| 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 |
|
| Name |
Albendazole |
| Drug Type |
|
| 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 |
- Albenza
- Eskazole
- Valbazen
- Zentel
|
| Brand Mixtures |
Not Available |
| Chemical IUPAC Name |
methyl N-(6-propylsulfanyl-1H-benzimidazol-2-yl)carbamate |
| Chemical Formula |
C12H15N3O2S |
| Chemical 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  |
| KEGG Compound |
C01779  |
| PubChem Compound |
2082  |
| PubChem Substance |
4909  |
| ChEBI ID |
16664  |
| PharmGKB ID |
PA448058  |
| HET ID |
ALW  |
| GenBank ID |
Not Available |
| Drug ID Number [DIN] |
01904779  |
| RxList Link |
http://www.rxlist.com/cgi/generic/albendazole.htm  |
| PDRhealth Link |
Not Available |
| Wikipedia Link |
http://en.wikipedia.org/wiki/Albendazole  |
| 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 | Download  |
| SDF File |
Show | Download  |
| PDB File |
Show | Download  |
| 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  |
| Interactions |
Show  |
| Drug Interactions |
Not Available
|
| Food Interactions |
Not Available
|
| Pathways |
Not Available
|
| General References |
- 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
]
- 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
]
- 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
]
- Haque A, Hollister WS, Willcox A, Canning EU: The antimicrosporidial activity of albendazole. J Invertebr Pathol. 1993 Sep;62(2):171-7. [PubMed
]
- Wikipedia

- RxList

|
| Organisms Affected |
- Helminthic Microorganisms
|
| Phase 1 Metabolizing Enzymes |
- Cytochrome P450 3A4 (CYP3A4)
|
| Targets |
- Tubulin alpha chain
- Tubulin beta-1 chain
|
|
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 |
|
| Target 1 Transmembrane Regions |
|
| Target 1 Essentiality |
Essential |
| Target 1 GenBank ID Protein |
159155  |
| Target 1 UniProtKB/Swiss-Prot ID |
P50719  |
| Target 1 UniProtKB/Swiss-Prot Entry Name |
TBA_HAECO  |
| Target 1 PDB ID |
1SA1  |
| Target 1 PDB File |
Show |
| Target 1 3D Structure |
|
| Target 1 Cellular Location |
|
| 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 |
- 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
]
|
| Target 1 Drug References |
- 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
]
|
|
Drug Target 2
[top]
|
| Target 2 ID |
4204 |
| Target 2 Name |
Tubulin beta-1 chain |
| Target 2 Synonyms |
- 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 |
|
| Target 2 Transmembrane Regions |
|
| Target 2 Essentiality |
Essential |
| Target 2 GenBank ID Protein |
Not Available |
| Target 2 UniProtKB/Swiss-Prot ID |
P18241  |
| Target 2 UniProtKB/Swiss-Prot Entry Name |
TBB1_BRUPA  |
| Target 2 PDB ID |
1SA1  |
| Target 2 PDB File |
Show |
| Target 2 3D Structure |
|
| Target 2 Cellular Location |
|
| 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 |
- 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
]
- 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
]
|
| Target 2 Drug References |
- 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
]
|