Drug Information
| Drug General Information | Top | |||
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| Drug ID |
D08HVR
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| Former ID |
DIB006947
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| Drug Name |
Levodopa
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| Synonyms |
Levodopa (optimized formulation, Parkinson's disease); More effective levodopa (Parkinson's disease), Orion; Levodopa (optimized formulation, Parkinson's disease), Orion
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| Drug Type |
Small molecular drug
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| Indication | Parkinson disease [ICD-11: 8A00.0; ICD-9: 332] | Approved | [1] | |
| Company |
Orion Corp
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| Structure |
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Download2D MOL |
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| Formula |
C9H11NO4
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| Canonical SMILES |
C1=CC(=C(C=C1CC(C(=O)O)N)O)O
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| InChI |
1S/C9H11NO4/c10-6(9(13)14)3-5-1-2-7(11)8(12)4-5/h1-2,4,6,11-12H,3,10H2,(H,13,14)/t6-/m0/s1
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| InChIKey |
WTDRDQBEARUVNC-LURJTMIESA-N
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| CAS Number |
CAS 59-92-7
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| PubChem Compound ID | ||||
| PubChem Substance ID |
3648, 222573, 555833, 3136680, 7847127, 7886892, 7979689, 8001566, 8143351, 8150164, 8153771, 10321285, 11111115, 11112155, 11335627, 11360866, 11363348, 11365910, 11368472, 11374316, 11376634, 11461838, 11466045, 11467165, 11484127, 11485710, 11488312, 11492354, 11494268, 11532916, 11537951, 15120911, 15219946, 17405017, 24277914, 24863554, 26613179, 26679497, 26719283, 26746620, 26753566, 29225059, 46508120, 47216726, 47291084, 47440197, 47440198, 47736420, 47810699, 47959681
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| ChEBI ID |
CHEBI:15765
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| ADReCS Drug ID | BADD_D02439 | |||
| 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): Campylobacterales | ||||
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Studied Microbe: Helicobacter pylori
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|
[2] | |||
| Hierarchy | ||||
| Metabolic Reaction | Dehydroxylation | |||
| Resulting Metabolite | M-hydroxyphenylacetic acid | |||
| Metabolic Effect | Decrease activity | |||
| Description | Levodopa can be metabolized to M-hydroxyphenylacetic acid by Helicobacter pylori through dehydroxylation, which results in the decrease of the drug's activity. | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Eggerthellales | ||||
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Studied Microbe: Eggerthella lenta
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|
[3], [4] | |||
| Hierarchy | ||||
| Microbial Enzyme | Molybdenum dependent dehydroxylase | |||
| Resulting Metabolite | M-tyramine | |||
| Metabolic Effect | Decrease activity; Increase toxicity | |||
| Description | Levodopa can be metabolized to M-tyramine by the molybdenum dependent dehydroxylase of Eggerthella lenta, which results in the decrease of drug's activity and the increase of the drug's toxicity. | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Lactobacillales | ||||
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Studied Microbe: Enterococcus faecalis
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|
[3], [4], [5] | |||
| Hierarchy | ||||
| Microbial Enzyme | Tyrosine decarboxylase | |||
| Metabolic Reaction | Decarboxylation | |||
| Resulting Metabolite | Dopamine | |||
| Metabolic Effect | Decrease activity | |||
| Description | Levodopa can be metabolized to Dopamine by the tyrosine decarboxylase of Enterococcus faecalis through decarboxylation, which results in the decrease of the drug's activity. | |||
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Studied Microbe: Enterococcus faecium
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|
[3], [4], [5] | |||
| Hierarchy | ||||
| Microbial Enzyme | Tyrosine decarboxylase | |||
| Metabolic Reaction | Decarboxylation | |||
| Resulting Metabolite | Dopamine | |||
| Metabolic Effect | Decrease activity | |||
| Description | Levodopa can be metabolized to Dopamine by the tyrosine decarboxylase of Enterococcus faecium through decarboxylation, which results in the decrease of the drug's activity. | |||
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Studied Microbe: Lactobacillus
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|
[4], [5] | |||
| Hierarchy | ||||
| Microbial Enzyme | Tyrosine decarboxylase | |||
| Metabolic Reaction | Decarboxylation | |||
| Resulting Metabolite | Dopamine | |||
| Metabolic Effect | Decrease activity | |||
| Description | Levodopa can be metabolized to Dopamine by the tyrosine decarboxylase of Lactobacillus through decarboxylation, which results in the decrease of the drug's activity. | |||
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Studied Microbe: Lactobacillus brevis
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|
[6] | |||
| Hierarchy | ||||
| Microbial Enzyme | Tyrosine decarboxylase | |||
| Metabolic Reaction | Decarboxylation and p-dehydroxylation | |||
| Resulting Metabolite | M-tyramine | |||
| Description | Levodopa can be metabolized to M-tyramine by the tyrosine decarboxylase of Lactobacillus brevis through decarboxylation and p-dehydroxylation. | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Gut microbiota | ||||
| Studied Microbe: Gut microbiota unspecific | [7], [8] | |||
| Microbial Enzyme | Tyrosine decarboxylase | |||
| Metabolic Reaction | Dehydroxylation | |||
| Resulting Metabolite | M-tyrosine; M-tyramine; M-hydroxyphenylacetic acid | |||
| Metabolic Effect | Decrease activity | |||
| Description | Levodopa can be metabolized to M-tyrosine and M-tyramine and M-hydroxyphenylacetic acid by the tyrosine decarboxylase of gut microbiota through dehydroxylation, which results in the decrease of the drug's activity. | |||
| References | Top | |||
|---|---|---|---|---|
| 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: 3639). | |||
| REF 2 | Gut microbiota modulates drug pharmacokinetics. Drug Metab Rev. 2018 Aug;50(3):357-368. | |||
| REF 3 | Discovery and inhibition of an interspecies gut bacterial pathway for Levodopa metabolism. Science. 2019 Jun 14;364(6445):eaau6323. | |||
| REF 4 | Interaction between drugs and the gut microbiome. Gut. 2020 Aug;69(8):1510-1519. | |||
| REF 5 | Gut bacterial tyrosine decarboxylases restrict levels of levodopa in the treatment of Parkinson's disease. Nat Commun. 2019 Jan 18;10(1):310. | |||
| REF 6 | Chemical transformation of xenobiotics by the human gut microbiota. Science. 2017 Jun 23;356(6344):eaag2770. | |||
| REF 7 | The influence of gut microbiota on drug metabolism and toxicity. Expert Opin Drug Metab Toxicol. 2016;12(1):31-40. | |||
| REF 8 | Gut Reactions: Breaking Down Xenobiotic-Microbiome Interactions. Pharmacol Rev. 2019 Apr;71(2):198-224. | |||
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