Penicillin g

• CAS: 61-33-6
• Catalog Number: ACM61336
• Category: Main Products
• Molecular Weight: 334.39
• Molecular Formula: C₁₆H₁₈N₂O₄S
• Synonyms: PENICILLIN G K-SALT;PENICILLIN G POTASSIUM;PENICILLIN G POTASSIUM SALT;(5r,6r)-benzylpenicillin;(phenylmethyl)-penicilli;(phenylmethyl)penicillin;(phenylmethyl)-penicillinicaci;(phenylmethyl)penicillinicacid
• IUPAC Name: (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid
• Canonical SMILES: CC1(C(N2C(S1)C(C2=O)NC(=O)CC3=CC=CC=C3)C(=O)O)C
• InChI Key: JGSARLDLIJGVTE-MBNYWOFBSA-N
• Boiling Point: 663.3ºC at 760 mmHg
• Flash Point: 355ºC
• Density: 1.42g/cm³
• Appearance: powder
• Application: Penicillin G, also known as benzylpenicillin, is the drug of choice for infections caused by sensitive organisms such as streptococci infections (except enterococci), gonococci, and meningococci that do not produce beta-lactam anaerobes. It is commonly used for croupous and focal pneumonia, skin infections, soft tissue and mucous membranes, peritonitis, cystitis, syphilis, diphtheria, and other infectious diseases. Penicillin G is an antimicrobial agent with antibacterial properties.
• EC Number: 200-506-3
• Exact Mass: 334.09900
• Hazard Statements: Xn
• Safety Description: 36/37
• WGK Germany: 2

Case Study

Effects of pH and temperature on the decomposition of penicillin G

Kheirolomoom, A., et al. Process Biochemistry 35.1-2 (1999): 205-211.

The stability of penicillin G as a function of temperature and pH was analyzed, and the combined effects of pH and temperature were studied by proposing a second-order polynomial model for the decomposition reaction rate constant of penicillin G. The simulation results of the first-order decomposition reaction of penicillin G were in good agreement with the experimental data in the pH range of 1.8-10.0 and the temperature range of 0-52°C. The stability analysis showed that penicillin G was more stable in the pH range of 5.0-8.0 than outside the pH range, and the temperature for subsequent separation was lower. The maximum stability of penicillin G was around pH 6.0, and its instability at acidic pH values was much higher than that at alkaline pH values. For all pH values, the stability of penicillin G decreased with increasing temperature. The stability results and the proposed second-order model for the decomposition reaction rate constant of penicillin G can be used to study the loss of penicillin G during the separation process.
Penicillin G solutions of different pH values (1.8 to 10) were prepared using different buffers. KCl-HCl buffers with pH values between 1.8 and 2.5, citrate buffers with pH values between 4.0 and 6.0, phosphate buffers with pH values between 6.0 and 8.0, and glycine-NaOH buffer solutions with pH values between 8.5 and 10 were used. Penicillin G potassium salt buffer solutions with different pH values were incubated at 0, 5, 10, 25, 37 and 52°C, and the residual penicillin G concentration values at the specified pH and temperature values and at different time intervals were used to determine the decomposition rate constant. The value of the decomposition rate constant was obtained from the slope of the linear equation of the first-order decomposition reaction of penicillin G.

Identification of Penicillin G Metabolites Using UHPLC-MS/MS

Aldeek, Fadi, et al. Journal of agricultural and food chemistry 64.31 (2016): 6100-6107.

The stability of penicillin G under various conditions including acidic, alkaline, natural acidic matrices, and after treatment of citrus trees infected with citrus greening disease was investigated. Penicillin G and its various metabolites were identified, confirmed, and quantified using two UHPLC-MS/MS systems with variable capabilities. Our data showed that 100 ng/mL of penicillin G degraded rapidly under both acidic and alkaline conditions with a half-life of approximately 2 hours determined. Penicillic acid, penicillinic acid, and penicillic acid were found to be the most abundant metabolites of penicillin G. These major metabolites along with isopenicillinic acid were found when penicillin G was used to treat trees infected with citrus greening disease.
Solutions of penicillin G potassium salt, penicillic acid, and penicillic acid were prepared at 1000 μg/mL by dissolving the standards (after adjustment for salt content and purity) in a mixture of water and acetonitrile (1:1, v/v), while a separate stock solution of penicillic acid at 1000 μg/mL was prepared by first dissolving the standards with 300 μL DMSO and then adding phosphate buffer. These standard stock solutions were stored at -20°C for extended periods of time (>5 months) without degradation. These stock solutions, all at a concentration of 1000 μg/mL, were used to prepare 1 μg/mL standard solutions of each compound. These solutions were prepared by adding 100 μL of each separate stock solution to an appropriate 100 mL volumetric flask and filling each flask to the mark with phosphate buffer (0.1 M, pH 7) to yield a solution at a concentration of 1 μg/mL.

A new analytical method for the detection of penicillin G

Li, Dong, et al. Water Research 42.1-2 (2008): 307-317.

There is a new analytical method for the simultaneous detection of penicillin G (PEN G) and five degradation products using liquid chromatography-electrospray ionization mass spectrometry (LC-ESI/MS). PEN G had been transformed before entering the wastewater treatment plant (WWTP) and the concentration in the raw effluent was 15374 mg/L. After continuous treatment with anaerobic, hydrolytic and two aerobic units with a hydraulic retention time (HRT) of 30 h, most of the PEN G could be eliminated and the final concentration in the treated water was 1.6870.48 mg/L. In the receiving river, the PEN G concentration decreased from 0.3170.04 mg/L at the discharge point to below the detection limit (0.03 mg/L) at the last sampling point (about 30 km from the discharge point). The degradation products of PEN G in the surface water were mainly penicillic acid, penicillic acid and isopenicillic acid, accounting for 65.8%, 20.4% and 12.9% of the total concentration at the last station, respectively. This is the first study to investigate the behavior of PEN G and its major degradation products in wastewater treatment processes and aquatic environments.
Prior to analysis, water samples were serially diluted 10-fold using ultrapure water because the concentrations of most analytes in the original samples exceeded the upper limit of their calibration curves (100 mg/L for penicillin G and 500 mg/L for penicillin G L for other analytes as described in Section 2.5). The samples were then analyzed using LC-ESI/MS after being filtered through a 0.2 mm polyethersulfone syringe filter and spiked with PEN V as an internal standard (IS) at a concentration of 10 mg/L. PEN V is commonly used as an internal standard for the determination of β-lactam antibiotics in some analytical methods and has been confirmed to be undetectable in all water samples in this study.

T cell recognition of penicillin G

Padovan, Elisabetta, et al. European journal of immunology 26.1 (1996): 42-48.

Penicillin G (Pen G) and other β-lactam antibiotics frequently induce allergic reactions, which are classic examples of human immune responses to haptens. In fact, penicillins represent a unique group of haptens based on the same protein-reactive β-lactam backbone with remarkable structural variability. Although both cellular and humoral responses have been implicated in drug-induced allergy, little is known about T cell reactivity to penicillins. To understand which structural features determine antigenic specificity, we isolated a panel of MHC-restricted Pen G-reactive T cell clones from different penicillin-allergic patients and tested their ability to proliferate in the presence of other penicillin derivatives. We found that the antigenic epitope consists of amide-linked side chains, which are different for each member of the penicillin family, as well as a thiazolidine ring common to all penicillin derivatives. We also demonstrated the existence of two distinct types of penicillin-specific T cells, one dependent on antigen processing by autologous antigen-presenting cells and the other independent of antigen processing by autologous antigen-presenting cells. Our data strongly suggest that penicillins form part of the epitope that contacts the T cell antigen receptor.
For in vitro assays, penicillin G (Pen G), Pen V, oxacillin, methicillin, cloxacillin, and carbenicillin were used at 1 mg/ml and diluted three-fold or two-fold; cefaclor and 6-APA were toxic to T cells at concentrations above 0.25 mg/ml. T cell clones were generated from the Pen G-specific T cell line after one or two consecutive antibiotic stimulations. with different dilutions of Pen G. After another 4 days, the cultures were checked for cell growth; positive wells were then pooled and expanded in medium containing IL-2. If the response was poor, the cell lines were restimulated with Pen G in the presence of irradiated autologous PBMCs, expanded again in IL-2, and then cloned by limiting dilution according to published methods.

Custom Q&A

What is the molecular formula of Penicillin G?

The molecular formula of Penicillin G is C16H18N2O4S.

What are some synonyms for Penicillin G?

Some synonyms for Penicillin G are Benzylpenicillin, Benzylpenicillin G, and Benzylpenicillinic acid.

What is the Chemical Safety information for Penicillin G?

Penicillin G is categorized as an Irritant, Health Hazard, and Environmental Hazard.

What is the CAS number for Penicillin G?

The CAS number for Penicillin G is 61-33-6.

What is the 3D structure of Penicillin G?

The 3D structure of Penicillin G is not provided in the reference.

What are some brand names for Penicillin G?

Some brand names for Penicillin G are Dropcillin, Gelacillin, and Liquacillin.

What is the pharmacological classification of Penicillin G?

The pharmacological classification of Penicillin G is J01CE01.

What is the chemical formula of Penicillin G potassium?

The chemical formula of Penicillin G potassium is C16H18N2O4S.K.

What are some alternative names for Penicillin G?

Some alternative names for Penicillin G are Benzylpenicillin and Bencilpenicilina.

What is the trade name for Penicillin G?

The trade name for Penicillin G is Pfizerpen.