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Details

Stereochemistry ABSOLUTE
Molecular Formula C15H19N3OS
Molecular Weight 289.396
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BUTAMISOLE

SMILES

CC(C)C(=O)NC1=CC=CC(=C1)[C@H]2CN3CCSC3=N2

InChI

InChIKey=YWDWYOALXURQPZ-CYBMUJFWSA-N
InChI=1S/C15H19N3OS/c1-10(2)14(19)16-12-5-3-4-11(8-12)13-9-18-6-7-20-15(18)17-13/h3-5,8,10,13H,6-7,9H2,1-2H3,(H,16,19)/t13-/m1/s1

HIDE SMILES / InChI

Description
Curator's Comment: Description was created based on several sources, including https://books.google.ru/books?id=nq6Zeo5vng8C&pg=PA5144&lpg=PA5144&dq=BUTAMISOLE retrieved from Molecular Biochemistry and Physiology of Helminth Neuromuscular Systems edited by David Halton, p.5144

Butamisole is an injectable imidazothiazoles anthelmintic. In dogs it is used for the treatment of infections with whipworms (Trichuris vulpis ), and the hookworm (Ancylostoma caninum ). Nicotinic acetylcholine receptor agonist. Acts as agonist at nicotinic Ach receptor of nematode à ganglionic stimulation causes sustained muscle contraction initially followed by depolarising neuro muscular blockade which in turn leads to spastic paralysis.

Approval Year

PubMed

PubMed

TitleDatePubMed
The efficacy and safety of injectable butamisole in dogs.
1979 Apr
Critical test evaluation of butamisole against gastrointestinal parasites of horses and ponies.
1979 Jan
Anthelmintic actions on homomer-forming nicotinic acetylcholine receptor subunits: chicken alpha7 and ACR-16 from the nematode Caenorhabditis elegans.
2000
Patents

Sample Use Guides

Dogs: Administer 0.1 mg per pound of body weight by subcutaneous injection. In problem cases, retreatment for whipworms may be necessary in approximately 3 months. For hookworms, a second injection should be given 21 days after the initial treatment.
Route of Administration: Other
Butamisole was without agonist actions on either alpha7 or ACR-16 chicken nicotinic receptors in the range 10nM-1mM. However, butamisole (pIC(50)=4.9 for both alpha7 and ACR-16) antagonized responses of both alpha7 and ACR-16 receptors to acetylcholine. Application of butamisole in the concentration range 0.1 um-100 um for 30 s prior to application of 1 mM ACh in the continued presence of butamisole resulted in a dose-dependent reduction in the ACh current amplitude recorded from both receptors.
Name Type Language
BUTAMISOLE
INN   MI  
INN  
Official Name English
PROPANAMIDE, 2-METHYL-N-(3-(2,3,5,6-TETRAHYDROIMIDAZO(2,1-B)THIAZOL-6-YL)PHENYL)-, (-)-
Systematic Name English
(-)-2-METHYL-3'-(2,3,5,6-TETRAHYDROIMIDAZO(2,1-B)THIAZOL-6-YL)PROPIONANILIDE
Systematic Name English
butamisole [INN]
Common Name English
BUTAMISOLE [MI]
Common Name English
PROPANAMIDE, 2-METHYL-N-(3-((6S)-2,3,5,6-TETRAHYDROIMIDAZO(2,1-B)THIAZOL-6-YL)PHENYL)-
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C250
Created by admin on Sat Dec 16 17:44:59 GMT 2023 , Edited by admin on Sat Dec 16 17:44:59 GMT 2023
Code System Code Type Description
PUBCHEM
76964745
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PRIMARY
MERCK INDEX
m1048
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PRIMARY Merck Index
EVMPD
SUB06001MIG
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PRIMARY
NCI_THESAURUS
C79921
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MESH
C020238
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EPA CompTox
DTXSID8057770
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ChEMBL
CHEMBL2110807
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SMS_ID
100000088494
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INN
3918
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CAS
54400-59-8
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FDA UNII
XVB7982801
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