Rafoxanide

Last updated
Rafoxanide
Rafoxanide.svg
Names
Preferred IUPAC name
N-[3-Chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3,5-diiodobenzamide
Other names
Rafoxanid, raphoxanide
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.041.029 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 245-148-9
KEGG
MeSH D011888
PubChem CID
UNII
  • InChI=1S/C19H11Cl2I2NO3/c20-10-1-4-13(5-2-10)27-17-6-3-12(9-15(17)21)24-19(26)14-7-11(22)8-16(23)18(14)25/h1-9,25H,(H,24,26) X mark.svgN
    Key: NEMNPWINWMHUMR-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C19H11Cl2I2NO3/c20-10-1-4-13(5-2-10)27-17-6-3-12(9-15(17)21)24-19(26)14-7-11(22)8-16(23)18(14)25/h1-9,25H,(H,24,26)
    Key: NEMNPWINWMHUMR-UHFFFAOYAP
  • C1=CC(=CC=C1OC2=C(C=C(C=C2)NC(=O)C3=CC(=CC(=C3O)I)I)Cl)Cl
Properties
C19H11Cl2I2NO3
Molar mass 626.01 g/mol
AppearanceSlight yellowish-brown injectable solution and white oral solution
In oily solutes
Pharmacology
QP52AG05 ( WHO )
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Has low safety index (6 times as normal dose)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Rafoxanide is a salicylanilide used as an anthelmintic. [1] It is most commonly used in ruminant animals to treat adult liver flukes of the species Fasciola hepatica and Fasciola gigantica . [1]

Related Research Articles

A superinfection is a second infection superimposed on an earlier one, especially by a different microbial agent of exogenous or endogenous origin, that is resistant to the treatment being used against the first infection. Examples of this in bacteriology are the overgrowth of endogenous Clostridium difficile that occurs following treatment with a broad-spectrum antibiotic, and pneumonia or sepsis from Pseudomonas aeruginosa in some immunocompromised patients.

<span class="mw-page-title-main">Fasciolosis</span> Parasitic worm infection

Fasciolosis is a parasitic worm infection caused by the common liver fluke Fasciola hepatica as well as by Fasciola gigantica. The disease is a plant-borne trematode zoonosis, and is classified as a neglected tropical disease (NTD). It affects humans, but its main host is ruminants such as cattle and sheep. The disease progresses through four distinct phases; an initial incubation phase of between a few days up to three months with little or no symptoms; an invasive or acute phase which may manifest with: fever, malaise, abdominal pain, gastrointestinal symptoms, urticaria, anemia, jaundice, and respiratory symptoms. The disease later progresses to a latent phase with less symptoms and ultimately into a chronic or obstructive phase months to years later. In the chronic state the disease causes inflammation of the bile ducts, gall bladder and may cause gall stones as well as fibrosis. While chronic inflammation is connected to increased cancer rates, it is unclear whether fasciolosis is associated with increased cancer risk.

<i>Fasciola hepatica</i> Species of fluke

Fasciola hepatica, also known as the common liver fluke or sheep liver fluke, is a parasitic trematode of the class Trematoda, phylum Platyhelminthes. It infects the livers of various mammals, including humans, and is transmitted by sheep and cattle to humans all over the world. The disease caused by the fluke is called fasciolosis or fascioliasis, which is a type of helminthiasis and has been classified as a neglected tropical disease. Fasciolosis is currently classified as a plant/food-borne trematode infection, often acquired through eating the parasite's metacercariae encysted on plants. F. hepatica, which is distributed worldwide, has been known as an important parasite of sheep and cattle for decades and causes significant economic losses in these livestock species, up to £23 million in the UK alone. Because of its relatively large size and economic importance, it has been the subject of many scientific investigations and may be the best-known of any trematode species. F. hepatica's closest relative is Fasciola gigantica. These two flukes are sister species; they share many morphological features and can mate with each other.

<i>Fasciola</i> Genus of flukes

Fasciola, commonly known as the liver fluke, is a genus of parasitic trematodes. There are three species within the genus Fasciola: Fasciola nyanzae,Fasciolahepatica and Fasciolagigantica. Fasciola hepatica and F. gigantica are known to form hybrids. Both F. hepatica and F. gigantica and their hybrids infect the liver tissue of a wide variety of mammals, including humans, in a condition known as fascioliasis. F. hepatica measures up to 30 mm by 15 mm, while F. gigantica measures up to 75 mm by 15 mm. Fasciola nyanzae is thought to exclusively infect the common hippopotamus, Hippopotamus amphibius.

<i>Fasciola gigantica</i> Species of fluke

Fasciola gigantica is a parasitic flatworm of the class Trematoda, which causes tropical fascioliasis. It is regarded as one of the most important single platyhelminth infections of ruminants in Asia and Africa. Estimates of infection rates are as high as 80–100% in some countries. The infection is commonly called fasciolosis.

<i>Fascioloides magna</i> Species of fluke

Fascioloides magna, also known as giant liver fluke, large American liver fluke or deer fluke, is trematode parasite that occurs in wild and domestic ruminants in North America and Europe. Adult flukes occur in the liver of the definitive host and feed on blood. Mature flukes measure 4 to 10 centimetres in length × 2 to 3.5 centimetres in width, and have an oval dorso-ventrally flattened body with oral and ventral sucker. The flukes are reddish-brown in colour and are covered by tegument. As with other digenean trematodes, the life cycle includes intramolluscan phase in snails. The parasite is currently distributed in wild ruminants in North America and Europe, including Austria, Canada, the Czech Republic, Croatia, Germany, Hungary, Italy, Poland, Serbia, Slovakia, and the United States.

<span class="mw-page-title-main">Tribendimidine</span> Chemical compound

Tribendimidine is a broad-spectrum anthelmintic agent developed in China, at the National Institute of Parasitic Diseases in Shanghai. It is a derivative of amidantel.

<i>Apatura</i> Genus of brush-footed butterflies

Apatura is a genus of butterflies commonly known as the emperors.

The ribbon sawtail fish, Idiacanthus fasciola, is a barbeled dragonfish of the family Stomiidae, found around the world at depths over 500 m between latitudes 40° N and 54° S. Length is up to 35 cm in general for the female, and 15 cm for the male.

<i>Galba truncatula</i> Species of gastropod

Galba truncatula is a species of air-breathing freshwater snail, an aquatic pulmonate gastropod mollusk in the family Lymnaeidae, the pond snails.

<span class="mw-page-title-main">Liver fluke</span> Group of liver parasites

Liver fluke is a collective name of a polyphyletic group of parasitic trematodes under the phylum Platyhelminthes. They are principally parasites of the liver of various mammals, including humans. Capable of moving along the blood circulation, they can occur also in bile ducts, gallbladder, and liver parenchyma. In these organs, they produce pathological lesions leading to parasitic diseases. They have complex life cycles requiring two or three different hosts, with free-living larval stages in water.

<i>Lymnaea tomentosa</i> Species of gastropod

Lymnaea tomentosa is a species of freshwater snail, an aquatic gastropod mollusc in the family Lymnaeidae.

<span class="mw-page-title-main">Fasciolidae</span> Family of flukes

Fasciolidae is a family of trematodes and includes several parasites involved in the veterinary and medical sciences, which cause the disease Fasciolosis. Fasciolidae is divided into five genera by Olson et al. 2003. The family's various species are localised in liver, gall bladder, and intestine. Their life-cycle includes an intermediate host, freshwater snails from the family Lymnaeidae.

<i>Lampsilis</i> Genus of bivalves

Lampsilis is a genus of freshwater mussels, aquatic bivalve mollusks in the family Unionidae, the river mussels. There are over 100 species in the genus.

<i>Campylocentrum fasciola</i> Species of orchid

Campylocentrum fasciola is a species of orchid. It occurs in a region ranging from southern Mexico across Central America, the West Indies, and northern South America.

<i>Diacrotricha fasciola</i> Species of plume moth

Diacrotricha fasciola, commonly known as the starfruit flowermoth, is a species of moth in the family Pterophoridae. It is widely distributed throughout south-east Asia.

<i>Elachista fasciola</i> Species of moth

Elachista fasciola is a moth of the family Elachistidae. It is found from Europe east through Russia to Japan.

Austropeplea viridis is a species of air-breathing freshwater snail, an aquatic pulmonate gastropod mollusk in the family Lymnaeidae, the pond snails.

<span class="mw-page-title-main">Bromofenofos</span> Chemical compound

Bromofenofos is an anthelminthic agent used in veterinary medicine. It is used to treat common liver fluke infections in cattle and sheep.

References

  1. 1 2 Lanusse, Carlos E.; Alvarez, Luis I.; Virkel, Guillermo L. (2018). "Chapter 40. Anticestodal and antitrematodal drugs. Rafoxanide". In Riviere, Jim E.; Papich, Mark G. (eds.). Veterinary Pharmacology and Therapeutics (10th ed.). John Wiley & Sons. p. 1091. ISBN   9781118855829.