U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of CLORSULON

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

Description

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

Merck
216
Curator's Comment: # Merck

Approval Year

1990
108
Targets

Targets

Primary TargetPharmacologyConditionPotency
Fasciola phosphoglycerate kinase
1
Target ID: Fasciola phosphoglycerate kinase
Inhibitor
8297
 0.29 mM [Ki]
Fasciola phosphoglyceromutase
1
Target ID: Fasciola phosphoglyceromutase
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8429
CURATREM

Approved Use

For the treatment of immature and adult liver fluke (Fasciola hepatica) infestations in cattle.

Launch Date

9.8997122E11
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
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
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
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
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

PubMed

TitleDatePubMed
The effect of ivomec super on dogs experimentally infested with Sarcoptes scabiei isolated from a patient.
2001 Apr
Fasciola hepatica: ultrastructural effects of a combination of triclabendazole and clorsulon against mature fluke.
2007 Apr
Interaction of anthelmintic drugs with P-glycoprotein in recombinant LLC-PK1-mdr1a cells.
2010 Aug 5
Unchanged triclabendazole kinetics after co-administration with ivermectin and methimazole: failure of its therapeutic activity against triclabendazole-resistant liver flukes.
2010 Feb 3
Patents

Patents

US4064239 A
1
US4199569 A
1
US4853372 A
1

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
Name Type Language
CLORSULON
GREEN BOOK   INN   MART.   MI   USAN   USP   USP-RS  
USAN   INN  
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
Created by admin on Fri Dec 15 15:12:32 UTC 2023 , Edited by admin on Fri Dec 15 15:12:32 UTC 2023
NCI_THESAURUS C250
Created by admin on Fri Dec 15 15:12:32 UTC 2023 , Edited by admin on Fri Dec 15 15:12:32 UTC 2023
CFR 21 CFR 520.462
Created by admin on Fri Dec 15 15:12:32 UTC 2023 , Edited by admin on Fri Dec 15 15:12:32 UTC 2023
CFR 21 CFR 556.163
Created by admin on Fri Dec 15 15:12:32 UTC 2023 , Edited by admin on Fri Dec 15 15:12:32 UTC 2023
Code System Code Type Description
EVMPD
SUB06767MIG
Created by admin on Fri Dec 15 15:12:32 UTC 2023 , Edited by admin on Fri Dec 15 15:12:32 UTC 2023
PRIMARY
DAILYMED
EG1ZDO6LRD
Created by admin on Fri Dec 15 15:12:32 UTC 2023 , Edited by admin on Fri Dec 15 15:12:32 UTC 2023
PRIMARY
RXCUI
28303
Created by admin on Fri Dec 15 15:12:32 UTC 2023 , Edited by admin on Fri Dec 15 15:12:32 UTC 2023
PRIMARY RxNorm
MESH
C015675
Created by admin on Fri Dec 15 15:12:32 UTC 2023 , Edited by admin on Fri Dec 15 15:12:32 UTC 2023
PRIMARY
DRUG BANK
DB11389
Created by admin on Fri Dec 15 15:12:32 UTC 2023 , Edited by admin on Fri Dec 15 15:12:32 UTC 2023
PRIMARY
USAN
T-6
Created by admin on Fri Dec 15 15:12:32 UTC 2023 , Edited by admin on Fri Dec 15 15:12:32 UTC 2023
PRIMARY
ChEMBL
CHEMBL1474129
Created by admin on Fri Dec 15 15:12:32 UTC 2023 , Edited by admin on Fri Dec 15 15:12:32 UTC 2023
PRIMARY
SMS_ID
100000084011
Created by admin on Fri Dec 15 15:12:32 UTC 2023 , Edited by admin on Fri Dec 15 15:12:32 UTC 2023
PRIMARY
MERCK INDEX
m3665
Created by admin on Fri Dec 15 15:12:32 UTC 2023 , Edited by admin on Fri Dec 15 15:12:32 UTC 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
262-100-2
Created by admin on Fri Dec 15 15:12:32 UTC 2023 , Edited by admin on Fri Dec 15 15:12:32 UTC 2023
PRIMARY
NSC
758901
Created by admin on Fri Dec 15 15:12:32 UTC 2023 , Edited by admin on Fri Dec 15 15:12:32 UTC 2023
PRIMARY
RS_ITEM_NUM
1140702
Created by admin on Fri Dec 15 15:12:32 UTC 2023 , Edited by admin on Fri Dec 15 15:12:32 UTC 2023
PRIMARY
CAS
60200-06-8
Created by admin on Fri Dec 15 15:12:32 UTC 2023 , Edited by admin on Fri Dec 15 15:12:32 UTC 2023
PRIMARY
PUBCHEM
43231
Created by admin on Fri Dec 15 15:12:32 UTC 2023 , Edited by admin on Fri Dec 15 15:12:32 UTC 2023
PRIMARY
FDA UNII
EG1ZDO6LRD
Created by admin on Fri Dec 15 15:12:32 UTC 2023 , Edited by admin on Fri Dec 15 15:12:32 UTC 2023
PRIMARY
INN
5237
Created by admin on Fri Dec 15 15:12:32 UTC 2023 , Edited by admin on Fri Dec 15 15:12:32 UTC 2023
PRIMARY
NCI_THESAURUS
C75213
Created by admin on Fri Dec 15 15:12:32 UTC 2023 , Edited by admin on Fri Dec 15 15:12:32 UTC 2023
PRIMARY
EPA CompTox
DTXSID8045488
Created by admin on Fri Dec 15 15:12:32 UTC 2023 , Edited by admin on Fri Dec 15 15:12:32 UTC 2023
PRIMARY
ACTIVE MOIETY
Structure of CLORSULON
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966