Drug Information
| Drug General Information | Top | |||
|---|---|---|---|---|
| Drug ID |
D01XWG
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| Former ID |
DAP000788
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| Drug Name |
Daunorubicin
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| Synonyms |
daunorubicin; Daunomycin; 20830-81-3; Rubidomycin; Cerubidine; Daunorubicine; Acetyladriamycin; Leukaemomycin C; Daunorubicinum; Daunarubicinum; Daunorrubicina; Daunamycin; Cerubidin; DaunoXome; Rubomycin C; (+)-Daunomycin; Daunoblastin; Anthracyline; Rubomycin; Daunorubicinum [INN-Latin]; RP 13057; Daunorubicin [INN:BAN]; RCRA waste no U059; FI6339; NSC-82151; DAUNORUBICIN HCL; DaunoXome (TN); UNII-ZS7284E0ZP; CCRIS 914; ZS7284E0ZP; CHEBI:41977; HSDB 5095; C27H29NO10; NCI-C04693; EINECS 244-069-7; Ondena; NSC 83142; Acetyladriamycin; Daunoblastine; Antibiotics from Streptomyces coeruleorubidus; DM1; FI 6339; Dauno-Rubidomycine; Daunorubicin (INN); Daunorubicin (liposomal); Daunorubicin, Hydrochloride; VS-103; (1S,3S)-3-acetyl-3,5,12-trihydroxy-10-(methyloxy)-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranoside; (1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-a-L-lyxo-hexopyranoside; (7S,9R)-9-Acetyl-7-[(2S,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-oxan-2-yl]oxy-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione; (7S,9S)-9-acetyl-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione; (8S-cis)-8-Acetyl-10-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyrannosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-napthacenedione; (8S-cis)-8-Acetyl-10-[(3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-naphthacenedione; Anthracycline
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| Drug Type |
Small molecular drug
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| Indication | Acute myeloid leukaemia [ICD-11: 2A60] | Approved | [1], [2] | |
| Kaposi sarcoma [ICD-11: 2B57; ICD-9: 176] | Approved | [3] | ||
| Solid tumour/cancer [ICD-11: 2A00-2F9Z; ICD-10: C00-D48; ICD-9: 140-199, 210-229] | Phase 2 | [4] | ||
| Therapeutic Class |
Anticancer Agents
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| Structure |
 |
Download2D MOL |
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| Formula |
C27H29NO10
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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)C)O)N)O
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| InChI |
1S/C27H29NO10/c1-10-22(30)14(28)7-17(37-10)38-16-9-27(35,11(2)29)8-13-19(16)26(34)21-20(24(13)32)23(31)12-5-4-6-15(36-3)18(12)25(21)33/h4-6,10,14,16-17,22,30,32,34-35H,7-9,28H2,1-3H3/t10-,14-,16-,17-,22+,27-/m0/s1
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| InChIKey |
STQGQHZAVUOBTE-VGBVRHCVSA-N
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| CAS Number |
CAS 20830-81-3
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| PubChem Compound ID | ||||
| PubChem Substance ID |
5016, 596008, 866161, 7887073, 7979028, 8171488, 11114094, 14763056, 15481415, 24769892, 26697306, 26701813, 26704223, 26715132, 26718351, 26718779, 29215022, 34672588, 46508433, 47440436, 47736668, 48110630, 48415843, 49699346, 49855159, 50070917, 50104250, 53788227, 56465013, 57288764, 57310919, 74382025, 74462219, 85788867, 92307396, 92308820, 96024474, 103477782, 104066339, 104307942, 117393873, 124766118, 124886869, 124886870, 124886871, 125299287, 126663226, 127301039, 127301040, 127301041
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| ChEBI ID |
CHEBI:41977
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| ADReCS Drug ID | BADD_D00590 ; BADD_D00591 ; BADD_D00592 | |||
| SuperDrug ATC ID |
L01DB02
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| SuperDrug CAS ID |
cas=020830813
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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): Bacillales | ||||
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Studied Microbe: Listeria welshimeri serovar 6b str. SLCC5334
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[5] | |||
| Hierarchy | ||||
| Metabolic Effect | Decrease activity | |||
| Description | Daunorubicin can be metabolized by Listeria welshimeri serovar 6b str. SLCC5334, which results in the decrease of the drug's activity. | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Enterobacterales | ||||
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Studied Microbe: Escherichia coli Nissle 1917
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[5] | |||
| Hierarchy | ||||
| Metabolic Effect | Decrease activity | |||
| Description | Daunorubicin can be metabolized by Escherichia coli Nissle 1917, which results in the decrease of the drug's activity. | |||
| 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: Bacteroides caccae
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[6] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Bacteroides caccae was decreased by Daunorubicin hydrochloride (adjusted p-values: 1.05E-03). | |||
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Studied Microbe: Bacteroides ovatus
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[6] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Bacteroides ovatus was decreased by Daunorubicin hydrochloride (adjusted p-values: 5.85E-06). | |||
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Studied Microbe: Bacteroides thetaiotaomicron
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[6] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Bacteroides thetaiotaomicron was decreased by Daunorubicin hydrochloride (adjusted p-values: 3.24E-03). | |||
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Studied Microbe: Bacteroides vulgatus
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[6] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Bacteroides vulgatus was decreased by Daunorubicin hydrochloride (adjusted p-values: 3.08E-03). | |||
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Studied Microbe: Bacteroides xylanisolvens
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[6] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Bacteroides xylanisolvens was decreased by Daunorubicin hydrochloride (adjusted p-values: 3.77E-03). | |||
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Studied Microbe: Odoribacter splanchnicus
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[6] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Odoribacter splanchnicus was decreased by Daunorubicin hydrochloride (adjusted p-values: 5.04E-06). | |||
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Studied Microbe: Parabacteroides distasonis
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[6] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Parabacteroides distasonis was decreased by Daunorubicin hydrochloride (adjusted p-values: 3.22E-07). | |||
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Studied Microbe: Parabacteroides merdae
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[6] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Parabacteroides merdae was decreased by Daunorubicin hydrochloride (adjusted p-values: 2.81E-05). | |||
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Studied Microbe: Prevotella copri
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[6] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Prevotella copri was decreased by Daunorubicin hydrochloride (adjusted p-values: 7.74E-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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[6] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Bifidobacterium adolescentis was decreased by Daunorubicin hydrochloride (adjusted p-values: 5.04E-06). | |||
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Studied Microbe: Bifidobacterium longum
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[6] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Bifidobacterium longum was decreased by Daunorubicin 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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[6] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Collinsella aerofaciens was decreased by Daunorubicin hydrochloride (adjusted p-values: 4.93E-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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[6] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Eggerthella lenta was decreased by Daunorubicin hydrochloride (adjusted p-values: 1.30E-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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[6] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Erysipelatoclostridium ramosum was decreased by Daunorubicin hydrochloride (adjusted p-values: 5.04E-06). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Eubacteriales | ||||
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Studied Microbe: Blautia obeum
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[6] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Blautia obeum was decreased by Daunorubicin hydrochloride (adjusted p-values: 7.64E-07). | |||
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Studied Microbe: Clostridioides difficile
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[6] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Clostridioides difficile was decreased by Daunorubicin hydrochloride (adjusted p-values: 1.44E-03). | |||
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Studied Microbe: Clostridium perfringens
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[6] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Clostridium perfringens was decreased by Daunorubicin hydrochloride (adjusted p-values: 2.83E-04). | |||
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Studied Microbe: Coprococcus comes
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[6] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Coprococcus comes was decreased by Daunorubicin hydrochloride (adjusted p-values: 3.10E-05). | |||
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Studied Microbe: Dorea formicigenerans
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[6] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Dorea formicigenerans was decreased by Daunorubicin hydrochloride (adjusted p-values: 6.92E-06). | |||
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Studied Microbe: Enterocloster bolteae
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[6] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Enterocloster bolteae was decreased by Daunorubicin hydrochloride (adjusted p-values: 6.71E-06). | |||
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Studied Microbe: Eubacterium eligens
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[6] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Eubacterium eligens was decreased by Daunorubicin hydrochloride (adjusted p-values: 5.04E-03). | |||
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Studied Microbe: Eubacterium rectale
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[6] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Eubacterium rectale was decreased by Daunorubicin hydrochloride (adjusted p-values: 1.20E-03). | |||
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Studied Microbe: Lacrimispora saccharolytica
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[6] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Lacrimispora saccharolytica was decreased by Daunorubicin hydrochloride (adjusted p-values: 2.40E-03). | |||
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Studied Microbe: Roseburia hominis
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[6] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Roseburia hominis was decreased by Daunorubicin hydrochloride (adjusted p-values: 1.55E-05). | |||
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Studied Microbe: Roseburia intestinalis
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[6] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Roseburia intestinalis was decreased by Daunorubicin hydrochloride (adjusted p-values: 4.23E-04). | |||
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Studied Microbe: Ruminococcus bromii
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[6] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Ruminococcus bromii was decreased by Daunorubicin hydrochloride (adjusted p-values: 1.53E-05). | |||
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Studied Microbe: Ruminococcus gnavus
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[6] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Ruminococcus gnavus was decreased by Daunorubicin hydrochloride (adjusted p-values: 8.95E-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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[6] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Lactobacillus paracasei was decreased by Daunorubicin hydrochloride (adjusted p-values: 5.04E-06). | |||
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Studied Microbe: Streptococcus parasanguinis
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[6] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Streptococcus parasanguinis was decreased by Daunorubicin hydrochloride (adjusted p-values: 6.79E-07). | |||
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Studied Microbe: Streptococcus salivarius
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[6] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Streptococcus salivarius was decreased by Daunorubicin hydrochloride (adjusted p-values: 5.51E-07). | |||
| Drug Resistance Mutation (DRM) | Top | |||
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| DRM | DRM Info | |||
| Target and Pathway | Top | |||
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| Target(s) | DNA replication (DNA repli) | Target Info | Modulator | [7] |
| Human Deoxyribonucleic acid (hDNA) | Target Info | Intercalator | [8] | |
| 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: 7063). | |||
| 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 | Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015 | |||
| REF 4 | Multicentre, phase II study evaluating capecitabine monotherapy in patients with anthracycline- and taxane-pretreated metastatic breast cancer. Eur J Cancer. 2004 Mar;40(4):536-42. | |||
| REF 5 | Local bacteria affect the efficacy of chemotherapeutic drugs. Sci Rep. 2015 Sep 29;5:14554. | |||
| REF 6 | Extensive impact of non-antibiotic drugs on human gut bacteria. Nature. 2018 Mar 29;555(7698):623-628. | |||
| REF 7 | Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. | |||
| REF 8 | 31P NMR spectra of ethidium, quinacrine, and daunomycin complexes with poly(adenylic acid).poly(uridylic acid) RNA duplex and calf thymus DNA. Biochemistry. 1989 Apr 4;28(7):2804-12. | |||
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