Drug Details

General Information of the Drug (ID: DR9241)
Name
Gentamicin
Synonyms
gentamicin; Gentavet; Gentamicins; GENTAMYCIN; Gentamicin sulphate sterile; Gentacycol; 1403-66-3; Cidomycin; Gentamicinum; Gentamycinum; Refobacin; Garasol; Refobacin TM; Gentamicina; Gentamicine; Gentocin; Gentamycin-creme; Gentamycins; Gentamicine [INN-French]; Gentamicinum [INN-Latin]; Gentamycin-creme [German]; Gentamicina [INN-Spanish]; Oksitselanim; Centicin; Lyramycin; Septigen; Gentamicin (TN); Gentamicin (BAN); Gentamicin [INN]; HSDB 3087; Gentamicin [INN:BAN]; EINECS 215-765-8; 4,6-diamino-3-{[3-deoxy-4-c-methyl-3-(methylamino)pentopyranosyl]oxy}-2-hydroxycyclohexyl 2-amino-2,3,4,6,7-pentadeoxy-6-(methylamino)heptopyranoside; SCHEMBL537630; CHEMBL329592; GTPL2427; SCHEMBL19996168; STL454325; AKOS015961211; DB00798; J4.074F; 2-[4,6-diamino-3-[3-amino-6-(1-methylaminoethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-5-methyl-4-methylaminooxane-3,5-diol; AC-13386; FT-0626646; FT-0668965; D08013; 123871-EP2292088A1; 123871-EP2295422A2; 123871-EP2295439A1; Q422482
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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
C21H43N5O7
PubChem CID
3467
Canonical SMILES
CC(C1CCC(C(O1)OC2C(CC(C(C2O)OC3C(C(C(CO3)(C)O)NC)O)N)N)N)NC
InChI
1S/C21H43N5O7/c1-9(25-3)13-6-5-10(22)19(31-13)32-16-11(23)7-12(24)17(14(16)27)33-20-15(28)18(26-4)21(2,29)8-30-20/h9-20,25-29H,5-8,22-24H2,1-4H3
InChIKey
CEAZRRDELHUEMR-UHFFFAOYSA-N
CAS Number
CAS 1403-66-3
TTD Drug ID
D0L9UU
DrugBank ID
DB00798
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Acteoside      Cistanche     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 Staphylococcus aureus Microorganism model Staphylococcus aureus
Escherichia coli Microorganism model Escherichia coli
                    Experimental
                    Result(s)		 The co-administration of verbascoside and gentamicin was more effective and synergistic activities (FICI<1) against clinical isolates.
          Apalcillin      Escherichia coli     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-vivo Model For a xenograft model, mice were made neutropenic by intraperitoneal (ip) injection of cyclophosphamide at a dose of 100 mg/kg on days 0, 2,4.
                    Experimental
                    Result(s)		 Apalcillin when combined with gentamicin is effective in treating serious P. aeruginosa bacteraemia in neutropenic mice.
          Bisdemethoxycurcumin      Curcumin     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 [4]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression UL54  Molecule Info 
Pathway MAP
                    In-vitro Model Staphylococcus aureus strains Microorganism model Staphylococcus aureus
                    Experimental
                    Result(s)		 Antimicrobial effect of BDMC combined with antibiotics was superior to treatment with that of a single agent alone.
          Pannarin      Pannaria tavaresii     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 [5]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model Staphylococcus aureus Microorganism model Staphylococcus aureus
                    Experimental
                    Result(s)		 The natural compound pannarin might be a good candidate for the individualization of novel templates for the development of new antimicrobial agents or combinations of drugs for chemotherapy.
          Plumbagin      Plumbago europaea     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 [6]
                    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)		 Herbal compound plumbagin was identified to stimulate gentamicin uptake by CRKp via enhancing TCA efflux and PMF to achieve a synergistic antibacterial effect. Plumbagin may be used in combination with aminoglycosides for severe CRKp infection by potentiating their therapeutic efficacy and lowering dosage.
          1,8-cineole + Clavulanate     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 [8]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model Staphylococcus aureus Microorganism model Staphylococcus aureus
Susceptible Saureus Microorganism model Susceptible Saureus
                    In-vivo Model Forty-two female New Zealand white rabbits were used as animal model in this study.
                    Experimental
                    Result(s)		 1,8-cineole showed a synergistic effect in combination with both AMC and gentamicin, which offer possibilities for reducing antibiotic usage.
    β. A List of Natural Product(s) Able to Decrease the Adverse Effect of This Drug
          Alpha linolenic acid      Perilla frutescens     Click to Show/Hide the Molecular Data of This NP
                 Decreasing Adverse Drug Reaction     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [7]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression BAX  Molecule Info 
Pathway MAP
Up-regulation Expression BCL-2  Molecule Info 
Pathway MAP
Down-regulation Expression CASP3  Molecule Info 
Pathway MAP
Down-regulation Expression COX-2  Molecule Info 
Pathway MAP
Down-regulation Expression NOS2  Molecule Info 
Pathway MAP
                    In-vivo Model Eight-week-old balb/c albino male mice were used in this study.
                    Experimental
                    Result(s)		 The gentamicin administration causes nephrotoxicity and the use of alpha-linolenic acid can be helpful against this toxic effect.
Target and Pathway
Target(s) Bacterial 30S ribosomal RNA (Bact 30S rRNA)  Molecule Info  [9]
References
Reference 1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 2427).
Reference 2 In vitro evaluation of antibacterial activity of verbascoside, lemon verbena extract and caffeine in combination with gentamicin against drug-resistant Staphylococcus aureus and Escherichia coli clinical isolates. Avicenna J Phytomed. May-Jun 2018;8(3):246-253.
Reference 3 Synergistic activity of apalcillin and gentamicin in a combination therapy in experimental Pseudomonas bacteraemia of neutropenic mice. J Antimicrob Chemother. 1986 Apr;17(4):499-503.
Reference 4 The Mechanism of Bisdemethoxycurcumin Enhances Conventional Antibiotics against Methicillin-Resistant Staphylococcus aureus. Int J Mol Sci. 2020 Oct 26;21(21):7945.
Reference 5 In vitro antimicrobial activity of pannarin alone and in combination with antibiotics against methicillin-resistant Staphylococcus aureus clinical isolates. Phytomedicine. 2012 May 15;19(7):596-602.
Reference 6 Synergistic Effect and Mechanism of Plumbagin with Gentamicin Against Carbapenem-Resistant Klebsiella pneumoniae. Infect Drug Resist. 2020 Aug 7;13:2751-2759.
Reference 7 Protective effect of alpha-linolenic acid on gentamicin-induced ototoxicity in mice. Somatosens Mot Res. 2017 Sep;34(3):145-150.
Reference 8 The Antistaphylococcal Activity of Amoxicillin/Clavulanic Acid, Gentamicin, and 1,8-Cineole Alone or in Combination and Their Efficacy through a Rabbit Model of Methicillin-Resistant Staphylococcus aureus Osteomyelitis. Evid Based Complement Alternat Med. 2020 Apr 28;2020:4271017.
Reference 9 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
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