Basic information
- Standard SMILES
COC(=O)Nc1nc2ccc(C(=O)c3ccccc3)cc2[nH]1- InChIKey
OPXLLQIJSORQAM-UHFFFAOYSA-N- Molecular formula
- C16H13N3O3
- Average molar mass
- 295.29 g/mol
- Monoisotopic mass
- 295.09569129
Names & identifiers
- Preferred name
- Mebendazole
- IUPAC
- methyl N-(6-benzoyl-1H-benzimidazol-2-yl)carbamate
- English name
- Mebendazole
- Molecular formula
- C16H13N3O3
- Molecular weight
- 295.29
Names & synonyms
Show more names
Database identifiers
- CAS
31431-39-7- PubChem CID
- 4030
- DTXSID
DTXSID4040682- ChEMBL
CHEMBL685- ChEBI
CHEBI:6704- UNII
- 81G6I5V05I
- EC Number
- 104-806-4、250-635-4
- Nikkaji
- J2.773A
Properties
Computed structural properties
- XLogP
- 2.8
- Topological polar surface area
- 84.1 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 4
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 423
Physicochemical properties
- Melting point
- 288.5 °C · 288.5°C
- Boiling point
- 436.98 °C · 436.98°C (rough estimate)
- Density
- 1.1952 · 1.1952 (rough estimate)
- refractive index
- 1.65 · 1.6500 (estimate)
- storage temp.
- 2 · Sealed in dry,2-8°C
- solubility
- Practically insoluble in water, in alcohol and in methylene chloride.
- form
- Solid
- pka
- 3.43 · pKa 3.43/9.93(H2O,t =25,I=0.025) (Uncertain)
- color
- White to Pale Beige
- Water Solubility
- 35.4 mg/L · 35.4mg/L(25 ºC)
- Merck
- 14 · 14,5768
- BRN
- 759809 · 759809
- Henry's Law Constant
- 1.8 · 1.8×1010 mol/(m3Pa) at 25℃, HSDB (2015)
- BCS Class
- 2 · 2,4
- Major Application
- forensics and toxicologypharmaceutical (small molecule)
- 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
- SMILES
- COC(=O)Nc1nc2cc(ccc2[nH]1)C(=O)c3ccccc3
- CAS DataBase Reference
- 31431 · 31431-39-7(CAS DataBase Reference)
- FDA UNII
- 81 G6I5V05I · 81G6I5V05I
- Proposition 65 List
- Mebendazole
- NCI Drug Dictionary
- mebendazole
- ATC code
- 2 CA01,P02CA51 · P02CA01,P02CA51
- EPA Substance Registry System
- Mebendazole (31431-39-7)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Protein binding
- 95 % · 95%
- Excreted unchanged in urine
- 2 % · 2%
- Volume of distribution
- 1 · 1-1.2(L/kg)
- Biological half-life
- 0.93 · 0.93 / -
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302
- Precautionary statements
- 301 · P301+P312+P330
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xn
- Risk Statements
- 22 · 22
- Safety Statements
- 36 · 36
- RIDADR
- 2811 · UN 2811
- WGK Germany
- 3 · 3
- RTECS
- 8600000 · EY8600000
- HS Code
- 29339900 · 29339900
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 4 Oral · Acute Tox. 4 Oral
- Hazardous Substances Data
- 31431 · 31431-39-7(Hazardous Substances Data)
- Toxicity
- 50 orally: · LD50 orally: >80 mg/kg in sheep; >40 mg/kg in mice, rats and chickens (Van Gelder)
Safety & regulation
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- rtecs
- EY8600000
- ridadr
- UN 2811
- hs_code
- 29339900
- Toxicity
- LD50 orally: >80 mg/kg in sheep; >40 mg/kg in mice, rats and chickens (Van Gelder)
- risk_code
- 22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 36
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302
- Hazard Classifications
- Acute Tox. 4 Oral
- Precautionary statements
- P301+P312+P330
- Hazardous Substances Data
- 31431-39-7(Hazardous Substances Data)
Chemistry & industry
Applications
DescriptionMebendazole is a broad-spectrum anthelmintic that is active against both larval and adult stages of nematodes selectively binding the β-subunit of tubulin, thereby inhibiting intestinal microtubule synthesis in the parasite (IC50 = 0.19 μM for Giardia in vitro). As a tubulin-binding agent, mebendazole also possesses antitumor properties, inducing apoptosis of various human carcinomas both in vitro and in vivo, thus preventing their growth and migration. Furthermore, mebendazole has been used to inhibit hedgehog signaling in cancer cells via suppression of the formation of the primary cilium, a microtubule-based organelle that functions as a signaling hub for hedgehog pathway activation. Additionally, mebendazole has been shown to stabilize the transcriptional activator HIF-1α and its downstream targets, abrogating oxidative neuronal death in primary neurons.
UsesMebendazole Polymorph C is an Anthelmintic (Nematodes).
UsesFor 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.
General DescriptionWhite to slightly yellow powder. Pleasant taste. Practically water insoluble.
Upstream & downstream products
Upstream raw materials
Suppliers50 total
Additional notes
DefinitionChEBI: A carbamate ester that is methyl 1H-benzimidazol-2-ylcarbamate substituted by a benzoyl group at position 5.
Related reactions
No reaction records under the current filter.
Linked notes
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