CLORSULON

Details

Stereochemistry	ACHIRAL
Molecular Formula	C8H8Cl3N3O4S2
Molecular Weight	380.656
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC1=C(C=C(C(=C1)C(Cl)=C(Cl)Cl)S(N)(=O)=O)S(N)(=O)=O

InChI

InChIKey=QOVTVIYTBRHADL-UHFFFAOYSA-N

InChI=1S/C8H8Cl3N3O4S2/c9-7(8(10)11)3-1-4(12)6(20(14,17)18)2-5(3)19(13,15)16/h1-2H,12H2,(H2,13,15,16)(H2,14,17,18)

HIDE SMILES / InChI

Molecular Formula	C8H8Cl3N3O4S2
Molecular Weight	380.656
Charge	0
Count

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

Description
Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Maximum_Residue_Limits_-_Report/2009/11/WC500012623.pdf

Clorsulon is a compound belonging to the benzenesulphonamide family. It is used in veterinary medicine for the treatment of liver fluke (monotherapy), gasrtointestinal and lung worms, lice, grubs and mites (in combination with ivermectin) in cattles. Clorsulon inhibits the enzymes involved in the glycolytic pathways of the common liver fluke (Fasciola hepatica or Fasciola gigantica), namely phosphoglycerate kinase and phosphoglyceromutase.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Fasciola phosphoglycerate kinase 1 Target ID: Fasciola phosphoglycerate kinase Sources: https://www.ncbi.nlm.nih.gov/pubmed/7088033	Inhibitor 8297		0.29 mM [Ki]
Fasciola phosphoglyceromutase 1 Target ID: Fasciola phosphoglyceromutase Sources: https://www.ncbi.nlm.nih.gov/pubmed/7088033	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Liver fluke infection 1 Sources: https://www.drugs.com/pro/curatrem.html	Curative	Approved 8429	CURATREM Approved Use For the treatment of immature and adult liver fluke (Fasciola hepatica) infestations in cattle. Launch Date 9.8997122E11
Gastrointestinal roundworms infection 2 Sources: https://www.drugs.com/vet/ivomec-plus-injection-for-cattle.html	Curative	Approved 8429	IVOMEC Approved Use It is used for the treatment and control of gastrointestinal nematodes (adults and fourth-stage larvae) (Haemonchus placei, Ostertagia ostertagi (including inhibited larvae), O. lyrata, Trichostrongylus axei, T. colubriformis, Cooperia oncophora, C. punctate, C. pectinate, Oesophagostomum radiatum, Nematodirus helvetianus (adults only), N. spathiger (adults only), Bunostomum phlebotomum; lungworms (adults and fourth-stage larvae) (Dictyocaulus viviparous); liver flukes (adults only) (Fasciola hepatica); grubs (parasitic stages) (Hypoderma bovis, H. lineatum); lice (Linognathus vituli, Haematopinus eurysternus, Solenopotes capillatus); mites (Psoroptes ovis (syn. P. communis var. bovis), Sarcoptes scabiei var. bovis). It is also used to control infections of D. viviparous and O. radiatum for 28 days after treatment and O. ostertagi, T. axei and C. punctate for 21 days after treatment, and H. placei and C. oncophora, for 14 days after treatment. Launch Date 6.0644157E11
Lungworms infection 1 Sources: https://www.drugs.com/vet/ivomec-plus-injection-for-cattle.html	Curative	Approved 8429	IVOMEC Approved Use It is used for the treatment and control of gastrointestinal nematodes (adults and fourth-stage larvae) (Haemonchus placei, Ostertagia ostertagi (including inhibited larvae), O. lyrata, Trichostrongylus axei, T. colubriformis, Cooperia oncophora, C. punctate, C. pectinate, Oesophagostomum radiatum, Nematodirus helvetianus (adults only), N. spathiger (adults only), Bunostomum phlebotomum; lungworms (adults and fourth-stage larvae) (Dictyocaulus viviparous); liver flukes (adults only) (Fasciola hepatica); grubs (parasitic stages) (Hypoderma bovis, H. lineatum); lice (Linognathus vituli, Haematopinus eurysternus, Solenopotes capillatus); mites (Psoroptes ovis (syn. P. communis var. bovis), Sarcoptes scabiei var. bovis). It is also used to control infections of D. viviparous and O. radiatum for 28 days after treatment and O. ostertagi, T. axei and C. punctate for 21 days after treatment, and H. placei and C. oncophora, for 14 days after treatment. Launch Date 6.0644157E11
Grubs 1 Sources: https://www.drugs.com/vet/ivomec-plus-injection-for-cattle.html	Curative	Approved 8429	IVOMEC Approved Use It is used for the treatment and control of gastrointestinal nematodes (adults and fourth-stage larvae) (Haemonchus placei, Ostertagia ostertagi (including inhibited larvae), O. lyrata, Trichostrongylus axei, T. colubriformis, Cooperia oncophora, C. punctate, C. pectinate, Oesophagostomum radiatum, Nematodirus helvetianus (adults only), N. spathiger (adults only), Bunostomum phlebotomum; lungworms (adults and fourth-stage larvae) (Dictyocaulus viviparous); liver flukes (adults only) (Fasciola hepatica); grubs (parasitic stages) (Hypoderma bovis, H. lineatum); lice (Linognathus vituli, Haematopinus eurysternus, Solenopotes capillatus); mites (Psoroptes ovis (syn. P. communis var. bovis), Sarcoptes scabiei var. bovis). It is also used to control infections of D. viviparous and O. radiatum for 28 days after treatment and O. ostertagi, T. axei and C. punctate for 21 days after treatment, and H. placei and C. oncophora, for 14 days after treatment. Launch Date 6.0644157E11
Sucking lice 1 Sources: https://www.drugs.com/vet/ivomec-plus-injection-for-cattle.html	Curative	Approved 8429	IVOMEC Approved Use It is used for the treatment and control of gastrointestinal nematodes (adults and fourth-stage larvae) (Haemonchus placei, Ostertagia ostertagi (including inhibited larvae), O. lyrata, Trichostrongylus axei, T. colubriformis, Cooperia oncophora, C. punctate, C. pectinate, Oesophagostomum radiatum, Nematodirus helvetianus (adults only), N. spathiger (adults only), Bunostomum phlebotomum; lungworms (adults and fourth-stage larvae) (Dictyocaulus viviparous); liver flukes (adults only) (Fasciola hepatica); grubs (parasitic stages) (Hypoderma bovis, H. lineatum); lice (Linognathus vituli, Haematopinus eurysternus, Solenopotes capillatus); mites (Psoroptes ovis (syn. P. communis var. bovis), Sarcoptes scabiei var. bovis). It is also used to control infections of D. viviparous and O. radiatum for 28 days after treatment and O. ostertagi, T. axei and C. punctate for 21 days after treatment, and H. placei and C. oncophora, for 14 days after treatment. Launch Date 6.0644157E11
Mange mites 1 Sources: https://www.drugs.com/vet/ivomec-plus-injection-for-cattle.html	Curative	Approved 8429	IVOMEC Approved Use It is used for the treatment and control of gastrointestinal nematodes (adults and fourth-stage larvae) (Haemonchus placei, Ostertagia ostertagi (including inhibited larvae), O. lyrata, Trichostrongylus axei, T. colubriformis, Cooperia oncophora, C. punctate, C. pectinate, Oesophagostomum radiatum, Nematodirus helvetianus (adults only), N. spathiger (adults only), Bunostomum phlebotomum; lungworms (adults and fourth-stage larvae) (Dictyocaulus viviparous); liver flukes (adults only) (Fasciola hepatica); grubs (parasitic stages) (Hypoderma bovis, H. lineatum); lice (Linognathus vituli, Haematopinus eurysternus, Solenopotes capillatus); mites (Psoroptes ovis (syn. P. communis var. bovis), Sarcoptes scabiei var. bovis). It is also used to control infections of D. viviparous and O. radiatum for 28 days after treatment and O. ostertagi, T. axei and C. punctate for 21 days after treatment, and H. placei and C. oncophora, for 14 days after treatment. Launch Date 6.0644157E11

PubMed

Title	Date	PubMed
The effect of ivomec super on dogs experimentally infested with Sarcoptes scabiei isolated from a patient.	2001 Apr	12557931
Ivermectin and clorsulon (ivomec super) in treatment of goats naturally infested with scab mites and biting lice.	2001 Aug	11478437
Efficacy of combined chemotherapy against gastrointestinal nematodes and Fasciola hepatica in cattle.	2001 Aug 20	11502367
Activity of oxyclozanide, nitroxynil, clorsulon and albendazole against adult triclabendazole-resistant Fasciola hepatica.	2001 Jun 9	11430684
Effects of parenteral administration of doramectin or a combination of ivermectin and clorsulon on control of gastrointestinal nematode and liver fluke infections and on growth performance in cattle.	2001 May 1	11345312
Effect of gastrointestinal nematode and liver fluke infections on weight gain and reproductive performance of beef heifers.	2002 Aug 2	12127252
Fasciola hepatica: effects of the fasciolicide clorsulon in vitro and in vivo on the tegumental surface, and a comparison of the effects on young- and old-mature flukes.	2003 Oct	12937959
Field trial on the efficacy of an experimental fasciolicide compared with some commercial compounds in naturally infected cattle.	2003 Sep	12844256
Transmission electron microscope study of the ultrastructural changes induced in the tegument and gut of Fasciola hepatica following in vivo drug treatment with clorsulon.	2004 Feb	14714178
Ultrastructural observations on oral ingestion and trans-tegumental uptake of clorsulon by the liver fluke, Fasciola hepatica.	2005 Feb	15645289
A scanning electron microscope study on the route of entry of clorsulon into the liver fluke, Fasciola hepatica.	2005 Jan	15592937
Field trial on comparative efficacy of four fasciolicides against natural liver fluke infection in cattle.	2006 Feb 18	16289862
Fasciola hepatica: morphological effects of a combination of triclabendazole and clorsulon against mature fluke.	2006 Oct	16896655
The efficacy of antihelminthic compound; Clorsulon against experimental Schistosoma mansoni infection.	2007 Apr	17580576
Fasciola hepatica: ultrastructural effects of a combination of triclabendazole and clorsulon against mature fluke.	2007 Apr	17180691
Comparison of the time required to administer three different fluke and worm combination products to commercial beef cattle at housing.	2008 Spring	18415946
Efficacy of an injectable combination anthelmintic (nitroxynil+clorsulon+ivermectin) against early immature Fasciola hepatica compared to triclabendazole combination flukicides given orally or topically to cattle.	2009 Jun 10	19375232
Interaction of anthelmintic drugs with P-glycoprotein in recombinant LLC-PK1-mdr1a cells.	2010 Aug 5	20513441
Unchanged triclabendazole kinetics after co-administration with ivermectin and methimazole: failure of its therapeutic activity against triclabendazole-resistant liver flukes.	2010 Feb 3	20128898

Patents

Sample Use Guides

In Vivo Use Guide

Bovine liver fluke: one-quarter fluid ounce per 200 pounds of body weight (7 milligrams per kilogram or 3.2 milligrams per pound of body weight). 200 mcg ivermectin and 2 mg/kg body weight (1 mL/110 lb body weight). Bovine astrointestinal nematodes, lungworms, liver flukes, grubs, lice, and mites: 1 milliliter (10 milligrams of ivermectin and 100 milligrams of clorsulon) per 50 kilograms (110 pounds) as subcutaneous injection.

Route of Administration: Other

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:12:32 UTC 2023` Edited by `admin` on `Fri Dec 15 15:12:32 UTC 2023`
Record UNII	EG1ZDO6LRD
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CLORSULON

Official Name

English

CLORSULON [MART.]

Common Name

English

CLORSULON [USP MONOGRAPH]

Common Name

English

CLORSULON [USP-RS]

Common Name

English

CURATREM

Brand Name

English

4-AMINO-6-(TRICHLOROVINYL)-M-BENZENEDISULFONAMIDE

Common Name

English

clorsulon [INN]

Common Name

English

CLORSURON [JAN]

Common Name

English

CLORSULON [USAN]

Common Name

English

NSC-758901

Code

English

CLORSULON [MI]

Common Name

English

MK-401

Code

English

1,3-BENZENEDISULFONAMIDE, 4-AMINO-6-(TRICHLOROETHENYL)-

Systematic Name

English

CLORSULON [GREEN BOOK]

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 522.1193