phenoxymethylpenicillin Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
antibiotics, 6-aminopenicillanic acid derivatives 2083 87-08-1

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • penicillin v
  • penicillin v potassium
  • phenopenicillin
  • meropenin
  • phenoxymethylpenicillin
  • phenoxymethylpenicillinic acid
A broad-spectrum penicillin antibiotic used orally in the treatment of mild to moderate infections by susceptible gram-positive organisms.
  • Molecular weight: 350.39
  • Formula: C16H18N2O5S
  • CLOGP: 1.94
  • LIPINSKI: 0
  • HAC: 7
  • HDO: 2
  • TPSA: 95.94
  • ALOGS: -2.89
  • ROTB: 5

Drug dosage:

DoseUnitRoute
2 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 4 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.25 mg/mL Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 71.35 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
Vd (Volume of distribution) 0.41 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 6.80 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.45 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 0.84 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Jan. 13, 1958 FDA WYETH AYERST

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug hypersensitivity 502.50 56.64 134 363 46509 2311079
Rash 247.03 56.64 83 414 59475 2298113
Lip swelling 105.38 56.64 25 472 4796 2352792
Swelling face 102.43 56.64 28 469 9465 2348123
Hypersensitivity 88.78 56.64 31 466 23562 2334026
Malaise 69.19 56.64 33 464 55552 2302036

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug hypersensitivity 217.03 68.39 55 242 15080 1731404
Rash 195.21 68.39 62 235 38631 1707853
Swelling face 86.87 68.39 21 276 4462 1742022
Swelling 72.89 68.39 20 277 6976 1739508

Pharmacologic Action:

SourceCodeDescription
ATC J01CE02 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
BETA-LACTAM ANTIBACTERIALS, PENICILLINS
Beta-lactamase sensitive penicillins
FDA EPC N0000175497 Penicillin-class Antibacterial
FDA CS M0016152 Penicillins
MeSH PA D000900 Anti-Bacterial Agents
MeSH PA D000890 Anti-Infective Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Acute otitis media indication 3110003
Infection of skin AND/OR subcutaneous tissue indication 19824006
Gingivostomatitis indication 20607006
Scarlet fever indication 30242009 DOID:8596
Streptococcal tonsillitis indication 41582007
Erysipelas indication 44653001 DOID:11330
Upper respiratory infection indication 54150009
Streptococcus pyogenes infection indication 302809008
Infective otitis media indication 312218008
Fusospirochetal pharyngitis indication 399095008
Pharyngitis indication 405737000 DOID:2275
Infection due to Staphylococcus aureus indication 406602003
Pneumococcal Acute Otitis Media indication
Upper Respiratory Pneumococcal Infection indication
Infection Prevention from Tooth Extraction indication
Rheumatic Fever Prevention indication
Upper Respiratory Streptococcal Infection indication
Actinomycotic infection off-label use 11817007 DOID:8478
Lyme disease off-label use 23502006 DOID:11729
Infection due to anaerobic bacteria off-label use 423451008
Pneumococcal Infection Prevention in Sickle Cell Disease off-label use
Kidney disease contraindication 90708001 DOID:557
Infectious mononucleosis contraindication 271558008 DOID:8568
Pseudomembranous enterocolitis contraindication 397683000

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 2.79 acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Bacterial penicillin-binding protein Enzyme INHIBITOR CHEMBL CHEMBL
Penicillin-binding protein 1A Enzyme WOMBAT-PK

External reference:

IDSource
N0000011298 NUI
C0030840 UMLSCUI
D05411 KEGG_DRUG
146T0TU1JB UNII
132-98-9 SECONDARY_CAS_RN
39359008 SNOMEDCT_US
7984 RXNORM
002684 NDDF
372725003 SNOMEDCT_US
CHEMBL615 ChEMBL_ID
DB00417 DRUGBANK_ID
CHEMBL1200852 ChEMBL_ID
PNV PDB_CHEM_ID
CHEBI:27446 CHEBI
518 INN_ID
D010404 MESH_DESCRIPTOR_UI
6869 PUBCHEM_CID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Penicillin V Potassium HUMAN PRESCRIPTION DRUG LABEL 1 0093-1172 TABLET 250 mg ORAL ANDA 13 sections
Penicillin V Potassium HUMAN PRESCRIPTION DRUG LABEL 1 0093-1174 TABLET 500 mg ORAL ANDA 13 sections
Penicillin V Potassium HUMAN PRESCRIPTION DRUG LABEL 1 0093-4125 POWDER, FOR SOLUTION 125 mg ORAL ANDA 13 sections
Penicillin V Potassium HUMAN PRESCRIPTION DRUG LABEL 1 0093-4127 POWDER, FOR SOLUTION 250 mg ORAL ANDA 13 sections
Penicillin V Potassium HUMAN PRESCRIPTION DRUG LABEL 1 0143-9836 TABLET, FILM COATED 500 mg ORAL ANDA 13 sections
Penicillin V Potassium HUMAN PRESCRIPTION DRUG LABEL 1 0143-9837 TABLET, FILM COATED 250 mg ORAL ANDA 13 sections
Penicillin V Potassium HUMAN PRESCRIPTION DRUG LABEL 1 0440-2055 TABLET 250 mg ORAL ANDA 12 sections
Penicillin V Potassium HUMAN PRESCRIPTION DRUG LABEL 1 0440-8055 TABLET 250 mg ORAL ANDA 11 sections
Penicillin V Potassium HUMAN PRESCRIPTION DRUG LABEL 1 0440-8056 TABLET 500 mg ORAL ANDA 12 sections
Penicillin V Potasium HUMAN PRESCRIPTION DRUG LABEL 1 0781-1205 TABLET 250 mg ORAL ANDA 12 sections
Penicillin V Potasium HUMAN PRESCRIPTION DRUG LABEL 1 0781-1655 TABLET 500 mg OROPHARYNGEAL ANDA 12 sections
Penicillin V Potassium HUMAN PRESCRIPTION DRUG LABEL 1 10544-075 TABLET, FILM COATED 500 mg ORAL ANDA 12 sections
Penicillin V Potassium HUMAN PRESCRIPTION DRUG LABEL 1 10544-296 TABLET 250 mg ORAL ANDA 12 sections
Penicillin V Potassium HUMAN PRESCRIPTION DRUG LABEL 1 10544-297 TABLET 500 mg ORAL ANDA 12 sections
Penicillin V Potassium HUMAN PRESCRIPTION DRUG LABEL 1 10544-500 TABLET 500 mg ORAL ANDA 13 sections
Penicillin V Potasium HUMAN PRESCRIPTION DRUG LABEL 1 10544-975 TABLET 500 mg ORAL ANDA 12 sections
Penicillin V Potassium HUMAN PRESCRIPTION DRUG LABEL 1 16714-234 TABLET, FILM COATED 250 mg ORAL ANDA 12 sections
Penicillin V Potassium HUMAN PRESCRIPTION DRUG LABEL 1 16714-235 TABLET, FILM COATED 500 mg ORAL ANDA 12 sections
Penicillin V Potassium HUMAN PRESCRIPTION DRUG LABEL 1 21695-318 TABLET 500 mg ORAL ANDA 11 sections
Penicillin V Potassium HUMAN PRESCRIPTION DRUG LABEL 1 21695-559 POWDER, FOR SOLUTION 250 mg ORAL ANDA 12 sections
Penicillin V Potassium HUMAN PRESCRIPTION DRUG LABEL 1 21695-772 POWDER, FOR SOLUTION 125 mg ORAL ANDA 12 sections
Penicillin V Potassium HUMAN PRESCRIPTION DRUG LABEL 1 33261-134 TABLET 250 mg ORAL ANDA 12 sections
Penicillin V Potassium HUMAN PRESCRIPTION DRUG LABEL 1 33261-138 TABLET 500 mg ORAL ANDA 12 sections
Penicillin V Potassium HUMAN PRESCRIPTION DRUG LABEL 1 42708-098 TABLET, FILM COATED 500 mg ORAL ANDA 12 sections
Penicillin V Potassium HUMAN PRESCRIPTION DRUG LABEL 1 43063-557 TABLET, FILM COATED 500 mg ORAL ANDA 12 sections
Penicillin V Potassium HUMAN PRESCRIPTION DRUG LABEL 1 43063-576 TABLET, FILM COATED 500 mg ORAL ANDA 12 sections
Penicillin V Potassium HUMAN PRESCRIPTION DRUG LABEL 1 43063-614 TABLET, FILM COATED 500 mg ORAL ANDA 12 sections
Penicillin V Potassium HUMAN PRESCRIPTION DRUG LABEL 1 43063-622 TABLET, FILM COATED 250 mg ORAL ANDA 12 sections
Penicillin V Potassium HUMAN PRESCRIPTION DRUG LABEL 1 43063-680 TABLET, FILM COATED 500 mg ORAL ANDA 12 sections
Penicillin V Potassium HUMAN PRESCRIPTION DRUG LABEL 1 43063-704 TABLET, FILM COATED 250 mg ORAL ANDA 12 sections