Drug Information
| Drug General Information | Top | |||
|---|---|---|---|---|
| Drug ID |
D05LEO
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| Former ID |
DAP000829
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| Drug Name |
Fluorouracil
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| Synonyms |
5-Fluorouracil; 51-21-8; fluorouracil; 5-FU; Fluoroplex; Adrucil; Efudex; Carac; Fluracil; Fluoroblastin; 5-fluoropyrimidine-2,4(1H,3H)-dione; Kecimeton; Timazin; Carzonal; Efudix; Arumel; Fluril; Queroplex; Fluracilum; Ulup; 5-Fluoracil; Phthoruracil; Fluro Uracil; 5-Fluoro-2,4(1H,3H)-pyrimidinedione; Ftoruracil; Fluorouracilum; Efurix; Fluri; 5 Fluorouracil; Effluderm (free base); 5-fluoro-1H-pyrimidine-2,4-dione; Fluorouracilo; Fluroblastin; Phtoruracil; 2,4-Dihydroxy-5-fluoropyrimidine; 2,4(1H,3H)-Pyrimidinedione, 5-fluoro-; Adrucil; Effluderm; Fluorouracile; Fluoruracil; Fluracedyl; Flurodex; Neofluor; Onkofluor; Ribofluor; Tetratogen; URF; Allergan Brand of Fluorouracil; Biosyn Brand of Fluorouracil; CSP Brand of Fluorouracil; Cinco FU; Dakota Brand of Fluorouracil; Dermatech Brand of Fluorouracil; Dermik Brandof Fluorouracil; Ferrer Brand of Fluorouracil; Fluoro Uracile ICN; Fluorouracil GRY; Fluorouracil Mononitrate; Fluorouracil Monopotassium Salt; Fluorouracil Monosodium Salt; Fluorouracil Potassium Salt; Fluorouracil Teva Brand; Fluorouracile Dakota; Fluorouracile [DCIT]; Fluorouracilo Ferrer Far; Gry Brand of Fluorouracil; Haemato Brand of Fluorouracil; Haemato fu; Hexal Brand of Fluorouracil; ICN Brand of Fluorouracil; Inhibits thymilidate synthetase; Medac Brand of Fluorouracil; Neocorp Brand of Fluorouracil; Onkoworks Brand of Fluorouracil; Ribosepharm Brand of Fluorouracil; Riemser Brand of Fluorouracil; Roche Brand of Fluorouracil; Teva Brand of Fluorouracil; F 6627; F0151; IN1335; U 8953; Adrucil (TN); Carac (TN); Dakota, Fluorouracile; Efudex (TN); Fluoro-Uracile ICN; Fluoro-uracile; Fluoro-uracilo; Fluoroplex (TN); Fluorouracil-GRY; Fluorouracilo [INN-Spanish]; Fluorouracilum [INN-Latin]; Haemato-fu; Ro 2-9757; U-8953; Ro-2-9757; Fluorouracil (JP15/USP/INN); Fluorouracil [USAN:INN:BAN:JAN]; 1-fluoro-1h-pyrimidine-2,4-dione; 2,4-Dioxo-5-fluoropryimidine; 2,4-Dioxo-5-fluoropyrimidine; 5 FU Lederle; 5 FU medac; 5 Fluorouracil biosyn; 5 HU Hexal; 5-FU (TN); 5-FU Lederle; 5-FU medac; 5-Faracil; 5-Fluor-2,4(1H,3H)-pyrimidindion; 5-Fluor-2,4(1H,3H)-pyrimidindion [Czech]; 5-Fluor-2,4-dihydroxypyrimidin; 5-Fluor-2,4-dihydroxypyrimidin [Czech]; 5-Fluor-2,4-pyrimidindiol; 5-Fluor-2,4-pyrimidindiol [Czech]; 5-Fluoracil [German]; 5-Fluoracyl; 5-Fluoro-2,4-pyrimidinedione; 5-Fluoropyrimidin-2,4-diol; 5-Fluoropyrimidine-2,4-dione; 5-Fluorouracil-biosyn; 5-Fluoruracil; 5-Fluoruracil [German]; 5-Ftouracyl; 5-HU Hexal; 5-fluoro uracil; 5FU
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] | |
| Colorectal cancer [ICD-11: 2B91.Z] | Investigative | [2] | ||
| Tumour [ICD-11: 2A00-2F9Z; ICD-10: C00-D48; ICD-9: 140-199, 210-229] | Investigative | [3] | ||
| Therapeutic Class |
Immunosuppressive Agents
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| Company |
Hoffmann-La Roche pharmaceutical company
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| Structure |
 |
Download2D MOL |
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| Formula |
C4H3FN2O2
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| Canonical SMILES |
C1=C(C(=O)NC(=O)N1)F
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| InChI |
1S/C4H3FN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9)
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| InChIKey |
GHASVSINZRGABV-UHFFFAOYSA-N
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| CAS Number |
CAS 51-21-8
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| PubChem Compound ID | ||||
| PubChem Substance ID |
9851, 82653, 595836, 603131, 841046, 3139714, 5132902, 5367838, 7847650, 7891022, 7978600, 8139872, 8149350, 8152156, 10524722, 11111190, 11335229, 11360468, 11363735, 11366297, 11368859, 11371368, 11374392, 11377021, 11406045, 11461440, 11484027, 11487892, 11490250, 11492372, 11494655, 11538022, 15218968, 17389875, 17405099, 22391543, 24276773, 24278439, 24871165, 24894963, 25346604, 25621761, 26611750, 26679238, 26697058, 26747342, 26747343, 26747344, 26752979, 26758708
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| ChEBI ID |
CHEBI:46345
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| ADReCS Drug ID | BADD_D00931 | |||
| SuperDrug ATC ID |
L01BC02
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| SuperDrug CAS ID |
cas=000051218
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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 | ||||
|
Studied Microbe: Escherichia coli
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[4], [5] | |||
| Hierarchy | ||||
| Microbial Enzyme | Uracil phosphoribosyltransferase | |||
| Metabolic Reaction | Phosphorylation | |||
| Resulting Metabolite | 5-fluorouridine monophospate | |||
| Metabolic Effect | Increase activity | |||
| Description | 5-fluorouracil can be metabolized to 5-fluorouridine monophospate by the uracil phosphoribosyltransferase of Escherichia coli through phosphorylation, which results in the increase of the drug's activity. | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Gut microbiota | ||||
| Studied Microbe: Gut microbiota unspecific | [6] | |||
| Metabolic Effect | Increase side effect | |||
| Description | 5-fluorouracil can be metabolized by gut microbiota, which results in the increase of the drug's side effect. | |||
| The Abundace of Studied Microbe(s) Regulated by Drug | ||||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Bacillales | ||||
|
Studied Microbe: Staphylococcus spp.
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[7] | |||
| Hierarchy | ||||
| Abundance Change | Increase | |||
| Experimental Species | Dark Agouti rat | Experimental Sample | Faeces | |
| Disease or Condition | Healthy | |||
| Description | The abundance of Staphylococcus spp. was increased by 5-fluorouracil (p < 0.05). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Bacteroidales | ||||
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Studied Microbe: Bacteroides caccae
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[8] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Bacteroides caccae was decreased by 5-fluorouracil (adjusted p-values: 1.73E-05). | |||
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Studied Microbe: Bacteroides fragilis enterotoxigenic
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[8] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Bacteroides fragilis enterotoxigenic was decreased by 5-fluorouracil (adjusted p-values: 7.00E-04). | |||
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Studied Microbe: Bacteroides fragilis nontoxigenic
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[8] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Bacteroides fragilis nontoxigenic was decreased by 5-fluorouracil (adjusted p-values: 6.96E-06). | |||
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Studied Microbe: Bacteroides ovatus
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|
[8] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Bacteroides ovatus was decreased by 5-fluorouracil (adjusted p-values: 5.04E-06). | |||
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Studied Microbe: Bacteroides spp.
Show/Hide Hierarchy
|
[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | Dark Agouti rat | Experimental Sample | Faeces | |
| Disease or Condition | Healthy | |||
| Description | The abundance of Bacteroides spp. was decreased by 5-fluorouracil (p < 0.05). | |||
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Studied Microbe: Bacteroides thetaiotaomicron
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[8] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Bacteroides thetaiotaomicron was decreased by 5-fluorouracil (adjusted p-values: 2.55E-03). | |||
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Studied Microbe: Bacteroides vulgatus
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[8] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Bacteroides vulgatus was decreased by 5-fluorouracil (adjusted p-values: 1.39E-05). | |||
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Studied Microbe: Bacteroides xylanisolvens
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[8] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Bacteroides xylanisolvens was decreased by 5-fluorouracil (adjusted p-values: 4.93E-07). | |||
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Studied Microbe: Odoribacter splanchnicus
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|
[8] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Odoribacter splanchnicus was decreased by 5-fluorouracil (adjusted p-values: 5.04E-06). | |||
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Studied Microbe: Parabacteroides distasonis
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|
[8] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Parabacteroides distasonis was decreased by 5-fluorouracil (adjusted p-values: 4.85E-05). | |||
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Studied Microbe: Parabacteroides merdae
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[8] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Parabacteroides merdae was decreased by 5-fluorouracil (adjusted p-values: 2.58E-03). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Bifidobacteriales | ||||
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Studied Microbe: Bifidobacterium adolescentis
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[8] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Bifidobacterium adolescentis was decreased by 5-fluorouracil (adjusted p-values: 5.04E-06). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Eggerthellales | ||||
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Studied Microbe: Eggerthella lenta
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[8] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Eggerthella lenta was decreased by 5-fluorouracil (adjusted p-values: 2.54E-03). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Enterobacterales | ||||
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Studied Microbe: Escherichia coli
Show/Hide Hierarchy
|
[7] | |||
| Hierarchy | ||||
| Abundance Change | Increase | |||
| Experimental Species | Dark Agouti rat | Experimental Sample | Jejunum sample | |
| Disease or Condition | Healthy | |||
| Description | The abundance of Escherichia coli was increased by 5-fluorouracil. | |||
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Studied Microbe: Escherichia coli ED1a
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|
[8] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Escherichia coli ED1a was decreased by 5-fluorouracil (adjusted p-values: 6.41E-05). | |||
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Studied Microbe: Escherichia coli IAI1
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[8] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Escherichia coli IAI1 was decreased by 5-fluorouracil (adjusted p-values: 2.51E-03). | |||
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Studied Microbe: Proteus spp.
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|
[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | Dark Agouti rat | Experimental Sample | Faeces | |
| Disease or Condition | Healthy | |||
| Description | The abundance of Proteus spp. was decreased by 5-fluorouracil. | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Erysipelotrichales | ||||
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Studied Microbe: Erysipelatoclostridium ramosum
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|
[8] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Erysipelatoclostridium ramosum was decreased by 5-fluorouracil (adjusted p-values: 4.92E-04). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Eubacteriales | ||||
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Studied Microbe: Clostridioides difficile
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|
[8] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Clostridioides difficile was decreased by 5-fluorouracil (adjusted p-values: 2.71E-05). | |||
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Studied Microbe: Clostridium perfringens
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|
[8] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Clostridium perfringens was decreased by 5-fluorouracil (adjusted p-values: 1.01E-04). | |||
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Studied Microbe: Clostridium spp.
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[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | Dark Agouti rat | Experimental Sample | Faeces | |
| Disease or Condition | Healthy | |||
| Description | The abundance of Clostridium spp. was decreased by 5-fluorouracil (p < 0.05). | |||
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Studied Microbe: Clostridium spp.
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[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | Dark Agouti rat | Experimental Sample | Jejunum sample | |
| Disease or Condition | Healthy | |||
| Description | The abundance of Clostridium spp. was decreased by 5-fluorouracil. | |||
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Studied Microbe: Clostridium spp.
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[7] | |||
| Hierarchy | ||||
| Abundance Change | Increase | |||
| Experimental Species | Dark Agouti rat | Experimental Sample | Colon sample | |
| Disease or Condition | Healthy | |||
| Description | The abundance of Clostridium spp. was increased by 5-fluorouracil. | |||
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Studied Microbe: Coprococcus comes
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[8] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Coprococcus comes was decreased by 5-fluorouracil (adjusted p-values: 7.45E-03). | |||
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Studied Microbe: Enterocloster bolteae
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[8] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Enterocloster bolteae was decreased by 5-fluorouracil (adjusted p-values: 6.62E-04). | |||
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Studied Microbe: Eubacterium rectale
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[8] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Eubacterium rectale was decreased by 5-fluorouracil (adjusted p-values: 5.03E-03). | |||
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Studied Microbe: Roseburia hominis
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[8] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Roseburia hominis was decreased by 5-fluorouracil (adjusted p-values: 2.27E-05). | |||
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Studied Microbe: Roseburia intestinalis
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[8] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Roseburia intestinalis was decreased by 5-fluorouracil (adjusted p-values: 1.98E-03). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Lactobacillales | ||||
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Studied Microbe: Lactobacillus paracasei
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[8] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Lactobacillus paracasei was decreased by 5-fluorouracil (adjusted p-values: 9.03E-06). | |||
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Studied Microbe: Lactobacillus spp.
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[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | Dark Agouti rat | Experimental Sample | Jejunum sample | |
| Disease or Condition | Healthy | |||
| Description | The abundance of Lactobacillus spp. was decreased by 5-fluorouracil (p < 0.05). | |||
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Studied Microbe: Lactobacillus spp.
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[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | Dark Agouti rat | Experimental Sample | Colon sample | |
| Disease or Condition | Healthy | |||
| Description | The abundance of Lactobacillus spp. was decreased by 5-fluorouracil. | |||
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Studied Microbe: Streptococcus spp.
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|
[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | Dark Agouti rat | Experimental Sample | Jejunum sample | |
| Disease or Condition | Healthy | |||
| Description | The abundance of Streptococcus spp. was decreased by 5-fluorouracil (p < 0.05). | |||
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Studied Microbe: Streptococcus spp.
Show/Hide Hierarchy
|
[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | Dark Agouti rat | Experimental Sample | Colon sample | |
| Disease or Condition | Healthy | |||
| Description | The abundance of Streptococcus spp. was decreased by 5-fluorouracil. | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Veillonellales | ||||
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Studied Microbe: Veillonella parvula
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[8] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Veillonella parvula was decreased by 5-fluorouracil (adjusted p-values: 5.04E-06). | |||
| References | Top | |||
|---|---|---|---|---|
| REF 1 | Natural products as sources of new drugs over the last 25 years. J Nat Prod. 2007 Mar;70(3):461-77. | |||
| REF 2 | The ChEMBL database in 2017. Nucleic Acids Res. 2017 Jan 4;45(D1):D945-D954. | |||
| REF 3 | Design and development of antisense drugs. Expert Opin. Drug Discov. 2008 3(10):1189-1207. | |||
| REF 4 | Gut Reactions: Breaking Down Xenobiotic-Microbiome Interactions. Pharmacol Rev. 2019 Apr;71(2):198-224. | |||
| REF 5 | Bacterial Metabolism Affects the C.?elegans Response to Cancer Chemotherapeutics. Cell. 2017 Apr 20;169(3):431-441.e8. | |||
| REF 6 | Toxicomicrobiomics: The Human Microbiome vs. Pharmaceutical, Dietary, and Environmental Xenobiotics. Front Pharmacol. 2020 Apr 16;11:390. | |||
| REF 7 | Gastrointestinal microflora and mucins may play a critical role in the development of 5-Fluorouracil-induced gastrointestinal mucositis. Exp Biol Med (Maywood). 2009 Apr;234(4):430-41. | |||
| REF 8 | Extensive impact of non-antibiotic drugs on human gut bacteria. Nature. 2018 Mar 29;555(7698):623-628. | |||
| REF 9 | The efficacy of the combination therapy of 5-fluorouracil, cisplatin and leucovorin for hepatocellular carcinoma and its predictable factors. Cancer Chemother Pharmacol. 2004 Apr;53(4):296-304. | |||
| REF 10 | Association of gastric and intestinal phenotypic marker expression of gastric carcinomas with tumor thymidylate synthase expression and response to... J Cancer Res Clin Oncol. 2003 Dec;129(12):683-90. | |||
| REF 11 | Thymidylate synthase expression in patients with colorectal carcinoma using a polyclonal thymidylate synthase antibody in comparison to the TS 106 monoclonal antibody. J Histochem Cytochem. 2000 Jun;48(6):755-60. | |||
| REF 12 | Acquisition of resistance to anticancer agents by overproduction of target enzymes. Nippon Rinsho. 1997 May;55(5):1030-7. | |||
| REF 13 | Enhancement of the antitumour activity of 5-fluorouracil (5-FU) by inhibiting dihydropyrimidine dehydrogenase activity (DPD) using 5-chloro-2,4-dihydroxypyridine (CDHP) in human tumour cells. Eur J Cancer. 2002 Jun;38(9):1271-7. | |||
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