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31431-39-7 molecular structure
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methyl N-(6-benzoyl-1H-1,3-benzodiazol-2-yl)carbamate

ChemBase ID: 525
Molecular Formular: C16H13N3O3
Molecular Mass: 295.29272
Monoisotopic Mass: 295.09569129
SMILES and InChIs

SMILES:
O=C(c1cc2[nH]c(nc2cc1)NC(=O)OC)c1ccccc1
Canonical SMILES:
COC(=O)Nc1nc2c([nH]1)cc(cc2)C(=O)c1ccccc1
InChI:
InChI=1S/C16H13N3O3/c1-22-16(21)19-15-17-12-8-7-11(9-13(12)18-15)14(20)10-5-3-2-4-6-10/h2-9H,1H3,(H2,17,18,19,21)
InChIKey:
OPXLLQIJSORQAM-UHFFFAOYSA-N

Cite this record

CBID:525 http://www.chembase.cn/molecule-525.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
methyl N-(6-benzoyl-1H-1,3-benzodiazol-2-yl)carbamate
methyl N-(5-benzoyl-1H-1,3-benzodiazol-2-yl)carbamate
IUPAC Traditional name
telmin
mebendazole
methyl N-(6-benzoyl-1H-1,3-benzodiazol-2-yl)carbamate
vermox
Brand Name
Vermirax
Vermox
Vermox (TN)
Verpanyl
Bantenol
Besantin
Equivurm Plus
Lomper
MBDZ
MEBENDAZOLE, 99%
Mebendazole (JAN/USP)
Mebendazole(USAN)
Mebenoazole
Mebenvet
Mebex
Mebutar
Noverme
Ovitelmin
Pantelmin
Telmin
Vermicidin
Synonyms
Mebendazole
N-(6-Benzoyl-1H-benzimidazol-2-yl)carbamic Acid Methyl Ester
Bantenol
Besantin
Mebenvet
Mebex
Noverme
Ovitelmin
Pantelmin
R 17635
methyl N-(6-benzoyl-1H-1,3-benzodiazol-2-yl)carbamate
5-benzoyl-2-benzimidazolylcarbamic acid methyl ester
Equivurm Plus
Lomper
MBDZ
Mebenoazole
Mebutar
Telmin
Vermicidin
Vermirax
Vermox
Verpanyl
Mebendazole
methyl (5-benzoyl-1H-benzo[d]imidazol-2-yl)carbamate
5-Benzoyl-2-benzimidazolecarbamic acid methyl ester
Mebendazol
Methyl N-(5-benzoyl-1H-benzimidazol-2-yl)carbamate
methyl (5-benzoyl-1H-benzimidazol-2-yl)carbamate
5-苯甲酰-2-苯并咪唑胺甲酸甲酯
N-(5-苯甲酰-1H-苯并咪唑-2-基)氨基甲酸甲酯
甲苯咪唑
甲苯达唑
CAS Number
31431-39-7
EC Number
250-635-4
MDL Number
MFCD00408814
MFCD00057872
Beilstein Number
759809
PubChem SID
160963988
24896742
24870130
46508807
PubChem CID
4030

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 9.168718  H Acceptors
H Donor LogD (pH = 5.5) 3.2565598 
LogD (pH = 7.4) 3.2536292  Log P 3.2601085 
Molar Refractivity 81.5039 cm3 Polarizability 31.87077 Å3
Polar Surface Area 84.08 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 2.95  LOG S -3.88 
Solubility (Water) 3.87e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
71.3 mg/L expand Show data source
DMSO expand Show data source
Apperance
White Solid expand Show data source
Melting Point
>273°C (dec.) expand Show data source
304 - 306°C expand Show data source
Hydrophobicity(logP)
2.8 expand Show data source
3.077 expand Show data source
Storage Condition
Refrigerator expand Show data source
RTECS
EY8600000 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
22 expand Show data source
Safety Statements
36 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H302 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Mechanism of Action
Glucose uptake inhibitor expand Show data source
Microtubule inhibitor expand Show data source
Purity
≥98% (NT/TLC) expand Show data source
95% expand Show data source
98% expand Show data source
Grade
VETRANAL™, analytical standard expand Show data source
Certificate of Analysis
Download expand Show data source
Application(s)
Broad-spectrum anthelmintic expand Show data source
Empirical Formula (Hill Notation)
C16H13N3O3 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB00643 external link
Item Information
Drug Groups approved
Description A benzimidazole that acts by interfering with carbohydrate metabolism and inhibiting polymerization of microtubules. [PubChem]
Indication For the treatment of Enterobius vermicularis (pinworm), Trichuris trichiura (whipworm), Ascaris lumbricoides (common roundworm), Ancylostoma duodenale (common hookworm), Necator americanus (American hookworm) in single or mixed infections.
Pharmacology Mebendazole is a (synthetic) broad-spectrum anthelmintic. The principal mode of action for Mebendazole is by its inhibitory effect on tubulin polymerization which results in the loss of cytoplasmic microtubules.
Toxicity Acute oral toxicity (LD50): 620 mg/kg [Mouse]. Symptoms of overdose include elevated liver enzymes, headaches, hair loss, low levels of white blood cells (neutropenia), fever, and itching.
Affected Organisms
Helminthic Microorganisms
Biotransformation Primarily hepatic. Primary metabolite is 2-amino-5-benzoylbenzimidazole, but also metabolized to inactive hydroxy and hydroxyamino metabolites. All metabolites are devoid of anthelmintic activity.
Absorption Poorly absorbed (approximately 5 to 10%) from gastrointestinal tract. Fatty food increases absorption.
Half Life 2.5 to 5.5 hours (range 2.5 to 9 hours) in patients with normal hepatic function. Approximately 35 hours in patients with impaired hepatic function (cholestasis).
Protein Binding 90-95%
Elimination In man, approximately 2% of administered mebendazole is excreted in urine and the remainder in the feces as unchanged drug or a primary metabolite.
References
[Link]
External Links
Wikipedia
RxList
Drugs.com
Sigma Aldrich - 46404 external link
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC
Toronto Research Chemicals - M200500 external link
Anthelmintic (Nematodes).

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • •  Link
  • • Al-Badr, A.A., et al.: Anal. Profiles Drug Subs., 16, 291 (1987)
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PATENTS

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