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Showing drug card for Mebendazole (DB00643)

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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-06-23 18:08:11
Primary Accession Number DB00643
Secondary Accession Number
  • APRD01086
Name Mebendazole
Drug Type
  • Approved
  • Small Molecule
Description A benzimidazole that acts by interfering with carbohydrate metabolism and inhibiting polymerization of microtubules. [PubChem]
Synonyms Not Available
Brand Names
  1. Bantenol
  2. Besantin
  3. Equivurm Plus
  4. Lomper
  5. MBDZ
  6. MEBENDAZOLE, 99%
  7. Mebendazole (JAN/USP)
  8. Mebendazole(USAN)
  9. Mebenoazole
  10. Mebenvet
  11. Mebex
  12. Mebutar
  13. Noverme
  14. Ovitelmin
  15. Pantelmin
  16. Telmin
  17. Vermicidin
  18. Vermirax
  19. Vermox
  20. Vermox (TN)
  21. Verpanyl
Brand Mixtures
  1. Bot-Plus Syringe Formula Equine Wormer (Mebendazole + Trichlorfon)
  2. Equiverm B Pst (Mebendazole + Trichlorfon)
  3. Telmin B Syringe Formula (Mebendazole + Trichlorfon)
Chemical IUPAC Name methyl N-[6-(benzoyl)-1H-benzimidazol-2-yl]carbamate
Chemical Formula C16H13N3O3
Chemical Structure Structure
CAS Registry Number 31431-39-7
InChI Identifier InChI=1/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)/f/h18-19H
InChI Key OPXLLQIJSORQAM-VEWCPZSHCR
KEGG Drug D00368 Link Image
KEGG Compound Not Available
PubChem Compound 4030 Link Image
PubChem Substance 7847434 Link Image
ChEBI ID Not Available
PharmGKB ID PA450333 Link Image
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] 00556734 Link Image
RxList Link http://www.rxlist.com/cgi/generic3/mebend.htm Link Image
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Mebendazole Link Image
FDA Label Not Available
Material Safety Data Sheet (MSDS)
Synthesis Reference Not Available
Average Molecular Weight 295.2927
Monoisotopic Molecular Weight 295.0957
State Solid
Melting Point 288.5 oC
Experimental Water Solubility 71.3 mg/L Source: PhysProp
Predicted Water Solubility 3.87e-02 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity 2.8 Source: PhysProp
Predicted LogP 2.95 Calculated using ALOGPS
Experimental LogS -3.88 [ADME Research, USCD]
Predicted LogS -3.88 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES COC(=O)NC1=NC2=C(N1)C=C(C=C2)C(=O)C1=CC=CC=C1
Canonical SMILES COC(=O)NC1=NC2=C(N1)C=C(C=C2)C(=O)C1=CC=CC=C1
Drug Category
  • Antinematodal Agents
  • Tubulin Modulators
ATC Codes
AHFS Codes
  • 08:08.00
Indication For 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.
Pharmacology Mebendazole is a (synthetic) broad-spectrum anthelmintic. The principal mode of action for albendazole is by its inhibitory effect on tubulin polymerization which results in the loss of cytoplasmic microtubules.
Mechanism of Action Mebendazole 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.
Absorption Poorly absorbed (approximately 5 to 10%) from gastrointestinal tract. Fatty food increases absorption.
Toxicity Acute 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.
Protein Binding 90-95%
Biotransformation 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.
Half Life 2.5 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).
Dosage Forms
Form Route
Tablet Oral
Patient Information Show Link Image
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions
Drug Interaction
Ethotoin The hydantoin decreases the efficiency of mebendazole
Fosphenytoin The hydantoin decreases the efficiency of mebendazole
Mephenytoin The hydantoin decreases the efficiency of mebendazole
Phenytoin The hydantoin decreases the efficiency of mebendazole
Food Interactions
  • Lipid rich meals may improve absorption.
  • Take with food.
Pathways Not Available
General References
  1. http://en.wikipedia.org/wiki/Mebendazole
  2. Drugs.com Link Image
  3. Wikipedia Link Image
  4. RxList Link Image
Organisms Affected
  • Helminthic Microorganisms
Phase 1 Metabolizing Enzymes
  1. Cytochrome P450 3A4 (CYP3A4)
Targets
  1. Tubulin alpha chain
  2. Tubulin beta chain
Phase 1 Metabolizing Enzyme 1 [top]
Enzyme 1 Name Cytochrome P450 3A4 (CYP3A4)
Enzyme 1 Gene Name CYP3A4
Enzyme 1 SwissProt ID P08684 Link Image
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 Protein Sequence >sp|P08684|CP3A4_HUMAN Cytochrome P450 3A4 (EC 1.14.13.67) 
ALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNILSYHKGFCMFD
MECHKKYGKVWGFYDGQQPVLAITDPDMIKTVLVKECYSVFTNRRPFGPVGFMKSAISIA
EDEEWKRLRSLLSPTFTSGKLKEMVPIIAQYGDVLVRNLRREAETGKPVTLKDVFGAYSM
DVITSTSFGVNIDSLNNPQDPFVENTKKLLRFDFLDPFFLSITVFPFLIPILEVLNICVF
PREVTNFLRKSVKRMKESRLEDTQKHRVDFLQLMIDSQNSKETESHKALSDLELVAQSII
FIFAGYETTSSVLSFIMYELATHPDVQQKLQEEIDAVLPNKAPPTYDTVLQMEYLDMVVN
ETLRLFPIAMRLERVCKKDVEINGMFIPKGWVVMIPSYALHRDPKYWTEPEKFLPERFSK
KNKDNIDPYIYTPFGSGPRNCIGMRFALMNMKLALIRVLQNFSFKPCKETQIPLKLSLGG
LLQPEKPVVLKVESRDGTVSGA
Drug Target 1 [top]
Target 1 ID 160
Target 1 Name Tubulin alpha chain
Target 1 Synonyms Not Available
Target 1 Gene Name Not Available
Target 1 Protein Sequence >Tubulin alpha chain 
MREVISIHIGQAGVQIGNACWELYCLEHGIQPDGQMPSDKSLGGCDDSFSTFFSETGSGR
HVPRAVMIDLEPTVIDEIRTGTYRSLFHPEQLITGKEDAANNYARGHYTIGKEIIDLTLD
RIRRLADNCTGLQGFLVFHSFGGGTGSGFTSLLMERLSVDYGKKAKLEFSVYPAPQVSTA
VVEPYNSILTTHTTLEHSDCSFMVDNEAIYDICRRNLDIERPSYTNLNRLIGQIVSSITA
SLRFDGALNVDLTEFQTNLVPYPRIHFPLATFSPVISAEKAYHEQLSVAEITNMCFEPHN
QMVKCDPRHGKYMAVCLLFRGDVVPKDVNAAIATIKTKRSIQFVDWCPTGFKVGINYQPP
TVVPGGDLAKVPRAVCMLSNTTAIAEAWARLDHKFDLMYAKRAFVHWYVGEGMEEGEFSE
AREDLAALEKDYEEVGVDSLEDNGEEGDEY
Target 1 Number of Residues 457
Target 1 Molecular Weight 50111
Target 1 Theoretical pI 4.78
Target 1 GO Classification
Function
binding
nucleotide binding
purine nucleotide binding
guanyl nucleotide binding
GTP binding
catalytic activity
hydrolase activity
hydrolase activity, acting on acid anhydrides
hydrolase activity, acting on acid anhydrides, in phosphorus-containing anhydrides
pyrophosphatase activity
nucleoside-triphosphatase activity
GTPase activity
structural molecule activity
Process
metabolism
macromolecule metabolism
protein metabolism
cellular protein metabolism
protein polymerization
physiological process
cellular physiological process
cell organization and biogenesis
organelle organization and biogenesis
cytoskeleton organization and biogenesis
microtubule-based process
microtubule-based movement
Component
protein complex
organelle
non-membrane-bound organelle
intracellular non-membrane-bound organelle
cytoskeleton
microtubule cytoskeleton
microtubule
Target 1 General Function Involved in structural molecule activity
Target 1 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
Target 1 Pathways Not Available
Target 1 Reactions Not Available
Target 1 Pfam Domain Function
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • None
Target 1 Essentiality Essential
Target 1 GenBank ID Protein 159155 Link Image
Target 1 UniProtKB/Swiss-Prot ID P50719 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name TBA_HAECO Link Image
Target 1 PDB ID 1SA1 Link Image
Target 1 PDB File Show
Target 1 3D Structure
Target 1 Cellular Location
  • Cytoplasmic
Target 1 Gene Sequence >1353 bp 
ATGCGTGAGGTGATTTCCATTCACATCGGCCAGGCTGGAGTACAGATTGGTAATGCTTGC
TGGGAGCTGTACTGTCTAGAACATGGAATCCAGCCTGATGGCCAAATGCCGTCAGATAAA
TCGCTCGGAGGTTGCGATGACTCGTTCTCGACGTTCTTCTCCGAGACCGGCAGTGGTCGC
CATGTCCCACGAGCGGTGATGATCGATCTTGAACCCACCGTCATCGATGAGATTCGCACC
GGGACCTACCGATCACTGTTCCATCCAGAACAACTCATCACCGGCAAAGAAGACGCCGCA
AACAACTATGCTCGAGGACACTATACCATCGGAAAGGAGATCATCGACCTCACATTGGAT
CGTATCCGGCGTCTTGCTGACAACTGCACCGGACTCCAGGGTTTCCTTGTGTTCCATTCG
TTCGGTGGCGGTACTGGCTCTGGATTCACATCTCTTCTCATGGAAAGGCTCTCAGTTGAC
TATGGAAAGAAGGCAAAACTTGAATTCTCCGTCTACCCAGCTCCACAGGTGTCGACAGCC
GTTGTCGAGCCATACAACTCAATTCTGACTACACACACCACACTCGAGCACTCGGATTGC
TCATTTATGGTCGATAATGAGGCCATCTATGACATTTGCCGACGAAATCTCGATATTGAA
CGACCCAGCTATACCAACTTGAACCGACTGATCGGCCAAATTGTCTCGTCGATCACAGCT
TCACTACGCTTCGATGGAGCTCTAAATGTAGACTTGACCGAATTCCAGACCAATCTCGTA
CCGTACCCTCGCATCCACTTTCCGCTTGCAACTTTCTCGCCTGTAATTTCTGCTGAAAAA
GCTTATCATGAGCAGCTATCAGTGGCCGAAATTACCAACATGTGTTTTGAACCGCATAAT
CAGATGGTAAAATGCGATCCACGACATGGGAAATACATGGCCGTATGCCTATTGTTCCGT
GGTGACGTGGTACCAAAAGATGTCAACGCTGCCATTGCCACTATCAAGACGAAACGCTCG
ATTCAGTTCGTCGACTGGTGTCCCACTGGTTTCAAGGTCGGAATCAATTATCAACCACCG
ACGGTTGTGCCAGGTGGCGATCTTGCCAAGGTACCACGTGCTGTCTGCATGCTGTCAAAC
ACGACGGCCATCGCCGAAGCTTGGGCTAGACTCGATCACAAATTCGATTTAATGTATGCC
AAAAGGGCATTCGTGCATTGGTACGTAGGTGAAGGTATGGAAGAAGGAGAGTTTTCGGAA
GCACGTGAAGATCTAGCAGCTTTGGAAAAAGACTACGAAGAGGTTGGCGTCGACTCCCTC
GAAGACAACGGTGAGGAAGGCGATGAGTATTGA
Target 1 GenBank Gene ID
Target 1 GeneCard ID Not Available
Target 1 GenAtlas ID Not Available
Target 1 HGNC ID Not Available
Target 1 Chromosome Location Not Available
Target 1 Locus Not Available
Target 1 SNPs Not Available
Target 1 General References
  1. Klein RD, Nulf SC, Alexander-Bowman SJ, Mainone CB, Winterrowd CA, Geary TG: Cloning of a cDNA encoding alpha-tubulin from Haemonchus contortus. Mol Biochem Parasitol. 1992 Dec;56(2):345-8. [PubMed Link Image]
Target 1 Drug References
  1. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed Link Image]
  2. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed Link Image]
Drug Target 2 [top]
Target 2 ID 4108
Target 2 Name Tubulin beta chain
Target 2 Synonyms
  1. Beta tubulin
Target 2 Gene Name Not Available
Target 2 Protein Sequence >Tubulin beta chain 
MREIVHIQAGQCGNQIGAKFWEVISDEHGIDPTGTYHGDSDLQLERINVYYNEASGGKYV
PRAILVDLEPGTMDSVRAGPFGTLFRPDNFIFGQSGAGNNWAKGHYTEGAELVDNVLDVV
RKESESCDCLQGFQLTHSLGGGTGSGMGTLLISKIREEYPDRIMTTFSVVPSPKVSDTVV
EPYNATLSVHQLVENTDETFCIDNEALYDICFRTLKLTTPTYGDLNHLVSATMSGVTTCL
RFPGQLNADLRKLAVNMVPFPRLHFFMPGFAPLTSRGSQGYRALTVPELTQQMFDAKNMM
AACDPRHGRYLTVAAIFRGRMSMKEVDEQMLNVQNKNNAYFVEWIPNNVKTAVCDIPPRG
LKMSATFIGNSTAIQELFKRISEQFTAMFRRKAFLHWYTGEGMDEMEFTEAESNMNDLVS
EYQQYQEATVEDEDFEEEGDYERE
Target 2 Number of Residues 451
Target 2 Molecular Weight 49849
Target 2 Theoretical pI 4.56
Target 2 GO Classification
Function
catalytic activity
hydrolase activity
hydrolase activity, acting on acid anhydrides
hydrolase activity, acting on acid anhydrides, in phosphorus-containing anhydrides
pyrophosphatase activity
nucleoside-triphosphatase activity
GTPase activity
binding
nucleotide binding
purine nucleotide binding
guanyl nucleotide binding
GTP binding
structural molecule activity
Process
metabolism
macromolecule metabolism
protein metabolism
cellular protein metabolism
protein polymerization
physiological process
cellular physiological process
cell organization and biogenesis
organelle organization and biogenesis
cytoskeleton organization and biogenesis
microtubule-based process
microtubule-based movement
Component
protein complex
cell
intracellular
cytoplasm
organelle
non-membrane-bound organelle
intracellular non-membrane-bound organelle
cytoskeleton
microtubule cytoskeleton
microtubule
Target 2 General Function Cell cycle control, cell division, chromosome partitioning
Target 2 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
Target 2 Pathways Not Available
Target 2 Reactions Not Available
Target 2 Pfam Domain Function
Target 2 Signals
  • None
Target 2 Transmembrane Regions
  • None
Target 2 Essentiality Essential
Target 2 GenBank ID Protein 2827988 Link Image
Target 2 UniProtKB/Swiss-Prot ID O44388 Link Image
Target 2 UniProtKB/Swiss-Prot Entry Name TBB_TRITR Link Image
Target 2 PDB ID 1SA1 Link Image
Target 2 PDB File Show
Target 2 3D Structure
Target 2 Cellular Location
  • Cytoplasmic
Target 2 Gene Sequence >1335 bp 
ATGCGTGAGATTGTGCATATCCAAGCCGGCCAATGTGGTAATCAAATTGGTGCGAAGTTC
TGGGAAGTCATCTCGGATGAACATGGTATCGATCCCACAGGAACTTACCACGGTGACTCG
GACCTGCAACTTGAACGCATAAATGTTTACTACAACGAAGCTTCTGGTGGCAAATACGTT
CCTAGGGCCATACTTGTTGACCTCGAGCCTGGTACTATGGACAGTGTGCGCGCAGGTCCG
TTCGGAACACTTTTTCGACCAGATAATTTTATTTTTGGGCAAAGTGGCGCCGGTAATAAT
TGGGCTAAAGGGCACTATACGGAAGGTGCCGAACTAGTTGACAATGTGCTTGATGTAGTC
CGCAAGGAATCGGAAAGCTGCGACTGCCTGCAAGGGTTTCAGTTGACTCATTCCCTCGGC
GGCGGAACTGGGAGTGGAATGGGTACGCTTCTGATATCTAAAATTCGGGAAGAGTATCCT
GACCGAATTATGACAACTTTTAGTGTCGTTCCGTCTCCGAAGGTTTCAGATACAGTTGTA
GAACCATATAATGCAACTCTGTCAGTCCACCAGTTGGTAGAGAACACGGACGAAACATTC
TGCATAGATAATGAAGCGCTTTACGATATTTGTTTCCGAACTTTGAAGTTAACAACACCA
ACTTACGGAGACTTAAATCATTTGGTTTCGGCAACCATGTCTGGAGTAACGACATGCCTA
CGCTTTCCTGGTCAGTTGAATGCTGACTTGCGGAAGCTGGCAGTCAATATGGTGCCTTTT
CCACGTTTGCATTTCTTTATGCCTGGCTTTGCGCCTCTAACTTCAAGAGGAAGTCAGGGT
TATCGTGCTCTGACGGTTCCTGAGCTTACTCAGCAAATGTTCGACGCAAAGAACATGATG
GCTGCTTGTGATCCTCGTCACGGGCGTTACTTAACTGTAGCTGCAATTTTCCGTGGGCGT
ATGTCTATGAAGGAAGTTGACGAGCAAATGCTGAACGTTCAGAACAAAAACAATGCCTAT
TTTGTGGAATGGATTCCAAATAACGTGAAGACGGCTGTCTGTGACATACCACCCCGTGGA
CTGAAGATGTCGGCTACGTTCATTGGAAATTCAACTGCTATTCAAGAATTGTTTAAACGC
ATATCTGAACAATTCACAGCGATGTTTCGCCGTAAAGCTTTTCTCCATTGGTATACGGGG
GAGGGTATGGACGAAATGGAGTTTACAGAAGCAGAAAGTAACATGAACGATCTAGTTAGC
GAATATCAACAATATCAGGAGGCCACAGTTGAAGATGAAGACTTCGAAGAAGAAGGCGAT
TACGAACGTGAATGA
Target 2 GenBank Gene ID
Target 2 GeneCard ID Not Available
Target 2 GenAtlas ID Not Available
Target 2 HGNC ID Not Available
Target 2 Chromosome Location Not Available
Target 2 Locus Not Available
Target 2 SNPs Not Available
Target 2 General References
  1. Bennett AB, Barker GC, Bundy DA: A beta-tubulin gene from Trichuris trichiura. Mol Biochem Parasitol. 1999 Sep 20;103(1):111-6. [PubMed Link Image]
Target 2 Drug References
  1. 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 Link Image]
  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 Link Image]
  3. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed Link Image]
  4. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed Link Image]
  5. 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 Link Image]

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