benzylpenicillin Indications/Contra | FAERs | Orange Book | BioActivity |

Stem definitionDrug idCAS RN
antibiotics, 6-aminopenicillanic acid derivatives 2082 61-33-6

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • penicillin g
  • benzylpenicillin
  • benzylpenicillin G
  • free penicillin G
  • benzylpenicillinic acid
  • penicillin G potassium
  • penicillin
  • penicillin G sodium
  • benzylpenicillin potassium
  • benzylpenicillin sodium
A group of antibiotics that contain 6-aminopenicillanic acid with a side chain attached to the 6-amino group. The penicillin nucleus is the chief structural requirement for biological activity. The side-chain structure determines many of the antibacterial and pharmacological characteristics. (Goodman and Gilman's The Pharmacological Basis of Therapeutics, 8th ed, p1065)
  • Molecular weight: 334.39
  • Formula: C16H18N2O4S
  • CLOGP: 1.75
  • LIPINSKI: 0
  • HAC: 6
  • HDO: 2
  • TPSA: 86.71
  • ALOGS: -3.07
  • ROTB: 4

Drug dosage:

DoseUnitRoute
3.60 g P

Approvals:

DateAgencyCompanyOrphan
Feb. 6, 1947 FDA PFIZER

FDA Adverse Event Reporting System

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 3506.02 38.33 754 797 67646 4569795
Rash 350.67 38.33 149 1402 108239 4529202
Anaphylactic reaction 292.38 38.33 83 1468 17827 4619614
Urticaria 242.73 38.33 87 1464 39486 4597955
Drug intolerance 204.57 38.33 66 1485 21680 4615761
Toxic epidermal necrolysis 158.36 38.33 41 1510 6151 4631290
Sleep disorder due to general medical condition, insomnia type 118.41 38.33 21 1530 509 4636932
Hypersensitivity 113.49 38.33 50 1501 38371 4599070
Pruritus 110.49 38.33 60 1491 72512 4564929
Swelling 96.00 38.33 39 1512 24443 4612998
Drug ineffective 89.33 38.33 75 1476 185986 4451455
Rash maculo-papular 88.61 38.33 28 1523 8501 4628940
Drug reaction with eosinophilia and systemic symptoms 87.64 38.33 30 1521 11683 4625758
Clostridium difficile infection 83.97 38.33 24 1527 5180 4632261
Rheumatoid arthritis 81.75 38.33 35 1516 24964 4612477
Pyrexia 81.71 38.33 57 1494 107087 4530354
Acute generalised exanthematous pustulosis 77.05 38.33 20 1531 3010 4634431
White blood cell count decreased 75.42 38.33 36 1515 33029 4604412
Angioedema 72.36 38.33 30 1521 19735 4617706
Dyspnoea 70.59 38.33 58 1493 138927 4498514
Type IV hypersensitivity reaction 69.62 38.33 15 1536 1012 4636429
Jarisch-Herxheimer reaction 65.53 38.33 12 1539 349 4637092
Chest discomfort 58.20 38.33 27 1524 23183 4614258
Eczema herpeticum 53.66 38.33 8 1543 61 4637380
Hypotension 49.20 38.33 35 1516 67365 4570076
Osteomyelitis salmonella 46.92 38.33 6 1545 11 4637430
Follicular mucinosis 45.94 38.33 6 1545 14 4637427
Condition aggravated 44.27 38.33 31 1520 58140 4579301
Migraine 44.10 38.33 19 1532 13690 4623751
Dysuria 42.59 38.33 16 1535 8094 4629347
Tachycardia 42.36 38.33 24 1527 31121 4606320
Hypervolaemia 41.30 38.33 8 1543 316 4637125
Lipoedema 40.69 38.33 6 1545 42 4637399

Pharmacologic Action:

SourceCodeDescription
ATC J01CE01 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
BETA-LACTAM ANTIBACTERIALS, PENICILLINS
Beta-lactamase sensitive penicillins
ATC S01AA14 SENSORY ORGANS
OPHTHALMOLOGICALS
ANTIINFECTIVES
Antibiotics
FDA EPC N0000175497 Penicillin-class Antibacterial
FDA CS M0016152 Penicillins
CHEBI has role CHEBI:36047 antibacterial drug
CHEBI has role CHEBI:88188 drug allergen
MeSH PA D000900 Anti-Bacterial Agents
MeSH PA D000890 Anti-Infective Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Rat bite fever indication 1685005
Acute otitis media indication 3110003
Meningococcemia indication 4089001
Streptococcal meningitis indication 4510004 DOID:11574
Gangrenous pneumonia indication 7063008
Inhalational anthrax indication 11389007
Actinomycotic infection indication 11817007 DOID:8478
Anthrax septicemia indication 14972006
Infection of skin AND/OR subcutaneous tissue indication 19824006
Gingivostomatitis indication 20607006
Pulmonary actinomycosis indication 21846001
Pinta indication 22064009 DOID:1022
Cervicofacial actinomycosis indication 23014006
Neurosyphilis indication 26039008 DOID:9988
Gonococcal conjunctivitis neonatorum indication 28438004
Scarlet fever indication 30242009 DOID:8596
Listeria meningitis indication 31568009 DOID:11572
Pneumonia due to Streptococcus indication 34020007
Congenital syphilis indication 35742006 DOID:9856
Streptococcal tonsillitis indication 41582007
Abdominal actinomycosis indication 43894001
Erysipelas indication 44653001 DOID:11330
Gonococcal infection of joint indication 44743006
Pneumococcal meningitis indication 51169003
Upper respiratory infection indication 54150009
Yaws indication 70647001 DOID:10371
Late syphilis indication 72083004 DOID:8200
Abscess of lung indication 73452002 DOID:0060317
Syphilis indication 76272004
Tetanus indication 76902006 DOID:11338
Pasteurella infection indication 83172007 DOID:11055
Cutaneous anthrax indication 84980006 DOID:7426
Streptococcal infectious disease indication 85769006
Tertiary lesion of yaws indication 88037009
Gastrointestinal anthrax indication 111798006 DOID:13386
Listerial endocarditis indication 186318004
Primary genital syphilis indication 186847001
Latent early syphilis indication 186867005
Late latent syphilis indication 186903006
Latent yaws indication 186973005
Meningococcal meningitis indication 192644005
Infection by Pasteurella multocida indication 197718007
Sepsis of the newborn indication 206376005
Pneumococcal pneumonia indication 233607000
Neonatal pneumonia indication 233619008
Streptococcal toxic shock syndrome indication 240451000
Secondary syphilis indication 240557004 DOID:4157
Bejel indication 240686008 DOID:13431
Gas gangrene caused by clostridium perfringens indication 266093005
Neonatal meningitis indication 276674008
Bacterial endocarditis indication 301183007
Streptococcus pyogenes infection indication 302809008
Septicemia due to enterococcus indication 310669007
Infective otitis media indication 312218008
Diphtheria indication 397428000
Infection due to Clostridium botulinum indication 398565003
Fusospirochetal pharyngitis indication 399095008
Erysipeloid indication 400105005
Pharyngitis indication 405737000 DOID:2275
Infection due to Staphylococcus aureus indication 406602003
Anthrax indication 409498004 DOID:7427
Aspiration pneumonia indication 422588002 DOID:3240
Latent syphilis indication 444150000 DOID:9531
Streptococcus Myositis indication
Disseminated Gonococcal Infection indication
Tertiary Bejel indication
Pneumococcal Acute Otitis Media indication
Necrotizing Fasciitis Streptococcus Infection indication
Upper Respiratory Infection due to Neisseria Meningitidis indication
Streptococcus Empyema indication
Pneumococcus Endocarditis indication
Streptococcal Endocarditis indication
Upper Respiratory Pneumococcal Infection indication
Latent Bejel indication
Upper Respiratory Streptococcal Infection indication
Streptococcus Pericarditis indication
Rheumatic Fever Prevention indication
Clostridium Perfringens Empyema indication
Neonatal Group B Streptococcal Septicemia indication
Asymptomatic Congenital Syphilis indication
Granulomatosis Infantiseptica indication
Infection Prevention from Tooth Extraction indication
Lyme disease off-label use 23502006 DOID:11729
Lyme arthritis off-label use 33937009
Neonatal conjunctivitis off-label use 34298002 DOID:9699
Omphalitis of the newborn off-label use 42052009
Lyme carditis off-label use 77863005
Relapsing fever off-label use 420079008 DOID:13034
Infection due to anaerobic bacteria off-label use 423451008
Pneumococcal Infection Prevention in Sickle Cell Disease off-label use
Lyme Disease of the Central Nervous System 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
Beta-lactamase TEM Enzyme Ki 4.70 CHEMBL

External reference:

IDSource
4017440 VUID
N0000145828 NUI
C0030827 UMLSCUI
D01053 KEGG_DRUG
323389000 SNOMEDCT_US
78507004 SNOMEDCT_US
4017440 VANDF
7980 RXNORM
004977 NDDF
CHEMBL29 ChEMBL_ID
CHEMBL1126 ChEMBL_ID
CHEMBL1223 ChEMBL_ID
DB01053 DRUGBANK_ID
Q42T66VG0C UNII
58 INN_ID
113-98-4 SECONDARY_CAS_RN
PNK PDB_CHEM_ID
PNN PDB_CHEM_ID
CHEBI:18208 CHEBI
5904 PUBCHEM_CID
D010400 MESH_DESCRIPTOR_UI
D010406 MESH_DESCRIPTOR_UI
4796 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Pfizerpen HUMAN PRESCRIPTION DRUG LABEL 1 0049-0420 POWDER, FOR SOLUTION 5000000 [iU] INTRAVENOUS ANDA 13 sections
Pfizerpen HUMAN PRESCRIPTION DRUG LABEL 1 0049-0430 POWDER, FOR SOLUTION 20000000 [iU] INTRAVENOUS ANDA 13 sections
Pfizerpen HUMAN PRESCRIPTION DRUG LABEL 1 0049-0520 POWDER, FOR SOLUTION 5000000 [iU] INTRAVENOUS ANDA 12 sections
Pfizerpen HUMAN PRESCRIPTION DRUG LABEL 1 0049-0530 POWDER, FOR SOLUTION 20000000 [iU] INTRAVENOUS ANDA 12 sections
PENICILLIN G POTASSIUM HUMAN PRESCRIPTION DRUG LABEL 1 0338-1021 INJECTION, SOLUTION 1000000 [iU] INTRAVENOUS NDA 12 sections
PENICILLIN G POTASSIUM HUMAN PRESCRIPTION DRUG LABEL 1 0338-1023 INJECTION, SOLUTION 2000000 [iU] INTRAVENOUS NDA 12 sections
PENICILLIN G POTASSIUM HUMAN PRESCRIPTION DRUG LABEL 1 0338-1025 INJECTION, SOLUTION 3000000 [iU] INTRAVENOUS NDA 12 sections
Penicillin G Potassium HUMAN PRESCRIPTION DRUG LABEL 1 0781-6135 INJECTION, POWDER, FOR SOLUTION 5000000 [iU] INTRAVENOUS ANDA 13 sections
Penicillin G Potassium HUMAN PRESCRIPTION DRUG LABEL 1 0781-6136 INJECTION, POWDER, FOR SOLUTION 20000000 [iU] INTRAVENOUS ANDA 13 sections
Penicillin G Sodium HUMAN PRESCRIPTION DRUG LABEL 1 0781-6153 INJECTION, POWDER, FOR SOLUTION 5000000 [USP'U] INTRAMUSCULAR ANDA 13 sections
Penicillin G Potassium HUMAN PRESCRIPTION DRUG LABEL 1 44567-310 INJECTION, POWDER, FOR SOLUTION 1000000 [iU] INTRAVENOUS ANDA 12 sections
Penicillin G Potassium HUMAN PRESCRIPTION DRUG LABEL 1 44567-311 INJECTION, POWDER, FOR SOLUTION 5000000 [iU] INTRAVENOUS ANDA 12 sections
Penicillin G Potassium HUMAN PRESCRIPTION DRUG LABEL 1 44567-312 INJECTION, POWDER, FOR SOLUTION 20000000 [iU] INTRAVENOUS ANDA 12 sections
BUFFERED PENICILLIN G POTASSIUM HUMAN PRESCRIPTION DRUG LABEL 1 51662-1436 INJECTION, POWDER, FOR SOLUTION 5000000 [iU] INTRAMUSCULAR ANDA 13 sections
Penicillin G Potassium HUMAN PRESCRIPTION DRUG LABEL 1 70860-126 INJECTION, POWDER, FOR SOLUTION 5000000 [iU] INTRAVENOUS ANDA 12 sections
Penicillin G Potassium HUMAN PRESCRIPTION DRUG LABEL 1 70860-127 INJECTION, POWDER, FOR SOLUTION 20000000 [iU] INTRAVENOUS ANDA 12 sections