(2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenoxyacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

• ChemBase ID: 300
• Molecular Formular: C16H18N2O5S
• Molecular Mass: 350.38952
• Monoisotopic Mass: 350.09364269
• SMILES: S1[C@H]2N([C@H](C1(C)C)C(=O)O)C(=O)[C@H]2NC(=O)COc1ccccc1
• Canonical SMILES: O=C(N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C)COc1ccccc1
• InChI: InChI=1S/C16H18N2O5S/c1-16(2)12(15(21)22)18-13(20)11(14(18)24-16)17-10(19)8-23-9-6-4-3-5-7-9/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22)/t11-,12+,14-/m1/s1
• InChIKey: BPLBGHOLXOTWMN-MBNYWOFBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenoxyacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• IUPAC Traditional name: penicillin V; (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenoxyacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• Brand Name: Acipen V; Apopen; Beepen-Vk; Beromycin; Betapen-Vk; Calcipen; Compocillin V; Crystapen V; Distaquaine V; Eskacillian V; Eskacillin V; Fenacilin; Fenospen; Fenoxypen; Ledercillin Vk; Meropenin; Oracillin; Oratren; Ospen; Pen-Oral; Pen-V; Pen-Vee; Pen-Vee K; Penapar-Vk; Penicillin Vk; Penicillin-Vk; Pfizerpen Vk; Phenocillin; Phenomycilline; Phenopenicillin; 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'
• Synonyms: Fenossimetilpenicillina [Dcit]; Fenoximetilpenicilina [INN-Spanish]; Penicillin Phenoxymethyl; Penicillin V Potassium; Phenoxymethylpenicillinic Acid; Phenoxymethylpenicillinic Acid Potassium Salt; Phenoxymethylpenicillin Potassium; Phenoxymethylenepenicillinic Acid; Phenoxymethyl Penicillin; Phenoximethylpenicillinum; Penicillin V; Apopen; Fenacillin; Fenocin; Fenospen; Fenoxypen; Meropenin; Oracillin; Oratren; Ospen; Pen-Vee; Phenocillin; Stabicillin; Vebecillin; Phenoxymethylpenicillin

Database IDs

• CAS Number: 87-08-1
• PubChem SID: 46507164; 160963763
• PubChem CID: 6869

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.390268
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -1.3336357
• LogD (pH = 7.4): -2.6421306
• Log P: 0.7632417
• Molar Refractivity: 85.768 cm^3
• Polarizability: 34.069244 Å^3
• Polar Surface Area: 95.94 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.78
• LOG S: -2.89
• Solubility (Water): 4.54e-01 g/l

PROPERTIES

Physical Property

• Solubility: <0.1 g/100mL
• Hydrophobicity(logP): 1.4

Pharmacology Properties

• Mechanism of Action: Binds penicillin binding protein 1Bs; Binds penicillin binding protein 3; Cell-wall mucopeptide synthesis inhibitor

Product Information

• Application(s): Orally absorbed antibiotic active against gram-positive bacteria

DETAILS

DrugBank - DB00417

• Drug Groups: approved
• Description: Penicillin V is narrow spectrum antibiotic used to treat mild to moderate infections caused by susceptible bacteria. It is a natural penicillin antibiotic that is administered orally. Penicillin V may also be used in some cases as prophylaxis against susceptible organisms.; ; Natural penicillins are considered the drugs of choice for several infections caused by susceptible gram positive aerobic organisms, such as Streptococcus pneumoniae, groups A, B, C and G streptococci, nonenterococcal group D streptococci, viridans group streptococci, and non-penicillinase producing staphylococcus. Aminoglycosides may be added for synergy against group B streptococcus (S. agalactiae), S. viridans, and Enterococcus faecalis. The natural penicillins may also be used as first or second line agents against susceptible gram positive aerobic bacilli such as Bacillus anthracis, Corynebacterium diphtheriae, and Erysipelothrix rhusiopathiae. Natural penicillins have limited activity against gram negative organisms; however, they may be used in some cases to treat infections caused by Neisseria meningitidis and Pasteurella. They are not generally used to treat anaerobic infections. Resistance patterns, susceptibility and treatment guidelines vary across regions.
• Indication: For the treatment of mild to moderately severe infections (e.g. dental infection, infections in the heart, middle ear infections, rheumatic fever, scarlet fever, skin infections, upper and lower respiratory tract infections) due to microorganisms
• Pharmacology: Penicillin V is a penicillin beta-lactam antibiotic used in the treatment of bacterial infections caused by susceptible, usually gram-positive, organisms. The name "penicillin" can either refer to several variants of penicillin available, or to the group of antibiotics derived from the penicillins. Penicillin V has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria. The bactericidal activity of Penicillin V results from the inhibition of cell wall synthesis and is mediated through Penicillin V binding to penicillin binding proteins (PBPs). Penicillin V is stable against hydrolysis by a variety of beta-lactamases, including penicillinases, and cephalosporinases and extended spectrum beta-lactamases.
• Toxicity: LD₅₀ >1040 mg/kg (Orally in rats with Sodium salt); Nausea, vomiting, stomach pain, diarrhea, and, in rare cases, major motor seizures
• Affected Organisms: Bacteria
• Biotransformation: About 35-70% of an oral dose is metabolized to penicilloic acid, an inactive metabolite. Small amounts of 6-aminopenicillanic acid have been recovered in the urine of patients on penicillin G. A small percentage of the drug appears to be hydroxylated into one or more active metabolites, which are also excreted via urine.
• Absorption: 25% of the dose given is absorbed, 50-60% bioavailable
• Half Life: 30 to 40 minutes
• Protein Binding: 80%
• Elimination: Mostly renal. A small percentage is eliminated by feces and the biliary route.
• References: : Inadvertent use of Bicillin C-R to treat syphilis infection--Los Angeles, California, 1999-2004. MMWR Morb Mortal Wkly Rep. 2005 Mar 11;54(9):217-9. [Pubmed] ; Gruchalla RS, Pirmohamed M: Clinical practice. Antibiotic allergy. N Engl J Med. 2006 Feb 9;354(6):601-9. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

REFERENCES

• : Inadvertent use of Bicillin C-R to treat syphilis infection--Los Angeles, California, 1999-2004. MMWR Morb Mortal Wkly Rep. 2005 Mar 11;54(9):217-9. Pubmed
• Gruchalla RS, Pirmohamed M: Clinical practice. Antibiotic allergy. N Engl J Med. 2006 Feb 9;354(6):601-9. Pubmed
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