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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 of BUTAMISOLE HYDROCHLORIDE

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 ClH
Molecular Weight 36.461
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C15H19N3OS
Molecular Weight 289.396
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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 TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Butamisole

PubMed

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
Record UNII
QGM18599H5
Record Status Validated (UNII)
Record Version