Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR2457)
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 Pneumocystis pneumonia [ICD11: CA40] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 475.5 Topological Polar Surface Area 182
Heavy Atom Count 33 Rotatable Bond Count 7
Hydrogen Bond Donor Count 5 Hydrogen Bond Acceptor Count 9
Cross-matching ID
PubChem CID
150610
PubChem SID
7979182 ; 10250773 ; 14761086 ; 14785384 ; 46227255 ; 46506508 ; 50070556 ; 50071303 ; 50249601 ; 57347055 ; 85595963 ; 92714224 ; 96024604 ; 99450921 ; 103447288 ; 104428898 ; 126629618 ; 126655559 ; 126663131 ; 134337727 ; 135106916 ; 137003431 ; 139445158 ; 152034496 ; 160963651 ; 162174325 ; 163412145 ; 175265685 ; 179296050 ; 184527505 ; 196105532 ; 223556604 ; 223660209 ; 224339593 ; 226420912 ; 248087834 ; 249865868 ; 251916745 ; 251917984 ; 252075643 ; 252451452
ChEBI ID
CHEBI:404903
CAS Number
153832-46-3
TTD Drug ID
D0Q1MS
Formula
C22H25N3O7S
Canonical SMILES
CC1C2C(C(=O)N2C(=C1SC3CC(NC3)C(=O)NC4=CC=CC(=C4)C(=O)O)C(=O)O)C(C)O
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
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Ertapenem metabolite M1 DM001931
45105276
Unclear 1 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000929 Ertapenem Ertapenem metabolite M1 Unclear blaB [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Beta-lactamase (blaB) DME1699 Morganella morganii
AMPC_MORMO
3.5.2.6
[2]
Beta-lactamase (blaB) DME1223 Escherichia coli
BLAT_ECOLX
3.5.2.6
[2]
Beta-lactamase (blaB) DME1004 Enterobacter cloacae
A0A1S7IV31_ENTAS
3.5.2.6
[3]
References
1 Ertapenem was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 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.
3 FRI-4 carbapenemase-producing Enterobacter cloacae complex isolated in Tokyo, Japan. J Antimicrob Chemother. 2018 Nov 1;73(11):2969-2972.
4 Pharmacokinetics and pharmacodynamics of ertapenem: an overview for clinicians J Antimicrob Chemother. 2004 Jun;53 Suppl 2:ii23-8. doi: 10.1093/jac/dkh205.

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