Penicillin V

(CC) Image: David E. Volk
penicillin V
IUPAC name: see chemistry section Synonyms: see below Formula: C16H18N2O5S
Uses:	antibiotic drug
Properties:	beta-lactam
Hazards:	see drug interactions
Mass (g/mol): CAS #: 350.3895 87-08-1

Penicillin V, or phenoxymethyl penicillin, is a broad-spectrum, beta-lactam-based antibiotic used to treat mild to severe infections due to Gram-positive bacteria. It is used to treat dental, ear, middle ear, respiratory tract and skin infections, and can also treat rheumatic and scarlet fevers. As opposed to penicillin G, it is resistant to digestive acids and is effective when administered orally.

Mechanism of action

Like other penicillin-like drugs, penicillin V works by binding to specific penicillin-binding proteins in bacterial cell walls and blocking the final cross-linking step in the synthesis of bacterial cell walls. This induces autolysis of the bactertial cells by autolysins.

Chemistry

Penicillin V is stable against degradation by beta-lactamases, including penicillinases, and cephalosporinases. Its IUPAC chemical name is (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[[2-(phenoxy)acetyl]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid and it has molecular formula C₁₆H₁₈N₂O₅S (MM = 350.3895 g/mol).

Drug interactions

Tetracycline and its derivatives demeclocycline, doxycycline, methacycline, minocycline, oxytetracycline, rolitetracycline, and tetracycline are antagonists of penicillins. The effects of oral contraceptives, including [[ethinyl estradiol] and mestranol are decreased when using penicillin. Penicillins increases the effect and toxicity of methotrexate.[1]

Synonyms and brand names

synonyms Fenossimetilpenicillina Fenoximetilpenicilina Penicillin Phenoxymethyl Penicillin V Potassium Phenoxymethylpenicillinic Acid Phenoxymethylpenicillinic Acid Potassium Salt Phenoxymethylpenicillin Potassium Phenoxymethylenepenicillinic Acid Phenoxymethyl Penicillin Phenoximethylpenicillinum

Brand names Acipen V® Apopen® Beepen-Vk® Beromycin® Betapen-Vk® Calcipen® Compocillin V® Crystapen V® Distaquaine V® Eskacillian V® Eskacillin V® Fenacilin® Fenospen® Fenoxypen® Ledercillin Vk®

Brand names Meropenin® Oracillin® Oratren® Ospen® Pen-Oral® Pen-V® Pen-Vee® Pen-Vee K® Penapar-Vk® Penicillin Vk® Penicillin-Vk® Pfizerpen Vk® Phenocillin® Phenomycilline® Phenopenicillin®

Brand Names Robicillin® Rocilin® Stabicillin® Uticillin Vk® V-Cil® V-Cillin® V-Cillin K® V-Cylina® V-Cyline® V-Tablopen® Vebecillin® Veetids® Veetids '125'® Veetids '250'® Veetids '500'®

External links

The most up-to-date information about Penicillin V and other drugs can be found at the following sites.

• Penicillin V - FDA approved drug information (drug label) from DailyMed (U.S. National Library of Medicine).
• Penicillin V - Drug information for consumers from MedlinePlus (U.S. National Library of Medicine).
• Penicillin V - Detailed information from DrugBank.