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Identification
Name Albendazole
Accession Number DB00518 (APRD00782)
Type small molecule
Groups approved
Description

A benzimidazole broad-spectrum anthelmintic structurally related to mebendazole that is effective against many diseases. (From Martindale, The Extra Pharmacopoeia, 30th ed, p38)
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Salts Not Available
Brand names
Name Company
Albenza
Eskazole
Valbazen
Zentel
Brand mixtures Not Available
Categories
  • Anthelmintics
  • Anticestodal Agents
  • Antiprotozoal Agents
  • Tubulin Modulators
CAS number 54965-21-8
Weight Average: 265.331
Monoisotopic: 265.088497429
Chemical Formula C12H15N3O2S
InChI Key InChIKey=HXHWSAZORRCQMX-UHFFFAOYSA-N
InChI
InChI=1S/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)
Plain Text
IUPAC Name
methyl N-[6-(propylsulfanyl)-1H-1,3-benzodiazol-2-yl]carbamate
SMILES
CCCSC1=CC2=C(C=C1)N=C(NC(=O)OC)N2
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Benzimidazoles
Substructures
  • Ethers
  • Carbamates and Derivatives
  • Benzimidazoles
  • Benzene and Derivatives
  • Imidazoles
  • Heterocyclic compounds
  • Aromatic compounds
  • Cyanamides
Pharmacology
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.
Pharmacodynamics 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)
Volume of distribution Not Available
Protein binding 70% bound to plasma protein
Metabolism
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.

Important The metabolism module of DrugBank is currently in beta. Questions or suggestions? Please contact us.

Substrate Enzymes Product
Albendazole
    		albendazole sulfone Details
    Albendazole
      		albendazole sulfoxide Details
      Route of elimination Albendazole is 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. Urinary excretion of albendazole sulfoxide is a minor elimination pathway with less than 1% of the dose recovered in the urine. Biliary elimination presumably accounts for a portion of the elimination as evidenced by biliary concentrations of albendazole sulfoxide similar to those achieved in plasma.
      Half life Terminal elimination half-life ranges from 8 to 12 hours (single dose, 400mg).
      Clearance Not Available
      Toxicity Symptoms of overdose include elevated liver enzymes, headaches, hair loss, low levels of white blood cells (neutropenia), fever, and itching.
      Affected organisms
      • Helminthic Microorganisms
      Pathways Not Available
      Pharmacoeconomics
      Manufacturers
      • Glaxosmithkline llc
      Packagers
      Dosage forms
      Form Route Strength
      Tablet, film coated Oral
      Prices
      Unit description Cost Unit
      Albenza 200 mg tablet 1.91 USD tablet
      Albendazole powder 0.41 USD g
      DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
      Patents Not Available
      Properties
      State solid
      Experimental Properties
      Property Value Source
      melting point 209 °C PhysProp
      water solubility Practically insoluble Not Available
      logP 2.7 Not Available
      Predicted Properties
      Property Value Source
      water solubility 2.28e-02 g/l ALOGPS
      logP 3.22 ALOGPS
      logP 3.2 ChemAxon
      logS -4.1 ALOGPS
      pKa (strongest acidic) 9.51 ChemAxon
      pKa (strongest basic) 4.27 ChemAxon
      physiological charge 0 ChemAxon
      hydrogen acceptor count 3 ChemAxon
      hydrogen donor count 2 ChemAxon
      polar surface area 67.01 ChemAxon
      rotatable bond count 5 ChemAxon
      refractivity 73.01 ChemAxon
      polarizability 29.3 ChemAxon
      References
      Synthesis Reference Not Available
      General Reference
      1. 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
      2. 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
      3. 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
      4. Haque A, Hollister WS, Willcox A, Canning EU: The antimicrosporidial activity of albendazole. J Invertebr Pathol. 1993 Sep;62(2):171-7. Pubmed
      External Links
      Resource Link
      KEGG Drug D00134 Link_out
      KEGG Compound C01779 Link_out
      PubChem Compound 2082 Link_out
      PubChem Substance 46506472 Link_out
      ChemSpider 1998 Link_out
      BindingDB 50241293 Link_out
      ChEBI 16664 Link_out
      ChEMBL 16664 Link_out
      Therapeutic Targets Database DAP000951 Link_out
      PharmGKB PA164746058 Link_out
      HET ALW Link_out
      Drug Product Database 1904779 Link_out
      RxList http://www.rxlist.com/cgi/generic/albendazole.htm Link_out
      Drugs.com http://www.drugs.com/cdi/albendazole.html Link_out
      Wikipedia http://en.wikipedia.org/wiki/Albendazole Link_out
      ATC Codes
      • P02CA03
      AHFS Codes Not Available
      PDB Entries Not Available
      FDA label Not Available
      MSDS show (74.4 KB)
      Interactions
      Drug Interactions Not Available
      Food Interactions Not Available
      Targets

      1. Tubulin alpha-3 chain

      Pharmacological action: yes
      Actions: inhibitor

      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

      Organism class: human
      UniProt ID: Q71U36 Link_out
      Gene: TUBA1A Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      SNPs: SNPJam Report Link_out

      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
      2. Chu SW, Badar S, Morris DL, Pourgholami MH: Potent inhibition of tubulin polymerisation and proliferation of paclitaxel-resistant 1A9PTX22 human ovarian cancer cells by albendazole. Anticancer Res. 2009 Oct;29(10):3791-6. Pubmed
      3. 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-2C chain

      Pharmacological action: yes
      Actions: inhibitor

      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

      Organism class: human
      UniProt ID: P68371 Link_out
      Gene: TUBB2C Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      SNPs: SNPJam Report Link_out

      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
      2. Chu SW, Badar S, Morris DL, Pourgholami MH: Potent inhibition of tubulin polymerisation and proliferation of paclitaxel-resistant 1A9PTX22 human ovarian cancer cells by albendazole. Anticancer Res. 2009 Oct;29(10):3791-6. Pubmed
      3. 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

      3. Fumarate reductase flavoprotein subunit

      Pharmacological action: unknown
      Actions: inhibitor

      Catalyzes fumarate reduction using artificial electron donors such as methyl viologen. The physiological reductant is unknown, but evidence indicates that flavocytochrome c participates in electron transfer from formate to fumarate and possibly also to trimethylamine oxide (TMAO). This enzyme is essentially unidirectional

      Organism class: bacterial
      UniProt ID: P83223 Link_out
      Gene: SO_0970
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      SNPs: SNPJam Report Link_out

      References:
      1. Barrowman MM, Marriner SE, Bogan JA: The fumarate reductase system as a site of anthelmintic attack in Ascaris suum. Biosci Rep. 1984 Oct;4(10):879-83. Pubmed
      Enzymes

      1. Cytochrome P450 3A4

      Actions: substrate

      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 xenobiotics. The enzyme also hydroxylates etoposide

      UniProt ID: P08684 Link_out
      Gene: CYP3A4
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      SNPs: SNPJam Report Link_out

      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

      Actions: inducer

      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

      UniProt ID: P04798 Link_out
      Gene: CYP1A1 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      SNPs: SNPJam Report Link_out

      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

      3. Cytochrome P450 1A2

      Actions: substrate, inhibitor, inducer

      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. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen

      UniProt ID: P05177 Link_out
      Gene: CYP1A2
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      SNPs: SNPJam Report Link_out

      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

      Actions: inhibitor

      Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells

      UniProt ID: P08183 Link_out
      Gene: ABCB1 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      SNPs: SNPJam Report Link_out

      References:
      1. Merino G, Alvarez AI, Prieto JG, Kim RB: The anthelminthic agent albendazole does not interact with p-glycoprotein. Drug Metab Dispos. 2002 Apr;30(4):365-9. Pubmed
      Comments
      Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19