Mebendazole

Names

[ Name ]:
Mebendazole

[Synonym ]:
mebenvet
Methyl (5-benzoyl-1H-benzo[d]imidazol-2-yl)carbamate
telmin
Methyl-[5-(phenylcarbonyl)-1H-benzimidazol-2-yl]carbamat
Methyl [5-(Benzoyl)benzimidazol-2-yl]carbamate
lomper
Carbamic acid, N-(5-benzoyl-1H-benzimidazol-2-yl)-, methyl ester
5-benzoyl-2-benzimidazolecarbamic acid methyl ester
besantin
Mebendazole
Methyl 5-benzoyl benzimidazole-2-carbamate
EINECS 250-635-4
Mebex
MFCD00057872
Vermox
5-benzoyl-1H-benzimidazol-2-yl carbamic acid methyl ester
mbdz
[5-(phénylcarbonyl)-1H-benzimidazol-2-yl]carbamate de méthyle
Methyl (5-benzoyl-1H-benzimidazol-2-yl)carbamate
bantenol
noverme

Biological Activity

[Description]:

Mebendazole is a highly effective, broad-spectrum antihelmintic indicated for the treatment of nematode infestations; has been found as a hedgehog inhibitor.

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Parasite

Research Areas >> Infection

[References]

[1]. Liu C, et al. In vivo and in vitro efficacies of mebendazole, mefloquine and nitazoxanide against cyst echinococcosis. Parasitol Res. 2015 Mar 15.

[2]. Pawluk SA, et al. A review of pharmacokinetic drug-drug interactions with the anthelmintic medications albendazole and mebendazole. Clin Pharmacokinet. 2015 Apr;54(4):371-83.

[3]. Speich B, et al. Efficacy and safety of albendazole plus ivermectin, albendazole plus mebendazole, albendazole plus oxantel pamoate, and mebendazole alone against Trichuris trichiura and concomitant soil-transmitted helminth infections: a four-arm, random

[4]. Larsen AR, et al. Repurposing the antihelmintic mebendazole as a hedgehog inhibitor. Mol Cancer Ther. 2015 Jan;14(1):3-13.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Melting Point ]:
288.5°C

[ Molecular Formula ]:
C₁₆H₁₃N₃O₃

[ Molecular Weight ]:
295.293

[ Exact Mass ]:
295.095703

[ PSA ]:
84.08000

[ LogP ]:
2.83

[ Index of Refraction ]:
1.703

[ Storage condition ]:
0-6°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: EY8600000

CHEMICAL NAME :: Carbamic acid, N-(5-benzoylbenzimidazol-2-yl)-, methyl ester

CAS REGISTRY NUMBER :: 31431-39-7

LAST UPDATED :: 199606

DATA ITEMS CITED :: 25

MOLECULAR FORMULA :: C16-H13-N3-O3

MOLECULAR WEIGHT :: 295.32

WISWESSER LINE NOTATION :: T56 BM DNJ CMVO1 GVR

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 714 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 350 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 620 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 712 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 1280 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: >2 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: >640 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: >640 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: >1280 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Bird - chicken

DOSE/DURATION :: >40 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - domestic

DOSE/DURATION :: >80 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 3640 mg/kg/13W-I

TOXIC EFFECTS :: Gastrointestinal - other changes Liver - changes in liver weight Related to Chronic Data - changes in testicular weight

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 78400 ug/kg

SEX/DURATION :: female 8-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - Central Nervous System

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 78400 ug/kg

SEX/DURATION :: female 8-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - musculoskeletal system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 78400 ug/kg

SEX/DURATION :: female 8-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)

MUTATION DATA

TEST SYSTEM :: Rodent - mouse

DOSE/DURATION :: 200 mg/kg

REFERENCE :: PCBRD2 Progress in Clinical and Biological Research. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1975- Volume(issue)/page/year: 340E,225,1990 *** REVIEWS *** TOXICOLOGY REVIEW MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 32,151,1975

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Precautionary Statements ]:
P301 + P312 + P330

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xn:Harmful

[ Risk Phrases ]:
R22

[ Safety Phrases ]:
S36

[ RIDADR ]:
UN 2811

[ WGK Germany ]:
3

[ RTECS ]:
EY8600000

[ HS Code ]:
2933990090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.

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Drug-induced liver injury is a major issue of concern and has led to the withdrawal of a significant number of marketed drugs. An understanding of structure-activity relationships (SARs) of chemicals ...