Oxibendazole

HCID 4622CAS 20559-55-1

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

Oxibendazole20559-55-1Anthelcide EQFilaribits PlusOxibendazolumoxibendazolSK&F 30310Methyl 5-propoxy-2-benzimidazolecarbamateDTXSID5045625Methyl 5-n-propoxy-2-benzimidazole carbamateSK&F-303105-Propoxy-2-benzimidazolecarbamic acid methyl ester
Show more names
FENBENDAZOLE SULFOXIDEOxbendazoleobdzEquitacSKF-30310OxbidazoleObendazoleAnthdcide EQ
NSC-758459Anthelcide EQ PasteCarbamic acid, (5-propoxy-1H-benzimidazol-2-yl)-, methyl ester022N12KJ0XDTXCID3025625methyl 5-n-propoxy-2-benzimidazolecarbamateRefChem:57474Anthelcide EQ Suspension

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

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
Animal Drugs · 2 items

FDA approved animal drugs -> Active ingredient

Pharmaceuticals -> Animal Drugs -> Approved in Taiwan

Collision Cross Section · 3 items

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

Safety & regulation

GHS classification

GHS ClassificationNot Classified

Hazard information

Regulatory InformationOxibendazole: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - Carbamic acid, (5-propoxy-1H-benzimidazol-2-yl)-, methyl ester: Environment tier I assessment
Hazard Classes and CategoriesNot Classified

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

Chemistry & industry

Pharmacology

ATC CodeQP - Antiparasitic products, insecticides and repellents
Mechanism of Action · 1 item

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.

Metabolism/MetabolitesHepatic
MeSH Pharmacological ClassificationAgents that kill parasitic worms. They are used therapeutically in the treatment of HELMINTHIASIS in man and animal.

Uses & manufacturing

Use ClassificationPharmaceuticals -> Animal Drugs -> Approved in Taiwan

Applications

Usesalcohol and narcotic antagonist

UsesAnthelmintic.

Suppliers50 total

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
广州隽沐生物科技股份有限公司020-36607679; 13502246435 · [email protected]
湖北金梭生物科技有限公司00123456789 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
武汉易泰科技有限公司上海分公司18930552037 · [email protected]

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

0 records

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Linked notes

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