Penicillin G

• CAT Number: R001177
• CAS Number: 61-33-6
• Molecular Formula: C16H18N2O4S
• Molecular Weight: 334.39
• Purity: ≥95%
• Storage: -20°C
• 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
• 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
• InChIKey: JGSARLDLIJGVTE-MBNYWOFBSA-N
• SMILES: CC1(C(N2C(S1)C(C2=O)NC(=O)CC3=CC=CC=C3)C(=O)O)C

Penicillin is a member of the β-lactam antibiotics and was one of the first discovered antibiotics.β-lactams interfere with PBP (penicillin binding protein) activity involved in the final phase of peptidoglycan synthesis. PBP’s are enzymes which catalyze a pentaglycine crosslink between alanine and lysine residues providing additional strength to the cell wall. Without a pentaglycine crosslink, the integrity of the cell wall is severely compromised and ultimately leads to cell lysis and death. Resistance to β-lactams is commonly due to cells containing plasmid encoded β-lactamases.

Reference

Guzmán, Flavio, MD. /Beta Lactams Antibiotics (penicillins and Cephalosporins) Mechanism of Action.” Medical Pharmacology. Pharmacology Corner, 29 Nov. 2008. Web. 21 Aug. 2012.Pitout JD, Sanders CC, Sanders WE Jr. Antimicrobial resistance with focus on beta-lactam resistance in gram-negative bacilli. Am J Med 1997; 103:51.