Drug Information
| Drug General Information | Top | |||
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| Drug ID |
D0CF2Q
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| Former ID |
DAP000570
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| Drug Name |
Levamisole
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| Synonyms |
Ketrax; LEVOMYSOL; Lepuron; Levamisol; Levamisolum; Levotetramisole; Tetramisol; Wormicid; Levamisole Base;Nilverm base; P00039; Vermisol 150; Dl-Tetramisol; Dl-Tetramisole; Ergamisol (TN); Ketrax (TN); L-Tetramisole; Levamisol [INN-Spanish]; Levamisole (INN); Levamisole [INN:BAN]; Levamisolum [INN-Latin]; TCMDC-125847; L(-)-Levamisole; L-2,3,5,6-Tetrahyro-6-phenylimidazo(2,1-b)thiazole; (-)-Tetramisole; (6S)-6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole; (S)-(-)-Levamisole
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| Drug Type |
Small molecular drug
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| Indication | Parasitic infection [ICD-11: 1D0Y-1G2Z; ICD-10: B85-B89] | Approved | [1] | |
| Colon cancer [ICD-11: 2B90.Z] | Withdrawn from market | [2], [3] | ||
| Therapeutic Class |
Anticancer Agents
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| Company |
Janssen Pharmaceutica
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| Structure |
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Download2D MOL |
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| Formula |
C11H12N2S
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| Canonical SMILES |
C1CSC2=NC(CN21)C3=CC=CC=C3
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| InChI |
1S/C11H12N2S/c1-2-4-9(5-3-1)10-8-13-6-7-14-11(13)12-10/h1-5,10H,6-8H2/t10-/m1/s1
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| InChIKey |
HLFSDGLLUJUHTE-SNVBAGLBSA-N
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| CAS Number |
CAS 14769-73-4
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| PubChem Compound ID | ||||
| PubChem Substance ID |
9282, 602395, 7979761, 8169434, 10322011, 11335842, 11361081, 11364503, 11367065, 11369627, 11371883, 11374574, 11377789, 11405871, 11462053, 11466210, 11467330, 11484645, 11485760, 11488681, 11490777, 11492892, 11495423, 14748767, 15171780, 34669469, 46509052, 47440260, 47589003, 47736487, 47736488, 48035125, 48416165, 49761633, 49831041, 49981671, 50111118, 53790505, 56313649, 56313755, 57310333, 76000434, 85789251, 85860304, 90341409, 92309280, 92717075, 93166530, 96024804, 103523408
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| ChEBI ID |
CHEBI:6432
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| SuperDrug ATC ID |
P02CE01
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| SuperDrug CAS ID |
cas=014769734
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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
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[4], [5], [6] | |||
| Hierarchy | ||||
| Metabolic Reaction | Thiazole ring opening | |||
| Resulting Metabolite | Levametabol-I, Levametabol-II; Levametabol-III | |||
| Metabolic Effect | Increase activity | |||
| Description | Levamisole can be metabolized to Levametabol-I, Levametabol-II and Levametabol-III by Bacteroides through thiazole ring opening, which results in the increase of the drug's activity. | |||
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Studied Microbe: Bacteroides dorei DSM 17855
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[7] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Levamisole can be metabolized by Bacteroides dorei DSM 17855 (log2FC = -0.565; p = 0.028). | |||
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Studied Microbe: Bacteroides fragilis ATCC43859
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[7] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Levamisole can be metabolized by Bacteroides fragilis ATCC43859 (log2FC = -0.697; p = 0.009). | |||
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Studied Microbe: Bacteroides fragilis HMW 610
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[7] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Levamisole can be metabolized by Bacteroides fragilis HMW 610 (log2FC = -0.522; p = 0.004). | |||
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Studied Microbe: Bacteroides fragilis NCTC 9343
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[7] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Levamisole can be metabolized by Bacteroides fragilis NCTC 9343 (log2FC = -0.351; p = 0.003). | |||
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Studied Microbe: Bacteroides fragilis str. 3397 T10
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[7] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Levamisole can be metabolized by Bacteroides fragilis str. 3397 T10 (log2FC = -0.544; p = 0.001). | |||
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Studied Microbe: Bacteroides fragilis str. 3986 T(B)9
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[7] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Levamisole can be metabolized by Bacteroides fragilis str. 3986 T(B)9 (log2FC = -0.541; p = 0.0). | |||
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Studied Microbe: Bacteroides fragilis str. DS-208
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[7] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Levamisole can be metabolized by Bacteroides fragilis str. DS-208 (log2FC = -0.466; p = 0.003). | |||
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Studied Microbe: Bacteroides stercoris ATCC 43183
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[7] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Levamisole can be metabolized by Bacteroides stercoris ATCC 43183 (log2FC = -0.53; p = 0.039). | |||
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Studied Microbe: Bacteroides thetaiotaomicron 7330
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[7] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Levamisole can be metabolized by Bacteroides thetaiotaomicron 7330 (log2FC = -0.438; p = 0.006). | |||
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Studied Microbe: Bacteroides thetaiotaomicron VPI-5482
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[7] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Levamisole can be metabolized by Bacteroides thetaiotaomicron VPI-5482 (log2FC = -0.396; p = 0.004). | |||
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Studied Microbe: Bacteroides uniformis ATCC 8492
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[7] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Levamisole can be metabolized by Bacteroides uniformis ATCC 8492 (log2FC = -0.819; p = 0.0). | |||
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Studied Microbe: Bacteroides uniformis CL03T12C37
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[8] | |||
| Hierarchy | ||||
| Description | Levamisole can be metabolized by Bacteroides uniformis CL03T12C37. | |||
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Studied Microbe: Bacteroides vulgatus ATCC 8482
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[7] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Levamisole can be metabolized by Bacteroides vulgatus ATCC 8482 (log2FC = -0.43; p = 0.023). | |||
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Studied Microbe: Bacteroides xylanisolvens DSM18836
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[7] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Levamisole can be metabolized by Bacteroides xylanisolvens DSM18836 (log2FC = -0.384; p = 0.012). | |||
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Studied Microbe: Odoribacter splanchnicus
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[7] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Levamisole can be metabolized by Odoribacter splanchnicus (log2FC = -0.402; p = 0.004). | |||
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Studied Microbe: Parabacteroides johnsonii DSM 18315
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[7] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Levamisole can be metabolized by Parabacteroides johnsonii DSM 18315 (log2FC = -0.467; p = 0.004). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Bifidobacteriales | ||||
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Studied Microbe: Bifidobacterium animalis subsp.lactis BI-07
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[8] | |||
| Hierarchy | ||||
| Description | Levamisole can be metabolized by Bifidobacterium animalis subsp.lactis BI-07. | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Enterobacterales | ||||
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Studied Microbe: Edwardsiella tarda ATCC 23685
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[7] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Levamisole can be metabolized by Edwardsiella tarda ATCC 23685 (log2FC = -1.764; p = 0.002). | |||
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Studied Microbe: Escherichia coli BW25113
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[7] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Levamisole can be metabolized by Escherichia coli BW25113 (log2FC = -2.179; p = 0.0). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Eubacteriales | ||||
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Studied Microbe: Anaerotruncus colihominis DSM 17241
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[7] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Levamisole can be metabolized by Anaerotruncus colihominis DSM 17241 (log2FC = -1.183; p = 0.0). | |||
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Studied Microbe: Clostridium
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[4], [5], [6] | |||
| Hierarchy | ||||
| Metabolic Reaction | Thiazole ring opening | |||
| Resulting Metabolite | Levametabol-I, Levametabol-II; Levametabol-III | |||
| Metabolic Effect | Increase activity | |||
| Description | Levamisole can be metabolized to Levametabol-I, Levametabol-II and Levametabol-III by Clostridium through thiazole ring opening, which results in the increase of the drug's activity. | |||
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Studied Microbe: Clostridium difficile 120
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[7] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Levamisole can be metabolized by Clostridium difficile 120 (log2FC = -0.34; p = 0.003). | |||
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Studied Microbe: Clostridium saccharolyticum DSM 2544
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[8] | |||
| Hierarchy | ||||
| Description | Levamisole can be metabolized by Clostridium saccharolyticum DSM 2544. | |||
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Studied Microbe: Clostridium sp.
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[9] | |||
| Hierarchy | ||||
| Metabolic Reaction | Thiazole ring opening | |||
| Resulting Metabolite | Levametabol-I, Levametabol-II; Levametabol-III | |||
| Metabolic Effect | Increase activity | |||
| Description | Levamisole can be metabolized to Levametabol-I, Levametabol-II and Levametabol-III by Clostridium sp. through thiazole ring opening, which results in the increase of the drug's activity. | |||
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Studied Microbe: Clostridium sporogenes ATCC 15579
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[7] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Levamisole can be metabolized by Clostridium sporogenes ATCC 15579 (log2FC = -0.624; p = 0.002). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Fusobacteriales | ||||
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Studied Microbe: Fusobacterium nucleatum subsp. nucleatum ATCC 25586
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[8] | |||
| Hierarchy | ||||
| Description | Levamisole can be metabolized by Fusobacterium nucleatum subsp. nucleatum ATCC 25586. | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Lactobacillales | ||||
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Studied Microbe: Lactobacillus gasseri ATCC 33323
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[8] | |||
| Hierarchy | ||||
| Description | Levamisole can be metabolized by Lactobacillus gasseri ATCC 33323. | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Tissierellales | ||||
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Studied Microbe: Anaerococcus hydrogenalis DSM 7454
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[7] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Levamisole can be metabolized by Anaerococcus hydrogenalis DSM 7454 (log2FC = -1.096; p = 0.003). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Gut microbiota | ||||
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Studied Microbe: Bacteroidetes
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[9] | |||
| Hierarchy | ||||
| Metabolic Reaction | Thiazole ring opening | |||
| Resulting Metabolite | Levametabol-I, Levametabol-II; Levametabol-III | |||
| Metabolic Effect | Increase activity | |||
| Description | Levamisole can be metabolized to Levametabol-I, Levametabol-II and Levametabol-III by Bacteroidetes through thiazole ring opening, which results in the increase of the drug's activity. | |||
| Studied Microbe: Gut microbiota unspecific | [10] | |||
| Metabolic Reaction | Ring fission and reduction | |||
| Resulting Metabolite | Levametabol-I, Levametabol-II; Levametabol-III | |||
| Metabolic Effect | Increase activity | |||
| Description | Levamisole can be metabolized to Levametabol-I, Levametabol-II and Levametabol-III by gut microbiota through ring fission and reduction, which results in the increase of the drug's activity. | |||
| Target and Pathway | Top | |||
|---|---|---|---|---|
| Target(s) | Alkaline phosphatase tissue-nonspecific (ALPL) | Target Info | Inhibitor | [11] |
| KEGG Pathway | Folate biosynthesis | |||
| Metabolic pathways | ||||
| NetPath Pathway | FSH Signaling Pathway | |||
| Pathwhiz Pathway | Vitamin B6 Metabolism | |||
| WikiPathways | Endochondral Ossification | |||
| BDNF signaling pathway | ||||
| AGE/RAGE pathway | ||||
| References | Top | |||
|---|---|---|---|---|
| REF 1 | Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015 | |||
| REF 2 | 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: 7210). | |||
| REF 3 | New drugs in development for the treatment of endometriosis. Expert Opin Investig Drugs. 2008 Aug;17(8):1187-202. | |||
| REF 4 | The influence of gut microbiota on drug metabolism and toxicity. Expert Opin Drug Metab Toxicol. 2016;12(1):31-40. | |||
| REF 5 | Pharmacomicrobiomics: The Holy Grail to Variability in Drug Response?. Clin Pharmacol Ther. 2019 Aug;106(2):317-328. | |||
| REF 6 | Gut microbiota: what is its place in pharmacology?. Expert Rev Clin Pharmacol. 2019 Oct;12(10):921-930. | |||
| REF 7 | Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467. | |||
| REF 8 | Bioaccumulation of therapeutic drugs by human gut bacteria. Nature. 2021 Sep;597(7877):533-538. | |||
| REF 9 | Human gut microbiota plays a role in the metabolism of drugs. Biomed Pap Med Fac Univ Palacky Olomouc Czech Repub. 2016 Sep;160(3):317-26. | |||
| REF 10 | Gut Microbiota-Mediated Drug-Antibiotic Interactions. Drug Metab Dispos. 2015 Oct;43(10):1581-9. | |||
| REF 11 | Characterization of rat heart alkaline phosphatase isoenzymes and modulation of activity. Braz J Med Biol Res. 2008 Jul;41(7):600-9. | |||
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