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Identification
NameMebendazole
Accession NumberDB00643  (APRD01086)
TypeSmall Molecule
GroupsApproved
Description

A benzimidazole that acts by interfering with carbohydrate metabolism and inhibiting polymerization of microtubules. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
(5-benzoyl-1H-benzimidazol-2-yl)-carbamic acid methyl esterNot AvailableNot Available
MBDZNot AvailableNot Available
MebendazolGermanINN
MebendazolSpanishINN
MébendazoleFrenchINN
MebendazolumLatinINN
VermoxNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Mebendazoletablet, chewable100 mgoralPhysicians Total Care, Inc.1996-04-04Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Mebendazoletablet, chewable100 mgoralbryant ranch prepack2010-04-28Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Over the Counter ProductsNot Available
International Brands
NameCompany
LomperEsteve
MeberixAversi
MebexCipla
MebezolJohnson
MebfilFourrts Laboratories
MebutarAndromaco
MebzolJulphar
MendazoleGlaxoSmithKline
MezoleYuan Chou
MinyoozoleEmil
MopenLi Taka Pharmaceuticals
MultielminOsorio de Moraes
NecaminAché
OvexMcNeil
PanamoxJayson
PantelminJanssen
TesicalSintesina
ThelmoxRemedica
TicoquerRoot
VermoxBiotech
Brand mixtures
Brand NameIngredients
Equiverm BMebendazole and Trichlorfon
Mebex PlusMebendazole and Pyrantel
Telmin B Syringe FormulaMebendazole and Trichlorfon
SaltsNot Available
Categories
CAS number31431-39-7
WeightAverage: 295.2927
Monoisotopic: 295.095691297
Chemical FormulaC16H13N3O3
InChI KeyOPXLLQIJSORQAM-UHFFFAOYSA-N
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)
IUPAC Name
methyl N-(6-benzoyl-1H-1,3-benzodiazol-2-yl)carbamate
SMILES
COC(=O)NC1=NC2=C(N1)C=C(C=C2)C(=O)C1=CC=CC=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as benzophenones. These are organic compounds containing a ketone attached to two phenyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzophenones
Direct ParentBenzophenones
Alternative Parents
Substituents
  • Benzophenone
  • Benzimidazole
  • Acetophenone
  • Aryl ketone
  • Benzoyl
  • Aminoimidazole
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Ketone
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationFor 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.
PharmacodynamicsMebendazole 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.
Mechanism of actionMebendazole 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.
AbsorptionPoorly absorbed (approximately 5 to 10%) from gastrointestinal tract. Fatty food increases absorption.
Volume of distributionNot Available
Protein binding90-95%
Metabolism

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.

SubstrateEnzymesProduct
Mebendazole
Not Available
2-amino-5-benzoylbenzimidazoleDetails
Route of eliminationIn man, approximately 2% of administered mebendazole is excreted in urine and the remainder in the feces as unchanged drug or a primary metabolite.
Half life2.5 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).
ClearanceNot Available
ToxicityAcute 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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9932
Blood Brain Barrier+0.9261
Caco-2 permeable+0.7261
P-glycoprotein substrateNon-substrate0.6073
P-glycoprotein inhibitor IInhibitor0.5844
P-glycoprotein inhibitor IIInhibitor0.7534
Renal organic cation transporterNon-inhibitor0.8464
CYP450 2C9 substrateNon-substrate0.749
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.6532
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 substrateNon-inhibitor0.9071
CYP450 2D6 substrateNon-inhibitor0.9231
CYP450 2C19 substrateNon-inhibitor0.9025
CYP450 3A4 substrateNon-inhibitor0.8308
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6779
Ames testAMES toxic0.7212
CarcinogenicityNon-carcinogens0.9102
BiodegradationNot ready biodegradable0.994
Rat acute toxicity2.5855 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9515
hERG inhibition (predictor II)Non-inhibitor0.8028
Pharmacoeconomics
Manufacturers
  • Teva pharmaceuticals usa
  • Mcneil pediatrics
Packagers
Dosage forms
FormRouteStrength
Tablet, chewableoral100 mg
Prices
Unit descriptionCostUnit
Mebendazole 100 mg Chew Tabs16.42USD tab
Mebendazole 100 mg tablet chew5.32USD tablet
Mebendazole powder5.03USD g
Vermox 100 mg Chewable Tablet4.14USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point288.5 °CPhysProp
water solubility71.3 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP2.83SANGSTER (1994)
logS-3.88ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility0.0387 mg/mLALOGPS
logP2.95ALOGPS
logP3.26ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)8.44ChemAxon
pKa (Strongest Basic)3.93ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area84.08 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity81.5 m3·mol-1ChemAxon
Polarizability31.1 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

U.S. Patent 3,657,267.

General Reference
  1. Link
External Links
ATC CodesP02CA01
AHFS Codes
  • 08:08.00
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (72.8 KB)
Interactions
Drug Interactions
Drug
CarbamazepineCarBAMazepine may decrease the serum concentration of Mebendazole.
CimetidineCimetidine may increase the serum concentration of Mebendazole.
FosphenytoinMay decrease the serum concentration of Mebendazole.
PhenytoinPhenytoin may decrease the serum concentration of Mebendazole.
Food Interactions
  • Lipid rich meals may improve absorption.
  • Take with food.

Targets

1. Tubulin alpha-1A chain

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Tubulin alpha-1A chain Q71U36 Details

References:

  1. Lubega GW, Geary TG, Klein RD, Prichard RK: Expression of cloned beta-tubulin genes of Haemonchus contortus in Escherichia coli: interaction of recombinant beta-tubulin with native tubulin and mebendazole. Mol Biochem Parasitol. 1993 Dec;62(2):281-92. Pubmed
  2. MacDonald LM, Armson A, Thompson AR, Reynoldson JA: Characterisation of benzimidazole binding with recombinant tubulin from Giardia duodenalis, Encephalitozoon intestinalis, and Cryptosporidium parvum. Mol Biochem Parasitol. 2004 Nov;138(1):89-96. Pubmed
  3. Oxberry ME, Gear TG, Prichard RK: Assessment of benzimidazole binding to individual recombinant tubulin isotypes from Haemonchus contortus. Parasitology. 2001 Jun;122(Pt 6):683-7. Pubmed
  4. Ochola DO, Prichard RK, Lubega GW: Classical ligands bind tubulin of trypanosomes and inhibit their growth in vitro. J Parasitol. 2002 Jun;88(3):600-4. Pubmed
  5. Wampande EM, Richard McIntosh J, Lubega GW: Classical ligands interact with native and recombinant tubulin from Onchocerca volvulus with similar rank order of magnitude. Protein Expr Purif. 2007 Oct;55(2):236-45. Epub 2007 Apr 25. Pubmed
  6. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

2. Tubulin beta-4B chain

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Tubulin beta-4B chain P68371 Details

References:

  1. Lubega GW, Geary TG, Klein RD, Prichard RK: Expression of cloned beta-tubulin genes of Haemonchus contortus in Escherichia coli: interaction of recombinant beta-tubulin with native tubulin and mebendazole. Mol Biochem Parasitol. 1993 Dec;62(2):281-92. Pubmed
  2. MacDonald LM, Armson A, Thompson AR, Reynoldson JA: Characterisation of benzimidazole binding with recombinant tubulin from Giardia duodenalis, Encephalitozoon intestinalis, and Cryptosporidium parvum. Mol Biochem Parasitol. 2004 Nov;138(1):89-96. Pubmed
  3. Oxberry ME, Gear TG, Prichard RK: Assessment of benzimidazole binding to individual recombinant tubulin isotypes from Haemonchus contortus. Parasitology. 2001 Jun;122(Pt 6):683-7. Pubmed
  4. Ochola DO, Prichard RK, Lubega GW: Classical ligands bind tubulin of trypanosomes and inhibit their growth in vitro. J Parasitol. 2002 Jun;88(3):600-4. Pubmed
  5. Wampande EM, Richard McIntosh J, Lubega GW: Classical ligands interact with native and recombinant tubulin from Onchocerca volvulus with similar rank order of magnitude. Protein Expr Purif. 2007 Oct;55(2):236-45. Epub 2007 Apr 25. Pubmed
  6. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

Enzymes

1. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

2. Cytochrome P450 1A1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inducer

Components

Name UniProt ID Details
Cytochrome P450 1A1 P04798 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

Transporters

1. Multidrug resistance protein 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Multidrug resistance protein 1 P08183 Details

References:

  1. Polli JW, Wring SA, Humphreys JE, Huang L, Morgan JB, Webster LO, Serabjit-Singh CS: Rational use of in vitro P-glycoprotein assays in drug discovery. J Pharmacol Exp Ther. 2001 Nov;299(2):620-8. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on May 23, 2014 12:03