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 266.34 17.87 236 6030 243589 46436207
Rash 158.17 17.87 215 6051 356297 46323499
Myocardial depression 116.84 17.87 24 6242 484 46679312
Lip swelling 107.20 17.87 57 6209 25338 46654458
Decorticate posture 106.65 17.87 21 6245 339 46679457
Hypersensitivity 75.96 17.87 97 6169 150224 46529572
Swelling face 62.70 17.87 54 6212 53005 46626791
Ventricular hypokinesia 56.17 17.87 21 6245 4057 46675739
Urticaria 50.15 17.87 70 6196 117822 46561974
Lichen nitidus 44.92 17.87 8 6258 72 46679724
Hypothermia 44.86 17.87 25 6241 12158 46667638
Rash macular 43.75 17.87 29 6237 19231 46660565
Coma scale abnormal 38.62 17.87 17 6249 4989 46674807
Drug reaction with eosinophilia and systemic symptoms 36.77 17.87 31 6235 29517 46650279
Eosinophilia 36.70 17.87 26 6240 19191 46660605
Oral discomfort 34.02 17.87 18 6248 7900 46671896
Respiratory depression 27.64 17.87 18 6248 11582 46668214
Swollen tongue 27.13 17.87 26 6240 29206 46650590
Agranulocytosis 27.03 17.87 23 6243 22162 46657634
Pruritus 25.62 17.87 81 6185 242271 46437525
Acute respiratory distress syndrome 25.23 17.87 22 6244 21900 46657896
Intravascular haemolysis 24.44 17.87 6 6260 276 46679520
Encephalopathy 24.10 17.87 26 6240 33563 46646233
Hepatobiliary infection 24.03 17.87 4 6262 23 46679773
Unresponsive to stimuli 23.25 17.87 25 6241 32149 46647647
Intentional overdose 22.43 17.87 35 6231 64909 46614887
Lichenification 22.37 17.87 6 6260 393 46679403
Hepatocellular injury 21.44 17.87 23 6243 29499 46650297
Toxic epidermal necrolysis 21.02 17.87 20 6246 22258 46657538
Mouth swelling 20.56 17.87 10 6256 3679 46676117
Left ventricular dysfunction 19.86 17.87 14 6252 10241 46669555
Sickle cell anaemia with crisis 19.81 17.87 10 6256 3982 46675814
Vomiting projectile 18.69 17.87 7 6259 1358 46678438
Jaundice 18.40 17.87 21 6245 28824 46650972

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 102.96 16.94 93 5632 68426 29878327
Nocardiosis 81.42 16.94 29 5696 3426 29943327
Rash 68.14 16.94 127 5598 191762 29754991
Brief psychotic disorder with marked stressors 54.78 16.94 11 5714 135 29946618
Swelling face 51.20 16.94 38 5687 21166 29925587
Morganella infection 44.16 16.94 11 5714 374 29946379
Pleocytosis 41.94 16.94 11 5714 461 29946292
Acute generalised exanthematous pustulosis 40.92 16.94 21 5704 6077 29940676
Spinal muscular atrophy 40.47 16.94 9 5716 185 29946568
Bronchial haemorrhage 37.21 16.94 11 5714 718 29946035
Pyrexia 36.44 16.94 131 5594 294358 29652395
Respiratory tract infection bacterial 30.98 16.94 9 5716 552 29946201
Toxoplasmosis 29.36 16.94 10 5715 1033 29945720
Pneumococcal sepsis 29.16 16.94 9 5716 680 29946073
Thrombotic microangiopathy 29.15 16.94 19 5706 8591 29938162
Skin exfoliation 28.11 16.94 28 5697 23144 29923609
Prothrombin level abnormal 27.84 16.94 6 5719 106 29946647
Rash papular 26.66 16.94 18 5707 8627 29938126
Brain abscess 26.37 16.94 12 5713 2669 29944084
Skin swelling 26.35 16.94 9 5716 938 29945815
Sinusitis bacterial 26.31 16.94 7 5718 310 29946443
Drug reaction with eosinophilia and systemic symptoms 25.00 16.94 29 5696 28459 29918294
Death 23.94 16.94 20 5705 357263 29589490
Disease complication 23.58 16.94 11 5714 2588 29944165
Plasma cell myeloma 23.53 16.94 39 5686 53423 29893330
Antipsychotic drug level decreased 23.18 16.94 8 5717 860 29945893
Increased bronchial secretion 23.17 16.94 9 5716 1350 29945403
Swelling 22.61 16.94 31 5694 35944 29910809
Lip swelling 22.49 16.94 19 5706 12725 29934028
Parvovirus B19 infection 22.25 16.94 7 5718 563 29946190
Conjunctivitis bacterial 21.44 16.94 5 5720 128 29946625
Sputum increased 20.46 16.94 9 5716 1848 29944905
Tonsil cancer 20.20 16.94 7 5718 761 29945992
Mouth haemorrhage 19.29 16.94 12 5713 5005 29941748
Chest X-ray abnormal 17.65 16.94 10 5715 3517 29943236
Metabolic disorder 17.43 16.94 10 5715 3601 29943152
Sleep disorder due to general medical condition, insomnia type 17.13 16.94 7 5718 1199 29945554
Resuscitation 16.98 16.94 7 5718 1225 29945528
Inflammation 16.98 16.94 21 5704 22005 29924748

Pharmacologic Action:

SourceCodeDescription
ATC J01CE02 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
BETA-LACTAM ANTIBACTERIALS, PENICILLINS
Beta-lactamase sensitive penicillins
FDA CS M0016152 Penicillins
FDA EPC N0000175497 Penicillin-class Antibacterial
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
D05411 KEGG_DRUG
132-98-9 SECONDARY_CAS_RN
4017436 VANDF
C0030840 UMLSCUI
CHEBI:27446 CHEBI
PNV PDB_CHEM_ID
CHEMBL615 ChEMBL_ID
CHEMBL1200852 ChEMBL_ID
D010404 MESH_DESCRIPTOR_UI
DB00417 DRUGBANK_ID
10920 IUPHAR_LIGAND_ID
518 INN_ID
Z61I075U2W UNII
4731 PUBCHEM_CID
203195 RXNORM
179406 MMSL
2179 MMSL
5248 MMSL
d07730 MMSL
002684 NDDF
002686 NDDF
372725003 SNOMEDCT_US
39359008 SNOMEDCT_US
56723006 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Penicillin V Potassium HUMAN PRESCRIPTION DRUG LABEL 1 0093-1172 TABLET 250 mg ORAL ANDA 15 sections
Penicillin V Potassium HUMAN PRESCRIPTION DRUG LABEL 1 0093-1174 TABLET 500 mg ORAL ANDA 15 sections
Penicillin V Potassium HUMAN PRESCRIPTION DRUG LABEL 1 0093-4125 POWDER, FOR SOLUTION 125 mg ORAL ANDA 15 sections
Penicillin V Potassium HUMAN PRESCRIPTION DRUG LABEL 1 0093-4127 POWDER, FOR SOLUTION 250 mg ORAL ANDA 15 sections
Penicillin V Potassium HUMAN PRESCRIPTION DRUG LABEL 1 0143-9836 TABLET, FILM COATED 500 mg ORAL ANDA 15 sections
Penicillin V Potassium HUMAN PRESCRIPTION DRUG LABEL 1 0143-9837 TABLET, FILM COATED 250 mg ORAL ANDA 15 sections
Penicillin V Potassium HUMAN PRESCRIPTION DRUG LABEL 1 0440-2055 TABLET 250 mg ORAL ANDA 14 sections
Penicillin V Potassium HUMAN PRESCRIPTION DRUG LABEL 1 0440-8055 TABLET 250 mg ORAL ANDA 14 sections
Penicillin V Potassium HUMAN PRESCRIPTION DRUG LABEL 1 0440-8056 TABLET 500 mg ORAL ANDA 14 sections
Penicillin V Potasium HUMAN PRESCRIPTION DRUG LABEL 1 0781-1205 TABLET 250 mg ORAL ANDA 15 sections
Penicillin V Potasium HUMAN PRESCRIPTION DRUG LABEL 1 0781-1655 TABLET 500 mg OROPHARYNGEAL ANDA 15 sections
Penicillin V Potassium HUMAN PRESCRIPTION DRUG LABEL 1 10544-075 TABLET, FILM COATED 500 mg ORAL ANDA 14 sections
Penicillin V Potassium HUMAN PRESCRIPTION DRUG LABEL 1 10544-296 TABLET 250 mg ORAL ANDA 15 sections
Penicillin V Potassium HUMAN PRESCRIPTION DRUG LABEL 1 10544-297 TABLET 500 mg ORAL ANDA 15 sections
Penicillin V Potassium HUMAN PRESCRIPTION DRUG LABEL 1 10544-500 TABLET 500 mg ORAL ANDA 15 sections
Penicillin V Potasium HUMAN PRESCRIPTION DRUG LABEL 1 10544-975 TABLET 500 mg ORAL ANDA 16 sections
Penicillin V Potassium Human Prescription Drug Label 1 16714-234 TABLET, FILM COATED 250 mg ORAL ANDA 14 sections
Penicillin V Potassium Human Prescription Drug Label 1 16714-235 TABLET, FILM COATED 500 mg ORAL ANDA 14 sections
Penicillin V Potassium HUMAN PRESCRIPTION DRUG LABEL 1 21695-318 TABLET 500 mg ORAL ANDA 14 sections
Penicillin V Potassium HUMAN PRESCRIPTION DRUG LABEL 1 21695-559 POWDER, FOR SOLUTION 250 mg ORAL ANDA 14 sections
Penicillin V Potassium HUMAN PRESCRIPTION DRUG LABEL 1 21695-772 POWDER, FOR SOLUTION 125 mg ORAL ANDA 14 sections
Penicillin V Potassium HUMAN PRESCRIPTION DRUG LABEL 1 33261-134 TABLET 250 mg ORAL ANDA 14 sections
Penicillin V Potassium HUMAN PRESCRIPTION DRUG LABEL 1 33261-138 TABLET 500 mg ORAL ANDA 14 sections
Penicillin V Potassium HUMAN PRESCRIPTION DRUG LABEL 1 42708-098 TABLET, FILM COATED 500 mg ORAL ANDA 14 sections
Penicillin V Potassium HUMAN PRESCRIPTION DRUG LABEL 1 43063-557 TABLET, FILM COATED 500 mg ORAL ANDA 14 sections
Penicillin V Potassium HUMAN PRESCRIPTION DRUG LABEL 1 43063-576 TABLET, FILM COATED 500 mg ORAL ANDA 14 sections
Penicillin V Potassium HUMAN PRESCRIPTION DRUG LABEL 1 43063-614 TABLET, FILM COATED 500 mg ORAL ANDA 14 sections
Penicillin V Potassium HUMAN PRESCRIPTION DRUG LABEL 1 43063-622 TABLET, FILM COATED 250 mg ORAL ANDA 14 sections
Penicillin V Potassium HUMAN PRESCRIPTION DRUG LABEL 1 43063-680 TABLET, FILM COATED 500 mg ORAL ANDA 14 sections
Penicillin V Potassium HUMAN PRESCRIPTION DRUG LABEL 1 43063-704 TABLET, FILM COATED 250 mg ORAL ANDA 14 sections