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Identification
NameAlbendazole
Accession NumberDB00518  (APRD00782)
Typesmall molecule
Groupsapproved
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
Synonyms
SynonymLanguageCode
AlbendazolGermanINN
AlbendazolSpanishINN
AlbendazoleFrenchINN
AlbendazolumLatinINN
RicobendazoleNot AvailableIS
RycobendazoleNot AvailableIS
SaltsNot Available
Brand names
NameCompany
AbentelAristopharma
ABZIndoco
AcurePharmix
AdazolRoemmers
ALRadicura
AlbenzaCorePharma
BandVensat
BandyMankind
BazoleNeutro Pharma
Ben-AAcme
BenrodInvision
BentilAlliance
BenzolMercury Lab
BenzoleFlamingo Pharmacueticals
BevindazolVincenti
BiwomZydus
BruzolBruluart
BuxolBuffington's
CentalBrisafarma
ChampsCCM
CicloparWeider
CidazoleJuggat
ClearwormInvision
DalbenKrka
DesparIcofarma
EskazoleGlaxoSmithKline
ZentelGlaxoSmithKline
ZolbenSanofi-Aventis
Brand mixtures
Brand NameIngredients
Albazio PlusAlbendazole and Ivermectin
Benrod-IAlbendazole and Ivermectin
C CobistalAlbendazole and Secnidazole
CategoriesNot Available
CAS number54965-21-8
WeightAverage: 265.331
Monoisotopic: 265.088497429
Chemical FormulaC12H15N3O2S
InChI KeyInChIKey=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)
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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassBenzimidazoles
SubclassNot Available
Direct parentBenzimidazoles
Alternative parentsAminoimidazoles; Benzene and Substituted Derivatives; Carbamic Acids and Derivatives; Ethers; Polyamines; Thioethers
Substituentsaminoimidazole; benzene; azole; imidazole; carbamic acid derivative; thioether; polyamine; ether; amine; organonitrogen compound
Classification descriptionThis compound belongs to the benzimidazoles. These are organic compounds containing a benzene ring fused to an imidazole ring (five member ring containing a nitrogen atom, 4 carbon atoms, and two double bonds).
Pharmacology
IndicationFor 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.
PharmacodynamicsAlbendazole 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 actionAlbendazole 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.
AbsorptionPoorly 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 distributionNot Available
Protein binding70% 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.

SubstrateEnzymesProduct
Albendazole
    albendazole sulfoneDetails
    Albendazole
      albendazole sulfoxideDetails
      Route of eliminationAlbendazole 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 lifeTerminal elimination half-life ranges from 8 to 12 hours (single dose, 400mg).
      ClearanceNot Available
      ToxicitySymptoms 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
      ADMET
      Predicted ADMET features
      Property Value Probability
      Human Intestinal Absorption + 0.9944
      Blood Brain Barrier + 0.9381
      Caco-2 permeable - 0.8957
      P-glycoprotein substrate Non-substrate 0.6637
      P-glycoprotein inhibitor I Non-inhibitor 0.6928
      P-glycoprotein inhibitor II Non-inhibitor 0.6089
      Renal organic cation transporter Non-inhibitor 0.8433
      CYP450 2C9 substrate Non-substrate 0.7742
      CYP450 2D6 substrate Substrate 0.8918
      CYP450 3A4 substrate Non-substrate 0.6147
      CYP450 1A2 substrate Inhibitor 0.9106
      CYP450 2C9 substrate Non-inhibitor 0.907
      CYP450 2D6 substrate Non-inhibitor 0.9231
      CYP450 2C19 substrate Non-inhibitor 0.9025
      CYP450 3A4 substrate Non-inhibitor 0.8347
      CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8037
      Ames test Non AMES toxic 0.7894
      Carcinogenicity Non-carcinogens 0.9334
      Biodegradation Not ready biodegradable 1.0
      Rat acute toxicity 2.0752 LD50, mol/kg Not applicable
      hERG inhibition (predictor I) Weak inhibitor 0.9707
      hERG inhibition (predictor II) Non-inhibitor 0.8549
      Pharmacoeconomics
      Manufacturers
      • Glaxosmithkline llc
      Packagers
      Dosage forms
      FormRouteStrength
      Tablet, film coatedOral
      Prices
      Unit descriptionCostUnit
      Albenza 200 mg tablet1.91USDtablet
      Albendazole powder0.41USDg
      DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
      PatentsNot Available
      Properties
      Statesolid
      Experimental Properties
      PropertyValueSource
      melting point208-210Gyurik, R.J. and Theodorides, VJ.; US. Patent 3,915,986; October 28,1975; assigned to Smith Kline Corp.
      water solubilityPractically insolubleNot Available
      logP2.7Not Available
      Predicted Properties
      PropertyValueSource
      water solubility2.28e-02 g/lALOGPS
      logP3.22ALOGPS
      logP3.2ChemAxon
      logS-4.1ALOGPS
      pKa (strongest acidic)9.51ChemAxon
      pKa (strongest basic)4.27ChemAxon
      physiological charge0ChemAxon
      hydrogen acceptor count3ChemAxon
      hydrogen donor count2ChemAxon
      polar surface area67.01ChemAxon
      rotatable bond count5ChemAxon
      refractivity73.01ChemAxon
      polarizability29.3ChemAxon
      number of rings2ChemAxon
      bioavailability1ChemAxon
      rule of fiveYesChemAxon
      Ghose filterYesChemAxon
      Veber's ruleNoChemAxon
      MDDR-like ruleNoChemAxon
      Spectra
      SpectraNot Available
      References
      Synthesis Reference

      Gyurik, R.J. and Theodorides, VJ.; US. Patent 3,915,986; October 28,1975; assigned to
      Smith Kline Corp.

      US3915986
      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
      ResourceLink
      KEGG DrugD00134
      KEGG CompoundC01779
      PubChem Compound2082
      PubChem Substance46506472
      ChemSpider1998
      BindingDB50241293
      ChEBI16664
      ChEMBLCHEMBL1483
      Therapeutic Targets DatabaseDAP000951
      PharmGKBPA164746058
      HETALW
      Drug Product Database1904779
      RxListhttp://www.rxlist.com/cgi/generic/albendazole.htm
      Drugs.comhttp://www.drugs.com/cdi/albendazole.html
      WikipediaAlbendazole
      ATC CodesP02CA03
      AHFS CodesNot Available
      PDB EntriesNot Available
      FDA labelNot Available
      MSDSshow(74.4 KB)
      Interactions
      Drug InteractionsNot Available
      Food InteractionsNot Available

      1. Tubulin beta-2 chain

      Kind: protein

      Organism: Pig roundworm

      Pharmacological action: yes

      Actions: inhibitor

      Components

      Name UniProt ID Details
      Tubulin beta-2 chain F1L7U3 Details

      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. Tubulin alpha-1A chain

      Kind: protein

      Organism: Human

      Pharmacological action: no

      Actions: inhibitor

      Components

      Name UniProt ID Details
      Tubulin alpha-1A chain Q71U36 Details

      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

      3. Tubulin beta-4B chain

      Kind: protein

      Organism: Human

      Pharmacological action: no

      Actions: inhibitor

      Components

      Name UniProt ID Details
      Tubulin beta-4B chain P68371 Details

      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

      4. Fumarate reductase flavoprotein subunit

      Kind: protein

      Organism: Shewanella oneidensis (strain MR-1)

      Pharmacological action: unknown

      Actions: inhibitor

      Components

      Name UniProt ID Details
      Fumarate reductase flavoprotein subunit P83223 Details

      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

      1. Cytochrome P450 3A4

      Kind: protein

      Organism: Human

      Pharmacological action: unknown

      Actions: substrate

      Components

      Name UniProt ID Details
      Cytochrome P450 3A4 P08684 Details

      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

      Kind: protein

      Organism: Human

      Pharmacological action: unknown

      Actions: inducer

      Components

      Name UniProt ID Details
      Cytochrome P450 1A1 P04798 Details

      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

      Kind: protein

      Organism: Human

      Pharmacological action: unknown

      Actions: substrate inhibitor inducer

      Components

      Name UniProt ID Details
      Cytochrome P450 1A2 P05177 Details

      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

      1. Multidrug resistance protein 1

      Kind: protein

      Organism: Human

      Pharmacological action: unknown

      Actions: inhibitor

      Components

      Name UniProt ID Details
      Multidrug resistance protein 1 P08183 Details

      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 March 27, 2014 11:11