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Identification
NameMebendazole
Accession NumberDB00643  (APRD01086)
TypeSmall Molecule
GroupsApproved, Vet Approved
DescriptionA benzimidazole that acts by interfering with carbohydrate metabolism and inhibiting polymerization of microtubules. [PubChem]
Structure
Thumb
Synonyms
(5-benzoyl-1H-benzimidazol-2-yl)-carbamic acid methyl ester
MBDZ
Mebendazol
Mebendazol
Mébendazole
Mebendazolum
Vermox
External Identifiers
  • R 17635
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
VermoxTablet, chewable500 mg/1OralJanssen Pharmaceuticals, Inc.2016-10-20Not applicableUs
Vermox Tablets 100 mgTablet100 mgOralJanssen Inc1982-12-31Not applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
EmvermTablet, chewable100 mg/1OralAmedra Pharmaceuticals LLC2016-02-15Not applicableUs
MebendazoleTablet, chewable100 mg/1OralPhysicians Total Care, Inc.1996-04-04Not applicableUs
MebendazoleTablet, chewable100 mg/1Oralbryant ranch prepack2010-04-28Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not 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 mixturesNot Available
SaltsNot Available
Categories
UNII81G6I5V05I
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
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.
Structured Indications
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.
TargetKindPharmacological actionActionsOrganismUniProt ID
Tubulin alpha-1A chainProteinyes
inhibitor
HumanQ71U36 details
Tubulin beta-4B chainProteinyes
inhibitor
HumanP68371 details
Related Articles
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
Interactions
Drug Interactions
DrugInteractionDrug group
AcebutololThe serum concentration of Acebutolol can be increased when it is combined with Mebendazole.Approved
AcetaminophenThe serum concentration of Acetaminophen can be increased when it is combined with Mebendazole.Approved
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Mebendazole.Approved
Acetylsalicylic acidThe serum concentration of Acetylsalicylic acid can be increased when it is combined with Mebendazole.Approved, Vet Approved
AfatinibThe serum concentration of Afatinib can be increased when it is combined with Mebendazole.Approved
AldosteroneThe serum concentration of Aldosterone can be increased when it is combined with Mebendazole.Experimental
AlitretinoinThe serum concentration of Alitretinoin can be increased when it is combined with Mebendazole.Approved, Investigational
AmbrisentanThe serum concentration of Ambrisentan can be increased when it is combined with Mebendazole.Approved, Investigational
AmiodaroneThe metabolism of Mebendazole can be decreased when combined with Amiodarone.Approved, Investigational
AmitriptylineThe serum concentration of Amitriptyline can be increased when it is combined with Mebendazole.Approved
AmodiaquineThe serum concentration of Mebendazole can be decreased when it is combined with Amodiaquine.Approved
AnvirzelAnvirzel may decrease the cardiotoxic activities of Mebendazole.Investigational
ApixabanThe serum concentration of Apixaban can be increased when it is combined with Mebendazole.Approved
AprepitantThe serum concentration of Mebendazole can be increased when it is combined with Aprepitant.Approved, Investigational
Arsenic trioxideThe serum concentration of Arsenic trioxide can be increased when it is combined with Mebendazole.Approved, Investigational
AtazanavirThe metabolism of Mebendazole can be decreased when combined with Atazanavir.Approved, Investigational
AtenololThe serum concentration of Atenolol can be increased when it is combined with Mebendazole.Approved
AtomoxetineThe metabolism of Mebendazole can be decreased when combined with Atomoxetine.Approved
AxitinibThe serum concentration of Axitinib can be increased when it is combined with Mebendazole.Approved, Investigational
BetamethasoneThe serum concentration of Betamethasone can be increased when it is combined with Mebendazole.Approved, Vet Approved
BevacizumabBevacizumab may increase the cardiotoxic activities of Mebendazole.Approved, Investigational
BexaroteneThe serum concentration of Mebendazole can be decreased when it is combined with Bexarotene.Approved, Investigational
BoceprevirThe metabolism of Mebendazole can be decreased when combined with Boceprevir.Approved
BortezomibThe metabolism of Mebendazole can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Mebendazole can be decreased when it is combined with Bosentan.Approved, Investigational
BosutinibThe serum concentration of Bosutinib can be increased when it is combined with Mebendazole.Approved
Brentuximab vedotinThe serum concentration of Brentuximab vedotin can be increased when it is combined with Mebendazole.Approved
BromocriptineThe serum concentration of Bromocriptine can be increased when it is combined with Mebendazole.Approved, Investigational
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Mebendazole.Approved
CaffeineThe serum concentration of Caffeine can be increased when it is combined with Mebendazole.Approved
CamptothecinThe serum concentration of Camptothecin can be increased when it is combined with Mebendazole.Experimental
CanagliflozinThe serum concentration of Canagliflozin can be increased when it is combined with Mebendazole.Approved
CarbamazepineThe serum concentration of Mebendazole can be decreased when it is combined with Carbamazepine.Approved, Investigational
CarfilzomibThe serum concentration of Carfilzomib can be increased when it is combined with Mebendazole.Approved
CeritinibThe serum concentration of Mebendazole can be increased when it is combined with Ceritinib.Approved
CerivastatinThe serum concentration of Cerivastatin can be increased when it is combined with Mebendazole.Withdrawn
ChloroquineThe serum concentration of Mebendazole can be decreased when it is combined with Chloroquine.Approved, Vet Approved
ChlorpromazineThe serum concentration of Chlorpromazine can be increased when it is combined with Mebendazole.Approved, Vet Approved
CimetidineThe serum concentration of Mebendazole can be increased when it is combined with Cimetidine.Approved
CiprofloxacinThe serum concentration of Ciprofloxacin can be increased when it is combined with Mebendazole.Approved, Investigational
CisplatinThe serum concentration of Cisplatin can be increased when it is combined with Mebendazole.Approved
CitalopramThe serum concentration of Citalopram can be increased when it is combined with Mebendazole.Approved
ClarithromycinThe metabolism of Mebendazole can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Mebendazole can be decreased when combined with Clemastine.Approved
ClobazamThe serum concentration of Clobazam can be increased when it is combined with Mebendazole.Approved, Illicit
ClomifeneThe serum concentration of Clomifene can be increased when it is combined with Mebendazole.Approved, Investigational
ClonidineThe serum concentration of Clonidine can be increased when it is combined with Mebendazole.Approved
ClopidogrelThe serum concentration of Clopidogrel can be increased when it is combined with Mebendazole.Approved, Nutraceutical
ClotrimazoleThe metabolism of Mebendazole can be decreased when combined with Clotrimazole.Approved, Vet Approved
ClozapineThe serum concentration of Clozapine can be increased when it is combined with Mebendazole.Approved
CobicistatThe metabolism of Mebendazole can be decreased when combined with Cobicistat.Approved
CobimetinibThe serum concentration of Cobimetinib can be increased when it is combined with Mebendazole.Approved
ColchicineThe serum concentration of Colchicine can be increased when it is combined with Mebendazole.Approved
ConivaptanThe serum concentration of Mebendazole can be increased when it is combined with Conivaptan.Approved, Investigational
Conjugated Equine EstrogensThe serum concentration of Conjugated Equine Estrogens can be increased when it is combined with Mebendazole.Approved
CrizotinibThe metabolism of Mebendazole can be decreased when combined with Crizotinib.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Mebendazole.Approved, Investigational
CyclosporineThe metabolism of Mebendazole can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
Dabigatran etexilateThe serum concentration of the active metabolites of Dabigatran etexilate can be increased when Dabigatran etexilate is used in combination with Mebendazole.Approved
DabrafenibThe serum concentration of Mebendazole can be decreased when it is combined with Dabrafenib.Approved
DactinomycinThe serum concentration of Dactinomycin can be increased when it is combined with Mebendazole.Approved
DapagliflozinThe serum concentration of Dapagliflozin can be increased when it is combined with Mebendazole.Approved
DarunavirThe metabolism of Mebendazole can be decreased when combined with Darunavir.Approved
DasatinibThe serum concentration of Mebendazole can be increased when it is combined with Dasatinib.Approved, Investigational
DaunorubicinThe serum concentration of Daunorubicin can be increased when it is combined with Mebendazole.Approved
DebrisoquinThe serum concentration of Debrisoquin can be increased when it is combined with Mebendazole.Approved
DeferasiroxThe serum concentration of Mebendazole can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe metabolism of Mebendazole can be decreased when combined with Delavirdine.Approved
DeslanosideDeslanoside may decrease the cardiotoxic activities of Mebendazole.Approved
DexamethasoneThe serum concentration of Mebendazole can be decreased when it is combined with Dexamethasone.Approved, Investigational, Vet Approved
DiazepamThe serum concentration of Diazepam can be increased when it is combined with Mebendazole.Approved, Illicit, Vet Approved
DiethylstilbestrolThe serum concentration of Diethylstilbestrol can be increased when it is combined with Mebendazole.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Mebendazole.Approved
DigoxinDigoxin may decrease the cardiotoxic activities of Mebendazole.Approved
DihydroergotamineThe metabolism of Mebendazole can be decreased when combined with Dihydroergotamine.Approved
DihydrotestosteroneThe serum concentration of Dihydrotestosterone can be increased when it is combined with Mebendazole.Illicit
DiltiazemThe metabolism of Mebendazole can be decreased when combined with Diltiazem.Approved
DipyridamoleThe serum concentration of Dipyridamole can be increased when it is combined with Mebendazole.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Mebendazole.Approved, Investigational
DomperidoneThe serum concentration of Domperidone can be increased when it is combined with Mebendazole.Approved, Investigational, Vet Approved
DoxorubicinThe serum concentration of Doxorubicin can be increased when it is combined with Mebendazole.Approved, Investigational
DoxycyclineThe metabolism of Mebendazole can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe metabolism of Mebendazole can be decreased when combined with Dronedarone.Approved
EdoxabanThe serum concentration of Edoxaban can be increased when it is combined with Mebendazole.Approved
EfavirenzThe serum concentration of Mebendazole can be decreased when it is combined with Efavirenz.Approved, Investigational
EletriptanThe serum concentration of Eletriptan can be increased when it is combined with Mebendazole.Approved, Investigational
EnzalutamideThe serum concentration of Mebendazole can be decreased when it is combined with Enzalutamide.Approved
EpinastineThe serum concentration of Epinastine can be increased when it is combined with Mebendazole.Approved, Investigational
ErlotinibThe serum concentration of Erlotinib can be increased when it is combined with Mebendazole.Approved, Investigational
ErythromycinThe metabolism of Mebendazole can be decreased when combined with Erythromycin.Approved, Vet Approved
Eslicarbazepine acetateThe serum concentration of Mebendazole can be decreased when it is combined with Eslicarbazepine acetate.Approved
EstradiolThe serum concentration of Estradiol can be increased when it is combined with Mebendazole.Approved, Investigational, Vet Approved
EstriolThe serum concentration of Estriol can be increased when it is combined with Mebendazole.Approved, Vet Approved
EstroneThe serum concentration of Estrone can be increased when it is combined with Mebendazole.Approved
Ethinyl EstradiolThe serum concentration of Ethinyl Estradiol can be increased when it is combined with Mebendazole.Approved
EtoposideThe serum concentration of Etoposide can be increased when it is combined with Mebendazole.Approved
EtravirineThe serum concentration of Mebendazole can be decreased when it is combined with Etravirine.Approved
EverolimusThe serum concentration of Everolimus can be increased when it is combined with Mebendazole.Approved
EzetimibeThe serum concentration of Ezetimibe can be increased when it is combined with Mebendazole.Approved
FesoterodineThe serum concentration of Fesoterodine can be increased when it is combined with Mebendazole.Approved
FexofenadineThe serum concentration of Fexofenadine can be increased when it is combined with Mebendazole.Approved
FidaxomicinThe serum concentration of Fidaxomicin can be increased when it is combined with Mebendazole.Approved
FluconazoleThe metabolism of Mebendazole can be decreased when combined with Fluconazole.Approved
Fluticasone furoateThe serum concentration of Fluticasone furoate can be increased when it is combined with Mebendazole.Approved
FluvoxamineThe metabolism of Mebendazole can be decreased when combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe metabolism of Mebendazole can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Mebendazole can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe serum concentration of Mebendazole can be decreased when it is combined with Fosphenytoin.Approved
Fusidic AcidThe serum concentration of Mebendazole can be increased when it is combined with Fusidic Acid.Approved
GefitinibThe serum concentration of Gefitinib can be increased when it is combined with Mebendazole.Approved, Investigational
GemcitabineThe serum concentration of Gemcitabine can be increased when it is combined with Mebendazole.Approved
GrazoprevirThe serum concentration of Grazoprevir can be increased when it is combined with Mebendazole.Approved
GrepafloxacinThe serum concentration of Grepafloxacin can be increased when it is combined with Mebendazole.Withdrawn
HaloperidolThe serum concentration of Haloperidol can be increased when it is combined with Mebendazole.Approved
HydrocortisoneThe serum concentration of Hydrocortisone can be increased when it is combined with Mebendazole.Approved, Vet Approved
HydroxychloroquineThe serum concentration of Mebendazole can be decreased when it is combined with Hydroxychloroquine.Approved
IbuprofenThe serum concentration of Ibuprofen can be increased when it is combined with Mebendazole.Approved
IdelalisibThe serum concentration of Mebendazole can be increased when it is combined with Idelalisib.Approved
ImatinibThe metabolism of Mebendazole can be decreased when combined with Imatinib.Approved
ImipramineThe serum concentration of Imipramine can be increased when it is combined with Mebendazole.Approved
IndacaterolThe serum concentration of Indacaterol can be increased when it is combined with Mebendazole.Approved
IndinavirThe metabolism of Mebendazole can be decreased when combined with Indinavir.Approved
IndomethacinThe serum concentration of Indomethacin can be increased when it is combined with Mebendazole.Approved, Investigational
IrinotecanThe serum concentration of Irinotecan can be increased when it is combined with Mebendazole.Approved, Investigational
IsavuconazoniumThe metabolism of Mebendazole can be decreased when combined with Isavuconazonium.Approved, Investigational
IsradipineThe metabolism of Mebendazole can be decreased when combined with Isradipine.Approved
ItraconazoleThe metabolism of Mebendazole can be decreased when combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Mebendazole can be increased when it is combined with Ivacaftor.Approved
IvermectinThe serum concentration of Ivermectin can be increased when it is combined with Mebendazole.Approved, Vet Approved
KetazolamThe serum concentration of Ketazolam can be increased when it is combined with Mebendazole.Approved
KetoconazoleThe metabolism of Mebendazole can be decreased when combined with Ketoconazole.Approved, Investigational
LamivudineThe serum concentration of Lamivudine can be increased when it is combined with Mebendazole.Approved, Investigational
LamotrigineThe serum concentration of Lamotrigine can be increased when it is combined with Mebendazole.Approved, Investigational
LansoprazoleThe serum concentration of Lansoprazole can be increased when it is combined with Mebendazole.Approved, Investigational
LedipasvirThe serum concentration of Ledipasvir can be increased when it is combined with Mebendazole.Approved
LenalidomideThe serum concentration of Lenalidomide can be increased when it is combined with Mebendazole.Approved
LenvatinibThe serum concentration of Lenvatinib can be increased when it is combined with Mebendazole.Approved
LevetiracetamThe serum concentration of Levetiracetam can be increased when it is combined with Mebendazole.Approved, Investigational
LevofloxacinThe serum concentration of Levofloxacin can be increased when it is combined with Mebendazole.Approved, Investigational
LevomilnacipranThe serum concentration of Levomilnacipran can be increased when it is combined with Mebendazole.Approved
LinagliptinThe serum concentration of Linagliptin can be increased when it is combined with Mebendazole.Approved
LoperamideThe serum concentration of Loperamide can be increased when it is combined with Mebendazole.Approved
LopinavirThe metabolism of Mebendazole can be decreased when combined with Lopinavir.Approved
LosartanThe serum concentration of Losartan can be increased when it is combined with Mebendazole.Approved
LovastatinThe metabolism of Mebendazole can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Mebendazole can be increased when it is combined with Luliconazole.Approved
LumacaftorThe metabolism of Mebendazole can be increased when combined with Lumacaftor.Approved
MannitolThe serum concentration of Mannitol can be increased when it is combined with Mebendazole.Approved, Investigational
MethotrexateThe serum concentration of Methotrexate can be increased when it is combined with Mebendazole.Approved
MethylprednisoloneThe serum concentration of Methylprednisolone can be increased when it is combined with Mebendazole.Approved, Vet Approved
MetoprololThe serum concentration of Metoprolol can be increased when it is combined with Mebendazole.Approved, Investigational
MetronidazoleThe risk or severity of adverse effects can be increased when Mebendazole is combined with Metronidazole.Approved
MidazolamThe serum concentration of Midazolam can be increased when it is combined with Mebendazole.Approved, Illicit
MifepristoneThe serum concentration of Mebendazole can be increased when it is combined with Mifepristone.Approved, Investigational
MirabegronThe serum concentration of Mirabegron can be increased when it is combined with Mebendazole.Approved
MitotaneThe serum concentration of Mebendazole can be decreased when it is combined with Mitotane.Approved
MitoxantroneThe serum concentration of Mitoxantrone can be increased when it is combined with Mebendazole.Approved, Investigational
ModafinilThe serum concentration of Mebendazole can be decreased when it is combined with Modafinil.Approved, Investigational
MorphineThe serum concentration of Morphine can be increased when it is combined with Mebendazole.Approved, Investigational
Mycophenolate mofetilThe serum concentration of Mycophenolate mofetil can be increased when it is combined with Mebendazole.Approved, Investigational
NadololThe serum concentration of Nadolol can be increased when it is combined with Mebendazole.Approved
NafcillinThe serum concentration of Mebendazole can be decreased when it is combined with Nafcillin.Approved
NaloxegolThe serum concentration of Naloxegol can be increased when it is combined with Mebendazole.Approved
NaloxoneThe serum concentration of Naloxone can be increased when it is combined with Mebendazole.Approved, Vet Approved
NefazodoneThe metabolism of Mebendazole can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Mebendazole can be decreased when combined with Nelfinavir.Approved
NetupitantThe serum concentration of Mebendazole can be increased when it is combined with Netupitant.Approved
NevirapineThe metabolism of Mebendazole can be increased when combined with Nevirapine.Approved
NicardipineThe serum concentration of Nicardipine can be increased when it is combined with Mebendazole.Approved
NifedipineThe serum concentration of Nifedipine can be increased when it is combined with Mebendazole.Approved
NilotinibThe metabolism of Mebendazole can be decreased when combined with Nilotinib.Approved, Investigational
NintedanibThe serum concentration of Nintedanib can be increased when it is combined with Mebendazole.Approved
NizatidineThe serum concentration of Nizatidine can be increased when it is combined with Mebendazole.Approved
OlanzapineThe serum concentration of Olanzapine can be increased when it is combined with Mebendazole.Approved, Investigational
OlaparibThe metabolism of Mebendazole can be decreased when combined with Olaparib.Approved
OmbitasvirThe serum concentration of Ombitasvir can be increased when it is combined with Mebendazole.Approved
OsimertinibThe serum concentration of Mebendazole can be increased when it is combined with Osimertinib.Approved
OuabainOuabain may decrease the cardiotoxic activities of Mebendazole.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Mebendazole.Approved, Vet Approved
PalbociclibThe serum concentration of Mebendazole can be increased when it is combined with Palbociclib.Approved
PanobinostatThe serum concentration of Panobinostat can be increased when it is combined with Mebendazole.Approved, Investigational
PazopanibThe serum concentration of Pazopanib can be increased when it is combined with Mebendazole.Approved
PentobarbitalThe metabolism of Mebendazole can be increased when combined with Pentobarbital.Approved, Vet Approved
PhenobarbitalThe metabolism of Mebendazole can be increased when combined with Phenobarbital.Approved
PhenytoinThe serum concentration of Mebendazole can be decreased when it is combined with Phenytoin.Approved, Vet Approved
PitavastatinThe serum concentration of Pitavastatin can be increased when it is combined with Mebendazole.Approved
PomalidomideThe serum concentration of Pomalidomide can be increased when it is combined with Mebendazole.Approved
PonatinibThe serum concentration of Ponatinib can be increased when it is combined with Mebendazole.Approved
PosaconazoleThe metabolism of Mebendazole can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PravastatinThe serum concentration of Pravastatin can be increased when it is combined with Mebendazole.Approved
PrazosinThe serum concentration of Prazosin can be increased when it is combined with Mebendazole.Approved
PrednisoloneThe serum concentration of Prednisolone can be increased when it is combined with Mebendazole.Approved, Vet Approved
PrednisoneThe serum concentration of Prednisone can be increased when it is combined with Mebendazole.Approved, Vet Approved
PrimaquineThe serum concentration of Mebendazole can be decreased when it is combined with Primaquine.Approved
PrimidoneThe metabolism of Mebendazole can be increased when combined with Primidone.Approved, Vet Approved
ProgesteroneThe serum concentration of Progesterone can be increased when it is combined with Mebendazole.Approved, Vet Approved
PropranololThe serum concentration of Propranolol can be increased when it is combined with Mebendazole.Approved, Investigational
PrucaloprideThe serum concentration of Prucalopride can be increased when it is combined with Mebendazole.Approved
QuetiapineThe serum concentration of Quetiapine can be increased when it is combined with Mebendazole.Approved
QuinidineThe serum concentration of Quinidine can be increased when it is combined with Mebendazole.Approved
QuinineThe serum concentration of Quinine can be increased when it is combined with Mebendazole.Approved
RanitidineThe serum concentration of Ranitidine can be increased when it is combined with Mebendazole.Approved
RanolazineThe serum concentration of Ranolazine can be increased when it is combined with Mebendazole.Approved, Investigational
ReserpineThe serum concentration of Reserpine can be increased when it is combined with Mebendazole.Approved
RifabutinThe metabolism of Mebendazole can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Mebendazole can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Mebendazole can be increased when combined with Rifapentine.Approved
RifaximinThe serum concentration of Rifaximin can be increased when it is combined with Mebendazole.Approved, Investigational
RisperidoneThe serum concentration of Risperidone can be increased when it is combined with Mebendazole.Approved, Investigational
RitonavirThe metabolism of Mebendazole can be decreased when combined with Ritonavir.Approved, Investigational
RivaroxabanThe serum concentration of Rivaroxaban can be increased when it is combined with Mebendazole.Approved
RomidepsinThe serum concentration of Romidepsin can be increased when it is combined with Mebendazole.Approved, Investigational
Salicylic acidThe serum concentration of Salicylic acid can be increased when it is combined with Mebendazole.Approved, Vet Approved
SaquinavirThe metabolism of Mebendazole can be decreased when combined with Saquinavir.Approved, Investigational
SelexipagThe serum concentration of Selexipag can be increased when it is combined with Mebendazole.Approved
SildenafilThe metabolism of Mebendazole can be decreased when combined with Sildenafil.Approved, Investigational
SilodosinThe serum concentration of Silodosin can be increased when it is combined with Mebendazole.Approved
SiltuximabThe serum concentration of Mebendazole can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Mebendazole can be increased when it is combined with Simeprevir.Approved
SitagliptinThe serum concentration of Sitagliptin can be increased when it is combined with Mebendazole.Approved, Investigational
SofosbuvirThe serum concentration of Sofosbuvir can be increased when it is combined with Mebendazole.Approved
SorafenibThe serum concentration of Sorafenib can be increased when it is combined with Mebendazole.Approved, Investigational
SparfloxacinThe serum concentration of Sparfloxacin can be increased when it is combined with Mebendazole.Approved
SphingosineThe serum concentration of Sphingosine can be increased when it is combined with Mebendazole.Experimental
St. John's WortThe serum concentration of Mebendazole can be decreased when it is combined with St. John's Wort.Nutraceutical
StiripentolThe serum concentration of Mebendazole can be increased when it is combined with Stiripentol.Approved
SulfisoxazoleThe metabolism of Mebendazole can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
TacrolimusThe serum concentration of Tacrolimus can be increased when it is combined with Mebendazole.Approved, Investigational
TamoxifenThe serum concentration of Tamoxifen can be increased when it is combined with Mebendazole.Approved
Taurocholic AcidThe serum concentration of Taurocholic Acid can be increased when it is combined with Mebendazole.Experimental
Technetium Tc-99m sestamibiThe serum concentration of Technetium Tc-99m sestamibi can be increased when it is combined with Mebendazole.Approved
TelaprevirThe metabolism of Mebendazole can be decreased when combined with Telaprevir.Approved
TelithromycinThe metabolism of Mebendazole can be decreased when combined with Telithromycin.Approved
TemsirolimusThe serum concentration of Temsirolimus can be increased when it is combined with Mebendazole.Approved
TicagrelorThe serum concentration of Ticagrelor can be increased when it is combined with Mebendazole.Approved
TiclopidineThe metabolism of Mebendazole can be decreased when combined with Ticlopidine.Approved
TimololThe serum concentration of Timolol can be increased when it is combined with Mebendazole.Approved
TocilizumabThe serum concentration of Mebendazole can be decreased when it is combined with Tocilizumab.Approved
TolvaptanThe serum concentration of Tolvaptan can be increased when it is combined with Mebendazole.Approved
TopotecanThe serum concentration of Topotecan can be increased when it is combined with Mebendazole.Approved, Investigational
ToremifeneThe serum concentration of Toremifene can be increased when it is combined with Mebendazole.Approved, Investigational
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Mebendazole.Approved, Investigational
Trastuzumab emtansineThe serum concentration of Trastuzumab emtansine can be increased when it is combined with Mebendazole.Approved
UlipristalThe serum concentration of Ulipristal can be increased when it is combined with Mebendazole.Approved
UmeclidiniumThe serum concentration of Umeclidinium can be increased when it is combined with Mebendazole.Approved
VecuroniumThe serum concentration of Vecuronium can be increased when it is combined with Mebendazole.Approved
VenetoclaxThe serum concentration of Venetoclax can be increased when it is combined with Mebendazole.Approved
VenlafaxineThe metabolism of Mebendazole can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Mebendazole can be decreased when combined with Verapamil.Approved
VinblastineThe serum concentration of Vinblastine can be increased when it is combined with Mebendazole.Approved
VincristineThe serum concentration of Vincristine can be increased when it is combined with Mebendazole.Approved, Investigational
VismodegibThe serum concentration of Vismodegib can be increased when it is combined with Mebendazole.Approved
VoriconazoleThe metabolism of Mebendazole can be decreased when combined with Voriconazole.Approved, Investigational
ZidovudineThe serum concentration of Zidovudine can be increased when it is combined with Mebendazole.Approved
ZiprasidoneThe metabolism of Mebendazole can be decreased when combined with Ziprasidone.Approved
Food Interactions
  • Lipid rich meals may improve absorption.
  • Take with food.
References
Synthesis Reference

U.S. Patent 3,657,267.

General References
  1. Link [Link]
External Links
ATC CodesP02CA51P02CA01
AHFS Codes
  • 08:08.00
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (72.8 KB)
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 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Teva pharmaceuticals usa
  • Mcneil pediatrics
Packagers
Dosage forms
FormRouteStrength
Tablet, chewableOral100 mg/1
Tablet, chewableOral500 mg/1
TabletOral100 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
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
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

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Structural molecule activity
Specific Function:
Tubulin is the major constituent of microtubules. It binds two moles of GTP, one at an exchangeable site on the beta chain and one at a non-exchangeable site on the alpha chain.
Gene Name:
TUBA1A
Uniprot ID:
Q71U36
Molecular Weight:
50135.25 Da
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:8139621 ]
  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:15500920 ]
  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:11444621 ]
  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:12099434 ]
  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:17662615 ]
  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:10592235 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Unfolded protein binding
Specific Function:
Tubulin is the major constituent of microtubules. It binds two moles of GTP, one at an exchangeable site on the beta chain and one at a non-exchangeable site on the alpha chain.
Gene Name:
TUBB4B
Uniprot ID:
P68371
Molecular Weight:
49830.72 Da
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:8139621 ]
  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:15500920 ]
  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:11444621 ]
  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:12099434 ]
  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:17662615 ]
  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:10592235 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inducer
General Function:
Vitamin d 24-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP1A1
Uniprot ID:
P04798
Molecular Weight:
58164.815 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Xenobiotic-transporting atpase activity
Specific Function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular Weight:
141477.255 Da
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:11602674 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23