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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
(5-(Propylthio)-1H-benzimidazol-2-yl)carbamic acid methyl esterNot AvailableNot Available
5-(Propylthio)-2-carbomethoxyaminobenzimidazoleNot AvailableNot Available
AlbendazolGermanINN
AlbendazolSpanishINN
AlbendazoleFrenchINN
AlbendazolumLatinINN
AlbenzaNot AvailableNot Available
EskazoleNot AvailableNot Available
O-Methyl N-(5-(propylthio)-2-benzimidazolyl)carbamateNot AvailableNot Available
ProftrilNot AvailableNot Available
RicobendazoleNot AvailableIS
RycobendazoleNot AvailableIS
ValbazenNot AvailableNot Available
ZentelNot AvailableNot Available
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 KeyHXHWSAZORRCQMX-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
Not Available
albendazole sulfoneDetails
Albendazole
Not Available
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 Solubility0.0228ALOGPS
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 Area67.01 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity73.01 m3·mol-1ChemAxon
Polarizability29.3 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra1D NMR
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

Targets

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

Enzymes

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

Transporters

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

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Drug created on June 13, 2005 07:24 / Updated on March 27, 2014 11:11