Details of the Drug

General Information of Drug (ID: DM5EN79)

Drug Name
Levamisole
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
Indication
Disease Entry ICD 11 Status REF
Parasitic infection 1D0Y-1G2Z Approved [1]
Colon cancer 2B90.Z Withdrawn from market [2]
Therapeutic Class
Anticancer Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 204.29
Logarithm of the Partition Coefficient (xlogp) 1.8
Rotatable Bond Count (rotbonds) 1
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 2
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [3]
Bioavailability
65% of drug becomes completely available to its intended biological destination(s) [4]
Half-life
The concentration or amount of drug in body reduced by one-half in 4.4 - 5.6 hours (biphasic) [5]
Metabolism
The drug is metabolized via the hepatic []
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 4.07742 micromolar/kg/day [6]
Chemical Identifiers
Formula
C11H12N2S
IUPAC Name
(6S)-6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole
Canonical SMILES
C1CSC2=N[C@H](CN21)C3=CC=CC=C3
InChI
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
InChIKey
HLFSDGLLUJUHTE-SNVBAGLBSA-N
Cross-matching ID
PubChem CID
26879
ChEBI ID
CHEBI:6432
CAS Number
14769-73-4
DrugBank ID
DB00848
TTD ID
D0CF2Q
INTEDE ID
DR2400
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Alkaline phosphatase tissue-nonspecific (ALPL) TTMR5UV PPBT_HUMAN Inhibitor [7]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Apoptosis regulator Bcl-2 (BCL2) OT9DVHC0 BCL2_HUMAN Gene/Protein Processing [8]
Bcl-2 homologous antagonist/killer (BAK1) OTDP6ILW BAK_HUMAN Gene/Protein Processing [8]
Cellular tumor antigen p53 (TP53) OTIE1VH3 P53_HUMAN Gene/Protein Processing [8]
Clusterin (CLU) OTQGG0JM CLUS_HUMAN Gene/Protein Processing [8]
Endothelin-1 (EDN1) OTZCACEG EDN1_HUMAN Gene/Protein Processing [8]
Nitric oxide synthase 3 (NOS3) OTLDT7NR NOS3_HUMAN Gene/Protein Processing [8]
Retinoblastoma-associated protein (RB1) OTQJUJMZ RB_HUMAN Gene/Protein Processing [8]
Tumor necrosis factor (TNF) OT4IE164 TNFA_HUMAN Gene/Protein Processing [9]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Levamisole (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Roflumilast DMPGHY8 Moderate Additive immunosuppressive effects by the combination of Levamisole and Roflumilast. Asthma [CA23] [10]
Teriflunomide DMQ2FKJ Major Additive immunosuppressive effects by the combination of Levamisole and Teriflunomide. Hyper-lipoproteinaemia [5C80] [11]
Denosumab DMNI0KO Moderate Additive immunosuppressive effects by the combination of Levamisole and Denosumab. Low bone mass disorder [FB83] [12]
Tecfidera DM2OVDT Moderate Additive immunosuppressive effects by the combination of Levamisole and Tecfidera. Multiple sclerosis [8A40] [13]
Siponimod DM2R86O Major Additive immunosuppressive effects by the combination of Levamisole and Siponimod. Multiple sclerosis [8A40] [14]
Fingolimod DM5JVAN Major Additive immunosuppressive effects by the combination of Levamisole and Fingolimod. Multiple sclerosis [8A40] [15]
Ocrelizumab DMEZ2KH Moderate Additive immunosuppressive effects by the combination of Levamisole and Ocrelizumab. Multiple sclerosis [8A40] [16]
Ozanimod DMT6AM2 Major Additive immunosuppressive effects by the combination of Levamisole and Ozanimod. Multiple sclerosis [8A40] [10]
Omacetaxine mepesuccinate DMPU2WX Moderate Additive immunosuppressive effects by the combination of Levamisole and Omacetaxine mepesuccinate. Myeloproliferative neoplasm [2A20] [17]
Canakinumab DM8HLO5 Moderate Additive immunosuppressive effects by the combination of Levamisole and Canakinumab. Rheumatoid arthritis [FA20] [18]
Rilonacept DMGLUQS Moderate Additive immunosuppressive effects by the combination of Levamisole and Rilonacept. Rheumatoid arthritis [FA20] [18]
Golimumab DMHZV7X Major Additive immunosuppressive effects by the combination of Levamisole and Golimumab. Rheumatoid arthritis [FA20] [19]
Leflunomide DMR8ONJ Major Additive immunosuppressive effects by the combination of Levamisole and Leflunomide. Rheumatoid arthritis [FA20] [11]
Anthrax vaccine DM9GSWY Moderate Antagonize the effect of Levamisole when combined with Anthrax vaccine. Sepsis [1G40-1G41] [20]
Azathioprine DMMZSXQ Moderate Additive immunosuppressive effects by the combination of Levamisole and Azathioprine. Transplant rejection [NE84] [14]
Ganciclovir DM1MBYQ Moderate Additive myelosuppressive effects by the combination of Levamisole and Ganciclovir. Virus infection [1A24-1D9Z] [14]
Valganciclovir DMS2IUH Moderate Additive myelosuppressive effects by the combination of Levamisole and Valganciclovir. Virus infection [1A24-1D9Z] [14]
⏷ Show the Full List of 17 DDI Information of This Drug

References

1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
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).
3 BDDCS applied to over 900 drugs
4 Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
5 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
6 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
7 Characterization of rat heart alkaline phosphatase isoenzymes and modulation of activity. Braz J Med Biol Res. 2008 Jul;41(7):600-9.
8 Levamisole induced apoptosis in cultured vascular endothelial cells. Br J Pharmacol. 2000 Dec;131(8):1577-83.
9 Levamisole can reduce the high serum tumour necrosis factor-alpha level to a normal level in patients with erosive oral lichen planus. Clin Exp Dermatol. 2007 May;32(3):308-10. doi: 10.1111/j.1365-2230.2006.02343.x.
10 Cerner Multum, Inc. "UK Summary of Product Characteristics.".
11 Product Information. Arava (leflunomide). Hoechst Marion-Roussel Inc, Kansas City, MO.
12 Product Information. Prolia (denosumab). Amgen USA, Thousand Oaks, CA.
13 Product Information. Vumerity (diroximel fumarate). Alkermes, Inc, Cambridge, MA.
14 Cerner Multum, Inc. "Australian Product Information.".
15 Product Information. Gilenya (fingolimod). Novartis Pharmaceuticals, East Hanover, NJ.
16 Product Information. Ocrevus (ocrelizumab). Genentech, South San Francisco, CA.
17 Product Information. Synribo (omacetaxine). Teva Pharmaceuticals USA, North Wales, PA.
18 Product Information. Arcalyst (rilonacept). Regeneron Pharmaceuticals Inc, Tarrytown, NY.
19 Product Information. Cimzia (certolizumab). UCB Pharma Inc, Smyrna, GA.
20 CDC. Centers for Disease Control and Prevention/ "Recommendations of the advisory committtee on immunization practices (ACIP): use of vaccines and immune globulins in persons with altered immunocompetence." MMWR Morb Mortal Wkly Rep 42(RR-04) (1993): 1-18. [PMID: 20300058]