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Showing drug card for Albendazole (DB00518)

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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-06-23 18:08:14
Primary Accession Number DB00518
Secondary Accession Number
  • APRD00782
Name Albendazole
Drug Type
  • Approved
  • Small Molecule
Description A benzimidazole broad-spectrum anthelmintic structurally related to mebendazole that is effective against many diseases. (From Martindale, The Extra Pharmacopoeia, 30th ed, p38)
Synonyms Not Available
Brand Names
  1. Albenza
  2. Eskazole
  3. Valbazen
  4. Zentel
Brand Mixtures Not Available
Chemical IUPAC Name methyl N-(6-propylsulfanyl-1H-benzimidazol-2-yl)carbamate
Chemical Formula C12H15N3O2S
Chemical Structure Structure
CAS Registry Number 54965-21-8
InChI Identifier InChI=1/C12H15N3O2S/c1-3-6-18-8-4-5-9-10(7-8)14-11(13-9)15-12(16)17-2/h4-5,7H,3,6H2,1-2H3,(H2,13,14,15,16)/f/h14-15H
InChI Key HXHWSAZORRCQMX-VPQZEOPVCH
KEGG Drug D00134 Link Image
KEGG Compound C01779 Link Image
PubChem Compound 2082 Link Image
PubChem Substance 4909 Link Image
ChEBI ID 16664 Link Image
PharmGKB ID PA448058 Link Image
HET ID ALW Link Image
GenBank ID Not Available
Drug ID Number [DIN] 01904779 Link Image
RxList Link http://www.rxlist.com/cgi/generic/albendazole.htm Link Image
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Albendazole Link Image
FDA Label Not Available
Material Safety Data Sheet (MSDS)
Synthesis Reference Not Available
Average Molecular Weight 265.3310
Monoisotopic Molecular Weight 265.0885
State Solid
Melting Point 209 oC
Experimental Water Solubility Practically insoluble Source: PhysProp
Predicted Water Solubility 2.28e-02 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity 2.7 Source: PhysProp
Predicted LogP 3.22 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -4.07 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 CCCSC1=CC2=C(C=C1)N=C(NC(=O)OC)N2
Canonical SMILES CCCSC1=CC2=C(C=C1)N=C(NC(=O)OC)N2
Drug Category
  • Anthelmintics
  • Anticestodal Agents
  • Antiprotozoal Agents
  • Tubulin Modulators
ATC Codes
AHFS Codes Not Available
Indication For the treatment of parenchymal neurocysticercosis due to active lesions caused by larval forms of the pork tapeworm, Taenia solium and for the treatment of cystic hydatid disease of the liver, lung, and peritoneum, caused by the larval form of the dog tapeworm, Echinococcus granulosus.
Pharmacology Albendazole is a 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 Albendazole 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 from the gastrointestinal tract due to its low aqueous solubility. Oral bioavailability appears to be enhanced when coadministered with a fatty meal (estimated fat content 40 g)
Toxicity Symptoms of overdose include elevated liver enzymes, headaches, hair loss, low levels of white blood cells (neutropenia), fever, and itching.
Protein Binding 70% bound to plasma protein
Biotransformation Hepatic. Rapidly converted in the liver to the primary metabolite, albendazole sulfoxide, which is further metabolized to albendazole sulfone and other primary oxidative metabolites that have been identified in human urine.
Half Life Terminal elimination half-life ranges from 8 to 12 hours (single dose, 400mg).
Dosage Forms
Form Route
Tablet, film coated Oral
Patient Information Not Available
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions Not Available
Food Interactions Not Available
Pathways Not Available
General References
  1. Oxberry ME, Reynoldson JA, Thompson RC: The binding and distribution of albendazole and its principal metabolites in Giardia duodenalis. J Vet Pharmacol Ther. 2000 Jun;23(3):113-20. [PubMed Link Image]
  2. Ramirez T, Benitez-Bribiesca L, Ostrosky-Wegman P, Herrera LA: In vitro effects of albendazole and its metabolites on the cell proliferation kinetics and micronuclei frequency of stimulated human lymphocytes. Arch Med Res. 2001 Mar-Apr;32(2):119-22. [PubMed Link Image]
  3. Molina AJ, Merino G, Prieto JG, Real R, Mendoza G, Alvarez AI: Absorption and metabolism of albendazole after intestinal ischemia/reperfusion. Eur J Pharm Sci. 2007 May;31(1):16-24. Epub 2007 Feb 6. [PubMed Link Image]
  4. Haque A, Hollister WS, Willcox A, Canning EU: The antimicrosporidial activity of albendazole. J Invertebr Pathol. 1993 Sep;62(2):171-7. [PubMed Link Image]
  5. Wikipedia Link Image
  6. RxList Link Image
Organisms Affected
  • Helminthic Microorganisms
Phase 1 Metabolizing Enzymes
  1. Cytochrome P450 3A4 (CYP3A4)
Targets
  1. Tubulin alpha chain
  2. Tubulin beta-1 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. Ramirez T, Benitez-Bribiesca L, Ostrosky-Wegman P, Herrera LA: In vitro effects of albendazole and its metabolites on the cell proliferation kinetics and micronuclei frequency of stimulated human lymphocytes. Arch Med Res. 2001 Mar-Apr;32(2):119-22. [PubMed Link Image]
Drug Target 2 [top]
Target 2 ID 4204
Target 2 Name Tubulin beta-1 chain
Target 2 Synonyms
  1. Beta-1 tubulin
Target 2 Gene Name Not Available
Target 2 Protein Sequence >Tubulin beta-1 chain 
MREIVHVQAGQCGNQIGAKFWEVISDEHGVQPDGTYKGDSDLQIERINVYYNEANGGKYV
PRAVLVDLEPGTMDSIRGGEFGQLFRPDNFVFGQSGAGNNWAKGHYTEGAELVDNVLDVI
RKEAEGCDCLQGFQLTHSLGGGTGSGMGTLLISKIREEYPDRIMSSFSVVPSPKVSDVVL
EPYNATLSVHQLVENTDETFCIDNEALYDICFRTLKLANPTYGDLNHLVSVTMSGVTTCL
RFPGQLNADLRKLAVNMVPFPRLHFFMPGFAPLSARDAAAYRALNVAELTQQMFDAKNMM
AACDPRHGRYLTVAAMFRGRMSMREVDEQMMQVQNKNSSYFVEWIPNNVKTAVCDIPPRG
LKMSATFIGNTTAIQELFKRISEQFTAMFRRKAFLHWYTGEGMDEMEFTEAESNMNDLVS
EYQQYQDATADEEGDLQEGESEYIEQEE
Target 2 Number of Residues 455
Target 2 Molecular Weight 50192
Target 2 Theoretical pI 4.46
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 Involved in structural molecule activity
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 Not Available
Target 2 UniProtKB/Swiss-Prot ID P18241 Link Image
Target 2 UniProtKB/Swiss-Prot Entry Name TBB1_BRUPA 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 >1347 bp 
ATGAGAGAAATTGTCCACGTTCAAGCTGGTCAATGTGGCAACCAGATTGGTGCCAAGTTC
TGGGAAGTAATATCGGATGAACATGGTGTTCAACCTGATGGTACATACAAAGGTGATTCA
GACCTGCAAATTGAACGAATCAACGTCTACTATAATGAAGCGAATGGGGGCAAATATGTG
CCACGAGCAGTCCTTGTTGATTTGGAACCAGGTACCATGGATTCTATTCGAGGAGGTGAG
TTCGGGCAACTATTCCGACCTGACAATTTTGTTTTTGGGCAAAGTGGAGCTGGCAACAAC
TGGGCTAAGGGACATTATACGGAAGGTGCGGAACTAGTTGATAATGTGTTGGACGTGATA
CGAAAAGAAGCTGAGGGATGCGATTGTCTTCAGGGATTTCAACTAACGCATTCACTTGGT
GGTGGTACCGGTTCCGGCATGGGAACATTGCTGATCTCGAAAATTCGTGAGGAGTATCCG
GATCGAATTATGAGCTCTTTTTCGGTTGTGCCATCGCCCAAAGTATCAGATGTTGTGTTG
GAACCCTACAATGCAACATTATCAGTCCACCAACTAGTTGAAAACACTGACGAAACTTTC
TGCATTGATAACGAGGCTTTGTATGACATCTGCTTCCGAACGTTGAAGTTGGCAAATCCA
ACTTACGGTGACCTCAACCATTTGGTGTCTGTGACAATGTCGGGAGTAACAACTTGCTTA
CGTTTCCCTGGACAGTTGAACGCCGATCTCCGTAAACTTGCCGTCAATATGGTGCCATTC
CCACGGTTGCATTTCTTTATGCCAGGATTTGCTCCTCTCTCTGCTCGTGATGCTGCTGCT
TATCGAGCCCTCAATGTTGCTGAACTTACTCAACAGATGTTTGATGCCAAAAATATGATG
GCAGCATGTGATCCGCGTCATGGTCGTTACCTAACCGTAGCTGCCATGTTCCGAGGTAGA
ATGTCTATGCGGGAAGTAGACGAGCAAATGATGCAAGTACAGAATAAGAATTCATCGTAT
TTCGTTGAATGGATTCCAAATAACGTAAAGACAGCTGTTTGCGACATTCCACCACGTGGA
TTAAAGATGAGCGCAACATTTATTGGAAATACAACAGCTATACAAGAACTTTTCAAGCGA
ATTTCCGAACAGTTTACTGCCATGTTCCGACGTAAAGCATTCTTGCATTGGTATACTGGC
GAAGGTATGGATGAAATGGAATTCACGGAAGCGGAGAGTAATATGAATGACTTGGTGTCC
GAATATCAACAATATCAGGATGCGACGGCTGATGAAGAAGGTGATCTTCAGGAAGGTGAA
TCGGAATACATTGAACAGGAAGAGTGA
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. Guenette S, Prichard RK, Klein RD, Matlashewski G: Characterization of a beta-tubulin gene and a beta-tubulin gene products of Brugia pahangi. Mol Biochem Parasitol. 1991 Feb;44(2):153-64. [PubMed Link Image]
  2. Helm R, Selkirk ME, Bradley JE, Burns RG, Hamilton AJ, Croft S, Maizels RM: Localization and immunogenicity of tubulin in the filarial nematodes Brugia malayi and B. pahangi. Parasite Immunol. 1989 Sep;11(5):479-502. [PubMed Link Image]
Target 2 Drug References
  1. Solana HD, Sallovitz JM, Lanusse CE, Rodriguez JA: Enantioselective binding of albendazole sulphoxide to cytosolic proteins from helminth parasites. Methods Find Exp Clin Pharmacol. 2002 Jan-Feb;24(1):7-13. [PubMed Link Image]

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