Mebendazole

HCID 4030CAS 31431-39-7

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

mebendazole31431-39-7VermoxOvitelminPantelminTelminMebenvetVermicidinVermiraxVerpanylMBDZBesantin
Show more names
Methyl (5-benzoyl-1H-benzo[d]iMidazol-2-yl)carbaMate(5-Benzoyl-1H-benzimidazol-2-yl)carbamicacidmethylesterMebexlomperr17635
NovermeMebendazolMebendazolumMethyl 5-benzoyl-2-benzimidazolecarbamatemethyl N-(6-benzoyl-1H-benzimidazol-2-yl)carbamate5-Benzoyl-2-benzimidazolecarbamic acid methyl esterEmvermCarbamic acid, (5-benzoyl-1H-benzimidazol-2-yl)-, methyl ester

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

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.

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)

Chemistry & industry

Applications · 4 items

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.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
湖北威德利化学试剂有限公司181-6332-1995 18062128043 · [email protected]

Additional notes

DefinitionChEBI: A carbamate ester that is methyl 1H-benzimidazol-2-ylcarbamate substituted by a benzoyl group at position 5.

Related reactions

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