ertapenem ๐Ÿถ Veterinary Use | 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: -0.83
  • 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 ยตM/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
Macular degeneration 612.71 22.52 159 4317 14229 50586419
Seizure 139.70 22.52 101 4375 117773 50482875
Hallucination 121.52 22.52 66 4410 46591 50554057
Drug ineffective 118.18 22.52 236 4240 819097 49781551
Confusional state 103.26 22.52 103 4373 185825 50414823
Encephalopathy 88.59 22.52 48 4428 33663 50566985
Renal graft infection 68.80 22.52 12 4464 150 50600498
Mental status changes 59.28 22.52 38 4438 36234 50564414
Product use in unapproved indication 54.81 22.52 59 4417 115760 50484888
Clostridium difficile infection 52.66 22.52 31 4445 25408 50575240
Avian influenza 49.92 22.52 8 4468 57 50600591
Status epilepticus 49.43 22.52 24 4452 13382 50587266
Mitochondrial toxicity 47.59 22.52 10 4466 348 50600300
Skin odour abnormal 42.43 22.52 12 4464 1460 50599188
Acute generalised exanthematous pustulosis 42.24 22.52 19 4457 8919 50591729
Generalised tonic-clonic seizure 41.58 22.52 27 4449 26283 50574365
Epilepsy 41.29 22.52 25 4451 21542 50579106
Delirium 38.97 22.52 30 4446 38162 50562486
Clostridium test positive 38.38 22.52 12 4464 2060 50598588
Drug reaction with eosinophilia and systemic symptoms 37.32 22.52 26 4450 28398 50572250
Bone marrow eosinophilic leukocyte count increased 33.24 22.52 5 4471 22 50600626
Allergic hepatitis 32.24 22.52 5 4471 28 50600620
Wound secretion 31.20 22.52 12 4464 3805 50596843
Hallucination, visual 31.17 22.52 19 4457 16563 50584085
Urinary tract infection pseudomonal 29.97 22.52 8 4468 785 50599863
Klebsiella infection 29.93 22.52 14 4462 7180 50593468
Tooth discolouration 29.16 22.52 8 4468 871 50599777
Neurotoxicity 27.99 22.52 17 4459 14723 50585925
Enterococcal infection 27.40 22.52 13 4463 6885 50593763
Cross sensitivity reaction 26.69 22.52 9 4467 1960 50598688
Pathogen resistance 26.58 22.52 12 4464 5677 50594971
Hypoglycaemia 26.54 22.52 28 4448 53553 50547095
Escherichia test positive 26.09 22.52 9 4467 2098 50598550
Seizure like phenomena 23.71 22.52 7 4469 991 50599657
Choriocarcinoma 23.48 22.52 4 4472 43 50600605
Scar 23.39 22.52 14 4462 11804 50588844

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 219.01 22.49 173 4567 127704 29442083
Seizure 208.35 22.49 148 4592 92975 29476812
Hallucination 130.56 22.49 84 4656 44628 29525159
Encephalopathy 104.83 22.49 64 4676 30979 29538808
Hallucination, visual 89.38 22.49 45 4695 14970 29554817
Myoclonus 85.47 22.49 42 4698 13267 29556520
Delirium 79.46 22.49 59 4681 39338 29530449
Product use in unapproved indication 69.03 22.49 77 4663 86798 29482989
Generalised tonic-clonic seizure 65.93 22.49 40 4700 19099 29550688
Status epilepticus 51.76 22.49 28 4712 10766 29559021
Serotonin syndrome 51.23 22.49 33 4707 17479 29552308
Pathogen resistance 47.32 22.49 24 4716 8092 29561695
Epilepsy 47.28 22.49 32 4708 18400 29551387
Biliary sepsis 46.43 22.49 12 4728 568 29569219
Agitation 41.57 22.49 46 4694 51258 29518529
Drug interaction 41.53 22.49 95 4645 197290 29372497
Neurotoxicity 41.42 22.49 27 4713 14586 29555201
Clostridium difficile colitis 41.38 22.49 26 4714 13186 29556601
Toxic encephalopathy 40.24 22.49 18 4722 4594 29565193
Disorientation 39.87 22.49 35 4705 29480 29540307
Myasthenia gravis crisis 38.54 22.49 10 4730 481 29569306
Pseudomonal sepsis 37.39 22.49 15 4725 2927 29566860
Neuromyopathy 36.84 22.49 11 4729 888 29568899
Drug resistance 34.13 22.49 28 4712 21512 29548275
Eosinophilia 31.38 22.49 27 4713 22134 29547653
Appendicitis perforated 29.95 22.49 11 4729 1692 29568095
Rash morbilliform 25.88 22.49 11 4729 2482 29567305
Metabolic acidosis 24.20 22.49 30 4710 37632 29532155
Vitamin B1 deficiency 23.80 22.49 6 4734 257 29569530
Vitamin A deficiency 23.32 22.49 4 4736 23 29569764
Anticonvulsant drug level decreased 23.30 22.49 8 4732 1011 29568776

FDA Adverse Event Reporting System (Geriatric)

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 300.19 19.65 256 8053 260888 64229535
Seizure 280.82 19.65 205 8104 166687 64323736
Hallucination 251.61 19.65 141 8168 72647 64417776
Encephalopathy 184.48 19.65 107 8202 58712 64431711
Delirium 118.21 19.65 86 8223 69108 64421315
Hallucination, visual 112.82 19.65 60 8249 27774 64462649
Myoclonus 107.06 19.65 56 8253 25062 64465361
Product use in unapproved indication 101.19 19.65 119 8190 176499 64313924
Generalised tonic-clonic seizure 100.29 19.65 63 8246 39794 64450629
Status epilepticus 97.21 19.65 50 8259 21613 64468810
Epilepsy 89.40 19.65 55 8254 33476 64456947
Mental status changes 71.90 19.65 61 8248 61101 64429322
Pathogen resistance 68.23 19.65 33 8276 12510 64477913
Neurotoxicity 68.12 19.65 43 8266 27361 64463062
Clostridium difficile infection 64.10 19.65 46 8263 36117 64454306
Clostridium test positive 60.52 19.65 22 8287 4093 64486330
Clostridium difficile colitis 58.53 19.65 39 8270 27184 64463239
Renal graft infection 53.08 19.65 12 8297 401 64490022
Drug reaction with eosinophilia and systemic symptoms 49.69 19.65 47 8262 54170 64436253
Disorientation 48.52 19.65 47 8262 55781 64434642
Toxic encephalopathy 47.94 19.65 24 8285 9791 64480632
Drug resistance 45.36 19.65 37 8272 35065 64455358
Avian influenza 44.58 19.65 8 8301 79 64490344
Eosinophilia 42.73 19.65 37 8272 38039 64452384
Agitation 40.01 19.65 53 8256 88314 64402109
Cross sensitivity reaction 38.60 19.65 15 8294 3352 64487071
Myasthenia gravis crisis 34.87 19.65 10 8299 874 64489549
Acute generalised exanthematous pustulosis 34.77 19.65 22 8287 14036 64476387
Neuromyopathy 34.66 19.65 11 8298 1357 64489066
Biliary sepsis 34.19 19.65 11 8298 1417 64489006
Bone marrow eosinophilic leukocyte count increased 31.36 19.65 5 8304 22 64490401
Skin odour abnormal 31.30 19.65 11 8298 1856 64488567
Eosinophilic pneumonia 30.94 19.65 14 8295 4563 64485860
Escherichia test positive 30.32 19.65 12 8297 2813 64487610
Allergic hepatitis 29.92 19.65 5 8304 31 64490392
Tooth discolouration 29.67 19.65 9 8300 956 64489467
Pseudomonal sepsis 29.31 19.65 14 8295 5158 64485265
Disorganised speech 28.73 19.65 10 8299 1640 64488783
Metabolic acidosis 28.24 19.65 40 8269 70918 64419505
Fatigue 27.24 19.65 34 8275 748696 63741727
Pyrexia 26.77 19.65 142 8167 558502 63931921
Urinary tract infection pseudomonal 26.16 19.65 9 8300 1425 64488998
Seizure like phenomena 24.92 19.65 9 8300 1643 64488780
Arthralgia 24.88 19.65 13 8296 442247 64048176
Vitamin B1 deficiency 24.86 19.65 7 8302 573 64489850
Drug interaction 24.64 19.65 102 8207 361981 64128442
Anticonvulsant drug level decreased 24.02 19.65 9 8300 1821 64488602
Mitochondrial toxicity 23.92 19.65 10 8299 2696 64487727
Metabolic encephalopathy 23.53 19.65 14 8295 8011 64482412
Appendicitis perforated 23.52 19.65 10 8299 2810 64487613
Rash morbilliform 23.43 19.65 12 8297 5129 64485294
Wound secretion 23.24 19.65 12 8297 5220 64485203
Enterococcal infection 23.10 19.65 17 8292 13849 64476574
Off label use 22.66 19.65 149 8160 632657 63857766
Pain in extremity 21.87 19.65 6 8303 303079 64187344
Klebsiella infection 21.49 19.65 16 8293 13265 64477158
Unresponsive to stimuli 20.93 19.65 29 8280 50364 64440059
Vitamin A deficiency 20.62 19.65 4 8305 62 64490361
Choriocarcinoma 20.62 19.65 4 8305 62 64490361
Endotracheal intubation 20.43 19.65 10 8299 3885 64486538
Haematidrosis 20.39 19.65 4 8305 66 64490357
HER2 positive breast cancer 19.93 19.65 5 8304 262 64490161

FDA Adverse Event Reporting System (Pediatric)

None

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




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ Veterinary products

None

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
D-alanyl-D-alanine carboxypeptidase DacB Enzyme INHIBITOR DRUGBANK CHEMBL
Penicillin-binding protein 1A Enzyme INHIBITOR DRUGBANK CHEMBL
Penicillin-binding protein 1B 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
CHEMBL1359 ChEMBL_ID
CHEMBL1232 ChEMBL_ID
D000077727 MESH_DESCRIPTOR_UI
DB00303 DRUGBANK_ID
10906 IUPHAR_LIGAND_ID
8049 INN_ID
G32F6EID2H UNII
150610 PUBCHEM_CID
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
1RG PDB_CHEM_ID
2RG PDB_CHEM_ID

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 0006-3843 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
INVANZ HUMAN PRESCRIPTION DRUG LABEL 1 0006-3845 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 g INTRAVENOUS NDA 28 sections
ertapenem sodium HUMAN PRESCRIPTION DRUG LABEL 1 0143-9398 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 g INTRAMUSCULAR ANDA 28 sections
Ertapenem HUMAN PRESCRIPTION DRUG LABEL 1 0409-3510 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 g INTRAMUSCULAR ANDA 28 sections
ERTAPENEM SODIUM HUMAN PRESCRIPTION DRUG LABEL 1 16714-889 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 g INTRAVENOUS ANDA 25 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 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 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 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
Ertapenem HUMAN PRESCRIPTION DRUG LABEL 1 68001-408 INJECTION 1 g INTRAVENOUS ANDA 29 sections
Ertapenem Human Prescription Drug Label 1 68083-351 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 g INTRAVENOUS ANDA 25 sections
Ertapenem Human Prescription Drug Label 1 68083-351 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 g INTRAVENOUS ANDA 25 sections
Ertapenem HUMAN PRESCRIPTION DRUG LABEL 1 72266-159 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 g INTRAVENOUS ANDA 25 sections
Ertapenem HUMAN PRESCRIPTION DRUG LABEL 1 72266-159 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 g INTRAVENOUS ANDA 25 sections