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Colon cancer	2B90.Z	Withdrawn from market	[2], [3]

Therapeutic Class

Anticancer Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

204.29

Topological Polar Surface Area (xlogp)

1.8

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [4]
Bioavailability: 65% of drug becomes completely available to its intended biological destination(s) [5]
Half-life: The concentration or amount of drug in body reduced by one-half in 4.4 - 5.6 hours (biphasic) [6]
Metabolism: The drug is metabolized via the hepatic [7]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 4.07742 micromolar/kg/day [8]

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

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	[9]

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Molecular Interaction Atlas (MIA)

MIA Detail

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]	[11]
Teriflunomide	DMQ2FKJ	Major	Additive immunosuppressive effects by the combination of Levamisole and Teriflunomide.	Hyper-lipoproteinaemia [5C80]	[12]
Denosumab	DMNI0KO	Moderate	Additive immunosuppressive effects by the combination of Levamisole and Denosumab.	Low bone mass disorder [FB83]	[13]
Tecfidera	DM2OVDT	Moderate	Additive immunosuppressive effects by the combination of Levamisole and Tecfidera.	Multiple sclerosis [8A40]	[14]
Siponimod	DM2R86O	Major	Additive immunosuppressive effects by the combination of Levamisole and Siponimod.	Multiple sclerosis [8A40]	[15]
Fingolimod	DM5JVAN	Major	Additive immunosuppressive effects by the combination of Levamisole and Fingolimod.	Multiple sclerosis [8A40]	[16]
Ocrelizumab	DMEZ2KH	Moderate	Additive immunosuppressive effects by the combination of Levamisole and Ocrelizumab.	Multiple sclerosis [8A40]	[17]
Ozanimod	DMT6AM2	Major	Additive immunosuppressive effects by the combination of Levamisole and Ozanimod.	Multiple sclerosis [8A40]	[11]
Omacetaxine mepesuccinate	DMPU2WX	Moderate	Additive immunosuppressive effects by the combination of Levamisole and Omacetaxine mepesuccinate.	Myeloproliferative neoplasm [2A20]	[18]
Canakinumab	DM8HLO5	Moderate	Additive immunosuppressive effects by the combination of Levamisole and Canakinumab.	Rheumatoid arthritis [FA20]	[19]
Rilonacept	DMGLUQS	Moderate	Additive immunosuppressive effects by the combination of Levamisole and Rilonacept.	Rheumatoid arthritis [FA20]	[19]
Golimumab	DMHZV7X	Major	Additive immunosuppressive effects by the combination of Levamisole and Golimumab.	Rheumatoid arthritis [FA20]	[20]
Leflunomide	DMR8ONJ	Major	Additive immunosuppressive effects by the combination of Levamisole and Leflunomide.	Rheumatoid arthritis [FA20]	[12]
Anthrax vaccine	DM9GSWY	Moderate	Antagonize the effect of Levamisole when combined with Anthrax vaccine.	Sepsis [1G40-1G41]	[21]
Azathioprine	DMMZSXQ	Moderate	Additive immunosuppressive effects by the combination of Levamisole and Azathioprine.	Transplant rejection [NE84]	[15]
Ganciclovir	DM1MBYQ	Moderate	Additive myelosuppressive effects by the combination of Levamisole and Ganciclovir.	Virus infection [1A24-1D9Z]	[15]
Valganciclovir	DMS2IUH	Moderate	Additive myelosuppressive effects by the combination of Levamisole and Valganciclovir.	Virus infection [1A24-1D9Z]	[15]
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⏷ 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	New drugs in development for the treatment of endometriosis. Expert Opin Investig Drugs. 2008 Aug;17(8):1187-202.
4	BDDCS applied to over 900 drugs
5	Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
6	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
7	FDA approval: ado-trastuzumab emtansine for the treatment of patients with HER2-positive metastatic breast cancer. Clin Cancer Res. 2014 Sep 1;20(17):4436-41.
8	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
9	Characterization of rat heart alkaline phosphatase isoenzymes and modulation of activity. Braz J Med Biol Res. 2008 Jul;41(7):600-9.
10	Enzyme-replacement therapy in life-threatening hypophosphatasia. N Engl J Med. 2012 Mar 8;366(10):904-13.
11	Cerner Multum, Inc. "UK Summary of Product Characteristics.".
12	Product Information. Arava (leflunomide). Hoechst Marion-Roussel Inc, Kansas City, MO.
13	Product Information. Prolia (denosumab). Amgen USA, Thousand Oaks, CA.
14	Product Information. Vumerity (diroximel fumarate). Alkermes, Inc, Cambridge, MA.
15	Cerner Multum, Inc. "Australian Product Information.".
16	Product Information. Gilenya (fingolimod). Novartis Pharmaceuticals, East Hanover, NJ.
17	Product Information. Ocrevus (ocrelizumab). Genentech, South San Francisco, CA.
18	Product Information. Synribo (omacetaxine). Teva Pharmaceuticals USA, North Wales, PA.
19	Product Information. Arcalyst (rilonacept). Regeneron Pharmaceuticals Inc, Tarrytown, NY.
20	Product Information. Cimzia (certolizumab). UCB Pharma Inc, Smyrna, GA.
21	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]