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Rafoxanide (Standard)

CAT: 0804-HY-17598R-01Size: 10 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-17598R-01Size:10 mg
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Description
Rafoxanide (Standard) is the analytical standard of Rafoxanide. This product is intended for research and analytical applications. Rafoxanide is a poent, orally active halogenated salicylaniline agent with antiparasitic activity. Rafoxanide interferes with energy metabolism in trematodes by uncoupling oxidative phosphorylation. Rafoxanide is also found to be a potent inhibitor of the BRAF V600E mutant protein, which is important in colorectal cancer. Rafoxanide can be used for the control of infestation with Hemonchus species or Fasciola species in sheep and cattle as well as Oestrus ovis in sheep. Rafoxanide can also be used for cancer research[1][2][3].
CAS Number
22662-39-1
UNSPSC
12352005
Target
Apoptosis; Oxidative Phosphorylation; p38 MAPK; Parasite; Raf; Reference Standards
Type
Reference Standards
Related Pathways
Anti-infection; Apoptosis; MAPK/ERK Pathway; Metabolic Enzyme/Protease; Others
Field of Research
Cancer; Infection
Assay Protocol
https://www.medchemexpress.com/rafoxanide-standard.html
Solubility
DMSO : ≥ 31 mg/mL
Smiles
O=C(NC1=CC=C(OC2=CC=C(Cl)C=C2)C(Cl)=C1)C3=CC(I)=CC(I)=C3O
Molecular Formula
C19H11Cl2I2NO3
Molecular Weight
626.01
References & Citations
[1]El-Banna HA, et, al. Comparative pharmacokinetics of ivermectin alone and a novel formulation of ivermectin and rafoxanide in calves and sheep. Parasitol Res. 2008 May;102 (6) :1337-42.|[2]van Wyk JA, et, al. Two field strains of Haemonchus contortus resistant to rafoxanide. Onderstepoort J Vet Res. 1987 Jun;54 (2) :143-6.|[3]Laudisi F, et al. Induction of endoplasmic reticulum stress and inhibition of colon carcinogenesis by the anti-helmintic drug rafoxanide. Cancer Lett. 2019;462:1-11.
Shipping Conditions
Room temperature
Scientific Category
Reference Standards
Clinical Information
No Development Reported

Chemical Information

Rafoxanide

Rafoxanide is a salicylanilide resulting from the formal condensation of the carboxy group of 2-hydroxy-3,5-diiodobenzoic acid with the amino group of 3-chloro-4-(4-chlorophenoxy)aniline. It is a broad-spectrum anthelmintic used for the treatment of parasitic infections in cattle and sheep. It has a role as an autophagy inducer, a chemosensitiser, an antibacterial agent, an anthelminthic drug, an antineoplastic agent, an antifungal agent, a DNA synthesis inhibitor, a B-Raf inhibitor and an EC 2.7.11.22 (cyclin-dependent kinase) inhibitor. It is a secondary carboxamide, a member of benzamides, a member of phenols, an aromatic ether, an organoiodine compound, a member of salicylanilides and a member of monochlorobenzenes.

CAS Number22662-39-1
PubChem CID31475
IUPAC NameN-[3-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3,5-diiodobenzamide
Molecular FormulaC19H11Cl2I2NO3
Molecular Weight626.0
XLogP7
Topological Polar Surface Area58.6
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count3
Rotatable Bond Count4
Heavy Atom Count27
Formal Charge0
Complexity507
SMILES
C1=CC(=CC=C1OC2=C(C=C(C=C2)NC(=O)C3=C(C(=CC(=C3)I)I)O)Cl)Cl
InChI
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)
InChIKey
NEMNPWINWMHUMR-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of Rafoxanide
CAS: 22662-39-1
CID: 31475
Formula: C19H11Cl2I2NO3
MW: 626.0
Interactive 3D Structure
Loading 3D structure...
Computed Properties
PropertyValue
Molecular Weight626.0
XLogP37
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count3
Rotatable Bond Count4
Exact Mass624.82054
Monoisotopic Mass624.82054
Topological Polar Surface Area58.6 Ų
Heavy Atom Count27
Formal Charge0
Complexity507
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes