Drug Details

General Information of the Drug (ID: DR7727)
Name
Ertapenem
Synonyms
Ertapenem; 153832-46-3; Invanz; UNII-G32F6EID2H; (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; Invanz (TN); G32F6EID2H; C22H25N3O7S; CHEBI:404903; (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; Ertapenem (INN); Ertapenem [INN:BAN]; HSDB 8020; (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; CHEMBL1359; SCHEMBL34454; GTPL10906; AOB6700; DTXSID50165456; ZINC3918453; AKOS015895077; AC-6814; DB00303; NCGC00387409-02; 1-Azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid, 3-(((3S,5S)-5-(((3-carboxyphenyl)amino)carbonyl)-3-pyrrolidinyl)thio)-6-((1R)-1-hydroxyethyl-4-methyl-7-oxo-, (4R,5S,6S)-; 1-Azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid, 3-((5-(((3-carboxyphenyl)amino)carbonyl)-3-pyrrolidinyl)thio)-6-(1-hydroxyethyl)-4-methyl-7-oxo-, (4R-(3(3S*,5S*),4alpha,5beta,6beta(R*)))-; D07908; 832E463; Q553220
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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

ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability
Clearance
The clearance of drug is 1.8 L/h
Elimination
38% of drug is excreted from urine in the unchanged form
Half-life
The concentration or amount of drug in body reduced by one-half in 4 hours
Metabolism
The drug is metabolized via the hydrolysis of the beta-lactam ring
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 28.715 micromolar/kg/day
Unbound Fraction
The unbound fraction of drug in plasma is 0.1%
Vd
The volume of distribution (Vd) of drug is 0.12 L/kg
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Formula
C22H25N3O7S
PubChem CID
150610
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
CAS Number
CAS 153832-46-3
ChEBI ID
CHEBI:404903
TTD Drug ID
D0Q1MS
DrugBank ID
DB00303
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Reverse the Resistance of This Drug
          Propolis      Streptophyta     Click to Show/Hide the Molecular Data of This NP
                 Reversing Drug Resistance     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 Escherichia coli isolates NECS892841 Microorganism model Escherichia coli
Escherichia coli isolates NECS30090 Microorganism model Escherichia coli
Escherichia coli isolates NECS858785 Microorganism model Escherichia coli
Escherichia coli isolates NECS864598 Microorganism model Escherichia coli
Escherichia coli isolates NEC892420 Microorganism model Escherichia coli
Escherichia coli isolates NEC118564 Microorganism model Escherichia coli
                    Experimental
                    Result(s)		 Propolis could enhance the efficiency of antibiotics used in UTIs and could represent an alternative solution.
Target and Pathway
Target(s) Bacterial Penicillin binding protein (Bact PBP)  Molecule Info  [3]
References
Reference 1 Natural products as sources of new drugs over the last 25 years. J Nat Prod. 2007 Mar;70(3):461-77.
Reference 2 Synergistic Effect of Propolis and Antibiotics on Uropathogenic Escherichia coli. Antibiotics (Basel). 2020 Oct 27;9(11):739.
Reference 3 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.
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