Drug Information
| Drug General Information | Top | |||
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| Drug ID |
D07VLY
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| Former ID |
DAP000192
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| Drug Name |
Doxorubicin
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| Synonyms |
doxorubicin; 23214-92-8; Doxil; Doxorubicine; Adriablastin; Doxorubicinum; 14-Hydroxydaunomycin; 14-Hydroxydaunorubicine; Doxorubicina; Adriamycin semiquinone; Doxorubicinum [INN-Latin]; Doxorubicine [INN-French]; Doxorubicina [INN-Spanish]; Myocet; FI 106; Doxorubicin [USAN:INN:BAN]; CCRIS 739; NDC 38242-874; HSDB 3070; UNII-80168379AG; NCI-C01514; EINECS 245-495-6; CHEMBL53463; CHEBI:28748; 5,12-Naphthacenedione,; ADM; ADR; ThermoDox; Aerosolized Doxorubicin; Doxorubicin citrate; RDF Rubex; Conjugate of doxorubicin with humanized monoclonal antibody LL1 against CD74; DM2; JT9100000; Adiblastine (hydrochloride salt); Adr iablatina (hydrochloride salt); Adriablastine (hydrochloride salt); Adriablatina (hydrochloride salt); Adriacin (hydrochloride salt); Adriamycin PFS (TN); Adriamycin PFS (hydrochloride salt); Adriamycin RDF (TN); Adriamycin RDF (hydrochloride salt); Adriblastina (TN); Adriblastina (hydrochloride salt); Adriblatina (hydrochloride salt); Caelyx (TN); Conjugate of doxorubicin with monoclonal antibody P4/D10 against GP120; DOX-SL; Doxorubicin hydrochloride (hydrochloride salt); Doxorubicin-hLL1; Doxorubicin-hLL1 conjugate; Farmablastina (hydrochloride salt); Hydroxydaunomycin hydrochlor ide (hydrochloride salt); Hydroxydaunomycin hydrochloride (hydrochloride salt); Hydroxydaunorubicin hydrochloride (hydrochloride salt); Myocet (TN); Rubex (TN); Rubex (hydrochloride salt); TLC D-99; Doxorubicin (USAN/INN); Doxorubicin-P4/D10; Doxorubicin-P4/D10 conjugate; Cantide + adriamycin
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] | |
| Hepatocellular carcinoma [ICD-11: 2C12.02; ICD-10: C22.0; ICD-9: 155] | Phase 3 | [3] | ||
| Breast cancer [ICD-11: 2C60-2C65] | Phase 2 | [4] | ||
| Tumour [ICD-11: 2A00-2F9Z; ICD-10: C00-D48; ICD-9: 140-199, 210-229] | Investigative | [5] | ||
| Therapeutic Class |
Anticancer Agents
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| Company |
Sequus Pharmaceuticals Inc
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| Structure |
 |
Download2D MOL |
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| Formula |
C27H29NO11
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| Canonical SMILES |
CC1C(C(CC(O1)OC2CC(CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)CO)O)N)O
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| InChI |
1S/C27H29NO11/c1-10-22(31)13(28)6-17(38-10)39-15-8-27(36,16(30)9-29)7-12-19(15)26(35)21-20(24(12)33)23(32)11-4-3-5-14(37-2)18(11)25(21)34/h3-5,10,13,15,17,22,29,31,33,35-36H,6-9,28H2,1-2H3/t10-,13-,15-,17-,22+,27-/m0/s1
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| InChIKey |
AOJJSUZBOXZQNB-TZSSRYMLSA-N
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| CAS Number |
CAS 23214-92-8
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| PubChem Compound ID | ||||
| PubChem Substance ID |
4809, 596007, 7887074, 7979129, 8172352, 11466466, 11467586, 11486131, 11533222, 11538021, 14910387, 14910388, 17397983, 24769891, 26704333, 26709766, 34673809, 46507641, 47440542, 47515588, 47589229, 47736754, 47811027, 47811028, 48035406, 48185239, 48414671, 48415928, 49698493, 49846798, 49855190, 50063935, 53787595, 53837797, 56310844, 56311108, 56311939, 56312034, 56312063, 56312270, 56312524, 56312768, 56313130, 56313308, 56313325, 56313365, 56313675, 56313990, 56314080, 56314176
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| ChEBI ID |
CHEBI:28748
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| ADReCS Drug ID | BADD_D00723 ; BADD_D00724 | |||
| SuperDrug ATC ID |
L01DB01
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| SuperDrug CAS ID |
cas=023214928
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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 BW25113
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[6], [7] | |||
| Hierarchy | ||||
| Resulting Metabolite | 7-deoxydoxorubicinol; 7-deoxydoxorubicinolone | |||
| Metabolic Effect | Decrease toxicity | |||
| Description | Doxorubicin can be metabolized to 7-deoxydoxorubicinol and 7-deoxydoxorubicinolone by Escherichia coli BW25113, which results in the decrease of the drug's toxicity. | |||
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Studied Microbe: Escherichia coli Nissle 1917
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[8] | |||
| Hierarchy | ||||
| Metabolic Effect | Decrease activity | |||
| Description | Doxorubicin can be metabolized by Escherichia coli Nissle 1917, which results in the decrease of the drug's activity. | |||
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Studied Microbe: Klebsiella pneumoniae
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[9] | |||
| Hierarchy | ||||
| Metabolic Effect | Decrease activity | |||
| Description | Doxorubicin can be metabolized by Klebsiella pneumoniae, which results in the decrease of the drug's activity. | |||
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Studied Microbe: Raoultella planticola
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[6], [7], [9] | |||
| Hierarchy | ||||
| Metabolic Reaction | Reductive deglycosylation | |||
| Resulting Metabolite | 7-deoxydoxorubicinol; 7-deoxydoxorubicinolone | |||
| Metabolic Effect | Decrease toxicity; Decrease activity | |||
| Description | Doxorubicin can be metabolized to 7-deoxydoxorubicinol and 7-deoxydoxorubicinolone by Raoultella planticola through reductive deglycosylation, which results in the decrease of the drug's toxicity and activity. | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Gut microbiota | ||||
| Studied Microbe: Gut microbiota unspecific | [10] | |||
| Metabolic Effect | Increase side effect | |||
| Description | Doxorubicin 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): Bacteroidales | ||||
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Studied Microbe: Odoribacter splanchnicus
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[11] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Odoribacter splanchnicus was decreased by Doxorubicin hydrochloride (adjusted p-values: 5.04E-06). | |||
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Studied Microbe: Parabacteroides distasonis
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[11] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Parabacteroides distasonis was decreased by Doxorubicin hydrochloride (adjusted p-values: 2.14E-04). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Bifidobacteriales | ||||
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Studied Microbe: Bifidobacterium adolescentis
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[11] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Bifidobacterium adolescentis was decreased by Doxorubicin hydrochloride (adjusted p-values: 5.04E-06). | |||
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Studied Microbe: Bifidobacterium longum
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[11] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Bifidobacterium longum was decreased by Doxorubicin hydrochloride (adjusted p-values: 5.04E-06). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Coriobacteriales | ||||
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Studied Microbe: Collinsella aerofaciens
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[11] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Collinsella aerofaciens was decreased by Doxorubicin hydrochloride (adjusted p-values: 2.73E-07). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Eggerthellales | ||||
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Studied Microbe: Eggerthella lenta
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[11] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Eggerthella lenta was decreased by Doxorubicin hydrochloride (adjusted p-values: 6.47E-05). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Erysipelotrichales | ||||
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Studied Microbe: Erysipelatoclostridium ramosum
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[11] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Erysipelatoclostridium ramosum was decreased by Doxorubicin hydrochloride (adjusted p-values: 6.70E-05). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Eubacteriales | ||||
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Studied Microbe: Blautia obeum
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[11] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Blautia obeum was decreased by Doxorubicin hydrochloride (adjusted p-values: 1.07E-04). | |||
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Studied Microbe: Clostridioides difficile
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[11] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Clostridioides difficile was decreased by Doxorubicin hydrochloride (adjusted p-values: 1.73E-03). | |||
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Studied Microbe: Clostridium perfringens
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[11] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Clostridium perfringens was decreased by Doxorubicin hydrochloride (adjusted p-values: 2.94E-03). | |||
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Studied Microbe: Coprococcus comes
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[11] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Coprococcus comes was decreased by Doxorubicin hydrochloride (adjusted p-values: 7.69E-04). | |||
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Studied Microbe: Dorea formicigenerans
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[11] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Dorea formicigenerans was decreased by Doxorubicin hydrochloride (adjusted p-values: 3.45E-03). | |||
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Studied Microbe: Enterocloster bolteae
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[11] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Enterocloster bolteae was decreased by Doxorubicin hydrochloride (adjusted p-values: 5.15E-05). | |||
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Studied Microbe: Roseburia hominis
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[11] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Roseburia hominis was decreased by Doxorubicin hydrochloride (adjusted p-values: 2.32E-05). | |||
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Studied Microbe: Roseburia intestinalis
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[11] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Roseburia intestinalis was decreased by Doxorubicin hydrochloride (adjusted p-values: 4.84E-03). | |||
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Studied Microbe: Ruminococcus torques
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[11] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Ruminococcus torques was decreased by Doxorubicin hydrochloride (adjusted p-values: 2.40E-04). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Lactobacillales | ||||
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Studied Microbe: Lactobacillus paracasei
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[11] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Lactobacillus paracasei was decreased by Doxorubicin hydrochloride (adjusted p-values: 7.55E-05). | |||
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Studied Microbe: Streptococcus parasanguinis
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[11] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Streptococcus parasanguinis was decreased by Doxorubicin hydrochloride (adjusted p-values: 5.51E-07). | |||
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Studied Microbe: Streptococcus salivarius
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[11] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Streptococcus salivarius was decreased by Doxorubicin hydrochloride (adjusted p-values: 1.72E-06). | |||
| Target and Pathway | Top | |||
|---|---|---|---|---|
| Target(s) | DNA topoisomerase II (TOP2) | Target Info | Modulator | [12] |
| TERT messenger RNA (TERT mRNA) | Target Info | . | [5] | |
| KEGG Pathway | HTLV-I infection | |||
| NetPath Pathway | IL2 Signaling Pathway | |||
| Pathway Interaction Database | Validated targets of C-MYC transcriptional activation | |||
| Regulation of Telomerase | ||||
| IL2 signaling events mediated by PI3K | ||||
| Regulation of nuclear beta catenin signaling and target gene transcription | ||||
| HIF-1-alpha transcription factor network | ||||
| Reactome | Formation of the beta-catenin:TCF transactivating complex | |||
| WikiPathways | TGF beta Signaling Pathway | |||
| miR-targeted genes in lymphocytes - TarBase | ||||
| miR-targeted genes in epithelium - TarBase | ||||
| Telomere Maintenance | ||||
| 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: 7069). | |||
| 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 | ClinicalTrials.gov (NCT02112656) Study of ThermoDox With Standardized Radiofrequency Ablation (RFA) for Treatment of Hepatocellular Carcinoma (HCC) (OPTIMA). U.S. National Institutes of Health. | |||
| REF 4 | Antitumor activity of liposome-encapsulated doxorubicin in advanced breast cancer: phase II study. J Natl Cancer Inst. 1990 Nov 7;82(21):1706-10. | |||
| REF 5 | Design and development of antisense drugs. Expert Opin. Drug Discov. 2008 3(10):1189-1207. | |||
| REF 6 | Gut Reactions: Breaking Down Xenobiotic-Microbiome Interactions. Pharmacol Rev. 2019 Apr;71(2):198-224. | |||
| REF 7 | Transformation of the Anticancer Drug Doxorubicin in the Human Gut Microbiome. ACS Infect Dis. 2018 Jan 12;4(1):68-76. | |||
| REF 8 | Local bacteria affect the efficacy of chemotherapeutic drugs. Sci Rep. 2015 Sep 29;5:14554. | |||
| REF 9 | 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 10 | Toxicomicrobiomics: The Human Microbiome vs. Pharmaceutical, Dietary, and Environmental Xenobiotics. Front Pharmacol. 2020 Apr 16;11:390. | |||
| REF 11 | Extensive impact of non-antibiotic drugs on human gut bacteria. Nature. 2018 Mar 29;555(7698):623-628. | |||
| REF 12 | Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. | |||
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