W., et al.: Biochem. J., et al.: 26, 1907 (1929)