Drug Information
| Drug General Information | Top | |||
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| Drug ID |
D07HOB
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| Former ID |
DAP000647
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| Drug Name |
Irinotecan
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| Synonyms |
Biotecan; Camptosar; Irinotecanum; IRINOTECAN HYDROCHLORIDE Trihydrate; Irinotecan Hcl; Irinotecan hydrochloride; CP0; Biotecan (TN); Campto (TN); Camptosar (TN); Irinotecan (INN); Irinotecan [INN:BAN]; Irinotecanum [INN-Latin]; IRINOTECAN, CPT-11; Camptosar, Campto, CPT-11, Irinotecan; (+)-Irinotecan; (4S)-4,11-DIETHYL-4-HYDROXY-3,14-DIOXO-3,4,12,14-TETRAHYDRO-1H-PYRANO[3',4':6,7]INDOLIZINO[1,2-B]QUINOLIN-9-YL 1,4'-BIPIPERIDINE-1'-CARBOXYLATE; (4S)-4,11-Diethyl-4-hydroxy-3,14-dioxo-4,12-dihydro-1H-pyrano[3,4-f]quinolino[2,3-a]indolizin-9-yl 4-piperidylpiperidinecarboxylate; Irinotecan (TOPO1 inhibitor); Onivyde
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| Drug Type |
Small molecular drug
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| Indication | Colorectal cancer [ICD-11: 2B91.Z] | Approved | [1], [2] | |
| Therapeutic Class |
Anticancer Agents
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| Company |
Pfizer Pharmaceuticals
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| Structure |
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Download2D MOL |
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| Formula |
C33H38N4O6
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| Canonical SMILES |
CCC1=C2CN3C(=CC4=C(C3=O)COC(=O)C4(CC)O)C2=NC5=C1C=C(C=C5)OC(=O)N6CCC(CC6)N7CCCCC7
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| InChI |
1S/C33H38N4O6/c1-3-22-23-16-21(43-32(40)36-14-10-20(11-15-36)35-12-6-5-7-13-35)8-9-27(23)34-29-24(22)18-37-28(29)17-26-25(30(37)38)19-42-31(39)33(26,41)4-2/h8-9,16-17,20,41H,3-7,10-15,18-19H2,1-2H3/t33-/m0/s1
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| InChIKey |
UWKQSNNFCGGAFS-XIFFEERXSA-N
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| CAS Number |
CAS 97682-44-5
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| PubChem Compound ID | ||||
| PubChem Substance ID |
645391, 6436484, 7886725, 7979640, 8187089, 11409441, 14764625, 14911520, 43118176, 46393294, 46505871, 47811029, 48427687, 49835834, 49894524, 50422254, 51090967, 53788707, 56312891, 56314523, 57288560, 57314141, 81092817, 85789488, 92711320, 96024776, 103169165, 104020044, 104253165, 104321776, 117623718, 118049657, 124757074, 124893595, 125163878, 126630981, 126650121, 126663759, 129430288, 134337937, 134338553, 135032920, 136342503, 137001856, 142371089, 143493285, 143493286, 144116083, 152034388, 152240238
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| ChEBI ID |
CHEBI:80630
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| ADReCS Drug ID | BADD_D01195 ; BADD_D01196 | |||
| SuperDrug ATC ID |
L01XX19
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| SuperDrug CAS ID |
cas=097682445
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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): Bacteroidales | ||||
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Studied Microbe: Bacteroides fragilis
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[3] | |||
| Hierarchy | ||||
| Microbial Enzyme | Beta glucuronidase | |||
| Metabolic Reaction | Glucuronide hydrolysis | |||
| Resulting Metabolite | SN-38 glucuronide | |||
| Metabolic Effect | Increase toxicity | |||
| Description | Irinotecan can be metabolized to SN-38 glucuronide by the beta glucuronidase of Bacteroides fragilis through glucuronide hydrolysis, which results in the increase of the drug's toxicity. | |||
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Studied Microbe: Bacteroides vulgatus
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[4], [5] | |||
| Hierarchy | ||||
| Microbial Enzyme | Beta glucuronidase | |||
| Metabolic Reaction | Glucuronide hydrolysis | |||
| Resulting Metabolite | SN-38 | |||
| Metabolic Effect | Increase activity; Increase toxicity (gastrointestinal toxicity) | |||
| Description | Irinotecan can be metabolized to SN-38 by the beta glucuronidase of Bacteroides vulgatus through glucuronide hydrolysis, which results in the increase of drug's activity and toxicity (gastrointestinal toxicity). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Bifidobacteriales | ||||
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Studied Microbe: Bifidobacterium sp.
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[6] | |||
| Hierarchy | ||||
| Metabolic Reaction | Hydrolysis | |||
| Resulting Metabolite | SN-38 | |||
| Metabolic Effect | Increase toxicity (gastrointestinal toxicity) | |||
| Description | Irinotecan can be metabolized to SN-38 by Bifidobacterium sp. through hydrolysis, which results in the increase of the drug's toxicity (gastrointestinal toxicity). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Enterobacterales | ||||
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Studied Microbe: Escherichia coli
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[3], [5] | |||
| Hierarchy | ||||
| Microbial Enzyme | Beta glucuronidase | |||
| Metabolic Reaction | Glucuronide hydrolysis | |||
| Resulting Metabolite | SN-38 glucuronide | |||
| Metabolic Effect | Increase activity; Increase toxicity | |||
| Description | Irinotecan can be metabolized to SN-38 glucuronide by the beta glucuronidase of Escherichia coli through glucuronide hydrolysis, which results in the increase of drug's activity and toxicity. | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Erysipelotrichales | ||||
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Studied Microbe: Clostridium ramosum
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[4], [5] | |||
| Hierarchy | ||||
| Microbial Enzyme | Beta glucuronidase | |||
| Metabolic Reaction | Glucuronide hydrolysis | |||
| Resulting Metabolite | SN-38 | |||
| Metabolic Effect | Increase activity; Increase side effect (diarrhea) | |||
| Description | Irinotecan can be metabolized to SN-38 by the beta glucuronidase of Clostridium ramosum through glucuronide hydrolysis, which results in the increase of drug's activity and side effect (diarrhea). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Eubacteriales | ||||
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Studied Microbe: Clostridium
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[6] | |||
| Hierarchy | ||||
| Metabolic Reaction | Hydrolysis | |||
| Resulting Metabolite | SN-38 | |||
| Metabolic Effect | Increase toxicity (gastrointestinal toxicity) | |||
| Description | Irinotecan can be metabolized to SN-38 by Clostridium through hydrolysis, which results in the increase of the drug's toxicity (gastrointestinal toxicity). | |||
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Studied Microbe: Clostridium perfringens
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[3] | |||
| Hierarchy | ||||
| Microbial Enzyme | Beta glucuronidase | |||
| Metabolic Reaction | Glucuronide hydrolysis | |||
| Resulting Metabolite | SN-38 glucuronide | |||
| Metabolic Effect | Increase toxicity | |||
| Description | Irinotecan can be metabolized to SN-38 glucuronide by the beta glucuronidase of Clostridium perfringens through glucuronide hydrolysis, which results in 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: Streptococcus agalactiae
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[3] | |||
| Hierarchy | ||||
| Microbial Enzyme | Beta glucuronidase | |||
| Metabolic Reaction | Glucuronide hydrolysis | |||
| Resulting Metabolite | SN-38 glucuronide | |||
| Metabolic Effect | Increase toxicity | |||
| Description | Irinotecan can be metabolized to SN-38 glucuronide by the beta glucuronidase of Streptococcus agalactiae through glucuronide hydrolysis, which results in the increase of the drug's toxicity. | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Gut microbiota | ||||
| Studied Microbe: Gut microbiota unspecific | [4], [7] | |||
| Microbial Enzyme | Beta glucuronidase | |||
| Resulting Metabolite | SN-38 | |||
| Metabolic Effect | Increase activity; Increase side effect (diarrhea) | |||
| Description | Irinotecan can be metabolized to SN-38 by the beta glucuronidase of gut microbiota, which results in the increase of drug's activity and side effect (diarrhea). | |||
| The Abundace of Studied Microbe(s) Regulated by Drug | ||||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Enterobacterales | ||||
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Studied Microbe: Enterobacteriaceae
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[8] | |||
| Hierarchy | ||||
| Abundance Change | Increase | |||
| Experimental Species | Fisher 344 rat | Experimental Sample | Faeces | |
| Disease or Condition | Colon cancer | |||
| Description | The abundance of Enterobacteriaceae was increased by Irinotecan. | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Eubacteriales | ||||
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Studied Microbe: Peptoclostridium difficile
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[8] | |||
| Hierarchy | ||||
| Abundance Change | Increase | |||
| Experimental Species | Fisher 344 rat | Experimental Sample | Faeces | |
| Disease or Condition | Colon cancer | |||
| Description | The abundance of Peptoclostridium difficile was increased by Irinotecan. | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Gut microbiota | ||||
| Studied Microbe: Clostridium cluster XI | [8] | |||
| Abundance Change | Increase | |||
| Experimental Species | Fisher 344 rat | Experimental Sample | Faeces | |
| Disease or Condition | Colon cancer | |||
| Description | The abundance of Clostridium cluster XI was increased by Irinotecan. | |||
| Drug Resistance Mutation (DRM) | Top | |||
|---|---|---|---|---|
| DRM | DRM Info | |||
| Target and Pathway | Top | |||
|---|---|---|---|---|
| Target(s) | DNA topoisomerase I (TOP1) | Target Info | Modulator | [9] |
| NetPath Pathway | IL2 Signaling Pathway | |||
| Panther Pathway | DNA replication | |||
| Pathway Interaction Database | Caspase Cascade in Apoptosis | |||
| WikiPathways | Integrated Pancreatic Cancer Pathway | |||
| 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: 6823). | |||
| REF 2 | New drugs for the treatment of cancer, 1990-2001. Isr Med Assoc J. 2002 Dec;4(12):1124-31. | |||
| REF 3 | Structure and Inhibition of Microbiome beta-Glucuronidases Essential to the Alleviation of Cancer Drug Toxicity. Chem Biol. 2015 Sep 17;22(9):1238-49. | |||
| REF 4 | Alleviating cancer drug toxicity by inhibiting a bacterial enzyme. Science. 2010 Nov 5;330(6005):831-5. | |||
| REF 5 | Gut microbiota modulates drug pharmacokinetics. Drug Metab Rev. 2018 Aug;50(3):357-368. | |||
| REF 6 | Effects of Gut Microbiota on Drug Metabolism and Guidance for Rational Drug Use Under Hypoxic Conditions at High Altitudes. Curr Drug Metab. 2019;20(2):155-165. | |||
| REF 7 | Toxicomicrobiomics: The Human Microbiome vs. Pharmaceutical, Dietary, and Environmental Xenobiotics. Front Pharmacol. 2020 Apr 16;11:390. | |||
| REF 8 | Irinotecan (CPT-11) chemotherapy alters intestinal microbiota in tumour bearing rats. PLoS One. 2012;7(7):e39764. | |||
| REF 9 | Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. | |||
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