Drug Details

General Information of the Drug (ID: DR0490)
Name
Etoposide
Synonyms
etoposide; 33419-42-0; VePesid; Toposar; trans-Etoposide; Lastet; (-)-Etoposide; Zuyeyidal; Etoposido; Etoposidum; Etoposidum [INN-Latin]; VP-16; Etoposide (VP16); VP 16-213; VP 16 (pharmaceutical); Vepesid J; Etoposido [INN-Spanish]; Etopophos (phosphate salt); VP 16; VP-16-213; VP 16213; UNII-6PLQ3CP4P3; NK 171; NSC-141540; NSC 141540; CCRIS 2392; HSDB 6517; EINECS 251-509-1; Epipodophyllotoxin VP-162
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Molecular Type
Small molecule
Disease Testicular carcinoma [ICD-11: 2C80] Approved [1]
Prostate cancer [ICD-11: 2C82] Investigative
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 drug present in the plasma can be removed from the body at the rate of 0.5 mL/min/kg
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 5.7 hours
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 6.2986 micromolar/kg/day
Unbound Fraction
The unbound fraction of drug in plasma is 0.12%
Vd
Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 0.18 L/kg
Water Solubility
The ability of drug to dissolve in water is measured as 0.22 mg/mL
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Formula
C29H32O13
PubChem CID
36462
Canonical SMILES
CC1OCC2C(O1)C(C(C(O2)OC3C4COC(=O)C4C(C5=CC6=C(C=C35)OCO6)C7=CC(=C(C(=C7)OC)O)OC)O)O
InChI
1S/C29H32O13/c1-11-36-9-20-27(40-11)24(31)25(32)29(41-20)42-26-14-7-17-16(38-10-39-17)6-13(14)21(22-15(26)8-37-28(22)33)12-4-18(34-2)23(30)19(5-12)35-3/h4-7,11,15,20-22,24-27,29-32H,8-10H2,1-3H3/t11-,15+,20-,21-,22+,24-,25-,26-,27-,29+/m1/s1
InChIKey
VJJPUSNTGOMMGY-MRVIYFEKSA-N
CAS Number
CAS 33419-42-0
GDSC
Etoposide
TTD Drug ID
D06GMG
DrugBank ID
DB00773
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Arsenic trioxide      Realgar and orpiment     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
                    Molecule(s)
                    Regulation		 Up-regulation Cleavage CASP3  Molecule Info 
Pathway MAP
Up-regulation Cleavage PARP1  Molecule Info 
Pathway MAP
                    In-vitro Model A-673 CVCL_0080 Ewing sarcoma Homo sapiens
RD-ES CVCL_2169 Ewing sarcoma Homo sapiens
SK-N-MC CVCL_0530 Ewing sarcoma Homo sapiens
mesenchymal stem cell Healthy Homo sapiens
                    Experimental
                    Result(s)		 Arsenic trioxide potentiates the effectiveness of etoposide in Ewing sarcomas.
          Curcumin      Hellenia speciosa     Click to Show/Hide the Molecular Data of This NP
                 Augmenting Drug Sensitivity     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
                    Biological
                    Regulation		 Up-regulation ROS generation
                    In-vitro Model HL-60 CVCL_0002 Adult acute myeloid leukemia Homo sapiens
                    In-vivo Model 1*106 BNML cells in 0.5 mL of PBS injected into tail vein in male Brown Norway (BN/CrlCmd) rats.
                    Experimental
                    Result(s)		 Curcumin can increase the antileukemic effect of etoposide through reactive oxygen species in sensitive myeloid leukemia cells, and it is harmless to normal human cells.
          Elemene      Pogostemon cablin     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		 Up-regulation Expression BAX  Molecule Info 
Pathway MAP
Down-regulation Expression CCND1  Molecule Info 
Pathway MAP
Up-regulation Expression CDKN1A  Molecule Info 
Pathway MAP
Up-regulation Cleavage PARP1  Molecule Info 
Pathway MAP
Up-regulation Expression TP53  Molecule Info 
Pathway MAP
                    In-vitro Model A-549 CVCL_0023 Lung adenocarcinoma Homo sapiens
                    Experimental
                    Result(s)		 Synergistic antitumor effect of Beta-elemene and etoposide is mediated via induction of cell apoptosis and cell cycle arrest in non-small cell lung carcinoma cells.
          Fisetin      Toxicodendron succedaneum     Click to Show/Hide the Molecular Data of This NP
                 Augmenting Drug Sensitivity     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
                    Molecule(s)
                    Regulation		 Down-regulation Expression CCNB1  Molecule Info 
Pathway MAP
Down-regulation Expression CCNE1  Molecule Info 
Pathway MAP
                    In-vitro Model MG-63 CVCL_0426 Osteosarcoma Homo sapiens
SaOS-2 CVCL_0548 Osteosarcoma Homo sapiens
U2OS CVCL_0042 Osteosarcoma Homo sapiens
                    Experimental
                    Result(s)		 The combination of fisetin with etoposide has higher anti-proliferative effects in osteosarcoma associated with cell cycle arrest, allowing the use of lower doses of the chemotherapeutic agent.
          Hesperetin      Citrus limon     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
                    Biological
                    Regulation		 Induction Cell cycle arrest in G2 phase
                    In-vitro Model U2OS CVCL_0042 Osteosarcoma Homo sapiens
                    Experimental
                    Result(s)		 Hesperetin combined with etoposide showed additive effects on the inhibition of cell growth.
          Resveratrol      Gnetum parvifolium     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 [7]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Expression TP53  Molecule Info 
Pathway MAP
                    In-vitro Model HCT 116 CVCL_0291 Colon carcinoma Homo sapiens
                    Experimental
                    Result(s)		 Combination of resveratrol and etoposide showed synergistic anti-proliferative effect on hepatocellular carcinoma cells.
References
Reference 1 FDA Approved Drug Products from FDA Official Website. 2019. Application Number: (ANDA) 075635.
Reference 2 Arsenic trioxide potentiates the effectiveness of etoposide in Ewing sarcomas. Int J Oncol. 2016 Nov;49(5):2135-2146.
Reference 3 Curcumin enhances the cytogenotoxic effect of etoposide in leukemia cells through induction of reactive oxygen species. Drug Des Devel Ther. 2016 Feb 4;10:557-70.
Reference 4 Synergistic antitumor effect of Beta-elemene and etoposide is mediated via induction of cell apoptosis and cell cycle arrest in non-small cell lung carcinoma cells. Mol Med Rep. Nov-Dec 2011;4(6):1189-93.
Reference 5 Combination of etoposide and fisetin results in anti-cancer efficiency against osteosarcoma cell models. Arch Toxicol. 2018 Mar;92(3):1205-1214.
Reference 6 Hesperetin-etoposide combinations induce cytotoxicity in U2OS cells: Implications on therapeutic developments for osteosarcoma. DNA Repair (Amst). 2017 Feb;50:36-42.
Reference 7 Synergistic anti-proliferative effect of resveratrol and etoposide on human hepatocellular and colon cancer cell lines. Eur J Pharmacol. 2013 Oct 15;718(1-3):34-40.
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