Basic information
- CAS
22662-39-1- Standard SMILES
O=C(Nc1ccc(Oc2ccc(Cl)cc2)c(Cl)c1)c1cc(I)cc(I)c1O- InChIKey
NEMNPWINWMHUMR-UHFFFAOYSA-N- Molecular formula
- C19H11Cl2I2NO3
- Average molar mass
- 626 g/mol
- Monoisotopic mass
- 624.82054457
Overview
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.
Names & identifiers
- Preferred name
- Rafoxanide
- IUPAC
- N-[3-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3,5-diiodobenzamide
- English name
- Rafoxanide
- Molecular formula
- C19H11Cl2I2NO3
- Molecular weight
- 626.01
Names & synonyms
Show more names
Database identifiers
- CAS
22662-39-1- PubChem CID
- 31475
- DTXSID
DTXSID5046227- ChEMBL
CHEMBL287542- ChEBI
CHEBI:234200- UNII
- 22F4FLA7DH
- EC Number
- 245-148-9
- Nikkaji
- J11.487A
Properties
Computed structural properties
- XLogP
- 7
- Topological polar surface area
- 58.6 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 4
- Heavy atoms
- 27
- Formal charge
- 0
- Complexity
- 507
Physicochemical properties
- Melting point
- 168 · 168-170°
- Boiling point
- 526.6 · 526.6±50.0 °C(Predicted)
- Density
- 2.05 · 2.050±0.06 g/cm3(Predicted)
- storage temp.
- 2 · Keep in dark place,Sealed in dry,2-8°C
- solubility
- Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly)
- pka
- 6.04 · 6.04±0.48(Predicted)
- form
- Solid
- color
- White to Off-White
- Merck
- 14 · 14,8097
- Major Application
- agricultureenvironmental
- 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
- SMILES
- C(NC1=CC=C(OC2=CC=C(Cl)C=C2)C(Cl)=C1)(=O)C1=CC(I)=CC(I)=C1O
- CAS DataBase Reference
- 22662 · 22662-39-1(CAS DataBase Reference)
- FDA UNII
- 22 F4FLA7DH · 22F4FLA7DH
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 2 · GHS02,GHS07
- Signal word
- Warning
- Hazard statements
- 413 · H413
- Precautionary statements
- 501 · P501-P273
- PPE
- 95 · Eyeshields, Gloves, type N95 (US)
- WGK Germany
- 3 · 3
- RTECS
- 7870000 · VN7870000
- HS Code
- 2924.29 · 2924.29.7790
- Storage Class
- 11 · 11 - Combustible Solids
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 6.5% (2 of 31) of reports.
Danger
H360D (90.3%): May damage the unborn child [Danger Reproductive toxicity]
P203, P260, P264, P270, P280, P308+P316, P318, P319, P321, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 31 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- rtecs
- VN7870000
- hs_code
- 2924.29.7790
- Signal word
- Warning
- Symbol(GHS)
- GHS02,GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H413
- Precautionary statements
- P501-P273
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Substances used in the treatment or control of nematode infestations. They are used also in veterinary practice.
Agents used to treat cestode, trematode, or other flatworm infestations in man or animals.
Applications
UsesRafoxanide is a thyroid hormone receptor.
Upstream & downstream products
Upstream raw materials
Suppliers100 total
Related reactions
Compound notes
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