Cloperastine hydrochloride

Names

[ Name ]:
Cloperastine hydrochloride

[Synonym ]:
1-(2-((p-chloro-a-phenylbenzyl)oxy)ethyl)piperidine hydrochloride
MFCD00079012
1-[2-[(4-Chlorophenyl)(phenyl)methoxy]ethyl]piperidine Hydrochloride
Piperidine, 1-(2-((4-chlorophenyl)phenylmethoxy)ethyl)-, hydrochloride (9CI)
Piperidine, 1-[2-[(4-chlorophenyl)phenylmethoxy]ethyl]-, hydrochloride (1:1)
Cloperastine hydrochloride
4-Chlorobenzhydryl 2-(1-Piperidyl)ethyl Ether Hydrochloride
1-{2-[(4-Chlorophenyl)(phenyl)methoxy]ethyl}piperidine hydrochloride (1:1)
1-[2-[(4-chlorophenyl)-phenylmethoxy]ethyl]piperidine,hydrochloride
EINECS 239-067-8

Biological Activity

[Description]:

Cloperastine hydrochloride inhibits the hERG K+ currents in a concentration-dependent manner with an IC50 value of 27 nM[1].

[Related Catalog]:

Research Areas >> Inflammation/Immunology

Signaling Pathways >> Membrane Transporter/Ion Channel >> Potassium Channel

[Target]

27 nM (K+ currents)[1]

[In Vitro]

Cloperastine inhibits the hERG K+ currents in a concentrationdependent manner with an IC50 value of 27 nM[1]. Among the antitussive agents, Cloperastine, which possesses antitussive and antiedemic activity, also relaxes the bronchial musculature. Cloperastine is a drug with a central antitussive effect, and is also endowed with an antihistaminic and papaverine-like activity similar to codeine but without its narcotic effects[2].

[In Vivo]

In the anesthetized guinea pigs, Cloperastine at a therapeutic dose of 1 mg/kg prolonged the QT interval and monophasicaction potential (MAP) duration without affecting PR interval or QRS width[1]. Cloperastine hydrochloride shows relatively low acute toxicity when administered by the intraperitoneal route in rats and mice, and shows minor toxicity by the oral route when administered as Cloperastine fendizoate, the LD50 in rats and mice for the two administration routes exceeds 1000 and 2000 mg/kg, respectively[2].

[References]

[1]. Takahara A, et al. Effects of the antitussive drug cloperastine on ventricular repolarization in halothane-anesthetized guinea pigs. J Pharmacol Sci. 2012;120(3):165-75.

[2]. Catania MA, et al. Pharmacological and clinical overview of cloperastine in treatment of cough. Ther Clin Risk Manag. 2011;7:83-92.

Chemical & Physical Properties

[ Boiling Point ]:
84°C 35mm

[ Molecular Formula ]:
C₂₀H₂₅Cl₂NO

[ Molecular Weight ]:
366.325

[ Flash Point ]:
210.2ºC

[ Exact Mass ]:
365.131317

[ PSA ]:
12.47000

[ LogP ]:
5.67180

[ Vapour Pressure ]:
2.15E-07mmHg at 25°C

[ Index of Refraction ]:
1.414

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: TM6491500

CHEMICAL NAME :: Piperidine, 1-(2-((p-chloro-alpha-phenylbenzyl)oxy)ethyl)-, hydrochloride

CAS REGISTRY NUMBER :: 14984-68-0

LAST UPDATED :: 199706

DATA ITEMS CITED :: 5

MOLECULAR FORMULA :: C20-H24-Cl-N-O.Cl-H

MOLECULAR WEIGHT :: 366.36

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1986 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: BCFAAI Bollettino Chimico Farmaceutico. (Societa Editoriale Farmaceutica, Via Ausonio 12, 20123 Milan, Italy) V.33- 1894- Volume(issue)/page/year: 122,384,1983

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 150 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: BCFAAI Bollettino Chimico Farmaceutico. (Societa Editoriale Farmaceutica, Via Ausonio 12, 20123 Milan, Italy) V.33- 1894- Volume(issue)/page/year: 122,384,1983

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 553 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: BCFAAI Bollettino Chimico Farmaceutico. (Societa Editoriale Farmaceutica, Via Ausonio 12, 20123 Milan, Italy) V.33- 1894- Volume(issue)/page/year: 122,384,1983

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 140 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: BCFAAI Bollettino Chimico Farmaceutico. (Societa Editoriale Farmaceutica, Via Ausonio 12, 20123 Milan, Italy) V.33- 1894- Volume(issue)/page/year: 122,384,1983

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1300 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: YKKZAJ Yakugaku Zasshi. Journal of Pharmacy. (Nippon Yakugakkai, 2-12-15 Shibuya, Shibuya-ku, Tokyo 150, Japan) No.1- 1881- Volume(issue)/page/year: 80,1759,1960

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xn:Harmful;

[ Risk Phrases ]:
R22

[ Safety Phrases ]:
S36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
TM6491500

[ HS Code ]:
2933399090

Customs

[ HS Code ]: 2933399090

[ Summary ]:
2933399090. other compounds containing an unfused pyridine ring (whether or not hydrogenated) in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

[Novel antidepressant-like action of drugs possessing GIRK channel blocking action in rats].

Yakugaku Zasshi 130(5) , 699-705, (2010)

We have previously found that antitussive drugs inhibit G protein-coupled inwardly rectifying potassium (GIRK) channel currents in brain neurons. Potassium efflux through GIRK channels causes membrane...

Effects of the antitussive drug cloperastine on ventricular repolarization in halothane-anesthetized guinea pigs.

J. Pharmacol. Sci. 120(3) , 165-75, (2012)

Cloperastine is an antitussive drug, which can be received as an over-the-counter cold medicine. The chemical structure of cloperastine is quite similar to that of the antihistamine drug diphenhydrami...

Levocloperastine in the treatment of chronic nonproductive cough: comparative efficacy versus standard antitussive agents.

Drugs Exp. Clin. Res. 30(4) , 133-41, (2004)

The medical and social impact of cough is substantial. Current antitussive agents at effective doses have adverse events such as drowsiness, nausea and constipation that limit their use. There is also...