Page last updated: 2024-11-04

tetramisole

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Tetramisole is a synthetic imidazothiazole derivative with anthelmintic, immunostimulatory, and anti-inflammatory properties. It is synthesized through a multi-step process involving the reaction of 2-mercaptoethanol with 2-chloro-N-(2-chloroethyl)benzamide. Tetramisole acts as a cholinesterase inhibitor, leading to the paralysis and expulsion of parasitic worms. It is also known to enhance the immune response by activating T lymphocytes and increasing the production of cytokines. The importance of tetramisole lies in its historical use as a broad-spectrum anthelmintic, particularly for the treatment of gastrointestinal parasites in humans and animals. However, its use has declined due to concerns about potential side effects and the emergence of drug resistance. Tetramisole is still studied for its immunomodulatory properties, with potential applications in cancer therapy and autoimmune diseases. Research is ongoing to investigate its mechanism of action and to develop safer and more effective derivatives for therapeutic use.'

6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole : An imidazothiazole that is imidazo[2,1-b][1,3]thiazole in which the double bonds at the 2-3 and 5-6 positions have been reduced to single bonds and in which one of the hydrogens at position 6 is replaced by a phenyl group. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

tetramisole : A racemate comprising equimolar amounts of levamisole and dexamisole. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID3913
CHEMBL ID277775
CHEBI ID77278
SCHEMBL ID167819
MeSH IDM0021246

Synonyms (85)

Synonym
HMS1674C22
BRD-A46393198-003-04-2
nsc-614927
nsc614927
phenyl imidothiazole
imidazo[2,1-b]thiazole, 2,3,5,6-tetrahydro-6-phenyl-
BSPBIO_000589
PRESTWICK3_000182
BPBIO1_000115
BSPBIO_000103
LOPAC0_001194
PRESTWICK2_000545
SPBIO_002510
PRESTWICK1_000545
PRESTWICK0_000545
BPBIO1_000649
PRESTWICK3_000545
NCGC00162225-01
NCGC00162363-01
AC-11604
NCGC00015620-04
tetramizole
tetramisole
AKOS000605651
ascaverm (tn)
5036-02-2
D08576
tetramisole [veterinary] (tn)
tetramisole (inn)
STL019093
6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole
6649-23-6
tetramisol [inn-spanish]
unii-c8m7rfe4no
dl-tetramisole
c8m7rfe4no ,
dl-tetramisol
tetramisol
imidazo(2,1-b)thiazole, 2,3,5,6-tetrahydro-6-phenyl-
ici 50627
einecs 229-667-8
tetramisolum [inn-latin]
6-phenyl-2,3,5,6-tetrahydroimidazo(2,1-b)thiazole
imidazo(2,1-b)thiazole, 2,3,5,6-tetrahydro-6-phenyl-, (+-)-
einecs 225-729-3
nsc 102063
tetramisole [inn:ban]
CCG-205268
chebi:77278 ,
nsc-102063
ascaverm
levamisole dl-form
CHEMBL277775
r-8299
NCGC00015620-03
FT-0605226
(-)-2,3,5,6-tetrahydro-6-phenylimidazo(2,1-b)thiazole
(+/-)-2,3,5,6-tetrahydro-6-phenylimidazo(2,1-b)thiazole
tetramisole [who-dd]
levamisole dl-form [mi]
tetramisole [inn]
AKOS022087568
AKOS022142451
SCHEMBL167819
2,3,5,6-tetrahydro-6-phenylimidazo-[2,1-b]-thiazole
(-)-2,3,5,6-tetrahydro-6-phenylimidazol[2,1-b]thiazole
(-)-2,3,5,6-tetrahydro-6-phenylimidazo[2,1-b]thiazole
6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole-, (s)-
tetramisole, tetramisole hydrochloride
smr001550472
MLS006011861
6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole
mfcd00792481
SBI-0051161.P002
FT-0709104
DTXSID20860143
Q27146858
l-tetramisole; lepuron; levamisol; levamisole
levamisol 100 microg/ml in acetonitrile
BRD-A46393198-003-10-9
SDCCGSBI-0051161.P003
NCGC00015620-14
6-phenyl-2,3,5,6-tetrahydro imidazo [2,1-b]thiazole
SB67394
SY107591

Research Excerpts

Treatment

All tetramisole-treated mice showed crouching behavior and were nervous and difficult to handle. All tetram isole treatments significantly reduced the number of B. difficile cases.

ExcerptReferenceRelevance
"All tetramisole-treated mice showed crouching behavior and were nervous and difficult to handle."( Neurobehavioral effects of tetramisole in mice.
Ahmed, K; Faris, GA; Mohammad, FK; Rhayma, MS, 2006
)
1.11
"All tetramisole treatments significantly reduced the number of B."( Stimulation of anti-Brucella vaccination in mice by tetramisole, a phenyl-imidothiazole salt.
Renoux, G; Renoux, M, 1973
)
0.98

Dosage Studied

The most successful treatment occurred in SPF (Specific Pathogen Free) rats dosed with tetramisole loaded into zeolite. No worms were present in this group at autopsy eight days post-infection.

ExcerptRelevanceReference
" The results suggest that, under field conditions, a strategic dosing programme using a modern anthelmintic can prevent liveweight loss in ewe hoggs wintered either on the hill or "inbye"."( Influence of anthelmintic treatment on the liveweight of outwintered ewe hoggs.
Mackay, RR, 1975
)
0.25
" The most successful treatment occurred in SPF (Specific Pathogen Free) rats dosed with tetramisole loaded into zeolite and no worms were present in this group at autopsy eight days post-infection."( Treatment of Nippostrongylus brasiliensis in normal and SPF rats using tetramisole loaded into zeolite.
Dyer, A; Shaker, SK; Storey, DM, 1992
)
0.74
"Hamsters infected with laboratory-adapted preadult Necator americanus were dosed with 6 reference anthelmintics."( Response of preadult Necator americanus to some known anthelmintics in hamsters.
Bose, S; Deb, BN; Dhage, KR; Rajasekariah, GR, 1986
)
0.27
" Nilverm given to cattle in high dosage orally did not lead to Prototheca suppressing values in milk sera."( [Udder compatibility of tetramisole and levamisole hydrochloride and suggestion for the prescription of their intramammary use in cattle against Prototheca zopfii].
Bergmann, A, 1993
)
0.59
" Two groups were dosed with single therapeutic doses of closantel and tetramisole and the third group was given a low-level medication with albendazole through feed pellets for 30 days."( Comparative anthelmintic activity of strategic sustained low-level administration of albendazole in feed pellets compared to single doses of closantel and tetramisole against natural ovine parasitic gastroenteritis.
Bhagwan, PS; Khan, FA; Sanyal, PK; Singh, D; Swarnkar, CP, 1999
)
0.74
"A facile, rapid and sensitive methods for the determination of tetramisole hydrochloride in pure and in dosage forms are described."( Facile colorimetric methods for the quantitative determination of tetramisole hydrochloride.
Amin, AS; Dessouki, HA, 2002
)
0.79
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
xenobioticA xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
environmental contaminantAny minor or unwanted substance introduced into the environment that can have undesired effects.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (1)

ClassDescription
imidazothiazole
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (4)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
thioredoxin reductaseRattus norvegicus (Norway rat)Potency0.25120.100020.879379.4328AID588453
euchromatic histone-lysine N-methyltransferase 2Homo sapiens (human)Potency4.46680.035520.977089.1251AID504332
chromobox protein homolog 1Homo sapiens (human)Potency28.18380.006026.168889.1251AID488953
ATP-dependent phosphofructokinaseTrypanosoma brucei brucei TREU927Potency9.52830.060110.745337.9330AID485368
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (21)

Assay IDTitleYearJournalArticle
AID1347050Natriuretic polypeptide receptor (hNpr2) antagonism - Pilot subtype selectivity assay2019Science translational medicine, 07-10, Volume: 11, Issue:500
Inhibition of natriuretic peptide receptor 1 reduces itch in mice.
AID1347083qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347086qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347151Optimization of GU AMC qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID504836Inducers of the Endoplasmic Reticulum Stress Response (ERSR) in human glioma: Validation2002The Journal of biological chemistry, Apr-19, Volume: 277, Issue:16
Sustained ER Ca2+ depletion suppresses protein synthesis and induces activation-enhanced cell death in mast cells.
AID1347045Natriuretic polypeptide receptor (hNpr1) antagonism - Pilot counterscreen GloSensor control cell line2019Science translational medicine, 07-10, Volume: 11, Issue:500
Inhibition of natriuretic peptide receptor 1 reduces itch in mice.
AID1347058CD47-SIRPalpha protein protein interaction - HTRF assay qHTS validation2019PloS one, , Volume: 14, Issue:7
Quantitative high-throughput screening assays for the discovery and development of SIRPα-CD47 interaction inhibitors.
AID1347405qHTS to identify inhibitors of the type 1 interferon - major histocompatibility complex class I in skeletal muscle: primary screen against the NCATS LOPAC collection2020ACS chemical biology, 07-17, Volume: 15, Issue:7
High-Throughput Screening to Identify Inhibitors of the Type I Interferon-Major Histocompatibility Complex Class I Pathway in Skeletal Muscle.
AID1347059CD47-SIRPalpha protein protein interaction - Alpha assay qHTS validation2019PloS one, , Volume: 14, Issue:7
Quantitative high-throughput screening assays for the discovery and development of SIRPα-CD47 interaction inhibitors.
AID1347410qHTS for inhibitors of adenylyl cyclases using a fission yeast platform: a pilot screen against the NCATS LOPAC library2019Cellular signalling, 08, Volume: 60A fission yeast platform for heterologous expression of mammalian adenylyl cyclases and high throughput screening.
AID588378qHTS for Inhibitors of ATXN expression: Validation
AID1347057CD47-SIRPalpha protein protein interaction - LANCE assay qHTS validation2019PloS one, , Volume: 14, Issue:7
Quantitative high-throughput screening assays for the discovery and development of SIRPα-CD47 interaction inhibitors.
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID588349qHTS for Inhibitors of ATXN expression: Validation of Cytotoxic Assay
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID1347082qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347049Natriuretic polypeptide receptor (hNpr1) antagonism - Pilot screen2019Science translational medicine, 07-10, Volume: 11, Issue:500
Inhibition of natriuretic peptide receptor 1 reduces itch in mice.
AID588519A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities2011Antiviral research, Sep, Volume: 91, Issue:3
High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors.
AID540299A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis2010Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (257)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990160 (62.26)18.7374
1990's37 (14.40)18.2507
2000's18 (7.00)29.6817
2010's32 (12.45)24.3611
2020's10 (3.89)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 47.26

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index47.26 (24.57)
Research Supply Index5.63 (2.92)
Research Growth Index4.52 (4.65)
Search Engine Demand Index74.48 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (47.26)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials7 (2.57%)5.53%
Reviews9 (3.31%)6.00%
Case Studies4 (1.47%)4.05%
Observational0 (0.00%)0.25%
Other252 (92.65%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]