DT-Web

DB00417 - Penicillin V


Identification
Name Penicillin V
Accession Number DB00417 (APRD00423, DB08415)
Type small molecule
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.
Structure
MOL SDF PDB SMILES InChI
Categories (*)
Molecular Weight 350.39
Groups approved
Monoisotopic Weight 350.093642386
Pharmacology
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
Mechanism of action By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, Penicillin V inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that Penicillin V interferes with an autolysin inhibitor.
Absorption 25% of the dose given is absorbed, 50-60% bioavailable
Protein binding 80%
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.
Route of elimination Mostly renal. A small percentage is eliminated by feces and the biliary route.
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
Interactions
Drug Interactions
Drug Mechanism of interaction
Demeclocycline Possible antagonism of action
Doxycycline Possible antagonism of action
Fusidic Acid Fusidic acid may diminish the therapeutic effect of penicillins. To management this interaction, penicillin should be administered 2 hours before fusidic acid.
Mestranol This anti-infectious agent could decrease the effect of the oral contraceptive
Methacycline Possible antagonism of action
Methotrexate The penicillin increases the effect and toxicity of methotrexate
Minocycline Possible antagonism of action
Oxytetracycline Possible antagonism of action
Rolitetracycline Possible antagonism of action
Tetracycline Possible antagonism of action
Food Interactions
  • Absorption is increased when taken on an empty stomach (one hour before or two hours after meals).

Targets


Penicillin-binding proteins 1A/1B
Name Penicillin-binding proteins 1A/1B
Gene Name pbpA
Pharmacological action yes
Actions Not Available
References
  • Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. - Pubmed
  • Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. - Pubmed
DTHybrid score 1.0151
MecA PBP2' (penicillin binding protein 2')
Name MecA PBP2' (penicillin binding protein 2')
Gene Name mecA
Pharmacological action yes
Actions inhibitor
References
  • Lemaire S, Glupczynski Y, Duval V, Joris B, Tulkens PM, Van Bambeke F: Activities of ceftobiprole and other cephalosporins against extracellular and intracellular (THP-1 macrophages and keratinocytes) forms of methicillin-susceptible and methicillin-resistant Staphylococcus aureus. Antimicrob Agents Chemother. 2009 Jun;53(6):2289-97. Epub 2009 Mar 16. - Pubmed
DTHybrid score Not Available
Penicillin-binding protein 4
Name Penicillin-binding protein 4
Gene Name dacB
Pharmacological action unknown
Actions Not Available
References
  • Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. - Pubmed
DTHybrid score 0.6263
Penicillin acylase
Name Penicillin acylase
Gene Name Not Available
Pharmacological action unknown
Actions Not Available
References
  • Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. - Pubmed
DTHybrid score 1.068

Enzymes


Beta-lactamase
Name Beta-lactamase
Gene Name SHV-7
Actions substrate
References
  • Martin MT, Waley SG: Kinetic characterization of the acyl-enzyme mechanism for beta-lactamase I. Biochem J. 1988 Sep 15;254(3):923-5. - Pubmed
  • Chan PH, Chan KC, Liu HB, Chung WH, Leung YC, Wong KY: Fluorescein-labeled beta-lactamase mutant for high-throughput screening of bacterial beta-lactamases against beta-lactam antibiotics. Anal Chem. 2005 Aug 15;77(16):5268-76. - Pubmed
DTHybrid score 0.0133

Predictions


Id Partner name Gene Name Score
543 Penicillin-binding protein 1B mrcB 0.1717
6186 Penicillin-binding protein 1B ponB 0.1717
6822 Penicillin-binding protein 1b pbp1b 0.1717
6844 Penicillin-binding protein 1b pbp1b 0.1717
645 Penicillin-binding protein 1A mrcA 0.1692
5805 Penicillin-binding protein 1A ponA 0.1692
6185 Penicillin-binding protein 1A mrcA 0.1692
6799 Penicillin-binding protein 1A pbpA 0.1692
1539 Oligopeptide transporter, small intestine isoform SLC15A1 0.1243
2340 Beta-lactamase PSE-2 bla 0.0976
1974 Oligopeptide transporter, kidney isoform SLC15A2 0.084
6184 D-alanyl-D-alanine carboxypeptidase dacC dacC 0.058
867 Penicillin-binding protein 3 pbpC 0.0481
6119 Penicillin-binding protein 3 pbp3 0.0481
7154 Penicillin-binding protein 3 pbp3 0.0481
7157 Penicillin-binding protein 3 LMHCC_2184 0.0481
7162 Penicillin-binding protein 3 pbpB 0.0481
7172 Penicillin-binding protein 3 pbp3 0.0481
1729 Solute carrier family 22 member 6 SLC22A6 0.0479
2688 Peptide deformylase def 0.042
2708 Peptide deformylase def 0.042
3004 Peptide deformylase def 0.042
4337 Peptide deformylase def 0.042
4338 Peptide deformylase def 0.042
5368 Peptide deformylase def 0.042
5371 Peptide deformylase def 0.042
6375 Peptide deformylase def 0.042
6378 Peptide deformylase def 0.042
6379 Peptide deformylase def 0.042
6776 Peptide deformylase def 0.042
6900 Peptide deformylase def 0.042
5367 Peroxiredoxin prx 0.0419
4037 Hypothetical protein GPX1 0.0419
4297 Hypothetical protein SP_1951 0.0419
4521 Hypothetical protein BC_2969 0.0419
4540 Hypothetical protein TM_1070 0.0419
4555 Hypothetical protein MT1739 0.0419
4569 Hypothetical protein mshD 0.0419
4578 Hypothetical protein PA3270 0.0419
4747 Hypothetical protein PA3967 0.0419
5177 Hypothetical protein TM_0096 0.0419
5194 Hypothetical protein PA1204 0.0419
5240 Hypothetical protein Rv2991 0.0419
5370 Hypothetical protein TM_1158 0.0419
5710 Hypothetical protein Tb927.5.1360 0.0419
5366 Sugar-phosphate isomerase TM_1080 0.0419
5365 Metallo beta-lactamase blaVIM-2 0.0419
5369 Golgi-associated plant pathogenesis-related protein 1 GLIPR2 0.0419
4699 Methylaspartate ammonia-lyase Not Available 0.0419
3858 Cathepsin L CTSL1 0.0364
3596 Deoxynucleotide monophosphate kinase 1 0.036
3760 Penicillin-binding protein 5 precursor dacA 0.0345
3105 M-phase inducer phosphatase 2 CDC25B 0.0333
1 Peptidoglycan synthetase ftsI ftsI 0.0329
4155 Peptidoglycan synthetase ftsI ftsI 0.0329
2664 S-ribosylhomocysteine lyase luxS 0.0317
2725 S-ribosylhomocysteine lyase luxS 0.0317
587 Serum albumin ALB 0.0283
115 Penicillin-binding protein 2 mrdA 0.0278
6069 Penicillin-binding protein 2 mrdA 0.0278
6118 Penicillin-binding protein 2 penA 0.0278
6187 Penicillin-binding protein 2 pbpA 0.0278
6686 Penicillin-binding protein 2 pbp2 0.0278
6939 Penicillin-binding protein 2 mrdA 0.0278
7163 Penicillin-binding protein 2 pbpA 0.0278
615 3-oxoacyl-[acyl-carrier-protein] synthase 3 fabH 0.0275
3138 3-oxoacyl-[acyl-carrier-protein] synthase 3 fabH 0.0275
4568 3-oxoacyl-[acyl-carrier-protein] synthase 3 fabH 0.0275
6370 3-oxoacyl-[acyl-carrier-protein] synthase 3 fabH 0.0275
1024 Solute carrier family 22 member 11 SLC22A11 0.0199
118 Organic cation/carnitine transporter 2 SLC22A5 0.0186
687 Tyrosine-protein phosphatase non-receptor type 1 PTPN1 0.0185
6142 Solute carrier family 22 member 8 SLC22A8 0.0171
6067 Penicillin binding protein 2a mecA 0.0143
4512 Cytochrome P450 3A4 CYP3A4 0.014
1757 Myeloperoxidase MPO 0.0139
332 Beta-lactamase blaZ 0.0133
2478 Beta-lactamase ampC 0.0133
2613 Beta-lactamase ampC 0.0133
2635 Beta-lactamase ampC 0.0133
2700 Beta-lactamase penP 0.0133
5445 Beta-lactamase blaB 0.0133
6701 Beta-lactamase cphA 0.0133
159 Penicillin-binding protein 2B penA 0.0126
6121 Penicillin-binding protein 2B penA 0.0126
4252 Penicillin-binding protein 5 dacA 0.0117
6143 Solute carrier family 22 member 7 SLC22A7 0.0113
6016 Cytochrome P450 2C19 CYP2C19 0.0067
2461 D-alanyl-D-alanine carboxypeptidase Not Available 0.0045
5756 D-alanyl-D-alanine carboxypeptidase dac 0.0045
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