Details of the Drug

General Information of Drug (ID: DM4S3O8)

Drug Name
Ertapenem
Synonyms
Ertapenem [INN]; Ertapenem (INN); Invanz (TN); (1R,5S,6S,8R,2'S,4'S)-2-(2-(3-carboxyphenylcarbamoyl)pyrrolidin-4-ylthio)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid; (4R,5S,6S)-3-((3S,5S)-5-((3-carboxyphenyl)carbamoyl)pyrrolidin-3-ylthio)-6-((R)-1-hydroxyethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid; (4R,5S,6S)-3-({(3S,5S)-5-[(3-carboxyphenyl)carbamoyl]pyrrolidin-3-yl}sulfanyl)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid; (4R,5S,6S)-3-[(3S,5S)-5-[(3-carboxyphenyl)carbamoyl]pyrrolidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
Indication
Disease Entry ICD 11 Status REF
Bacterial infection 1A00-1C4Z Approved [1]
Endometritis N.A. Approved [2]
Peptostreptococcus infectious disease N.A. Approved [2]
Streptococcal pneumonia N.A. Approved [2]
Therapeutic Class
Antibiotics
Affected Organisms
Enteric bacteria and other eubacteriaStaphylococcus aureusStreptococcus agalactiaeStreptococcus pneumoniaeStreptococcus pyogenesEscherichia coliHaemophilus influenzaeKlebsiella pneumoniaeMoraxella catarrhalisProteus mirabilisBacteroides fragilisParabacteroides distasonisBacteroides ovatusBacteroides thetaiotaomicronBacteroides uniformisClostridium clostridioformeEubacterium spp.PeptostreptococcusPrevotella biviaPorphyromonas asaccharolytica
ATC Code
J01DH03: Ertapenem
J01DH: Carbapenems
J01D: OTHER BETA-LACTAM ANTIBACTERIALS
J01: ANTIBACTERIALS FOR SYSTEMIC USE
J: ANTIINFECTIVES FOR SYSTEMIC USE
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 475.5
Logarithm of the Partition Coefficient (xlogp) -1.5
Rotatable Bond Count (rotbonds) 7
Hydrogen Bond Donor Count (hbonddonor) 5
Hydrogen Bond Acceptor Count (hbondacc) 9
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [3]
Clearance
The clearance of drug is 1.8 L/h []
Elimination
38% of drug is excreted from urine in the unchanged form [3]
Half-life
The concentration or amount of drug in body reduced by one-half in 4 hours [4]
Metabolism
The drug is metabolized via the hydrolysis of the beta-lactam ring [5]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 28.715 micromolar/kg/day [6]
Unbound Fraction
The unbound fraction of drug in plasma is 0.1% [4]
Vd
The volume of distribution (Vd) of drug is 0.12 L/kg []
Chemical Identifiers
Formula
C22H25N3O7S
IUPAC Name
(4R,5S,6S)-3-[(3S,5S)-5-[(3-carboxyphenyl)carbamoyl]pyrrolidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
Canonical SMILES
C[C@@H]1[C@@H]2[C@H](C(=O)N2C(=C1S[C@H]3C[C@H](NC3)C(=O)NC4=CC=CC(=C4)C(=O)O)C(=O)O)[C@@H](C)O
InChI
InChI=1S/C22H25N3O7S/c1-9-16-15(10(2)26)20(28)25(16)17(22(31)32)18(9)33-13-7-14(23-8-13)19(27)24-12-5-3-4-11(6-12)21(29)30/h3-6,9-10,13-16,23,26H,7-8H2,1-2H3,(H,24,27)(H,29,30)(H,31,32)/t9-,10-,13+,14+,15-,16-/m1/s1
InChIKey
JUZNIMUFDBIJCM-ANEDZVCMSA-N
Cross-matching ID
PubChem CID
150610
ChEBI ID
CHEBI:404903
CAS Number
153832-46-3
UNII
G32F6EID2H
DrugBank ID
DB00303
TTD ID
D0Q1MS
INTEDE ID
DR2457
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Bacterial Penicillin binding protein (Bact PBP) TTJP4SM NOUNIPROTAC Binder [7]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Beta-lactamase (blaB) DEC3G7M A0A1S7IV31_ENTAS Substrate [8]
Beta-lactamase (blaB) DEMIUB2 BLAT_ECOLX Substrate [9]
Beta-lactamase (blaB) DECWSA9 AMPC_MORMO Substrate [9]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Ertapenem (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Mycophenolic acid DMRBMAU Moderate Altered absorption of Ertapenem due to GI flora changes caused by Mycophenolic acid. Crohn disease [DD70] [10]
Probenecid DMMFWOJ Minor Decreased elimination of Ertapenem caused by Probenecid mediated competitive inhibition of renal tubular secretion. Inborn purine/pyrimidine/nucleotide metabolism error [5C55] [11]
Polyethylene glycol DM4I1JP Moderate Increased risk of lowers seizure threshold by the combination of Ertapenem and Polyethylene glycol. Irritable bowel syndrome [DD91] [12]
Bupropion DM5PCS7 Major Increased risk of lowers seizure threshold by the combination of Ertapenem and Bupropion. Nicotine use disorder [6C4A] [13]
Lindane DMB8CNL Moderate Increased risk of lowers seizure threshold by the combination of Ertapenem and Lindane. Pediculosis [1G00] [14]
Mycophenolate mofetil DMPQAGE Moderate Altered absorption of Ertapenem due to GI flora changes caused by Mycophenolate mofetil. Transplant rejection [NE84] [10]
⏷ Show the Full List of 6 DDI Information of This Drug

References

1 Natural products as sources of new drugs over the last 25 years. J Nat Prod. 2007 Mar;70(3):461-77.
2 Ertapenem FDA Label
3 BDDCS applied to over 900 drugs
4 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
5 Pharmacokinetics and pharmacodynamics of ertapenem: an overview for clinicians
6 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
7 Role of penicillin-binding protein 2 (PBP2) in the antibiotic susceptibility and cell wall cross-linking of Staphylococcus aureus: evidence for the cooperative functioning of PBP2, PBP4, and PBP2A. JBacteriol. 2005 Mar;187(5):1815-24.
8 FRI-4 carbapenemase-producing Enterobacter cloacae complex isolated in Tokyo, Japan. J Antimicrob Chemother. 2018 Nov 1;73(11):2969-2972.
9 War wound treatment complications due to transfer of an IncN plasmid harboring bla(OXA-181) from Morganella morganii to CTX-M-27-producing sequence type 131 Escherichia coli. Antimicrob Agents Chemother. 2015;59(6):3556-62.
10 Product Information. CellCept (mycophenolate mofetil). Roche Laboratories, Nutley, NJ.
11 Product Information. Doribax (doripenem). Ortho McNeil Pharmaceutical, Raritan, NJ.
12 Product Information. Suprep Bowel Prep Kit (magnesium/potassium/sodium sulfates). Braintree Laboratories, Braintree, MA.
13 Product Information. Wellbutrin XL (buPROPion). GlaxoSmithKline, Philadelphia, PA.
14 Matsuoka LY "Convulsions following application of gamma benzene hexachloride." J Am Acad Dermatol 5 (1981): 98-9. [PMID: 6168673]