benzylpenicillin Indications/Contra | FAERs-F | FAERs-M | Orange Bk | 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

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
3.60 g P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 3 Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 564.67 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 30 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.24 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 6.90 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.40 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 0.70 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Feb. 6, 1947 FDA PFIZER

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 1432.43 15.27 782 8979 243043 46433258
Anaphylactic reaction 144.71 15.27 106 9655 53006 46623295
Urticaria 90.31 15.27 117 9644 117775 46558526
Rash 81.96 15.27 209 9552 356303 46319998
Toxic epidermal necrolysis 61.81 15.27 45 9716 22233 46654068
Loss of employment 58.37 15.27 18 9743 1238 46675063
Lymphoedema 53.44 15.27 29 9732 8583 46667718
Hypersensitivity 49.77 15.27 102 9659 150219 46526082
Exposure during pregnancy 46.40 15.27 82 9679 108130 46568171
Drug intolerance 43.13 15.27 95 9666 146954 46529347
Pneumococcal infection 38.08 15.27 10 9751 384 46675917
Oesophageal spasm 35.66 15.27 14 9747 1975 46674326
Oesophageal pain 35.64 15.27 15 9746 2528 46673773
Lipoedema 35.47 15.27 8 9753 160 46676141
X-ray abnormal 34.72 15.27 12 9749 1183 46675118
Eczema herpeticum 33.72 15.27 7 9754 93 46676208
Hepatitis infectious mononucleosis 33.51 15.27 7 9754 96 46676205
Dysbiosis 26.17 15.27 8 9753 534 46675767
Angioedema 23.95 15.27 35 9726 39307 46636994
Fall 23.00 15.27 21 9740 329076 46347225
Bronchial obstruction 22.63 15.27 9 9752 1313 46674988
Fistula discharge 21.98 15.27 8 9753 917 46675384
Sleep apnoea syndrome 21.76 15.27 25 9736 22176 46654125
Pharyngeal oedema 20.81 15.27 20 9741 14451 46661850
Tendon operation 20.81 15.27 6 9755 327 46675974
Completed suicide 20.59 15.27 3 9758 145917 46530384
Spinal cord disorder 20.39 15.27 8 9753 1126 46675175
Wrist surgery 19.41 15.27 7 9754 781 46675520
Phlebectomy 19.14 15.27 4 9757 55 46676246
Bladder spasm 18.34 15.27 8 9753 1471 46674830
Gastric disorder 18.08 15.27 25 9736 26680 46649621
Finger deformity 17.99 15.27 12 9749 5150 46671151
Death 17.47 15.27 27 9734 335521 46340780
Oligohydramnios 17.37 15.27 12 9749 5453 46670848
Hepatic steatosis 17.02 15.27 23 9738 24019 46652282
Myelopathy 16.97 15.27 9 9752 2543 46673758
Lipase increased 16.53 15.27 14 9747 8589 46667712
Fibromyalgia 16.07 15.27 28 9733 36435 46639866
Gonorrhoea 15.62 15.27 4 9757 139 46676162

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 481.77 15.25 259 6753 68260 29877206
Sleep disorder due to general medical condition, insomnia type 96.47 15.25 27 6985 1179 29944287
Rheumatoid arthritis 86.73 15.25 74 6938 41123 29904343
Oral surgery 65.50 15.25 17 6995 555 29944911
Jarisch-Herxheimer reaction 65.07 15.25 16 6996 418 29945048
Acute generalised exanthematous pustulosis 53.85 15.25 27 6985 6071 29939395
Oral disorder 51.26 15.25 23 6989 4039 29941427
Spinal muscular atrophy 38.65 15.25 9 7003 185 29945281
Rheumatoid nodule 36.34 15.25 14 6998 1676 29943790
Pneumococcal sepsis 35.62 15.25 11 7001 678 29944788
Drug reaction with eosinophilia and systemic symptoms 34.86 15.25 38 6974 28450 29917016
Drug intolerance 32.20 15.25 46 6966 45245 29900221
Hypersensitivity 31.47 15.25 50 6962 53978 29891488
Respiratory tract infection bacterial 29.18 15.25 9 7003 552 29944914
Bradycardia neonatal 28.64 15.25 10 7002 906 29944560
Radiation fibrosis - lung 28.56 15.25 5 7007 21 29945445
Toxic epidermal necrolysis 27.48 15.25 27 6985 17913 29927553
Osteomyelitis salmonella 26.05 15.25 5 7007 38 29945428
Impaired work ability 25.24 15.25 16 6996 5627 29939839
Increased bronchial secretion 24.80 15.25 10 7002 1349 29944117
Oedema peripheral 24.56 15.25 67 6945 105765 29839701
Pain in jaw 23.84 15.25 21 6991 12135 29933331
Rash 22.01 15.25 96 6916 191793 29753673
Urticaria 22.01 15.25 43 6969 54563 29890903
Tachypnoea 21.97 15.25 22 6990 14930 29930536
Foetal exposure during pregnancy 21.29 15.25 34 6978 36837 29908629
Follicular mucinosis 21.01 15.25 4 7008 29 29945437
Middle insomnia 20.09 15.25 14 6998 5759 29939707
Resuscitation 18.88 15.25 8 7004 1224 29944242
Sputum increased 18.71 15.25 9 7003 1848 29943618
Disease complication 18.61 15.25 10 7002 2589 29942877
Rash maculo-papular 18.32 15.25 26 6986 25392 29920074
Anaphylactic reaction 17.82 15.25 27 6985 27955 29917511
Chest discomfort 17.34 15.25 35 6977 45445 29900021
Resorption bone increased 16.96 15.25 4 7008 87 29945379
Sciatic nerve injury 16.43 15.25 4 7008 100 29945366
White blood cell count decreased 16.41 15.25 50 6962 83897 29861569
Death 15.81 15.25 38 6974 357245 29588221
Chest X-ray abnormal 15.77 15.25 10 7002 3517 29941949
Tongue biting 15.60 15.25 6 7006 714 29944752
Hypervolaemia 15.45 15.25 8 7004 1921 29943545

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 CS M0016152 Penicillins
FDA EPC N0000175497 Penicillin-class Antibacterial
MeSH PA D000900 Anti-Bacterial Agents
MeSH PA D000890 Anti-Infective Agents
CHEBI has role CHEBI:50904 allergene
CHEBI has role CHEBI:36047 antibacterial drugs
CHEBI has role CHEBI:53000 epitope function
CHEBI has role CHEBI:88188 allergenic drug

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
D01053 KEGG_DRUG
113-98-4 SECONDARY_CAS_RN
4017435 VANDF
4017438 VANDF
4017440 VANDF
4019880 VANDF
C0030827 UMLSCUI
CHEBI:18208 CHEBI
PNN PDB_CHEM_ID
CHEMBL29 ChEMBL_ID
CHEMBL1223 ChEMBL_ID
CHEMBL1126 ChEMBL_ID
DB01053 DRUGBANK_ID
D010406 MESH_DESCRIPTOR_UI
D010400 MESH_DESCRIPTOR_UI
5904 PUBCHEM_CID
4796 IUPHAR_LIGAND_ID
58 INN_ID
Q42T66VG0C UNII
203133 RXNORM
179173 MMSL
179425 MMSL
2147 MMSL
2169 MMSL
5245 MMSL
5247 MMSL
d00116 MMSL
d07728 MMSL
d07729 MMSL
002679 NDDF
002680 NDDF
004977 NDDF
016121 NDDF
11986009 SNOMEDCT_US
323389000 SNOMEDCT_US
373270004 SNOMEDCT_US
6369005 SNOMEDCT_US
764146007 SNOMEDCT_US
78507004 SNOMEDCT_US
89055006 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Pfizerpen HUMAN PRESCRIPTION DRUG LABEL 1 0049-0420 POWDER, FOR SOLUTION 5000000 [iU] INTRAVENOUS ANDA 26 sections
Pfizerpen HUMAN PRESCRIPTION DRUG LABEL 1 0049-0430 POWDER, FOR SOLUTION 20000000 [iU] INTRAVENOUS ANDA 26 sections
Pfizerpen HUMAN PRESCRIPTION DRUG LABEL 1 0049-0520 POWDER, FOR SOLUTION 5000000 [iU] INTRAVENOUS ANDA 25 sections
Pfizerpen HUMAN PRESCRIPTION DRUG LABEL 1 0049-0520 POWDER, FOR SOLUTION 5000000 [iU] INTRAVENOUS ANDA 25 sections
Pfizerpen HUMAN PRESCRIPTION DRUG LABEL 1 0049-0530 POWDER, FOR SOLUTION 20000000 [iU] INTRAVENOUS ANDA 25 sections
Pfizerpen HUMAN PRESCRIPTION DRUG LABEL 1 0049-0530 POWDER, FOR SOLUTION 20000000 [iU] INTRAVENOUS ANDA 25 sections
PENICILLIN G POTASSIUM HUMAN PRESCRIPTION DRUG LABEL 1 0338-1021 INJECTION, SOLUTION 1000000 [iU] INTRAVENOUS NDA 23 sections
PENICILLIN G POTASSIUM HUMAN PRESCRIPTION DRUG LABEL 1 0338-1023 INJECTION, SOLUTION 2000000 [iU] INTRAVENOUS NDA 23 sections
PENICILLIN G POTASSIUM HUMAN PRESCRIPTION DRUG LABEL 1 0338-1025 INJECTION, SOLUTION 3000000 [iU] INTRAVENOUS NDA 23 sections
Penicillin G Potassium HUMAN PRESCRIPTION DRUG LABEL 1 0781-6135 INJECTION, POWDER, FOR SOLUTION 5000000 [iU] INTRAVENOUS ANDA 22 sections
Penicillin G Potassium HUMAN PRESCRIPTION DRUG LABEL 1 0781-6136 INJECTION, POWDER, FOR SOLUTION 20000000 [iU] INTRAVENOUS ANDA 22 sections
Penicillin G Sodium HUMAN PRESCRIPTION DRUG LABEL 1 0781-6153 INJECTION, POWDER, FOR SOLUTION 5000000 [USPU] INTRAMUSCULAR ANDA 23 sections
Penicillin G Potassium HUMAN PRESCRIPTION DRUG LABEL 1 44567-310 INJECTION, POWDER, FOR SOLUTION 1000000 [iU] INTRAVENOUS ANDA 24 sections
Penicillin G Potassium HUMAN PRESCRIPTION DRUG LABEL 1 44567-311 INJECTION, POWDER, FOR SOLUTION 5000000 [iU] INTRAVENOUS ANDA 24 sections
Penicillin G Potassium HUMAN PRESCRIPTION DRUG LABEL 1 44567-312 INJECTION, POWDER, FOR SOLUTION 20000000 [iU] INTRAVENOUS ANDA 24 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 25 sections
Penicillin G Potassium HUMAN PRESCRIPTION DRUG LABEL 1 70860-127 INJECTION, POWDER, FOR SOLUTION 20000000 [iU] INTRAVENOUS ANDA 25 sections