Benzylpenicillin

Benzylpenicillin

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Category Antibiotics
Catalog number BBF-00295
CAS
Molecular Weight 334.39
Molecular Formula C16H18N2O4S

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Description

It is produced by the strain of Penicillum sp. Penicillin has a strong antibacterial effect on gram-positive bacteria, Neisseria, Haemophilus, anaerobes (except fragile bacilli), spirochetes and actinomycetes, but no effect on mycobacterium tuberculosis, rickettsia, fungi, protozoa and virus.

Specification

Related CAS 113-98-4 (monopotassium salt) 69-57-8 (monohydrochloride salt)
Synonyms penicillin g; Benzylpenicillinic acid; Pencillin G
IUPAC Name (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Canonical SMILES CC1(C(N2C(S1)C(C2=O)NC(=O)CC3=CC=CC=C3)C(=O)O)C
InChI InChI=1S/C16H18N2O4S/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)/t11-,12+,14-/m1/s1
InChI Key JGSARLDLIJGVTE-MBNYWOFBSA-N

Properties

Appearance White Amorphous Powder
Antibiotic Activity Spectrum gram-positive bacteria
Solubility Soluble in methanol, ethanol, ethyl acetate, ether, acetone, chloroform, benzene, slightly soluble in water, insoluble in petroleum ether.

Reference Reading

1. Cu(II)-catalyzed transformation of benzylpenicillin revisited: the overlooked oxidation
Jiabin Chen, Peizhe Sun, Xuefei Zhou, Yalei Zhang, Ching-Hua Huang Environ Sci Technol. 2015 Apr 7;49(7):4218-25. doi: 10.1021/es505114u. Epub 2015 Mar 20.
Penicillins, a class of widely used β-lactam antibiotics, are known to be susceptible to catalyzed hydrolysis by metal ions such as Cu(II). However, new results in this study strongly indicate that the role of Cu(II) is not merely a hydrolysis catalyst but also an oxidant. When benzylpenicillin (i.e., penicillin G (PG)) was exposed to Cu(II) ion at an equal molar ratio and pH 7, degradation of PG occurred rapidly in the oxygen-rich solution but gradually slowed down to a halt in the oxygen-limited solution. In-depth studies revealed that Cu(II) catalyzed hydrolysis of PG to benzylpenicilloic acid (PA) and oxidized PA to yield phenylacetamide and other products. The availability of oxygen played the role in reoxidizing Cu(I) back to Cu(II), which sustained fast degradation of PG over time. The overall reaction was also influenced by pH, with Cu(II)-catalyzed hydrolysis of PG occurring throughout pH 5, 7 and 9, while Cu(II) oxidation of PA occurring at pH 7 and 9. Note that the potential of Cu(II) to oxidize penicillins was largely overlooked in the previous literature, and catalyzed hydrolysis was frequently assumed as the only reaction. This study is among the first to identify the dual roles of Cu(II) in the entire degradation process of PG and systematically investigate the overlooked oxidation reaction to elucidate the mechanism. The new mechanistic knowledge has important implications for many other β-lactam antibiotics for their interactions with Cu(II), and significantly improves the ability to predict the environmental fate and transformation products of PG and related penicillins in systems where Cu(II) species are also present.
2. [Role of bacterial infection in the pathophysiology of benzylpenicillin allergy]
Przemysław Zdziarski Pol Merkur Lekarski. 2003 Jan;14(79):50-4.
In this paper current data on the pathogenesis of benzylpenicillin allergy is presented. Individual allergic reaction and susceptibility for the drug perhaps is not related to chemical properties of benzylpenicillin. An association between bacterial infection and allergy to benzylpenicillin is reviewed.
3. Stability of penethamate, a benzylpenicillin ester prodrug, in oily vehicles
Rohit Jain, Olaf Bork, Ian G Tucker Drug Dev Ind Pharm. 2015;41(11):1801-8. doi: 10.3109/03639045.2015.1009091. Epub 2015 Feb 12.
Penethamate (PNT) is an ester prodrug of benzylpenicillin which is marketed as dry powder for reconstitution with aqueous vehicle prior to injection. The purpose of this paper was to investigate the chemical stability of PNT in oily formulations to provide a basis for a ready-to-use (RTU) oil-based PNT formulation. The chemical stability of PNT solutions and suspensions in light liquid paraffin (LP), medium chain triglyceride (MIG), ethyl oleate (EO) and sunflower oil (SO) was investigated at 30 °C. Solid state stability of PNT powder and stability of PNT in EO suspensions with different moisture contents were also evaluated. The solubility of PNT in the oils was in order SO > EO > MIG > LP. Degradation of PNT was rapid in oily solutions and less than 10% remained after 7-15 days. Stability of PNT decreased with increase in moisture content in ethyl oleate suspensions. PNT was stable over four weeks in the solid state. Hydrolysis, due to moisture in the oil formulation is not the only degradation mechanism. PNT stability (% drug remaining) in oily suspensions after 3.5 months was in the order LP (96.2%) > MIG (95.4%) > EO (94.1%) > SO (86%). A shelf-life of up to 5.5 years at 30 °C may be achieved for PNT suspension in these oils.

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