Drug Information
| Drug General Information | Top | |||
|---|---|---|---|---|
| Drug ID |
D0B7EB
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| Former ID |
DAP000786
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| Drug Name |
Etoposide
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| Synonyms |
etoposide; 33419-42-0; VePesid; Toposar; trans-Etoposide; Lastet; (-)-Etoposide; Zuyeyidal; Etoposidum; Etoposido; Vepesid J; Eposin; Etoposidum [INN-Latin]; Etoposide (VP16); VP 16-213; VP 16 (pharmaceutical); Etoposido [INN-Spanish]; Etopophos (phosphate salt); VP-16-213; 4-Demethylepipodophyllotoxin beta-D-ethylideneglucoside; VP 16213; UNII-6PLQ3CP4P3; NK 171; NSC 141540; CCRIS 2392; HSDB 6517; 4'-Demethylepipodophyllotoxin 9-(4,6-O-(R)-ethylidene-beta-D-glucopyranoside); EINECS 251-509-1; NSC-141540; Eposide; Etopol; Etosid; Vepeside; Demethyl EpipodophyllotoxinEthylidine Glucoside; E0675; Demethyl-epiodophyllotoxin ethylidene glucoside; Epipodophyllotoxin VP-16213; Eposin (TN); Etopophos (TN); Trans-Etoposide; VePESID (TN); Vepesid (TN); DEMETHY-EPIPODOPHYLLOTOXIN, ETHYLIDENE GLUCOSIDE; VP-16 (TN); Demethylepipodophyllotoxin-beta-D-ethylideneglucoside; Etoposide (JP15/USP/INN); Etoposide [USAN:INN:BAN:JAN]; Eposin, Vepesid, VP-16, Toposar, Etoposide; Epipodophyllotoxin, 4'-demethyl-, 4,6-O-ethylidene-beta-D-glucopyranoside; Epipodophyllotoxin, 4'-demethyl-, 4,6-O-ethylidene-beta-D-glucopyranoside (8CI); Epipodophyllotoxin, 4'-demethyl-, 9-(4,6-O-ethylidene-beta-D-glucopyranoside); 4'-Demethyl-epipodophyllotoxin 9-[4,6-O-(R)-ethylidene-beta-D-glucopyranoside; 4'-Demethylepipodophyllotoxin 9-(4,6-O-ethylidene-beta-D-glucopyranoside); 4'-Demethylepipodophyllotoxin ethylidene-beta-D-glucoside; 4'-O-Demethyl-1-O-(4,6-O-ethylidene-beta-D-glucopyranosyl)epipodophyllotoxin; 4-Demethylepipodophyllotoxin-beta-D-ethylideneglucoside
Click to Show/Hide
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| Drug Type |
Small molecular drug
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| Indication | Solid tumour/cancer [ICD-11: 2A00-2F9Z; ICD-10: C76-C80; ICD-9: 140-229] | Approved | [1], [2] | |
| Therapeutic Class |
Anticancer Agents
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| Company |
Bristol Myers Squibb Co Pharmaceutical Research Institute
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| Structure |
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Download2D MOL |
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| Formula |
C29H32O13
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| 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
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| 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
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| InChIKey |
VJJPUSNTGOMMGY-MRVIYFEKSA-N
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| CAS Number |
CAS 33419-42-0
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| PubChem Compound ID | ||||
| PubChem Substance ID |
4733, 597749, 7847193, 7979208, 8145856, 8174504, 11110521, 12013288, 14886949, 14935915, 24278178, 24769897, 34677904, 46386954, 46500626, 46505434, 47362874, 48182835, 48332078, 49681767, 49699016, 49855364, 53787668, 56463308, 57311878, 71825014, 75974183, 85148351, 85788790, 89850276, 92308660, 92308790, 99437037, 104019076, 104234176, 104324084, 117664408, 117682510, 119525100, 121363248, 124349593, 124659141, 124757097, 124800231, 124893613, 125163901, 127298729, 127298730, 127298731, 127298732
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| ChEBI ID |
CHEBI:4911
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| ADReCS Drug ID | BADD_D00854 | |||
| SuperDrug ATC ID |
L01CB01
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| SuperDrug CAS ID |
cas=033419420
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| Interaction between the Drug and Microbe | Top | |||
|---|---|---|---|---|
| The Metabolism of Drug Affected by Studied Microbe(s) | ||||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Enterobacterales | ||||
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Studied Microbe: Escherichia coli Nissle 1917
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[3] | |||
| Hierarchy | ||||
| Metabolic Effect | Decrease activity | |||
| Description | Etoposide phosphate can be metabolized by Escherichia coli Nissle 1917, which results in the decrease of the drug's activity. | |||
| The Abundace of Studied Microbe(s) Regulated by Drug | ||||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Bacteroidales | ||||
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Studied Microbe: Parabacteroides
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[4], [5] | |||
| Hierarchy | ||||
| Abundance Change | Increase | |||
| Experimental Species | Human | Experimental Sample | Faeces | |
| Disease or Condition | Non-Hodgkin's lymphoma | |||
| Description | The abundance of Parabacteroides was increased by Combination of carmustine, etoposide, aracytine and melphalan (p < 0.05). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Bifidobacteriales | ||||
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Studied Microbe: Bifidobacterium
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[4], [5] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | Human | Experimental Sample | Faeces | |
| Disease or Condition | Non-Hodgkin's lymphoma | |||
| Description | The abundance of Bifidobacterium was decreased by Combination of carmustine, etoposide, aracytine and melphalan (p < 0.05). | |||
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Studied Microbe: Bifidobacterium adolescentis
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[6] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Bifidobacterium adolescentis was decreased by Etoposide (adjusted p-values: 3.47E-04). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Coriobacteriales | ||||
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Studied Microbe: Atopobium
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[4], [5] | |||
| Hierarchy | ||||
| Abundance Change | Increase | |||
| Experimental Species | Human | Experimental Sample | Faeces | |
| Disease or Condition | Non-Hodgkin's lymphoma | |||
| Description | The abundance of Atopobium was increased by Combination of carmustine, etoposide, aracytine and melphalan (p < 0.05). | |||
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Studied Microbe: Collinsella
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[4], [5] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | Human | Experimental Sample | Faeces | |
| Disease or Condition | Non-Hodgkin's lymphoma | |||
| Description | The abundance of Collinsella was decreased by Combination of carmustine, etoposide, aracytine and melphalan (p < 0.05). | |||
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Studied Microbe: Collinsella aerofaciens
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[6] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Collinsella aerofaciens was decreased by Etoposide (adjusted p-values: 3.20E-07). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Eggerthellales | ||||
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Studied Microbe: Adlercreutzia
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[4], [5] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | Human | Experimental Sample | Faeces | |
| Disease or Condition | Non-Hodgkin's lymphoma | |||
| Description | The abundance of Adlercreutzia was decreased by Combination of carmustine, etoposide, aracytine and melphalan (p < 0.05). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Enterobacterales | ||||
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Studied Microbe: Citrobacter
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|
[4], [5] | |||
| Hierarchy | ||||
| Abundance Change | Increase | |||
| Experimental Species | Human | Experimental Sample | Faeces | |
| Disease or Condition | Non-Hodgkin's lymphoma | |||
| Description | The abundance of Citrobacter was increased by Combination of carmustine, etoposide, aracytine and melphalan (p < 0.05). | |||
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Studied Microbe: Klebsiella
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[4], [5] | |||
| Hierarchy | ||||
| Abundance Change | Increase | |||
| Experimental Species | Human | Experimental Sample | Faeces | |
| Disease or Condition | Non-Hodgkin's lymphoma | |||
| Description | The abundance of Klebsiella was increased by Combination of carmustine, etoposide, aracytine and melphalan (p < 0.05). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Eubacteriales | ||||
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Studied Microbe: Blautia
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[4], [5] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | Human | Experimental Sample | Faeces | |
| Disease or Condition | Non-Hodgkin's lymphoma | |||
| Description | The abundance of Blautia was decreased by Combination of carmustine, etoposide, aracytine and melphalan (p < 0.05). | |||
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Studied Microbe: Blautia obeum
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[6] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Blautia obeum was decreased by Etoposide (adjusted p-values: 1.63E-04). | |||
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Studied Microbe: Clostridium
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[4], [5] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | Human | Experimental Sample | Faeces | |
| Disease or Condition | Non-Hodgkin's lymphoma | |||
| Description | The abundance of Clostridium was decreased by Combination of carmustine, etoposide, aracytine and melphalan (p < 0.05). | |||
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Studied Microbe: Clostridium perfringens
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[6] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Clostridium perfringens was decreased by Etoposide (adjusted p-values: 1.86E-04). | |||
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Studied Microbe: Coprococcus
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|
[4], [5] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | Human | Experimental Sample | Faeces | |
| Disease or Condition | Non-Hodgkin's lymphoma | |||
| Description | The abundance of Coprococcus was decreased by Combination of carmustine, etoposide, aracytine and melphalan (p < 0.05). | |||
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Studied Microbe: Coprococcus comes
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[6] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Coprococcus comes was decreased by Etoposide (adjusted p-values: 3.25E-05). | |||
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Studied Microbe: Dorea
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[4], [5] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | Human | Experimental Sample | Faeces | |
| Disease or Condition | Non-Hodgkin's lymphoma | |||
| Description | The abundance of Dorea was decreased by Combination of carmustine, etoposide, aracytine and melphalan (p < 0.05). | |||
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Studied Microbe: Dorea formicigenerans
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[6] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Dorea formicigenerans was decreased by Etoposide (adjusted p-values: 3.87E-04). | |||
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Studied Microbe: Enterocloster bolteae
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[6] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Enterocloster bolteae was decreased by Etoposide (adjusted p-values: 1.30E-05). | |||
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Studied Microbe: Eubacterium rectale
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|
[6] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Eubacterium rectale was decreased by Etoposide (adjusted p-values: 1.45E-03). | |||
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Studied Microbe: Lachnospira
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[4], [5] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | Human | Experimental Sample | Faeces | |
| Disease or Condition | Non-Hodgkin's lymphoma | |||
| Description | The abundance of Lachnospira was decreased by Combination of carmustine, etoposide, aracytine and melphalan (p < 0.05). | |||
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Studied Microbe: Lacrimispora saccharolytica
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[6] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Lacrimispora saccharolytica was decreased by Etoposide (adjusted p-values: 2.41E-05). | |||
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Studied Microbe: Oscillospira
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[4], [5] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | Human | Experimental Sample | Faeces | |
| Disease or Condition | Non-Hodgkin's lymphoma | |||
| Description | The abundance of Oscillospira was decreased by Combination of carmustine, etoposide, aracytine and melphalan (p < 0.05). | |||
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Studied Microbe: Roseburia
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[4], [5] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | Human | Experimental Sample | Faeces | |
| Disease or Condition | Non-Hodgkin's lymphoma | |||
| Description | The abundance of Roseburia was decreased by Combination of carmustine, etoposide, aracytine and melphalan (p < 0.05). | |||
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Studied Microbe: Roseburia hominis
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[6] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Roseburia hominis was decreased by Etoposide (adjusted p-values: 5.47E-05). | |||
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Studied Microbe: Roseburia intestinalis
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[6] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Roseburia intestinalis was decreased by Etoposide (adjusted p-values: 8.01E-04). | |||
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Studied Microbe: Ruminococcus
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[4], [5] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | Human | Experimental Sample | Faeces | |
| Disease or Condition | Non-Hodgkin's lymphoma | |||
| Description | The abundance of Ruminococcus was decreased by Combination of carmustine, etoposide, aracytine and melphalan (p < 0.05). | |||
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Studied Microbe: Ruminococcus gnavus
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[6] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Ruminococcus gnavus was decreased by Etoposide (adjusted p-values: 5.04E-06). | |||
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Studied Microbe: Ruminococcus torques
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[6] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Ruminococcus torques was decreased by Etoposide (adjusted p-values: 1.79E-05). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Lactobacillales | ||||
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Studied Microbe: Enterococcus
Show/Hide Hierarchy
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[4], [5] | |||
| Hierarchy | ||||
| Abundance Change | Increase | |||
| Experimental Species | Human | Experimental Sample | Faeces | |
| Disease or Condition | Non-Hodgkin's lymphoma | |||
| Description | The abundance of Enterococcus was increased by Combination of carmustine, etoposide, aracytine and melphalan (p < 0.05). | |||
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Studied Microbe: Lactobacillus paracasei
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[6] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Lactobacillus paracasei was decreased by Etoposide (adjusted p-values: 6.95E-06). | |||
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Studied Microbe: Streptococcus parasanguinis
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[6] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Streptococcus parasanguinis was decreased by Etoposide (adjusted p-values: 2.10E-05). | |||
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Studied Microbe: Streptococcus salivarius
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[6] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Streptococcus salivarius was decreased by Etoposide (adjusted p-values: 5.04E-06). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Tissierellales | ||||
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Studied Microbe: Anaerococcus
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[4], [5] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | Human | Experimental Sample | Faeces | |
| Disease or Condition | Non-Hodgkin's lymphoma | |||
| Description | The abundance of Anaerococcus was decreased by Combination of carmustine, etoposide, aracytine and melphalan (p < 0.05). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Veillonellales | ||||
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Studied Microbe: Megasphaera
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[4], [5] | |||
| Hierarchy | ||||
| Abundance Change | Increase | |||
| Experimental Species | Human | Experimental Sample | Faeces | |
| Disease or Condition | Non-Hodgkin's lymphoma | |||
| Description | The abundance of Megasphaera was increased by Combination of carmustine, etoposide, aracytine and melphalan (p < 0.05). | |||
| Drug Resistance Mutation (DRM) | Top | |||
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| DRM | DRM Info | |||
| Target and Pathway | Top | |||
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| Target(s) | DNA topoisomerase II (TOP2) | Target Info | Modulator | [7] |
| References | Top | |||
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| REF 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: 6815). | |||
| REF 2 | Natural products as sources of new drugs over the last 25 years. J Nat Prod. 2007 Mar;70(3):461-77. | |||
| REF 3 | Local bacteria affect the efficacy of chemotherapeutic drugs. Sci Rep. 2015 Sep 29;5:14554. | |||
| REF 4 | Chemotherapy-driven dysbiosis in the intestinal microbiome. Aliment Pharmacol Ther. 2015 Sep;42(5):515-28. | |||
| REF 5 | Pharmacomicrobiomics: exploiting the drug-microbiota interactions in anticancer therapies. Microbiome. 2018 May 22;6(1):92. | |||
| REF 6 | Extensive impact of non-antibiotic drugs on human gut bacteria. Nature. 2018 Mar 29;555(7698):623-628. | |||
| REF 7 | Etoposide, topoisomerase II and cancer.Curr Med Chem Anticancer Agents.2005 Jul;5(4):363-72. | |||
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