| Identification | More | [Name]
Clorsulon | [CAS]
60200-06-8 | [Synonyms]
4-AMINO-6-(TRICHLORO-ETHENYL)-1,3-BENZENEDISULFONAMIDE
4-AMINO-6-TRICHLOROVINYL-1,3-BENZENEDISULFONAMIDE
4-AMINO-6-(TRICHLOROVINYL)-M-BENZENEDISULFONAMIDE
CLORSULON
4-amino-6-(trichloroethenyl)-3-benzenedisulfonamide
curatrem
l631529
Foramsulfuron, Pestanal
1,3-Benzenedisulfonamide, 4-amino-6-(trichloroethenyl)-
chlorsulon
CLORSULON USP
4-AMINO-6-(TRICHLOROETHENYL)-1,3-BENZENEDISULPHONAMIDE
MK-401
4-AMINO-6-(1,2,2-TRICHLOROVINYL)BENZENE-1,3-DISULFONAMIDE
4-Amino-6-(1,2,2-trichloroethenyl)-1,3-benzenedisulfonamide | [EINECS(EC#)]
262-100-2 | [Molecular Formula]
C8H8Cl3N3O4S2 | [MDL Number]
MFCD00072006 | [Molecular Weight]
380.66 | [MOL File]
60200-06-8.mol |
| Chemical Properties | Back Directory | [Appearance]
Crystalline Solid | [Melting point ]
194-203°C | [Boiling point ]
651.7±65.0 °C(Predicted) | [density ]
1.800±0.06 g/cm3(Predicted) | [storage temp. ]
0-6°C | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
neat | [pka]
9.16±0.60(Predicted) | [color ]
White | [Usage]
A benzenedisulfonamide derivative with fasciolicidal activity. Anthelmintic (Trematodes) | [Major Application]
forensics and toxicology
pharmaceutical (small molecule) | [InChI]
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) | [InChIKey]
QOVTVIYTBRHADL-UHFFFAOYSA-N | [SMILES]
C1(S(N)(=O)=O)=C(/C(/Cl)=C(/Cl)\Cl)C=C(N)C(S(N)(=O)=O)=C1 | [CAS DataBase Reference]
60200-06-8(CAS DataBase Reference) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H319 | [Precautionary statements ]
P305+P351+P338 | [Safety Statements ]
24/25 | [WGK Germany ]
2 | [RTECS ]
CZ9090000 | [HS Code ]
29350090 | [Storage Class]
11 - Combustible Solids | [Toxicity]
LD50 in mice (mg/kg): 761 i.p.; >10,000 orally (Ostlind) |
| Hazard Information | Back Directory | [Description]
Clorsulon is a sulfonamide antiparasitic agent.1 It induces swelling and blebbing and reduces motility of F. hepatica mature flukes when used at a concentration of 10 μg/ml. In vivo, clorsulon (3.5-15 mg/kg) reduces the number of flukes in a goat model of F. hepatica infection.2 It completely eradicates naturally acquired F. hepatica adult flukes in sheep and cattle when administered at a dose of 7 mg/kg.3 Formulations containing clorsulon have been used in the treatment of liver flukes in sheep and cattle. | [Chemical Properties]
Crystalline Solid | [Uses]
A benzenedisulfonamide derivative with fasciolicidal activity. Anthelmintic (Trematodes) | [Uses]
A benzenedisulfonamide derivative with fasciolicidal activity. Anthelmintic (Trematodes). | [Uses]
analgesic, antiinflammatory | [Definition]
ChEBI: 4-amino-6-(1,2,2-trichloroethenyl)benzene-1,3-disulfonamide is a sulfonamide and a member of benzenes. | [Brand name]
Curatrem [Veterinary] (Merial). | [Synthesis]
The general procedure for the synthesis of 4-amino-6-(1,2,2-trichlorovinyl)benzene-1,3-disulfonamide from the compound (CAS: 60285-85-0) is as follows: 100 mL of ethanol and 350 mL of water were mixed and stirred well, then 20 g of ammonia and 2 g of activated carbon were added. The mixture was heated to reflux for 1 hour, followed by thermal filtration. The residue was washed with 50 mL of ethanol and 100 kg of water. The filtrate was slowly cooled to 10 °C, filtered and dried to give 16.5 g of chlorosulfuron in 82.5% yield. | [Veterinary Drugs and Treatments]
Clorsulon is approved for use in the treatment of immature and
adult forms of Fasciola hepatica (Liver fluke) in cattle. It is not effective
against immature flukes less than 8 weeks old. It also has activity
against Fasciola gigantica. Although not approved, the drug has
been used in practice in various other species (e.g., sheep, llamas).
It has activity against F. magna in sheep, but is not completely effective
in eradicating the organism after a single dose, thus severely
limiting its clinical usefulness against this parasite. Clorsulon is also
not effective against the rumen fluke (Paramphistomum). | [References]
[1] Patent: CN104230767, 2016, B. Location in patent: Paragraph 0035; 0036 |
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