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

Stem definitionDrug idCAS RN
analogues of penicillanic acid antibiotics modified in the five-membered ring 1046 153832-46-3

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • ertapenem
  • invanz
  • ertapenem sodium
Ertapenem has in vitro activity against Gram-positive and Gram-negative aerobic and anaerobic bacteria. The bactericidal activity of ertapenem results from the inhibition of cell wall synthesis and is mediated through ertapenem binding to penicillin binding proteins (PBPs). In Escherichia coli, it has strong affinity toward PBPs 1a, 1b, 2, 3, 4 and 5 with preference for PBPs 2 and 3.
  • Molecular weight: 475.52
  • Formula: C22H25N3O7S
  • CLOGP: -1.82
  • LIPINSKI: 0
  • HAC: 10
  • HDO: 5
  • TPSA: 156.27
  • ALOGS: -3.22
  • ROTB: 7

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
1 g P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 3 Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 38 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 28.72 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
Vd (Volume of distribution) 0.12 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 0.45 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.10 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 3.80 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
April 18, 2002 EMA Merck Sharp & Dohme Ltd
Nov. 21, 2001 FDA MERCK SHARP DOHME

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
Seizure 297.63 44.95 85 624 24381 2332995
Confusional state 197.03 44.95 62 647 24282 2333094
Hallucination 196.93 44.95 49 660 8099 2349277
Encephalopathy 83.17 44.95 22 687 4539 2352837
Delirium 71.01 44.95 20 689 5203 2352173
Generalised tonic-clonic seizure 70.45 44.95 20 689 5352 2352024
Hallucination, visual 67.05 44.95 17 692 2962 2354414
Mental status changes 65.23 44.95 19 690 5563 2351813
Epilepsy 64.12 44.95 18 691 4621 2352755
Rash 61.03 44.95 35 674 59523 2297853
Status epilepticus 60.02 44.95 15 694 2463 2354913
Drug reaction with eosinophilia and systemic symptoms 56.67 44.95 17 692 5501 2351875
Drug ineffective 55.17 44.95 40 669 101584 2255792

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
Seizure 387.81 40.51 119 804 20322 1725536
Confusional state 374.57 40.51 117 806 21161 1724697
Hallucination 220.81 40.51 63 860 8107 1737751
Delirium 144.64 40.51 43 880 6319 1739539
Myoclonus 125.34 40.51 31 892 2264 1743594
Hallucination, visual 106.95 40.51 28 895 2564 1743294
Generalised tonic-clonic seizure 99.01 40.51 29 894 4017 1741841
Agitation 84.47 40.51 33 890 10993 1734865
Encephalopathy 79.28 40.51 25 898 4427 1741431
Disorientation 74.22 40.51 25 898 5444 1740414
Status epilepticus 64.99 40.51 18 905 2028 1743830
Epilepsy 61.29 40.51 20 903 3939 1741919
Clostridium difficile colitis 59.75 40.51 16 907 1588 1744270
Mental status changes 56.56 40.51 21 902 6054 1739804
Drug ineffective 50.41 40.51 43 880 63758 1682100
Acute kidney injury 46.09 40.51 32 891 34912 1710946
Biliary sepsis 45.46 40.51 8 915 105 1745753
Rash 45.42 40.51 33 890 38660 1707198

Pharmacologic Action:

SourceCodeDescription
ATC J01DH03 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
OTHER BETA-LACTAM ANTIBACTERIALS
Carbapenems
FDA Chemical/Ingredient N0000011294 Carbapenems
FDA EPC N0000175496 Penem Antibacterial
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)

DiseaseRelationSNOMED_IDDOID
Acute bacterial peritonitis indication 31860008
Bacterial pneumonia indication 53084003 DOID:874
Miscarriage with sepsis indication 67465009
Haemophilus influenzae pneumonia indication 70036007
Abdominal abscess indication 75100008
Female genital tract infection indication 125585007
Infectious disease of abdomen indication 128070006
Pneumococcal pneumonia indication 233607000
Escherichia coli urinary tract infection indication 301011002
Peptostreptococcus infection indication 135341000119101
Urinary tract infection caused by Klebsiella indication 369001000119100
Complicated Bacterial Peritonitis indication
Complicated Skin and Skin Structure Streptococcus Pyogenes Infection indication
Septic Abortion due to Porphyromonas indication
Post-Op Gynecologic Infection due to Porphyromonas indication
Klebsiella Pyelonephritis indication
Post-Op Gynecological Peptostreptococcus Infection indication
Complicated E. Coli Peritonitis indication
Postpartum Endomyometritis due to E. Coli indication
Postpartum Endomyometritis due to Streptococcus indication
Diabetic Foot Infection indication
Streptococcal Septic Abortion indication
Postpartum Endomyometritis due to Peptostreptococcus indication
Post-Op Gynecologic Infection due to Bacteroides indication
Postpartum Endomyometritis due to Bacteroides indication
E. Coli Septic Abortion indication
E. Coli Pyelonephritis indication
Complicated Skin and Skin Structure Staphylococcus Aureus Infection indication
Complicated Skin and Skin Structure E. Coli Infection indication
Peptostreptococcus Septic Abortion indication
Complicated Bacteroides Peritonitis indication
Moraxella Catarrhalis Pneumonia indication
Post-Op Gynecologic Infection due to Prevotella indication
Bacteroides Septic Abortion indication
Colorectal Surgery Infection Prevention indication
Postpartum Endomyometritis due to Porphyromonas indication
Post-Op Gynecological Infection due to E. Coli indication
Postpartum Endomyometritis due to Prevotella indication
Post-Op Gynecologic Infection, due to Streptococcus indication
Prevotella Septic Abortion indication
Complicated Skin and Skin Structure Infection indication
Gas gangrene caused by clostridium perfringens off-label use 266093005
Clostridium Perfringens Empyema off-label use
Acute nephropathy contraindication 58574008
Kidney disease contraindication 90708001 DOID:557
Seizure disorder contraindication 128613002
Lesion of brain contraindication 301766008
Pseudomembranous enterocolitis contraindication 397683000

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 2.79 acidic
pKa2 4.1 acidic
pKa3 6.83 Basic

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
Penicillin-binding protein 1B Enzyme INHIBITOR DRUGBANK CHEMBL
Penicillin-binding protein 1A Enzyme INHIBITOR DRUGBANK CHEMBL
D-alanyl-D-alanine carboxypeptidase DacB Enzyme INHIBITOR DRUGBANK CHEMBL
Penicillin-binding protein 1 Enzyme WOMBAT-PK
Penicillin-binding protein 2 Enzyme WOMBAT-PK
D-alanyl-D-alanine carboxypeptidase; D-alanyl-D-alanine carboxypeptidase penicillin-binding protein 6 Enzyme WOMBAT-PK
Penicillin-binding protein 4 Enzyme WOMBAT-PK
D-ala-D-ala-carboxypeptidase; D-alanyl-D-alanine carboxypeptidase; D-alanyl-D-alanine carboxypeptidase family protein; Penicillin-binding protein 5 Enzyme WOMBAT-PK

External reference:

IDSource
D000077727 MESH_DESCRIPTOR_UI
4021283 VUID
N0000148720 NUI
C1120106 UMLSCUI
D04049 KEGG_DRUG
2T90KE67L0 UNII
153773-82-1 SECONDARY_CAS_RN
274067 MMSL
385574002 SNOMEDCT_US
d04783 MMSL
325642 RXNORM
4021283 VANDF
396346003 SNOMEDCT_US
009554 NDDF
CHEMBL1232 ChEMBL_ID
CHEMBL1359 ChEMBL_ID
DB00303 DRUGBANK_ID
8049 INN_ID
1RG PDB_CHEM_ID
2RG PDB_CHEM_ID
CHEBI:404903 CHEBI
150610 PUBCHEM_CID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
INVANZ HUMAN PRESCRIPTION DRUG LABEL 1 0006-3843 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 g INTRAMUSCULAR NDA 18 sections
INVANZ HUMAN PRESCRIPTION DRUG LABEL 1 0006-3845 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 g INTRAVENOUS NDA 18 sections
ERTAPENEM HUMAN PRESCRIPTION DRUG LABEL 1 42023-221 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 g INTRAMUSCULAR NDA 18 sections
ertapenem sodium HUMAN PRESCRIPTION DRUG LABEL 1 44567-820 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 g INTRAMUSCULAR ANDA 18 sections
Ertapenem HUMAN PRESCRIPTION DRUG LABEL 1 44647-051 INJECTION 1 g INTRAVENOUS ANDA 17 sections
Ertapenem HUMAN PRESCRIPTION DRUG LABEL 1 55150-282 INJECTION 1 g INTRAVENOUS ANDA 18 sections
Ertapenem HUMAN PRESCRIPTION DRUG LABEL 1 60505-6196 INJECTION 1 g INTRAVENOUS ANDA 17 sections
Ertapenem HUMAN PRESCRIPTION DRUG LABEL 1 63323-823 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 g INTRAVENOUS ANDA 16 sections
Ertapenem HUMAN PRESCRIPTION DRUG LABEL 1 68001-408 INJECTION 1 g INTRAVENOUS ANDA 17 sections