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
Acute otitis media AB00 Approved [1]
Bacterial infection 1A00-1C4Z Approved [2]
Erysipelas N.A. Approved [1]
Respiratory tract infection CA45 Approved [1]
Staphylococcus aureus infection N.A. Approved [1]
Therapeutic Class
Antibiotics
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 350.4
Logarithm of the Partition Coefficient (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 [3]
Absorption Tmax
The time to maximum plasma concentration (Tmax) is 2 h [3]
Bioavailability
The bioavailability of drug is 25-60% [3]
Half-life
The concentration or amount of drug in body reduced by one-half in 30 minutes [4]
Vd
The volume of distribution (Vd) of drug is 35.4 L [5]
Adverse Drug Reaction (ADR)
ADR Term Variation Related DOT DOT ID REF
Adverse drug reaction Not Available GFAP OTQ01ZAS [6]
Depression Not Available FOS OTJBUVWS [6]
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
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

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 [7]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Cytochrome P450 3A4 (CYP3A4) OTQGYY83 CP3A4_HUMAN Gene/Protein Processing [8]
Glial fibrillary acidic protein (GFAP) OTQ01ZAS GFAP_HUMAN Drug Response [6]
Glutamate--cysteine ligase regulatory subunit (GCLM) OT6CP234 GSH0_HUMAN Gene/Protein Processing [9]
Interleukin-8 (CXCL8) OTS7T5VH IL8_HUMAN Gene/Protein Processing [9]
Liver carboxylesterase 1 (CES1) OT9L0LR8 EST1_HUMAN Gene/Protein Processing [9]
NAD(P)H dehydrogenase 1 (NQO1) OTZGGIVK NQO1_HUMAN Gene/Protein Processing [9]
Pirin (PIR) OT8ALXHU PIR_HUMAN Gene/Protein Processing [9]
Protein c-Fos (FOS) OTJBUVWS FOS_HUMAN Drug Response [6]
Tripartite motif-containing protein 16 (TRIM16) OTLRXYOZ TRI16_HUMAN Gene/Protein Processing [9]
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] [10]
Anisindione DM2C48U Moderate Increased risk of bleeding by the combination of Penicillin V and Anisindione. Coagulation defect [3B10] [11]
Mycophenolic acid DMRBMAU Moderate Altered absorption of Penicillin V due to GI flora changes caused by Mycophenolic acid. Crohn disease [DD70] [12]
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] [13]
Methotrexate DM2TEOL Major Decreased elimination of Penicillin V caused by Methotrexate mediated competitive inhibition of renal tubular secretion. Leukaemia [2A60-2B33] [14]
Warfarin DMJYCVW Moderate Increased risk of bleeding by the combination of Penicillin V and Warfarin. Supraventricular tachyarrhythmia [BC81] [11]
Mycophenolate mofetil DMPQAGE Moderate Altered absorption of Penicillin V due to GI flora changes caused by Mycophenolate mofetil. Transplant rejection [NE84] [12]
⏷ 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 Penicillin V FDA Label
2 How many modes of action should an antibiotic have Curr Opin Pharmacol. 2008 Oct;8(5):564-73.
3 Josefsson K, Bergan T: Pharmacokinetics of phenoxymethylpenicillin in volunteers. Chemotherapy. 1982;28(4):241-6. doi: 10.1159/000238084.
4 Phenoxymethyl Penicillin 250mg/5ml Oral Solution Sugar Free (syringe) - eMC
5 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.
6 ADReCS-Target: target profiles for aiding drug safety research and application. Nucleic Acids Res. 2018 Jan 4;46(D1):D911-D917. doi: 10.1093/nar/gkx899.
7 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.
8 A comprehensive in vitro and in silico analysis of antibiotics that activate pregnane X receptor and induce CYP3A4 in liver and intestine. Drug Metab Dispos. 2008 Aug;36(8):1689-97.
9 Evaluation of the sensitizing potential of antibiotics in vitro using the human cell lines THP-1 and MUTZ-LC and primary monocyte-derived dendritic cells. Toxicol Appl Pharmacol. 2012 Aug 1;262(3):283-92.
10 Agencia Espaola de Medicamentos y Productos Sanitarios Healthcare "Centro de informacion online de medicamentos de la AEMPS - CIMA.".
11 Alexander DP, Russo ME, Fohrman DE, Rothstein G "Nafcillin-induced platelet dysfunction and bleeding." Antimicrob Agents Chemother 23 (1983): 59-62. [PMID: 6830209]
12 Product Information. CellCept (mycophenolate mofetil). Roche Laboratories, Nutley, NJ.
13 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]
14 Dean R, Nachman J, Lorenzana AN "Possible methotrexate-mezlocillin interaction." Am J Pediatr Hematol Oncol 14 (1992): 88-92. [PMID: 1550270]