BUTAMISOLE HYDROCHLORIDE

Possibly Marketed Outside US

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C15H19N3OS.ClH
Molecular Weight	325.857
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=FXYKKPLSQTYWRY-BTQNPOSSSA-N

InChI=1S/C15H19N3OS.ClH/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);1H/t13-;/m1./s1

HIDE SMILES / InChI

Molecular Formula	C15H19N3OS
Molecular Weight	289.396
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:37:20 GMT 2023` Edited by `admin` on `Fri Dec 15 17:37:20 GMT 2023`
Record UNII	QGM18599H5
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BUTAMISOLE HYDROCHLORIDE

Official Name

English

(-)-2-METHYL-3'-(2,3,5,6-TETRAHYDROIMIDAZO(2,1-B)THIAZOL-6-YL)PROPIONANILIDE MONOHYDROCHLORIDE

Systematic Name

English

BUTAMISOLE HYDROCHLORIDE [MI]

Common Name

English

BUTAMISOLE HYDROCHLORIDE [USAN]

Common Name

English

PROPANAMIDE, 2-METHYL-N-(3-((6S)-2,3,5,6-TETRAHYDROIMIDAZO(2,1-B)THIAZOL-6-YL)PHENYL)-, HYDROCHLORIDE

Systematic Name

English

BUTAMISOLE HYDROCHLORIDE [GREEN BOOK]

Common Name

English

CL 206,214

Code

English

CL-206214

Code

English

PROPANAMIDE, 2-METHYL-N-(3-(2,3,5,6-TETRAHYDROIMIDAZO(2,1-B)THIAZOL-6-YL)PHENYL)-, MONOHYDROCHLORIDE, (-)-

Common Name

English

BUTAMISOLE HCL

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 522.234