Closantel

Names

[ Name ]:
Closantel

[Synonym ]:
MFCD00661151
Closantel
N-{5-Chloro-4-[(4-chlorophenyl)(cyano)methyl]-2-methylphenyl}-2-hydroxy-3,5-diiodobenzamide
rac-N-[5-chloro-4-[(R)-(4-chlorophenyl)cyanomethyl]-2-methylphenyl]-2-hydroxy-3,5-diiodobenzamide
N-[5-Chloro-4-[(4-chlorophenyl)cyanomethyl]-2-methylphenyl]-2-hydroxy-3,5-diiodobenzamide
(RS)-5’-chloro-4’-(4-chloro-α-cyanobenzyl)-3,5-diiodosalicyl-o-toluidide
N-{5-Chlor-4-[(4-chlorphenyl)(cyan)methyl]-2-methylphenyl}-2-hydroxy-3,5-diiodbenzolcarboxamid
N-(5-Chloro-4-((4-chlorophenyl)(cyano)methyl)-2-methylphenyl)-2-hydroxy-3,5-diiodobenzamide
Benzamide, N-[5-chloro-4-[(4-chlorophenyl)cyanomethyl]-2-methylphenyl]-2-hydroxy-3,5-diiodo-
UNII:EUL532EI54
EINECS 260-967-1

Biological Activity

[Description]:

Closantel is a salicylanilide anthelmintic compound; exhibits different anthelmintic spectra and apparent toxicity in mammals.

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Parasite

Research Areas >> Infection

[References]

[1]. Bacon JA, et al. Comparative in vitro effects of closantel and selected beta-ketoamide anthelmintics on a gastrointestinal nematode and vertebrate liver cells. J Vet Pharmacol Ther. 1998 Jun;21(3):190-8.

[2]. Macielag MJ, et al. Substituted salicylanilides as inhibitors of two-component regulatory systems in bacteria. J Med Chem. 1998 Jul 30;41(16):2939-45.

[3]. Waruiru RM. Efficacy of closantel, albendazole and levamisole on an ivermectin resistant strain of Haemonchus contortus in sheep. Vet Parasitol. 1997 Dec 15;73(1-2):65-71.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.9±0.1 g/cm3

[ Boiling Point ]:
590.5±50.0 °C at 760 mmHg

[ Melting Point ]:
210 - 22ºC

[ Molecular Formula ]:
C₂₂H₁₄Cl₂I₂N₂O₂

[ Molecular Weight ]:
663.074

[ Flash Point ]:
310.9±30.1 °C

[ Exact Mass ]:
661.852173

[ PSA ]:
73.12000

[ LogP ]:
9.08

[ Vapour Pressure ]:
0.0±1.7 mmHg at 25°C

[ Index of Refraction ]:
1.736

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: CV2444250

CHEMICAL NAME :: Benzamide, N-(5-chloro-4-((4-chlorophenyl)cyanomethyl)-2-methylp henyl)-2-hydroxy-3,5- diiodo-

CAS REGISTRY NUMBER :: 57808-65-8

LAST UPDATED :: 199412

DATA ITEMS CITED :: 9

MOLECULAR FORMULA :: C22-H14-Cl2-I2-N2-O2

MOLECULAR WEIGHT :: 663.08

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 :: 262 mg/kg

TOXIC EFFECTS :: Behavioral - ataxia Lungs, Thorax, or Respiration - dyspnea Gastrointestinal - hypermotility, diarrhea

REFERENCE :: DCTODJ Drug and Chemical Toxicology. (Marcel Dekker, 270 Madison Ave., New York, NY 10016) V.1- 1977/78- Volume(issue)/page/year: 8,101,1985

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

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 28400 ug/kg

TOXIC EFFECTS :: Behavioral - ataxia Lungs, Thorax, or Respiration - dyspnea Gastrointestinal - hypermotility, diarrhea

REFERENCE :: DCTODJ Drug and Chemical Toxicology. (Marcel Dekker, 270 Madison Ave., New York, NY 10016) V.1- 1977/78- Volume(issue)/page/year: 8,101,1985

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 331 mg/kg

TOXIC EFFECTS :: Behavioral - ataxia Lungs, Thorax, or Respiration - dyspnea Gastrointestinal - hypermotility, diarrhea

REFERENCE :: DCTODJ Drug and Chemical Toxicology. (Marcel Dekker, 270 Madison Ave., New York, NY 10016) V.1- 1977/78- Volume(issue)/page/year: 8,101,1985

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

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 56800 ug/kg

TOXIC EFFECTS :: Behavioral - ataxia Lungs, Thorax, or Respiration - dyspnea Gastrointestinal - hypermotility, diarrhea

REFERENCE :: DCTODJ Drug and Chemical Toxicology. (Marcel Dekker, 270 Madison Ave., New York, NY 10016) V.1- 1977/78- Volume(issue)/page/year: 8,101,1985

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - domestic

DOSE/DURATION :: 70 mg/kg

TOXIC EFFECTS :: Peripheral Nerve and Sensation - spastic paralysis with or without sensory change Sense Organs and Special Senses (Eye) - visual field changes Behavioral - muscle weakness

REFERENCE :: DCTODJ Drug and Chemical Toxicology. (Marcel Dekker, 270 Madison Ave., New York, NY 10016) V.1- 1977/78- Volume(issue)/page/year: 8,101,1985

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Mammal - domestic

DOSE/DURATION :: 40 mg/kg

TOXIC EFFECTS :: Peripheral Nerve and Sensation - spastic paralysis with or without sensory change Sense Organs and Special Senses (Eye) - visual field changes Behavioral - muscle weakness

REFERENCE :: DCTODJ Drug and Chemical Toxicology. (Marcel Dekker, 270 Madison Ave., New York, NY 10016) V.1- 1977/78- Volume(issue)/page/year: 8,101,1985

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Mammal - cattle

DOSE/DURATION :: 35 mg/kg

TOXIC EFFECTS :: Peripheral Nerve and Sensation - spastic paralysis with or without sensory change Sense Organs and Special Senses (Eye) - visual field changes Behavioral - muscle weakness

REFERENCE :: DCTODJ Drug and Chemical Toxicology. (Marcel Dekker, 270 Madison Ave., New York, NY 10016) V.1- 1977/78- Volume(issue)/page/year: 8,101,1985 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 3640 mg/kg/91D-C

TOXIC EFFECTS :: Related to Chronic Data - changes in testicular weight

REFERENCE :: DCTODJ Drug and Chemical Toxicology. (Marcel Dekker, 270 Madison Ave., New York, NY 10016) V.1- 1977/78- Volume(issue)/page/year: 8,101,1985 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 3600 mg/kg

SEX/DURATION :: male 90 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - testes, epididymis, sperm duct

REFERENCE :: DCTODJ Drug and Chemical Toxicology. (Marcel Dekker, 270 Madison Ave., New York, NY 10016) V.1- 1977/78- Volume(issue)/page/year: 8,101,1985

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H301-H413

[ Precautionary Statements ]:
P301 + P310

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

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
R22

[ RIDADR ]:
2811

[ RTECS ]:
CV2444250

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

The efficacy of trichlorphon and naphthalophos against multiple anthelmintic-resistant nematodes of naturally infected sheep in Argentina.

Parasitol. Res. 109 Suppl 1 , S139-48, (2011)

An anthelmintic efficacy trial was conducted in sheep harbouring anthelmintic-resistant worms in Argentina. Seventy lambs were selected from a flock that had been grazed on pastures infected with tric...

Emergency slaughter of casualty cattle increases the prevalence of anthelmintic drug residues in muscle.

Food Addit. Contam. Part A. Chem. Anal. Control. Expo. Risk Assess. 29(8) , 1263-71, (2012)

The ProSafeBeef project studied the prevalence of residues of anthelmintic drugs used to control parasitic worms and fluke in beef cattle in Ireland. Injured (casualty) cattle may enter the human food...

An improved thyroid hormone reporter assay to determine the thyroid hormone-like activity of amiodarone, bithionol, closantel and rafoxanide.

Toxicol. Lett. 208(1) , 30-5, (2012)

A number of environmental chemicals have been reported to exhibit thyroid hormone-like activity. Since thyroid hormones play a crucial role in development, it is important to identify chemicals in the...