piperacillin indications/contra

Stem definitionDrug idCAS RN
antibiotics, 6-aminopenicillanic acid derivatives 2187 61477-96-1

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • piperacillin hydrate
  • piperacillin
  • piperacillin sodium
  • pipracil
  • piperacillin sodium salt
Semisynthetic, broad-spectrum, AMPICILLIN derived ureidopenicillin antibiotic proposed for PSEUDOMONAS infections. It is also used in combination with other antibiotics.
  • Molecular weight: 517.56
  • Formula: C23H27N5O7S
  • CLOGP: 1.36
  • LIPINSKI: 2
  • HAC: 12
  • HDO: 3
  • TPSA: 156.43
  • ALOGS: -3.64
  • ROTB: 6

Drug dosage:

DoseUnitRoute
14 g P
14 g P

Approvals:

DateAgencyCompanyOrphan
Dec. 29, 1981 FDA

FDA Adverse Event Reporting System

scroll-->
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
Acute kidney injury 926.80 46.03 318 2801 49365 3333375
Pyrexia 548.45 46.03 250 2869 80865 3301875
Tubulointerstitial nephritis 486.48 46.03 114 3005 4272 3378468
Thrombocytopenia 426.31 46.03 165 2954 35103 3347637
Toxic epidermal necrolysis 379.47 46.03 94 3025 4451 3378289
Rash 365.81 46.03 182 2937 70639 3312101
Drug reaction with eosinophilia and systemic symptoms 305.68 46.03 89 3030 7806 3374934
Renal tubular necrosis 278.03 46.03 68 3051 3040 3379700
Rash maculo-papular 235.19 46.03 68 3051 5799 3376941
Stevens-Johnson syndrome 234.22 46.03 70 3049 6702 3376038
Eosinophilia 224.66 46.03 63 3056 4810 3377930
Pancytopenia 212.13 46.03 84 3035 18736 3364004
Neutropenia 211.25 46.03 99 3020 33287 3349453
Clostridium difficile colitis 200.40 46.03 52 3067 2951 3379789
Blood creatinine increased 200.12 46.03 84 3035 21734 3361006
Nephropathy toxic 198.94 46.03 52 3067 3037 3379703
Diarrhoea 180.02 46.03 133 2986 104215 3278525
Agranulocytosis 179.66 46.03 54 3065 5258 3377482
Hepatic function abnormal 172.93 46.03 63 3056 11164 3371576
Renal failure 167.00 46.03 84 3035 32856 3349884
Multiple organ dysfunction syndrome 164.63 46.03 65 3054 14345 3368395
Drug interaction 157.80 46.03 91 3028 46721 3336019
Acute respiratory distress syndrome 157.40 46.03 50 3069 5844 3376896
Sepsis 156.62 46.03 80 3039 32293 3350447
Drug hypersensitivity 154.94 46.03 82 3037 35598 3347142
Clostridium difficile infection 150.03 46.03 42 3077 3176 3379564
Renal impairment 149.75 46.03 65 3054 18196 3364544
Anaphylactic reaction 145.99 46.03 58 3061 12996 3369744
Clostridial infection 145.86 46.03 35 3084 1435 3381305
Septic shock 142.78 46.03 56 3063 12128 3370612

Pharmacologic Action:

scroll-->
SourceCodeDescription
ATC J01CA12 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
BETA-LACTAM ANTIBACTERIALS, PENICILLINS
Penicillins with extended spectrum
ATC J01CR05 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
BETA-LACTAM ANTIBACTERIALS, PENICILLINS
Combinations of penicillins, incl. beta-lactamase inhibitors
MeSH PA D000900 Anti-Bacterial Agents
MeSH PA D000890 Anti-Infective Agents
CHEBI has role CHEBI:36047 antibacterial drug

Drug Use (View source of the data)

scroll-->
DiseaseRelationSNOMED_IDDOID
Septicemia due to Escherichia coli indication 9323009
Bacterial septicemia indication 10001005
Infection due to Pseudomonas aeruginosa indication 11218009
Gonorrhea indication 15628003 DOID:7551
Infection of skin AND/OR subcutaneous tissue indication 19824006
Acute gonococcal cervicitis indication 20943002 DOID:10615
Streptococcal septicemia indication 29577008
Acute gonococcal urethritis indication 29864006
Postoperative infection indication 33910007
Pneumonia due to Pseudomonas indication 41381004
Peritonitis indication 48661000
Lower respiratory tract infection indication 50417007
Pneumonia due to Escherichia coli indication 51530003
Bacterial pneumonia indication 53084003 DOID:874
Klebsiella cystitis indication 60867007
Acute gonococcal endometritis indication 65295003 DOID:7527
Urinary tract infectious disease indication 68566005
Haemophilus influenzae pneumonia indication 70036007
Infection due to Escherichia coli indication 71057007
Bacterial infection due to Serratia indication 71120004
Rhinoscleroma indication 72409005 DOID:11336
Appendicitis indication 74400008 DOID:8337
Abdominal abscess indication 75100008
Septicemia due to Bacteroides indication 79587009
Septicemia due to Serratia indication 82091000
Infection of bone indication 111253001
Female genital tract infection indication 125585007
Infectious disease of abdomen indication 128070006
Infection due to Enterobacteriaceae indication 128945009
Bacterial infection due to Klebsiella pneumoniae indication 186435004
Proteus septicemia indication 300986008
Escherichia coli urinary tract infection indication 301011002
Proteus urinary tract infection indication 301012009
Septicemia due to enterococcus indication 310669007
Infectious disorder of joint indication 363162000 DOID:381
Infection due to Staphylococcus aureus indication 406602003
Nosocomial pneumonia indication 425464007
Sepsis due to Pseudomonas indication 448813005
Sepsis due to Gram negative bacteria indication 449082003
Urinary tract infection caused by Klebsiella indication 369001000119100
Skin and Skin Structure Bacteroides Fragilis Infection indication
E. Coli Appendicitis indication
Bacteroides Pneumonia indication
Complicated Skin and Skin Structure Staphylococcus Aureus Infection indication
Bacteroides Peritonitis indication
Skin and Skin Structure Enterococcus Infection indication
Prevention of Perioperative Infection indication
Pseudomonas Aeruginosa Urinary Tract Infection indication
Bacteroides Pelvic Inflammatory Disease indication
Bacteroides Pelvic Cellulitis indication
Bacteroides Endometritis indication
E. Coli Peritonitis indication
Pseudomonas Aeruginosa Joint Infection indication
Bacteroides Complicated Appendicitis indication
Enterococcus Urinary Tract Infection indication
E. Coli Pelvic Inflammatory Disease indication
Skin and Skin Structure Serratia Infection indication
Bacteroides Appendicitis indication
Enterobacter Pneumonia indication
Enterococcus Peritonitis indication
Cesarean Section Infection Prevention indication
Vaginal Hysterectomy Infection Prevention indication
Enterococcus Pelvic Inflammatory Disease indication
Bacteroides Osteomyelitis indication
Infection Prevention for GI Surgery indication
Enterococcus Joint Infection indication
Clostridium Peritonitis indication
Complicated Skin and Skin Structure Infection indication
Inflammatory Disease of Female Pelvic Organs indication
Pseudomonas Aeruginosa Osteomyelitis indication
Peptostreptococcus Pelvic Inflammatory Disease indication
Complicated Proteus UTI indication
Staphylococcus Nosocomial Pneumonia indication
Skin and Skin Structure Acinetobacter Infection indication
Bacteroides Joint Infection indication
Enterococcus Complicated UTI indication
Skin and Skin Structure Proteus Infection indication
Neisseria Gonorrhea Pelvic Cellulitis indication
E. Coli Complicated Appendicitis indication
E. Coli Endometritis indication
Diabetic Foot Infection indication
Enterococcus Osteomyelitis indication
Enterococcus Endometritis indication
Complicated UTI with Pseudomonas Aeruginosa indication
Skin and Skin Structure Pseudomonas Aeruginosa Infection indication
Enterococcus Pelvic Cellulitis indication
Blood coagulation disorder contraindication 64779008 DOID:1247
Kidney disease contraindication 90708001 DOID:2527
Infectious mononucleosis contraindication 271558008 DOID:8568
Neutropenic disorder contraindication 303011007 DOID:1227
Pseudomembranous enterocolitis contraindication 397683000 DOID:0060185
Ecthyma gangrenosum off-label use 17732003
Sepsis of the newborn off-label use 206376005
Diverticulitis of gastrointestinal tract off-label use 271366000
Pseudomonas Respiratory Tract Infection in Cystic Fibrosis off-label use

Acid dissociation constants calculated using MoKa v3.0.0

scroll-->
Dissociation levelDissociation constantType (acidic/basic)
pKa1 2.79 acidic
pKa2 12.64 acidic

Orange Book patent data (new drug applications)

scroll-->
Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
EQ 2GM BASE/VIAL ZOSYN WYETH PHARMS INC N050684 Oct. 22, 1993 RX INJECTABLE INJECTION 6900184 April 14, 2023 METHOD OF TREATING BACTERIAL INFECTIONS
EQ 2GM BASE/VIAL ZOSYN WYETH PHARMS INC N050684 Oct. 22, 1993 RX INJECTABLE INJECTION 8133883 April 14, 2023 METHOD OF TREATING BACTERIAL INFECTIONS
EQ 36GM BASE/VIAL ZOSYN WYETH PHARMS INC N050684 Oct. 22, 1993 RX INJECTABLE INJECTION 6900184 April 14, 2023 METHOD OF TREATING BACTERIAL INFECTIONS
EQ 36GM BASE/VIAL ZOSYN WYETH PHARMS INC N050684 Oct. 22, 1993 RX INJECTABLE INJECTION 8133883 April 14, 2023 METHOD OF TREATING BACTERIAL INFECTIONS
EQ 3GM BASE/VIAL ZOSYN WYETH PHARMS INC N050684 Oct. 22, 1993 RX INJECTABLE INJECTION 6900184 April 14, 2023 METHOD OF TREATING BACTERIAL INFECTIONS
EQ 3GM BASE/VIAL ZOSYN WYETH PHARMS INC N050684 Oct. 22, 1993 RX INJECTABLE INJECTION 8133883 April 14, 2023 METHOD OF TREATING BACTERIAL INFECTIONS
EQ 4GM BASE/VIAL ZOSYN WYETH PHARMS INC N050684 Oct. 22, 1993 RX INJECTABLE INJECTION 6900184 April 14, 2023 METHOD OF TREATING BACTERIAL INFECTIONS
EQ 4GM BASE/VIAL ZOSYN WYETH PHARMS INC N050684 Oct. 22, 1993 RX INJECTABLE INJECTION 8133883 April 14, 2023 METHOD OF TREATING BACTERIAL INFECTIONS
EQ 40MG BASE/ML ZOSYN IN PLASTIC CONTAINER WYETH PHARMS INC N050750 Feb. 24, 1998 RX INJECTABLE INJECTION 6900184 April 14, 2023 METHOD OF TREATING BACTERIAL INFECTIONS
EQ 40MG BASE/ML ZOSYN IN PLASTIC CONTAINER WYETH PHARMS INC N050750 Feb. 24, 1998 RX INJECTABLE INJECTION 8133883 April 14, 2023 METHOD OF TREATING BACTERIAL INFECTIONS
EQ 4GM BASE/100ML ZOSYN IN PLASTIC CONTAINER WYETH PHARMS INC N050750 Feb. 24, 1998 RX INJECTABLE INJECTION 6900184 April 14, 2023 METHOD OF TREATING BACTERIAL INFECTIONS
EQ 4GM BASE/100ML ZOSYN IN PLASTIC CONTAINER WYETH PHARMS INC N050750 Feb. 24, 1998 RX INJECTABLE INJECTION 8133883 April 14, 2023 METHOD OF TREATING BACTERIAL INFECTIONS
EQ 60MG BASE/ML ZOSYN IN PLASTIC CONTAINER WYETH PHARMS INC N050750 Feb. 24, 1998 RX INJECTABLE INJECTION 6900184 April 14, 2023 METHOD OF TREATING BACTERIAL INFECTIONS
EQ 60MG BASE/ML ZOSYN IN PLASTIC CONTAINER WYETH PHARMS INC N050750 Feb. 24, 1998 RX INJECTABLE INJECTION 8133883 April 14, 2023 METHOD OF TREATING BACTERIAL INFECTIONS

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

scroll-->
TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Bacterial penicillin-binding protein Enzyme INHIBITOR CHEMBL CHEMBL
Penicillin-binding protein 1A Enzyme WOMBAT-PK
Streptokinase A Enzyme EC50 6.55 WOMBAT-PK
Beta-lactamase Enzyme Ki 6.70 CHEMBL

External reference:

scroll-->
IDSource
DB00319 DRUGBANK_ID
4019896 VUID
N0000147981 NUI
C0031955 UMLSCUI
D00466 KEGG_DRUG
CHEMBL702 ChEMBL_ID
4019896 VANDF
8339 RXNORM
372836004 SNOMEDCT_US
74575000 SNOMEDCT_US
d00057 MMSL
N0000006138 NDFRT
N0000147981 NDFRT
004832 NDDF
43672 PUBCHEM_CID
CHEMBL1200820 ChEMBL_ID
D010878 MESH_DESCRIPTOR_UI
M98T69Q7HP UNII
59703-84-3 SECONDARY_CAS_RN
CHEBI:8232 CHEBI
WPP PDB_CHEM_ID

Pharmaceutical products:

scroll-->
ProductCategoryIngredientsNDCFormQuantityRoute MarketingLabel
Zosyn HUMAN PRESCRIPTION DRUG LABEL 2 0206-2404 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 2 g INTRAVENOUS NDA 18 sections
Zosyn HUMAN PRESCRIPTION DRUG LABEL 2 0206-2405 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 3 g INTRAVENOUS NDA 18 sections
Zosyn HUMAN PRESCRIPTION DRUG LABEL 2 0206-2408 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 4 g INTRAVENOUS NDA 18 sections
Zosyn HUMAN PRESCRIPTION DRUG LABEL 2 0206-2409 INJECTION, SOLUTION 2 g INTRAVENOUS NDA 13 sections
Zosyn HUMAN PRESCRIPTION DRUG LABEL 2 0206-2411 INJECTION, SOLUTION 3 g INTRAVENOUS NDA 13 sections
Zosyn HUMAN PRESCRIPTION DRUG LABEL 2 0206-2413 INJECTION, SOLUTION 4 g INTRAVENOUS NDA 13 sections
Zosyn HUMAN PRESCRIPTION DRUG LABEL 2 0206-2416 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 36 g INTRAVENOUS NDA 13 sections
Zosyn HUMAN PRESCRIPTION DRUG LABEL 2 0206-5501 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 36 g INTRAVENOUS NDA 13 sections
Zosyn HUMAN PRESCRIPTION DRUG LABEL 2 0206-8852 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 2 g INTRAVENOUS NDA 18 sections
Zosyn HUMAN PRESCRIPTION DRUG LABEL 2 0206-8854 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 3 g INTRAVENOUS NDA 18 sections
Zosyn HUMAN PRESCRIPTION DRUG LABEL 2 0206-8855 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 4 g INTRAVENOUS NDA 18 sections
Zosyn HUMAN PRESCRIPTION DRUG LABEL 2 0206-8859 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 36 g INTRAVENOUS NDA 18 sections
Zosyn HUMAN PRESCRIPTION DRUG LABEL 2 0206-8860 INJECTION, SOLUTION 2 g INTRAVENOUS NDA 18 sections
Zosyn HUMAN PRESCRIPTION DRUG LABEL 2 0206-8861 INJECTION, SOLUTION 3 g INTRAVENOUS NDA 18 sections
Zosyn HUMAN PRESCRIPTION DRUG LABEL 2 0206-8862 INJECTION, SOLUTION 4 g INTRAVENOUS NDA 18 sections
Piperacillin and Tazobactam HUMAN PRESCRIPTION DRUG LABEL 2 0409-2999 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 12 g INTRAVENOUS ANDA 18 sections
Piperacillin and Tazobactam HUMAN PRESCRIPTION DRUG LABEL 2 0409-3374 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 2 g INTRAVENOUS ANDA 18 sections
Piperacillin and Tazobactam HUMAN PRESCRIPTION DRUG LABEL 2 0409-3378 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 3 g INTRAVENOUS ANDA 18 sections
Piperacillin and Tazobactam HUMAN PRESCRIPTION DRUG LABEL 2 0409-3379 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 4 g INTRAVENOUS ANDA 18 sections
Piperacillin and Tazobactam HUMAN PRESCRIPTION DRUG LABEL 2 0409-3383 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 2 g INTRAVENOUS ANDA 18 sections
Piperacillin and Tazobactam HUMAN PRESCRIPTION DRUG LABEL 2 0409-3385 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 3 g INTRAVENOUS ANDA 18 sections
Piperacillin and Tazobactam HUMAN PRESCRIPTION DRUG LABEL 2 0409-3390 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 4 g INTRAVENOUS ANDA 18 sections
Piperacillin and Tazobactam HUMAN PRESCRIPTION DRUG LABEL 2 0781-3110 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 2 g INTRAVENOUS ANDA 18 sections
Piperacillin and Tazobactam HUMAN PRESCRIPTION DRUG LABEL 2 0781-3113 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 3 g INTRAVENOUS ANDA 18 sections
Piperacillin and Tazobactam HUMAN PRESCRIPTION DRUG LABEL 2 0781-3114 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 4 g INTRAVENOUS ANDA 18 sections
Piperacillin and Tazobactam HUMAN PRESCRIPTION DRUG LABEL 2 0781-3344 INJECTION, POWDER, FOR SOLUTION 2 g INTRAVENOUS ANDA 17 sections
Piperacillin and Tazobactam HUMAN PRESCRIPTION DRUG LABEL 2 0781-3350 INJECTION, POWDER, FOR SOLUTION 3 g INTRAVENOUS ANDA 17 sections
Piperacillin and Tazobactam HUMAN PRESCRIPTION DRUG LABEL 2 0781-3367 INJECTION, POWDER, FOR SOLUTION 4 g INTRAVENOUS ANDA 17 sections
Piperacillin and Tazobactam HUMAN PRESCRIPTION DRUG LABEL 2 0781-9344 INJECTION, POWDER, FOR SOLUTION 2 g INTRAVENOUS ANDA 17 sections
Piperacillin and Tazobactam HUMAN PRESCRIPTION DRUG LABEL 2 0781-9350 INJECTION, POWDER, FOR SOLUTION 3 g INTRAVENOUS ANDA 17 sections