Basic information
- Standard SMILES
CCCOc1ccc2nc(NC(=O)OC)[nH]c2c1- InChIKey
RAOCRURYZCVHMG-UHFFFAOYSA-N- Molecular formula
- C12H15N3O3
- Average molar mass
- 249.27 g/mol
- Monoisotopic mass
- 249.11134134
Overview
N-(6-propoxy-1H-benzimidazol-2-yl)carbamic acid methyl ester is a member of benzimidazoles and a carbamate ester.
Names & identifiers
- Preferred name
- Oxibendazole
- IUPAC
- methyl N-(6-propoxy-1H-benzimidazol-2-yl)carbamate
- English name
- Oxibendazole
- Molecular formula
- C12H15N3O3
- Molecular weight
- 249.27
Names & synonyms
Show more names
Database identifiers
- CAS
20559-55-1- PubChem CID
- 4622
- DTXSID
DTXSID5045625- ChEMBL
CHEMBL1087630- ChEBI
CHEBI:92907- UNII
- 022N12KJ0X
- EC Number
- 243-877-7
- Nikkaji
- J10.991F
Properties
Computed structural properties
- XLogP
- 2.4
- Topological polar surface area
- 76.2 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 5
- Heavy atoms
- 18
- Formal charge
- 0
- Complexity
- 288
Experimental & physicochemical properties
Animal Drugs
FDA approved animal drugs -> Active ingredient
Pharmaceuticals -> Animal Drugs -> Approved in Taiwan
Collision Cross Section
156.71 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
173.5 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with Waters Major Mix]
157.5 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 230 · 230-231°C
- Density
- 1.301 · 1.301±0.06 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- solubility
- DMSO (Slightly, Heated), THF (Slightly, Heated)
- pka
- 10.6 · 10.60±0.10(Predicted)
- form
- Solid
- color
- Off-White
- Merck
- 14 · 14,6936
- InChI
- 1S/C12H15N3O3/c1-3-6-18-8-4-5-9-10(7-8)14-11(13-9)15-12(16)17-2/h4-5,7H,3,6H2,1-2H3,(H2,13,14,15,16)
- InChIKey
- RAOCRURYZCVHMG-UHFFFAOYSA-N
- SMILES
- CCCOc1ccc2[nH]c(NC(=O)OC)nc2c1
- CAS DataBase Reference
- 20559 · 20559-55-1(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 22 N12KJ0X · 022N12KJ0X
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
- Precautionary statements
- 261 · P261-P301+P312-P302+P352-P304+P340-P305+P351+P338
- WGK Germany
- 3 · 3
- RTECS
- 835000 · FD0835000
- HS Code
- 29339900 · 29339900
- Storage Class
- 11 · 11 - Combustible Solids
- Toxicity
- 32 gm/kg · mouse,LDLo,oral,32gm/kg (32000mg/kg),American Journal of Veterinary Research. Vol. 38, Pg. 809, 1977.
Safety & regulation
GHS classification
Hazard information
Safety data
- wgk
- 3
- rtecs
- FD0835000
- hs_code
- 29339900
- Toxicity
- mouse,LDLo,oral,32gm/kg (32000mg/kg),American Journal of Veterinary Research. Vol. 38, Pg. 809, 1977.
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P301+P312-P302+P352-P304+P340-P305+P351+P338
Chemistry & industry
Pharmacology
Mechanism of Action
Oxibendazole causes degenerative alterations in the tegument and intestinal cells of the worm by binding to the colchicine-sensitive site of tubulin, thus inhibiting its polymerization or assembly into microtubules. The loss of the cytoplasmic microtubules leads to impaired uptake of glucose by the larval and adult stages of the susceptible parasites, and depletes their glycogen stores. Degenerative changes in the endoplasmic reticulum, the mitochondria of the germinal layer, and the subsequent release of lysosomes result in decreased production of adenosine triphosphate (ATP), which is the energy required for the survival of the helminth. Due to diminished energy production, the parasite is immobilized and eventually dies.
Uses & manufacturing
Applications
Usesalcohol and narcotic antagonist
UsesAnthelmintic.
Upstream & downstream products
Upstream raw materials
Suppliers50 total
Additional notes
DefinitionChEBI: N-(6-propoxy-1H-benzimidazol-2-yl)carbamic acid methyl ester is a member of benzimidazoles and a carbamate ester.
Related reactions
No reaction records under the current filter.
Linked notes
Loading…