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 145.99 22.19 100 3506 122954 46559502
Confusional state 112.13 22.19 95 3511 159797 46522659
Hallucination 108.95 22.19 60 3546 49891 46632565
Mental status changes 57.26 22.19 36 3570 38052 46644404
Macular degeneration 55.86 22.19 21 3585 7184 46675272
Clostridium difficile infection 54.22 22.19 30 3576 25073 46657383
Mitochondrial toxicity 49.26 22.19 10 3596 337 46682119
Encephalopathy 46.13 22.19 30 3576 33559 46648897
Avian influenza 44.49 22.19 7 3599 51 46682405
Product use in unapproved indication 44.22 22.19 44 3562 90229 46592227
Skin odour abnormal 43.67 22.19 12 3594 1507 46680949
Delirium 43.33 22.19 30 3576 37198 46645258
Generalised tonic-clonic seizure 41.66 22.19 26 3580 27096 46655360
Hidradenitis 39.74 22.19 12 3594 2103 46680353
Epilepsy 39.63 22.19 24 3582 23714 46658742
Renal graft infection 39.23 22.19 7 3599 116 46682340
Status epilepticus 36.61 22.19 19 3587 13960 46668496
Bone marrow eosinophilic leukocyte count increased 33.74 22.19 5 3601 23 46682433
Klebsiella infection 32.79 22.19 14 3592 6648 46675808
Allergic hepatitis 32.76 22.19 5 3601 29 46682427
Wound secretion 32.60 22.19 12 3594 3868 46678588
Clostridium test positive 32.36 22.19 10 3596 1894 46680562
Acute generalised exanthematous pustulosis 31.17 22.19 15 3591 9390 46673066
Tooth discolouration 30.86 22.19 8 3598 804 46681652
Hallucination, visual 29.64 22.19 18 3588 17855 46664601
Hypoglycaemia 29.41 22.19 28 3578 54321 46628135
Drug reaction with eosinophilia and systemic symptoms 25.74 22.19 20 3586 29528 46652928
Urinary tract infection pseudomonal 25.73 22.19 7 3599 846 46681610
Scar 24.94 22.19 14 3592 12005 46670451
Seizure like phenomena 24.67 22.19 7 3599 988 46681468
Escherichia test positive 23.85 22.19 8 3598 1964 46680492
Myoclonus 22.64 22.19 14 3592 14338 46668118

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
Confusional state 199.57 23.46 160 4142 134674 29813502
Seizure 194.62 23.46 139 4163 98336 29849840
Hallucination 112.35 23.46 76 4226 48983 29899193
Myoclonus 83.71 23.46 40 4262 13272 29934904
Encephalopathy 83.61 23.46 54 4248 32151 29916025
Delirium 79.05 23.46 57 4245 40574 29907602
Hallucination, visual 76.47 23.46 40 4262 16073 29932103
Generalised tonic-clonic seizure 63.95 23.46 38 4264 19513 29928663
Serotonin syndrome 53.92 23.46 33 4269 17858 29930318
Status epilepticus 51.13 23.46 27 4275 11045 29937131
Product use in unapproved indication 46.45 23.46 55 4247 73638 29874538
Biliary sepsis 45.99 23.46 12 4290 660 29947516
Drug interaction 45.61 23.46 93 4209 199475 29748701
Agitation 41.99 23.46 45 4257 54028 29894148
Pseudomonal sepsis 38.71 23.46 15 4287 2985 29945191
Neuromyopathy 37.19 23.46 11 4291 961 29947215
Disorientation 35.29 23.46 32 4270 31386 29916790
Clostridium difficile colitis 34.54 23.46 22 4280 12746 29935430
Pathogen resistance 31.87 23.46 18 4284 8392 29939784
Eosinophilia 31.85 23.46 26 4276 22134 29926042
Appendicitis perforated 30.78 23.46 11 4291 1747 29946429
Epilepsy 29.70 23.46 24 4278 20145 29928031
Drug resistance 27.63 23.46 23 4279 20110 29928066
Metabolic acidosis 27.00 23.46 30 4272 37431 29910745
Vitamin B1 deficiency 25.46 23.46 6 4296 216 29947960
Neurotoxicity 24.46 23.46 18 4284 13164 29935012
Anticonvulsant drug level decreased 24.16 23.46 8 4294 1011 29947165
Vitamin A deficiency 23.76 23.46 4 4298 23 29948153

Pharmacologic Action:

SourceCodeDescription
ATC J01DH03 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
OTHER BETA-LACTAM ANTIBACTERIALS
Carbapenems
FDA CS M0024174 Carbapenems
FDA EPC N0000175496 Penem Antibacterial
MeSH PA D000900 Anti-Bacterial Agents
MeSH PA D000890 Anti-Infective Agents
CHEBI has role CHEBI:36047 antibacterial drugs

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
4021283 VUID
N0000148720 NUI
D04049 KEGG_DRUG
153773-82-1 SECONDARY_CAS_RN
4021283 VANDF
C1120106 UMLSCUI
CHEBI:404903 CHEBI
1RG PDB_CHEM_ID
2RG PDB_CHEM_ID
CHEMBL1359 ChEMBL_ID
CHEMBL1232 ChEMBL_ID
DB00303 DRUGBANK_ID
D000077727 MESH_DESCRIPTOR_UI
150610 PUBCHEM_CID
10906 IUPHAR_LIGAND_ID
8049 INN_ID
G32F6EID2H UNII
325642 RXNORM
16218 MMSL
173352 MMSL
274067 MMSL
42474 MMSL
d04783 MMSL
009554 NDDF
009555 NDDF
385573008 SNOMEDCT_US
385574002 SNOMEDCT_US
396346003 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
INVANZ HUMAN PRESCRIPTION DRUG LABEL 1 0006-3843 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 g INTRAMUSCULAR NDA 28 sections
INVANZ HUMAN PRESCRIPTION DRUG LABEL 1 0006-3845 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 g INTRAVENOUS NDA 28 sections
Ertapenem HUMAN PRESCRIPTION DRUG LABEL 1 0409-3510 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 g INTRAMUSCULAR ANDA 28 sections
ERTAPENEM HUMAN PRESCRIPTION DRUG LABEL 1 42023-221 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 g INTRAMUSCULAR NDA 29 sections
ERTAPENEM HUMAN PRESCRIPTION DRUG LABEL 1 42023-221 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 g INTRAMUSCULAR NDA 29 sections
ERTAPENEM SODIUM HUMAN PRESCRIPTION DRUG LABEL 1 43598-901 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 g INTRAVENOUS ANDA 25 sections
ertapenem HUMAN PRESCRIPTION DRUG LABEL 1 44567-820 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 g INTRAMUSCULAR ANDA 28 sections
Ertapenem HUMAN PRESCRIPTION DRUG LABEL 1 44647-051 INJECTION 1 g INTRAVENOUS ANDA 29 sections
Ertapenem Human Prescription Drug Label 1 55150-282 INJECTION 1 g INTRAVENOUS ANDA 25 sections
Ertapenem Human Prescription Drug Label 1 55150-282 INJECTION 1 g INTRAVENOUS ANDA 25 sections
Ertapenem HUMAN PRESCRIPTION DRUG LABEL 1 60505-6196 INJECTION 1 g INTRAVENOUS ANDA 29 sections
Ertapenem HUMAN PRESCRIPTION DRUG LABEL 1 63323-823 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 g INTRAVENOUS ANDA 29 sections
Ertapenem HUMAN PRESCRIPTION DRUG LABEL 1 68001-408 INJECTION 1 g INTRAVENOUS ANDA 29 sections
Ertapenam Human Prescription Drug Label 1 68083-351 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 g INTRAVENOUS ANDA 25 sections