BUTAMISOLE

Possibly Marketed Outside US

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 Search

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
Sources: https://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfcfr/CFRSearch.cfm?fr=522.234 | http://www.elearnvet.net/moodle/mod/resource/view.php?id=35233
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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Nicotinic acetylcholine receptor alpha subunit 5 Target ID: CHEMBL1884 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21189677 \| http://drjaggyvpt.blogspot.ru/2015/04/mode-of-action-of-anthelmintics.html \| https://www.ncbi.nlm.nih.gov/pubmed/11113327 \| http://www.elearnvet.net/moodle/mod/resource/view.php?id=35233 \| https://books.google.ru/books?id=nq6Zeo5vng8C&pg=PA5144&lpg=PA5144&dq=BUTAMISOLE	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Helminthiasis 39 Sources: https://www.ncbi.nlm.nih.gov/pubmed/256371 https://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfcfr/CFRSearch.cfm?fr=522.234	Curative		Approved 8429	Butamisole Approved Use Indications for use. For the treatment of infections with whipworms (Trichuris vulpis), and the hookworm (Ancylostoma caninum).

PubMed

Title	Date	PubMed
The efficacy and safety of injectable butamisole in dogs.	1979 Apr	256371
Critical test evaluation of butamisole against gastrointestinal parasites of horses and ponies.	1979 Jan	453676
Anthelmintic actions on homomer-forming nicotinic acetylcholine receptor subunits: chicken alpha7 and ACR-16 from the nematode Caenorhabditis elegans.	2000	11113327

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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

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