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

General Information of Drug (ID: DR2491)
Drug Name
Meropenem
Synonyms
Mepem (TN); Meronem; Meronem (TN); Meropen; Meropen (TN); Meropenem (INN); Meropenem anhydrous; Merrem; Merrem (TN); Merrem I.V. (TN); Neopenem (TN); SM-7338; MERONEM; (1R,5S,6S)-2-[(3S,5S)-5-(dimethylaminocarbonyl)pyrrolidin-3-ylthio]-6-[(R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylic acid trihydrate; (2S,3R,4R)-2-[(1S,2R)-1-carboxy-2-hydroxypropyl]-4-{[(3S,5R)-5-(dimethylcarbamoyl)pyrrolidin-3-yl]sulfanyl}-3-methyl-3,4-dihydro-2H-pyrrole-5-carboxylic acid; (4R,5S,6S)-3-[(3S,5S)-5-(dimethylcarbamoyl)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-(dimethylcarbamoyl)pyrrolidin-3-yl]thio}-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid; (5S,6S)-3-((3S,5S)-5-(dimethylcarbamoyl)pyrrolidin-3-ylthio)-6-((S)-1-hydroxyethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid; (6S)-2-{[(3S,5S)-5-(dimethylcarbamoyl)pyrrolidin-3-yl]sulfanyl}-6-[(1R)-1-hydroxyethyl]-1beta-methyl-2,3-didehydro-1-carbapenam-3-carboxylic acid; MEPM
Indication Pseudomonas infection [ICD11: 1G40] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 383.5 Topological Polar Surface Area 136
Heavy Atom Count 26 Rotatable Bond Count 5
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 7
Cross-matching ID
PubChem CID
441130
PubChem SID
7979907 ; 10298746 ; 11112878 ; 11467134 ; 11468254 ; 11486822 ; 12014124 ; 14780292 ; 14902620 ; 26744414 ; 36885035 ; 46386666 ; 46504928 ; 47217060 ; 47440550 ; 47589234 ; 47811032 ; 49681817 ; 49699298 ; 50123967 ; 57403544 ; 78847646 ; 92126058 ; 92308358 ; 92309041 ; 93167009 ; 96024875 ; 98569498 ; 103188146 ; 103914625 ; 104624717 ; 117664409 ; 117695442 ; 119525880 ; 121363729 ; 124658855 ; 124766033 ; 126592940 ; 127755594 ; 134221905 ; 135022991 ; 135684925 ; 135685918 ; 135692126 ; 135693793 ; 135727273 ; 136375187 ; 137003432 ; 137179129 ; 139117093
ChEBI ID
ChEBI:6770
CAS Number
119478-56-7
TTD Drug ID
D0O5FY
Formula
C17H25N3O5S
Canonical SMILES
CC1C2C(C(=O)N2C(=C1SC3CC(NC3)C(=O)N(C)C)C(=O)O)C(C)O
InChI
1S/C17H25N3O5S/c1-7-12-11(8(2)21)16(23)20(12)13(17(24)25)14(7)26-9-5-10(18-6-9)15(22)19(3)4/h7-12,18,21H,5-6H2,1-4H3,(H,24,25)/t7-,8-,9+,10+,11-,12-/m1/s1
InChIKey
DMJNNHOOLUXYBV-PQTSNVLCSA-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
Meropenem open ring DM015653
10340993
Unclear - Unclear 1 [9]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR009693 Meropenem Meropenem open ring Unclear - Unclear Unclear [9]
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) DME1004 Enterobacter cloacae
A0A1S7IV31_ENTAS
3.5.2.6
[3]
Beta-lactamase (blaB) DME1342 Acinetobacter baumannii
A0A1B1FBM9_ACIBA
3.5.2.6
[4]
Beta-lactamase (blaB) DME1095 Bacteroides fragilis
BLAB_BACFG
3.5.2.6
[5]
Carbapenemase (cphA) DME1731 Aeromonas hydrophila
BLAB_AERHY
3.5.2.6
[6] , [7]
New delhi metallo-beta-lactamase NDM-1 (blaNDM) DME1732 Salmonella enterica
A0A345N7K5_SALET
3.5.2.6
[8]
⏷ Show the Full List of 6  DME(s)
References
1 Meropenem was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Molecular investigation of extended-spectrum beta-lactamase genes and potential drug resistance in clinical isolates of Morganella morganii. Ann Saudi Med. 2016 May-Jun;36(3):223-8.
3 FRI-4 carbapenemase-producing Enterobacter cloacae complex isolated in Tokyo, Japan. J Antimicrob Chemother. 2018 Nov 1;73(11):2969-2972.
4 A high mortality rate associated with multidrug-resistant Acinetobacter baumannii ST79 and ST25 carrying OXA-23 in a Brazilian intensive care unit. PLoS One. 2018 Dec 28;13(12):e0209367.
5 Prevalence of antimicrobial resistance genes in Bacteroides spp. and Prevotella spp. Dutch clinical isolates. Clin Microbiol Infect. 2019 Sep;25(9):1156.e9-1156.e13.
6 A carbapenem-resistant clinical isolate of Aeromonas hydrophila in Japan harbouring an acquired gene encoding GES-24 beta-lactamase. J Med Microbiol. 2018 Nov;67(11):1535-1537.
7 Chronic colitis after Aeromonas infection. Gut. 1989 May;30(5):686-90. Case Reports
8 Genomic characterization of an extensively-drug resistance Salmonella enterica serotype Indiana strain harboring bla NDM-1 gene isolated from a chicken carcass in China. Microbiol Res. 2017 Nov;204:48-54.
9 An isotope-dilution LC-MS/MS method for the simultaneous quantification of meropenem and its open-ring metabolite in serum

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