Drug Information
| Drug General Information | Top | |||
|---|---|---|---|---|
| Drug ID |
D0C4YC
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| Former ID |
DAP000729
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| Drug Name |
Mesalazine
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| Synonyms |
Apriso; Asacol; Asacolitin; Asacolon; Asalit; Ascolitin; Canasa; Claversal; Fisalamine; Fivasa; Iialda; Ipocol; Lialda; Lixacol; Mesacol; Mesalamine; Mesalazina; Mesalazinum; Mesasal; Mesavance; Mesavancol; Mezavant; Pentacol; Pentasa; Rowasa; Salofalk; Salozinal; SfRowasa; Allphar Brand of Mesalamine; Antigen Brand of Mesalamine; Asacol HD; Axcan Brand of Mesalamine; Byk Brand of Mesalamine; Celltech Brand of Mesalamine; Falk Brand of Mesalamine; Farmasa Brand of Mesalamine; Ferring Brand of Mesalamine; GlaxoSmithKline Brand of Mesalamine; Henning Berlin Brand of Mesalamine; M Aminosalicylic Acid; Merckle Brand of Mesalamine; Mesalamine Hydrochloride; Mesalamine Monosodium Salt; Mesalamine [USAN]; Mesalazina[Spanish]; Mesalazine MMX; Mesalazinum [Latin]; Meta Aminosalicylic Acid; Mezavant XL; Minosalicylic acid; Norgine Brand of Mesalamine; Novopharm Brand of Mesalamine; Provalis Brand of Mesalamine; Sanofi Synthelabo Brand of Mesalamine; Schering Plough Brand of Mesalamine; SmithKline Brand of Mesalamine; Solvay Brand of Mesalamine; Yamanouchi Brand of Mesalamine; Novo 5 ASA; Novo5 ASA; AJG-501; Apriso (TN); Asacol (TN); Canasa (TN); Hydrochloride, Mesalamine; Iialda (TN); Ipocal (TN); Lialda (TN); M-A; M-Aminosalicylic acid; MAX-002; MD-0901; Masacol (TN); Mesalamine (USP); Meta-AminosalicylicAcid; Monosodium Salt, Mesalamine; Novo-5 ASA; P-Aminosalicylsaeure; P-Aminosalicylsaeure [German]; Pentasa (TN); Procter & Gamble Brand of Mesalamine; Rowasa (TN); SPD-476; SPD-480; Salofalk (TN); Salofalk Granu-Stix; Schering-Plough Brand of Mesalamine; Z-206; Mesalazine (JAN/INN); Salicylic acid, 5-amino-(8CI); 2-Hydroxy-5-aminobenzoic acid; 3-carboxy-4-hydroxyaniline; 5 Aminosalicylate; 5 Aminosalicylic Acid; 5-AS; 5-ASA; 5-Amino-2-hydroxybenzoic acid; 5-Aminosalicylate; 5-Aminosalicylic acid; 5-amino-2-hydroxy-benzoic acid; 5-aminosalicylic acid, Mesalazine, Asacol, Pentasa, Canasa, Mesalamine
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| Drug Type |
Small molecular drug
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| Indication | Ulcerative colitis [ICD-11: DD71; ICD-9: 556] | Approved | [1], [2] | |
| Therapeutic Class |
Antiinflammatory Agents
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| Structure |
 |
Download2D MOL |
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| Formula |
C7H7NO3
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| Canonical SMILES |
C1=CC(=C(C=C1N)C(=O)O)O
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| InChI |
1S/C7H7NO3/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,9H,8H2,(H,10,11)
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| InChIKey |
KBOPZPXVLCULAV-UHFFFAOYSA-N
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| CAS Number |
CAS 89-57-6
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| PubChem Compound ID | ||||
| PubChem Substance ID | ||||
| ChEBI ID |
CHEBI:6775
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| ADReCS Drug ID | BADD_D01397 ; BADD_D02414 | |||
| SuperDrug ATC ID |
A07EC02
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| SuperDrug CAS ID |
cas=000089576
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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: Citrobacter amalonaticus
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[3], [4] | |||
| Hierarchy | ||||
| Metabolic Reaction | N-acetylation | |||
| Resulting Metabolite | N-acetyl-5-aminosalicylic acid | |||
| Description | Mesalazine can be metabolized to N-acetyl-5-aminosalicylic acid by Citrobacter amalonaticus through N-acetylation. | |||
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Studied Microbe: Citrobacter farmeri
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[3], [4] | |||
| Hierarchy | ||||
| Metabolic Reaction | N-acetylation | |||
| Resulting Metabolite | N-acetyl-5-aminosalicylic acid | |||
| Description | Mesalazine can be metabolized to N-acetyl-5-aminosalicylic acid by Citrobacter farmeri through N-acetylation. | |||
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Studied Microbe: Citrobacter freundii
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[3], [4] | |||
| Hierarchy | ||||
| Metabolic Reaction | N-acetylation | |||
| Resulting Metabolite | N-acetyl-5-aminosalicylic acid | |||
| Description | Mesalazine can be metabolized to N-acetyl-5-aminosalicylic acid by Citrobacter freundii through N-acetylation. | |||
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Studied Microbe: Klebsiella oxytoca
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[3], [4] | |||
| Hierarchy | ||||
| Metabolic Reaction | N-acetylation | |||
| Resulting Metabolite | N-acetyl-5-aminosalicylic acid | |||
| Description | Mesalazine can be metabolized to N-acetyl-5-aminosalicylic acid by Klebsiella oxytoca through N-acetylation. | |||
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Studied Microbe: Klebsiella pneumoniae subsp. ozaenae
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[3], [4] | |||
| Hierarchy | ||||
| Metabolic Reaction | N-acetylation | |||
| Resulting Metabolite | N-acetyl-5-aminosalicylic acid | |||
| Description | Mesalazine can be metabolized to N-acetyl-5-aminosalicylic acid by Klebsiella pneumoniae subsp. ozaenae through N-acetylation. | |||
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Studied Microbe: Klebsiella pneumoniae subsp. rhinoscleromatis
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[3], [4] | |||
| Hierarchy | ||||
| Metabolic Reaction | N-acetylation | |||
| Resulting Metabolite | N-acetyl-5-aminosalicylic acid | |||
| Description | Mesalazine can be metabolized to N-acetyl-5-aminosalicylic acid by Klebsiella pneumoniae subsp. rhinoscleromatis through N-acetylation. | |||
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Studied Microbe: Morganella morganii
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[3], [4] | |||
| Hierarchy | ||||
| Metabolic Reaction | N-acetylation | |||
| Resulting Metabolite | N-acetyl-5-aminosalicylic acid | |||
| Description | Mesalazine can be metabolized to N-acetyl-5-aminosalicylic acid by Morganella morganii through N-acetylation. | |||
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Studied Microbe: Plesiomonas shigelloides
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[3], [4] | |||
| Hierarchy | ||||
| Metabolic Reaction | N-acetylation | |||
| Resulting Metabolite | N-acetyl-5-aminosalicylic acid | |||
| Description | Mesalazine can be metabolized to N-acetyl-5-aminosalicylic acid by Plesiomonas shigelloides through N-acetylation. | |||
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Studied Microbe: Serratia marcescens
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[3], [4] | |||
| Hierarchy | ||||
| Metabolic Reaction | N-acetylation | |||
| Resulting Metabolite | N-acetyl-5-aminosalicylic acid | |||
| Description | Mesalazine can be metabolized to N-acetyl-5-aminosalicylic acid by Serratia marcescens through N-acetylation. | |||
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Studied Microbe: Shigella flexneri
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|
[3], [4] | |||
| Hierarchy | ||||
| Metabolic Reaction | N-acetylation | |||
| Resulting Metabolite | N-acetyl-5-aminosalicylic acid | |||
| Description | Mesalazine can be metabolized to N-acetyl-5-aminosalicylic acid by Shigella flexneri through N-acetylation. | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Pseudomonadales | ||||
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Studied Microbe: Pseudomonas aeruginosa
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[3], [4] | |||
| Hierarchy | ||||
| Metabolic Reaction | N-acetylation | |||
| Resulting Metabolite | N-acetyl-5-aminosalicylic acid | |||
| Description | Mesalazine can be metabolized to N-acetyl-5-aminosalicylic acid by Pseudomonas aeruginosa through N-acetylation. | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Vibrionales | ||||
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Studied Microbe: Vibrio cholerae
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[3], [4] | |||
| Hierarchy | ||||
| Metabolic Reaction | N-acetylation | |||
| Resulting Metabolite | N-acetyl-5-aminosalicylic acid | |||
| Description | Mesalazine can be metabolized to N-acetyl-5-aminosalicylic acid by Vibrio cholerae through N-acetylation. | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Gut microbiota | ||||
| Studied Microbe: Gut microbiota unspecific | [5], [6] | |||
| Microbial Enzyme | N-acetyltransferase | |||
| Metabolic Reaction | N-acetylation | |||
| Resulting Metabolite | N-acetyl-5-aminosalicylic acid | |||
| Metabolic Effect | Decrease activity; Increase toxicity (pancreatic toxicity) | |||
| Description | Mesalazine can be metabolized to N-acetyl-5-aminosalicylic acid by the N-acetyltransferase of gut microbiota through N-acetylation, which results in the decrease of drug's activity and the increase of the drug's toxicity (pancreatic toxicity). | |||
| The Abundace of Studied Microbe(s) Regulated by Drug | ||||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Acidaminococcales | ||||
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Studied Microbe: Phascolarctobacterium
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[7], [8] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | Human | Experimental Sample | Mucosa | |
| Disease or Condition | Ulcerative colitis | |||
| Description | The abundance of Phascolarctobacterium was decreased by 5-aminosalicylic acid. | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Bacteroidales | ||||
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Studied Microbe: Bacteroides
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[7], [8] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | Human | Experimental Sample | Mucosa | |
| Disease or Condition | Ulcerative colitis | |||
| Description | The abundance of Bacteroides was decreased by 5-aminosalicylic acid. | |||
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Studied Microbe: Parabacteroides
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[7], [8] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | Human | Experimental Sample | Mucosa | |
| Disease or Condition | Ulcerative colitis | |||
| Description | The abundance of Parabacteroides was decreased by 5-aminosalicylic acid. | |||
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Studied Microbe: Prevotella
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[7], [8] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | Human | Experimental Sample | Mucosa | |
| Disease or Condition | Ulcerative colitis | |||
| Description | The abundance of Prevotella was decreased by 5-aminosalicylic acid. | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Burkholderiales | ||||
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Studied Microbe: Parasutterella
Show/Hide Hierarchy
|
[7], [8] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | Human | Experimental Sample | Mucosa | |
| Disease or Condition | Ulcerative colitis | |||
| Description | The abundance of Parasutterella was decreased by 5-aminosalicylic acid. | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Enterobacterales | ||||
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Studied Microbe: Escherichia/Shigella
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[7], [8] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | Human | Experimental Sample | Mucosa | |
| Disease or Condition | Ulcerative colitis | |||
| Description | The abundance of Escherichia/Shigella was decreased by 5-aminosalicylic acid. | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Erysipelotrichales | ||||
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Studied Microbe: Erysipelotrichaceae
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[9] | |||
| Hierarchy | ||||
| Abundance Change | Increase | |||
| Experimental Species | Human | Experimental Sample | Faeces | |
| Disease or Condition | Inflammatory bowel disease | |||
| Description | The abundance of Erysipelotrichaceae was increased by Mesalamine. | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Eubacteriales | ||||
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Studied Microbe: Eubacterium coprostanoligenes
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[7], [8] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | Human | Experimental Sample | Mucosa | |
| Disease or Condition | Ulcerative colitis | |||
| Description | The abundance of Eubacterium coprostanoligenes was decreased by 5-aminosalicylic acid. | |||
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Studied Microbe: Faecalibacterium
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[7], [8] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | Human | Experimental Sample | Mucosa | |
| Disease or Condition | Ulcerative colitis | |||
| Description | The abundance of Faecalibacterium was decreased by 5-aminosalicylic acid. | |||
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Studied Microbe: Lachnospiraceae bacterium NK4A136
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[7], [8] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | Human | Experimental Sample | Mucosa | |
| Disease or Condition | Ulcerative colitis | |||
| Description | The abundance of Lachnospiraceae_NK4A136 was decreased by 5-aminosalicylic acid. | |||
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Studied Microbe: Roseburia
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[7], [8] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | Human | Experimental Sample | Mucosa | |
| Disease or Condition | Ulcerative colitis | |||
| Description | The abundance of Roseburia was decreased by 5-aminosalicylic acid. | |||
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Studied Microbe: Ruminococcaceae UCG-002
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[7], [8] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | Human | Experimental Sample | Mucosa | |
| Disease or Condition | Ulcerative colitis | |||
| Description | The abundance of Ruminococcaceae UCG-002 was decreased by 5-aminosalicylic acid. | |||
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Studied Microbe: Ruminococcaceae UCG-014
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[7], [8] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | Human | Experimental Sample | Mucosa | |
| Disease or Condition | Ulcerative colitis | |||
| Description | The abundance of Ruminococcaceae UCG-014 was decreased by 5-aminosalicylic acid. | |||
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Studied Microbe: Ruminococcus
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[7], [8] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | Human | Experimental Sample | Mucosa | |
| Disease or Condition | Ulcerative colitis | |||
| Description | The abundance of Ruminococcus was decreased by 5-aminosalicylic acid. | |||
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Studied Microbe: Subdoligranulum
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[7], [8] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | Human | Experimental Sample | Mucosa | |
| Disease or Condition | Ulcerative colitis | |||
| Description | The abundance of Subdoligranulum was decreased by 5-aminosalicylic acid. | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Lactobacillales | ||||
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Studied Microbe: Enterococcus
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[7], [8] | |||
| Hierarchy | ||||
| Abundance Change | Increase | |||
| Experimental Species | Human | Experimental Sample | Mucosa | |
| Disease or Condition | Ulcerative colitis | |||
| Description | The abundance of Enterococcus was increased by 5-aminosalicylic acid. | |||
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Studied Microbe: Lactobacillus
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[7], [8] | |||
| Hierarchy | ||||
| Abundance Change | Increase | |||
| Experimental Species | Human | Experimental Sample | Mucosa | |
| Disease or Condition | Ulcerative colitis | |||
| Description | The abundance of Lactobacillus was increased by 5-aminosalicylic acid. | |||
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Studied Microbe: Lactococcus
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[7], [8] | |||
| Hierarchy | ||||
| Abundance Change | Increase | |||
| Experimental Species | Human | Experimental Sample | Mucosa | |
| Disease or Condition | Ulcerative colitis | |||
| Description | The abundance of Lactococcus was increased by 5-aminosalicylic acid. | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Veillonellales | ||||
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Studied Microbe: Dialister
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[7], [8] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | Human | Experimental Sample | Mucosa | |
| Disease or Condition | Ulcerative colitis | |||
| Description | The abundance of Dialister was decreased by 5-aminosalicylic acid. | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Verrucomicrobiales | ||||
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Studied Microbe: Akkermansia
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[7], [8] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | Human | Experimental Sample | Mucosa | |
| Disease or Condition | Ulcerative colitis | |||
| Description | The abundance of Akkermansia was decreased by 5-aminosalicylic acid. | |||
| Target and Pathway | Top | |||
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| Target(s) | Prostaglandin G/H synthase 1 (COX-1) | Target Info | Inhibitor | [10] |
| BioCyc | C20 prostanoid biosynthesis | |||
| KEGG Pathway | Arachidonic acid metabolism | |||
| Metabolic pathways | ||||
| Platelet activation | ||||
| Serotonergic synapse | ||||
| NetPath Pathway | TGF_beta_Receptor Signaling Pathway | |||
| Panther Pathway | Inflammation mediated by chemokine and cytokine signaling pathway | |||
| Pathwhiz Pathway | Arachidonic Acid Metabolism | |||
| WikiPathways | Prostaglandin Synthesis and Regulation | |||
| Arachidonic acid metabolism | ||||
| Phase 1 - Functionalization of compounds | ||||
| Eicosanoid Synthesis | ||||
| Selenium Micronutrient Network | ||||
| 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: 4655). | |||
| REF 2 | BiDil: assessing a race-based pharmaceutical. Ann Fam Med. 2006 Nov-Dec;4(6):556-60. | |||
| REF 3 | Bacterial acetylation of 5-aminosalicylic acid in faecal suspensions cultured under aerobic and anaerobic conditions. Eur J Clin Pharmacol. 1992;43(2):189-92. | |||
| REF 4 | Gut microbiome interactions with drug metabolism, efficacy, and toxicity. Transl Res. 2017 Jan;179:204-222. | |||
| REF 5 | Gut microbiota modulates drug pharmacokinetics. Drug Metab Rev. 2018 Aug;50(3):357-368. | |||
| REF 6 | Predicting and Understanding the Human Microbiome's Impact on Pharmacology. Trends Pharmacol Sci. 2019 Jul;40(7):495-505. | |||
| REF 7 | 5-Aminosalicylic Acid Alters the Gut Bacterial Microbiota in Patients With Ulcerative Colitis. Front Microbiol. 2018 Jun 13;9:1274. | |||
| REF 8 | Emerging Insights on the Interaction Between Anticancer and Immunosuppressant Drugs and Intestinal Microbiota in Pediatric Patients. Clin Transl Sci. 2020 Mar;13(2):238-259. | |||
| REF 9 | Impact of commonly used drugs on the composition and metabolic function of the gut microbiota. Nat Commun. 2020 Jan 17;11(1):362. | |||
| REF 10 | How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6. | |||
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