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

General Information of Drug (ID: DR2447)
Drug Name
Imipenem
Synonyms
Imipemide; Imipenem [INN]; Imipenem anhydrous; N-Formimidoylthienamycin; Primaxin (TN); Tienamycin; (5R,6S)-3-(2-Formimidoylamino-ethylsulfanyl)-6-((R)-1-hydroxy-ethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid; (5R,6S)-3-[2-(aminomethylideneamino)ethylsulfanyl]-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid; (5R,6S)-6-((R)-1-Hydroxyethyl)-3-(2-(iminomethylamino)ethylthio)-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carbonsaeure; (5R,6S)-6-[(1R)-1-hydroxyethyl]-3-({2-[(iminomethyl)amino]ethyl}thio)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid; Imipenem, N-Formimidoyl thienamycin; [5R-[5.alpha.,6.alpha.(R*)]]-6-(1-Hydroxyethyl)-3-[[2-[(iminomethyl)amino]ethyl]thio]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid monohydrate
Indication Acute pancreatitis [ICD11: DC31] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 299.35 Topological Polar Surface Area 142
Heavy Atom Count 20 Rotatable Bond Count 6
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
104838
PubChem SID
8890 ; 534389 ; 602889 ; 7979598 ; 10321787 ; 11466547 ; 11467667 ; 11486134 ; 15023235 ; 44434434 ; 46505744 ; 47349465 ; 47720707 ; 48094640 ; 48394036 ; 48416102 ; 49698536 ; 50112997 ; 50112998 ; 51091233 ; 57337871 ; 57394174 ; 78739513 ; 87322658 ; 90341794 ; 92125443 ; 92309011 ; 92719338 ; 93166844 ; 103071257 ; 103083352 ; 103204227 ; 103914272 ; 103980020 ; 104179221 ; 104373052 ; 119525091 ; 121360964 ; 121363114 ; 124766027 ; 126620895 ; 126655539 ; 129948482 ; 134222478 ; 134337754 ; 135007278 ; 135693794 ; 137117254 ; 142145336 ; 144076231
ChEBI ID
ChEBI:51799
CAS Number
74431-23-5
TTD Drug ID
D0H3TD
Formula
C12H17N3O4S
Canonical SMILES
CC(C1C2CC(=C(N2C1=O)C(=O)O)SCCN=CN)O
InChI
1S/C12H17N3O4S/c1-6(16)9-7-4-8(20-3-2-14-5-13)10(12(18)19)15(7)11(9)17/h5-7,9,16H,2-4H2,1H3,(H2,13,14)(H,18,19)/t6-,7-,9-/m1/s1
InChIKey
ZSKVGTPCRGIANV-ZXFLCMHBSA-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
Imipenem metabolite M1 DM002558
14240578
Unclear 1 [19]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001167 Imipenem Imipenem metabolite M1 Unclear Unclear [19]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
AmpC beta-lactamase (ampC) DME1192 Burkholderia multivorans
A0A0H3KQ39_BURM1
3.5.2.6
[2]
Beta-lactamase (blaB) DME1094 Citrobacter freundii
AMPC_CITFR
3.5.2.6
[3]
Beta-lactamase (blaB) DME1231 Serratia marcescens
AMPC_SERMA
3.5.2.6
[3] , [4]
Beta-lactamase (blaB) DME1699 Morganella morganii
AMPC_MORMO
3.5.2.6
[5]
Beta-lactamase (blaB) DME2029 Shigella boydii
A0A2S8DM15_SHIBO
3.5.2.6
[6]
Beta-lactamase (blaB) DME2023 Chryseobacterium oranimense
A0A1M5PLB6_9FLAO
3.5.2.6
[7]
Beta-lactamase (blaB) DME2026 Citrobacter farmeri
A0A223JZR3_9ENTR
3.5.2.6
[6]
Beta-lactamase (blaB) DME2031 Vibrio vulnificus
A0A3B7D7C4_9VIBR
3.5.2.6
[8]
Beta-lactamase (blaB) DME2024 Citrobacter braakii
K0GG60_CITBR
3.5.2.6
[6]
Beta-lactamase (blaB) DME1004 Enterobacter cloacae
A0A1S7IV31_ENTAS
3.5.2.6
[9] , [10]
Beta-lactamase (blaB) DME1484 Enterobacter cancerogenus
A0A1S7IV31_ENTAS
3.5.2.6
[11] , [12]
Beta-lactamase (blaB) DME1342 Acinetobacter baumannii
A0A1B1FBM9_ACIBA
3.5.2.6
[13]
Beta-lactamase (blaB) DME2027 Providencia stuartii
A0A291NY45_PROSP
3.5.2.6
[3]
Carbapenemase (cphA) DME2025 Citrobacter youngae
Q8L1M8_9ENTR
3.5.2.6
[14]
Carbapenemase (cphA) DME2021 Achromobacter xylosoxidans
A0A3G1JAD7_ALCXX
3.5.2.6
[15]
Carbapenemase (cphA) DME1731 Aeromonas hydrophila
BLAB_AERHY
3.5.2.6
[16] , [17]
Carbapenemase (cphA) DME2028 Pseudocitrobacter faecalis
A0A366EJX1_9ENTR
3.5.2.6
[18]
⏷ Show the Full List of 17  DME(s)
References
1 ClinicalTrials.gov (NCT02897206) Imipenem Prophylaxis in Patients With Acute Pancreatitis
2 Characterization of the AmpC beta-Lactamase from Burkholderia multivorans. Antimicrob Agents Chemother. 2018 Sep 24;62(10). pii: e01140-18.
3 Antibiotic therapy for inducible AmpC beta-lactamase-producing Gram-negative bacilli: what are the alternatives to carbapenems, quinolones and aminoglycosides? Int J Antimicrob Agents. 2012 Oct;40(4):297-305.
4 Serratia marcescens producing SME carbapenemases: an emerging resistance problem in the UK? J Antimicrob Chemother. 2017 May 1;72(5):1535-1537.
5 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.
6 Hospital sewage water: a reservoir for variants of New Delhi metallo-beta-lactamase (NDM)- and extended-spectrum beta-lactamase (ESBL)-producing Enterobacteriaceae. Int J Antimicrob Agents. 2018 Jan;51(1):82-88.
7 Whole-genome sequence of Chryseobacterium oranimense, a colistin-resistant bacterium isolated from a cystic fibrosis patient in France. Antimicrob Agents Chemother. 2015 Mar;59(3):1696-706.
8 Carbapenemase VCC-1-producing Vibrio cholerae in coastal waters of Germany. Emerg Infect Dis. 2017 Oct;23(10):1735-1737.
9 FRI-4 carbapenemase-producing Enterobacter cloacae complex isolated in Tokyo, Japan. J Antimicrob Chemother. 2018 Nov 1;73(11):2969-2972.
10 Survey of clinical extended-spectrum beta-lactamase-producing Enterobacter cloacae isolates in a Chinese Tertiary Hospital, 2012-2014. Microb Drug Resist. 2017 Jan;23(1):83-89.
11 AmpC beta-lactamase-producing Enterobacterales: what a clinician should know. Infection. 2019 Jun;47(3):363-375.
12 Molecular analysis of colonized bacteria in a human newborn infant gut. J Microbiol. 2005 Aug;43(4):345-53.
13 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.
14 Occurrence of a new metallo-beta-lactamase IMP-4 carried on a conjugative plasmid in Citrobacter youngae from the People's R
15 Proteomic identification of Axc, a novel beta-lactamase with carbapenemase activity in a meropenem-resistant clinical isolate of Achromobacter xylosoxidans. Sci Rep. 2018 May 25;8(1):8181.
16 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.
17 Chronic colitis after Aeromonas infection. Gut. 1989 May;30(5):686-90. Case Reports
18 Pseudocitrobacter gen. nov., a novel genus of the Enterobacteriaceae with two new species Pseudocitrobacter faecalis sp. nov., and Pseudocitrobacter anthropi sp. nov, isolated from fecal samples from hospitalized patients in Pakistan. Syst Appl Microbiol. 2014 Feb;37(1):17-22.
19 Urea as new stabilizing agent for imipenem determination: electrochemical study and determination of imipenem and its primary metabolite in human urine Talanta. 2008 Oct 19;77(1):241-8. doi: 10.1016/j.talanta.2008.06.013.

If you find any error in data or bug in web service, please kindly report it to Dr. Yin and Dr. Li.