Drug Details

General Information of the Drug (ID: DR0344)
Name
Imipenem
Synonyms
imipenem; 64221-86-9; Imipemide; N-Formimidoylthienamycin; Tienamycin; Imipenem anhydrous; Imipenemum; N-formimidoyl thienamycin; imipen; MK 0787; CHEBI:471744; 74431-23-5; Imipenem, N-Formimidoyl thienamycin; UNII-Q20IM7HE75; Imipenem (INN); Primaxin; (5R,6S)-6-((R)-1-Hydroxyethyl)-3-(2-(iminomethylamino)ethylthio)-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carbonsaeure; (5R,6S)-3-[2-(aminomethylideneamino)ethylsulfanyl]-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid; MK-0787; CHEMBL148; Q20IM7HE75; (5R,6S)-3-((2-(Formimidoylamino)ethyl)thio)-6-((R)-1-hydroxyethyl)-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid; Imipenem [INN]; (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; Imipenen; DSSTox_CID_3143; DSSTox_RID_76888; DSSTox_GSID_23143; 1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid,6-[(1R)-1-hydroxyethyl]-3-[[2-[(iminomethyl)amino]ethyl]thio]-7-oxo-,(5R,6S)-; 1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 6-[(1R)-1-hydroxyethyl]-3-[[2-[(iminomethyl)amino]ethyl]thio]-7-oxo-, (5R,6S)-; Imipenemum [Latin]; CAS-64221-86-9; SR-05000000294; NCGC00016928-01; (5R,6S)-6-[(1R)-1-hydroxyethyl]-3-(2-methanimidamidoethylsulfanyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid; 1-Azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid, 6-((1R)-1-hydroxyethyl)-3-((2-((iminomethyl)amino)ethyl)thio)-7-oxo-, (5R,6S)-; Prestwick_844; EINECS 264-734-5; MK-787; MK0787; Prestwick0_000519; Prestwick1_000519; Prestwick2_000519; Prestwick3_000519; Epitope ID:120384; BSPBio_000477; cc-394; BIDD:GT0686; SPBio_002398; BPBio1_000525; SCHEMBL1649260; SCHEMBL8781920; DTXSID2023143; GTPL10821; Primaxin (imipenem + cilastatin); HMS1569H19; HMS2090A15; HMS2096H19; HMS3260H20; HMS3713H19; Pharmakon1600-01506001; BCP13012; ZINC4097225; Tox21_110689; Tox21_500279; BDBM50049708; BDBM50213266; NSC717864; NSC759901; AKOS016010844; Tox21_110689_1; CCG-220519; CCG-221583; DB01598; LP00279; NSC-717864; NSC-759901; SDCCGSBI-0633697.P001; NCGC00167958-01; NCGC00167958-02; NCGC00167958-03; NCGC00167958-05; NCGC00167958-09; NCGC00260964-01; (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; AS-75130; C06665; D04515; X-2302; AB01563339_01; Recarbrio (imipenem + cilastatin + relebactam).; 847I667; Q425152; SR-05000000294-2; SR-05000000294-5; (5R,6S)-3-((2-formimidamidoethyl)thio)-6-((R)-1-hydroxyethyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid; (5R,6S)-3-({2-[(E)-(aminomethylidene)amino]ethyl}sulfanyl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid; (5R,6S)-3-(2-formimidamidoethylthio)-6-((R)-1-hydroxyethyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid; (5R,6S)-6-[(1R)-1-hydroxyethyl]-3-[(2-methanimidamidoethyl)sulfanyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid; [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; 1-Azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid, 6-(1-hydroxyethyl)-3-((2-((iminomethyl)amino)ethyl)thio)-7-oxo-, (5R-(5-alpha,6-alpha(R*)))-; 103730-39-8; 3-[(2-Aminoethyl)thio]-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (4-nitrophenyl)methylester monohydrochloride compd. with 1-methyl-2-pyrrolidinone (1:1)
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Molecular Type
Small molecule
Disease Bacterial infection [ICD-11: 1A00-1C4Z] Approved [1]
Structure
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2D MOL

3D MOL

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Formula
C12H17N3O4S
PubChem CID
104838
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
CAS Number
CAS 64221-86-9
ChEBI ID
CHEBI:471744
TTD Drug ID
D0H3TD
DrugBank ID
DB01598
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          1,4-naphthoquinone      Setaria palmifolia     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model Micrococcus luteus Microorganism model Micrococcus luteus
Bacillus cereus Microorganism model Bacillus cereus
Methicillin-sensitive Staphylococcus aureus Microorganism model Staphylococcus aureus
Methicillin-Resistant Staphylococcus aureus Microorganism model Staphylococcus aureus
Escherichia coli Microorganism model Escherichia coli
Klebsiella pneumoniae Microorganism model Klebsiella pneumoniae
Pseudomonas aeruginosa Microorganism model Pseudomonas aeruginosa
Salmonella choleraesuis Microorganism model Salmonella choleraesuis
                    Experimental
                    Result(s)		 1,4-naphthoquinone combined with ascorbate have significant antitumor effects against MCF-7 cells in vitro and Ehrlich-ascites carcinoma in mice.
          Tea Polyphenols      Theaceae     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model Klebsiella pneumoniae Microorganism model Klebsiella pneumoniae
                    Experimental
                    Result(s)		 Tea polyphenols used in combination with commonly used antibiotics showed synergistic bactericidal effect against multidrug-resistant Klebsiella pneumoniae.
Target and Pathway
Target(s) Bacterial Penicillin binding protein 2 (Bact mrdA)  Molecule Info  [4]
References
Reference 1 How many modes of action should an antibiotic have Curr Opin Pharmacol. 2008 Oct;8(5):564-73.
Reference 2 Synergistic Antibacterial Activity Between 1,4-Naphthoquinone and Beta-Lactam Antibiotics Against Methicillin-Resistant Staphylococcus aureus. Microb Drug Resist. 2021 Feb;27(2):234-240.
Reference 3 In-vitro antibacterial effect of tea polyphenols combined with common antibiotics on multidrug-resistant Klebsiella pneumoniae. Minerva Med. 2020 Dec;111(6):536-543.
Reference 4 A comparative trial of imipenem versus ceftazidime in the release of endotoxin and cytokine generation in patients with gram-negative urosepsis. Urosepsis Study Group. J Endotoxin Res. 2000;6(1):25-31.
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