tetramisole

Product Nametetramisole
CAS5036-02-2
MFC11H12N2S
MW204.29
EINECS225-729-3
MOL File5036-02-2.mol

Chemical Properties

Melting point	87-89°
Boiling point	344.4±45.0 °C(Predicted)
Density	1.32±0.1 g/cm3(Predicted)
storage temp.	2-8°C
solubility	DMSO; Methanol
form	Solid
pka	10.00±0.40(Predicted)
color	White (powder)
InChI	InChI=1S/C11H12N2S/c1-2-4-9(5-3-1)10-8-13-6-7-14-11(13)12-10/h1-5,10H,6-8H2
InChIKey	HLFSDGLLUJUHTE-UHFFFAOYSA-N
SMILES	S1CCN2CC(C3=CC=CC=C3)N=C12
EPA Substance Registry System	Tetramisole (5036-02-2)

Safety Information

TSCA	TSCA listed

Usage And Synthesis

Uses

Tetramisol is an isolated intermediate in the synthesis of 4-Hydroxy-tetramisole (H595270), a metabolite of Tetramisole, an anthelmintic.

Definition

ChEBI: 6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole is 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. It has a role as a xenobiotic and an environmental contaminant.

in vivo

Tetramisole (0.54 mg/kg; intravenous injection; single dose; 3 minutes pretreatment) significantly reduces the number and duration of ventricular arrhythmias and the incidence of ventricular fibrillation in the Sprague-Dawley rat model of myocardial infarction induced by coronary artery ligation, and this effect is reversed by the I_K1 channel blocker chloroquine (CQ)^[2].
Tetramisole (0.54 mg/kg; intraperitoneal injection; once a day; 10 days) improves cardiac contractile function, reduces cardiomyocyte hypertrophy and interstitial fibrosis, and inhibits the activation of the PKA signaling pathway in the Sprague-Dawley rat model of isoproterenol (Iso)-induced cardiac remodeling, and the effect is dependent on the I_K1 channel activity^[2].

Animal Model:	Male Sprague-Dawley rats (2 months old, weight not specified) + coronary ligation-induced acute myocardial infarction model^[2]
Dosage:	0.18, 0.54, 1.8 mg/kg (dissolved in saline)
Administration:	Intravenous injection 3 minutes before coronary artery occlusion; single dose
Result:	Significantly reduced premature ventricular contractions (PVC) from 134 to 16 episodes, shortened ventricular tachycardia (VT) duration from 59.4 s to 8.1 s, and eliminated ventricular fibrillation (VF) (duration 0 s, incidence 0%), compared to control. These anti-arrhythmic effects were largely reversed by co-administration of chloroquine (7.5 μg/kg), an I_K1 antagonist. Pretreatment for 10 days (0.54 mg/kg/day) also reduced VT duration (42.7 s to 6.5 s) and abolished VF, associated with upregulated Kir2.1 protein expression in ventricular tissue.

Animal Model:	Male Sprague-Dawley rats (2 months old, weight not specified) + isoproterenol (3 mg/kg/day, i.p., 10 days)-induced cardiac remodeling model^[2]
Dosage:	0.54 mg/kg/day (dissolved in saline)
Administration:	Intraperitoneal injection once daily for 10 days
Result:	Prevented Iso-induced increases in interventricular septum thickness and left ventricular wall thickness, normalized left ventricular ejection fraction (EF) and fractional shortening (FS), and reduced myocardial cell cross-sectional area by 22% compared to Iso group. Masson's trichrome staining showed a 35% reduction in interstitial fibrosis, accompanied by downregulated phosphorylated PKA (p-PKA) and upregulated Kir2.1/SAP97 signaling. Co-administration of chloroquine abolished these protective effects, confirming dependence on I_K1 channel activation.

tetramisole

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