Details of the Drug

General Information of Drug (ID: DMKVOYF)

Drug Name
Penicillin V
Synonyms
Apocillin; Apopen; Beromycin; Calcipen; Fenacilin; Fenospen; Fenossimetilpenicillina; Fenoximetilpenicilina; Fenoxymethylpenicillin; Fenoxypen; Meropenin; Oracillin; Oratren; Ospen; PNV; PVA; Phenocillin; Phenomycilline; Phenopenicillin; Phenoximethylpenicillinum; Phenoxomethylpenicillanyl; Phenoxomethylpenicillin; Phenoxymethylpenicillanyl; Phenoxymethylpenicillin; Phenoxymethylpenicilline; Phenoxymethylpenicillinum; Robicillin; Rocilin; Stabicillin; Vebecillin; Vegacillin; Acipen V; Compocillin V; Crystapen V; Distaquaine V; Eskacillian V; Eskacillin V; Fenossimetilpenicillina [DCIT]; Penicillin V [USAN]; Penicillin phenoxymethyl; Phenoxymethyl penicillin; Phenoxymethylenepenicillinic acid; Phenoxymethylpenicillinic acid; Phenoxymethylpenicillinic acid potassium salt; Acipen-v; Beromycin, Penicillin; Berromycin, Penicillin; Fenoximetilpenicilina [INN-Spanish]; Pen-Oral; Pen-V; Pen-vee; Penicillin V (USP); Penicillin, Phenoxymethyl; Phenoxymethylpenicillin (INN); Phenoxymethylpenicilline [INN-French]; Phenoxymethylpenicillinum [INN-Latin]; V-Cil; V-Cillin; V-Cylina; V-Cyline; V-Tablopen; P-Mega-Tablinen; V-Cillin (TN); (2S,5R,6R)-3,3-DIMETHYL-7-OXO-6-(2-PHENOXYACETAMIDO)-4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID; (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-(2-phenoxyacetamido)-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid; (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-[(phenoxyacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(2-phenoxyacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (2S,5R,6R)-3,3-dimethyl-7-oxo-6-{[(phenyloxy)acetyl]amino}-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; 2,2-dimethyl-6beta-[(phenoxyacetyl)amino]penam-3alpha-carbonyl; 2,2-dimethyl-6beta-[(phenoxyacetyl)amino]penam-3alpha-carboxylic acid; 3,3-Dimethyl-7-oxo-6-((phenyloxyacetyl)amino)-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid; 3,3-dimethyl-6beta-[(phenoxyacetyl)amino]penam-2alpha-carboxylic acid (PIN); 6-Phenoxyacetamidopenicillanic acid
Indication
Disease Entry ICD 11 Status REF
Bacterial infection 1A00-1C4Z Approved [1]
Therapeutic Class
Antibiotics
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 350.4
Topological Polar Surface Area (xlogp) 2.1
Rotatable Bond Count (rotbonds) 5
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 6
ADMET Property
Absorption Cmax
The maximum plasma concentration (Cmax) of drug is 200-700 mcg/L [2]
Absorption Tmax
The time to maximum plasma concentration (Tmax) is 2 h [2]
Bioavailability
The bioavailability of drug is 25-60% [2]
Half-life
The concentration or amount of drug in body reduced by one-half in 30 minutes [3]
Vd
The volume of distribution (Vd) of drug is 35.4 L [4]
Chemical Identifiers
Formula
C16H18N2O5S
IUPAC Name
(2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(2-phenoxyacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Canonical SMILES
CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)COC3=CC=CC=C3)C(=O)O)C
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
Cross-matching ID
PubChem CID
6869
ChEBI ID
CHEBI:27446
CAS Number
87-08-1
DrugBank ID
DB00417
TTD ID
D09CPR
VARIDT ID
DR00868
ACDINA ID
D00515

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Bacterial Penicillin binding protein (Bact PBP) TTJP4SM NOUNIPROTAC Binder [5]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Penicillin V (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Framycetin DMF8DNE Moderate Altered absorption of Penicillin V caused by Framycetin. Alcoholic liver disease [DB94] [15]
Anisindione DM2C48U Moderate Increased risk of bleeding by the combination of Penicillin V and Anisindione. Coagulation defect [3B10] [16]
Mycophenolic acid DMU65NK Moderate Altered absorption of Penicillin V due to GI flora changes caused by Mycophenolic acid. Crohn disease [DD70] [17]
Probenecid DMMFWOJ Minor Decreased elimination of Penicillin V caused by Probenecid mediated competitive inhibition of renal tubular secretion. Inborn purine/pyrimidine/nucleotide metabolism error [5C55] [18]
Methotrexate DM2TEOL Major Decreased elimination of Penicillin V caused by Methotrexate mediated competitive inhibition of renal tubular secretion. Leukaemia [2A60-2B33] [19]
Warfarin DMJYCVW Moderate Increased risk of bleeding by the combination of Penicillin V and Warfarin. Supraventricular tachyarrhythmia [BC81] [16]
Mycophenolate mofetil DMPQAGE Moderate Altered absorption of Penicillin V due to GI flora changes caused by Mycophenolate mofetil. Transplant rejection [NE84] [17]
⏷ Show the Full List of 7 DDI Information of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG
DIG Name DIG ID PubChem CID Functional Classification
Sodium citrate anhydrous E00102 6224 Alkalizing agent; Buffering agent; Complexing agent; Emulsifying agent
Sodium lauryl sulfate E00464 3423265 Emulsifying agent; Modified-release agent; Penetration agent; Solubilizing agent; Surfactant; lubricant
Beta-D-lactose E00099 6134 Diluent; Dry powder inhaler carrier; Lyophilization aid
Hypromellose E00634 Not Available Coating agent
Magnesium stearate E00208 11177 lubricant
Polyethylene glycol 400 E00653 Not Available Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Povidone E00667 Not Available Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
Silicon dioxide E00670 Not Available Anticaking agent; Opacifying agent; Viscosity-controlling agent
Talc E00520 16211421 Anticaking agent; Diluent; Glidant; lubricant
Titanium dioxide E00322 26042 Coating agent; Colorant; Opacifying agent
Cellulose microcrystalline E00698 Not Available Adsorbent; Suspending agent; Diluent
⏷ Show the Full List of 11 Pharmaceutical Excipients of This Drug
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Penicillin V 250 mg tablet 250 mg Oral Tablet Oral
Penicillin V 500 mg tablet 500 mg Oral Tablet Oral
Penicillin V 500mg tablet 500mg Tablet Oral
Penicillin V 250mg tablet 250mg Tablet Oral
Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1 How many modes of action should an antibiotic have Curr Opin Pharmacol. 2008 Oct;8(5):564-73.
2 Josefsson K, Bergan T: Pharmacokinetics of phenoxymethylpenicillin in volunteers. Chemotherapy. 1982;28(4):241-6. doi: 10.1159/000238084.
3 Phenoxymethyl Penicillin 250mg/5ml Oral Solution Sugar Free (syringe) - eMC
4 Overbosch D, Mattie H, van Furth R: Comparative pharmacodynamics and clinical pharmacokinetics of phenoxymethylpenicillin and pheneticillin. Br J Clin Pharmacol. 1985 May;19(5):657-68. doi: 10.1111/j.1365-2125.1985.tb02693.x.
5 Localization of penicillin-binding proteins to the splitting system of Staphylococcus aureus septa by using a mercury-penicillin V derivative. J Bacteriol. 1995 Jul;177(13):3631-40.
6 Effects of amino acid alterations in penicillin-binding proteins (PBPs) 1a, 2b, and 2x on PBP affinities of penicillin, ampicillin, amoxicillin, cefditoren, cefuroxime, cefprozil, and cefaclor in 18 clinical isolates of penicillin-susceptible, -intermediate, and -resistant pneumococci. Antimicrob Agents Chemother. 2002 May;46(5):1273-80.
7 Bacteriological characteristics of Staphylococcus aureus isolates from humans and bulk milk. J Dairy Sci. 2008 Feb;91(2):564-9.
8 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
9 Activities of antibiotics against methicillin-resistant Staphylococcus aureus with particular reference to synergetic effect between ticarcillin and fosfomycin on penicillinase non-producing methicillin-resistant S. aureus. Jpn J Antibiot. 1993 Jun;46(6):421-7.
10 Emerging drugs for bacterial urinary tract infections. Expert Opin Emerg Drugs. 2005 May;10(2):275-98.
11 Penicillin-binding protein sensitive to cephalexin in sporulation of Bacillus cereus. Microbiol Res. 1997 Sep;152(3):227-32.
12 Clofarabine: past, present, and future. Leuk Lymphoma. 2007 Oct;48(10):1922-30.
13 Relationship between penicillin-binding protein patterns and beta-lactamases in clinical isolates of Bacteroides fragilis with different susceptibility to beta-lactam antibiotics. J Med Microbiol. 2004 Mar;53(Pt 3):213-21.
14 Resistance of Pseudomonas aeruginosa to cefsulodin: modification of penicillin-binding protein 3 and mapping of its chromosomal gene. J Antimicrob Chemother. 1990 Apr;25(4):513-23.
15 Agencia Espaola de Medicamentos y Productos Sanitarios Healthcare "Centro de informacion online de medicamentos de la AEMPS - CIMA.".
16 Alexander DP, Russo ME, Fohrman DE, Rothstein G "Nafcillin-induced platelet dysfunction and bleeding." Antimicrob Agents Chemother 23 (1983): 59-62. [PMID: 6830209]
17 Product Information. CellCept (mycophenolate mofetil). Roche Laboratories, Nutley, NJ.
18 Allen MB, Fitzpatrick RW, Barratt A, Cole RB "The use of probenecid to increase the serum amoxycillin levels in patients with bronchiectasis." Respir Med 84 (1990): 143-6. [PMID: 2371437]
19 Dean R, Nachman J, Lorenzana AN "Possible methotrexate-mezlocillin interaction." Am J Pediatr Hematol Oncol 14 (1992): 88-92. [PMID: 1550270]