Identification

Name
Albendazole
Accession Number
DB00518  (APRD00782)
Type
Small Molecule
Groups
Approved, Vet 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
Synonyms
  • (5-(propylthio)-1H-benzimidazol-2-yl)carbamic acid methyl ester
  • 5-(propylthio)-2-carbomethoxyaminobenzimidazole
  • Albendazol
  • Albendazole
  • Albendazolum
  • Eskazole
  • O-methyl N-(5-(propylthio)-2-benzimidazolyl)carbamate
  • Proftril
External IDs
NSC-220008 / RS-8852 / SK&F-62979 / SKF 62979
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AlbenzaTablet, film coated200 mg/1OralAmedra Pharmaceuticals LLC1996-06-11Not applicableUs
AlbenzaTablet, film coated200 mg/1OralMckesson Rxpak Inc1996-06-11Not applicableUs
AlbenzaTablet, film coated200 mg/1OralImpax Specialty Pharma1996-06-11Not applicableUs
AlbenzaTablet, film coated200 mg/1OralDepartment Of State Health Services, Pharmacy Branch1996-06-11Not applicableUs
AlbenzaTablet, film coated200 mg/1OralCentral Texas Community Health Centers1996-06-11Not applicableUs
International/Other Brands
Abentel (Aristopharma) / ABZ (Indoco) / Acure (Pharmix) / Adazol (Roemmers) / AL (Radicura) / Band (Vensat) / Bandy (Mankind) / Bazole (Neutro Pharma) / Ben-A (Acme) / Benrod (Invision) / Bentil (Alliance) / Benzol (Mercury Lab) / Benzole (Flamingo Pharmacueticals) / Bevindazol (Vincenti) / Biwom (Zydus) / Bruzol (Bruluart) / Buxol (Buffington's) / Cental (Brisafarma) / Champs (CCM) / Ciclopar (Weider) / Cidazole (Juggat) / Clearworm (Invision) / Dalben (Krka) / Despar (Icofarma) / Eskazole (GlaxoSmithKline) / Valbazen / Zentel (GlaxoSmithKline) / Zolben (Sanofi-Aventis)
Categories
UNII
F4216019LN
CAS number
54965-21-8
Weight
Average: 265.331
Monoisotopic: 265.088497429
Chemical Formula
C12H15N3O2S
InChI Key
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

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.

Associated Conditions
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.

TargetActionsOrganism
ATubulin beta-2 chain
inhibitor
Pig roundworm
NTubulin alpha-1A chain
inhibitor
Human
NTubulin beta-4B chain
inhibitor
Human
UFumarate reductase flavoprotein subunit
inhibitor
Shewanella oneidensis (strain MR-1)
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.

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
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AbirateroneThe serum concentration of Albendazole can be increased when it is combined with Abiraterone.Approved
Acetyl sulfisoxazoleThe metabolism of Albendazole can be decreased when combined with Acetyl sulfisoxazole.Approved, Vet Approved
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Albendazole.Approved
AcetyldigoxinAcetyldigoxin may decrease the cardiotoxic activities of Albendazole.Experimental
AfatinibThe serum concentration of Afatinib can be increased when it is combined with Albendazole.Approved
AmiodaroneThe metabolism of Albendazole can be decreased when combined with Amiodarone.Approved, Investigational
AmodiaquineThe serum concentration of Albendazole can be decreased when it is combined with Amodiaquine.Approved, Investigational
AncestimThe risk or severity of cytotoxicity can be increased when Ancestim is combined with Albendazole.Approved, Investigational, Withdrawn
ApalutamideThe serum concentration of Albendazole can be decreased when it is combined with Apalutamide.Approved, Investigational
AprepitantThe serum concentration of Albendazole can be increased when it is combined with Aprepitant.Approved, Investigational
AtazanavirThe metabolism of Albendazole can be decreased when combined with Atazanavir.Approved, Investigational
AtomoxetineThe metabolism of Albendazole can be decreased when combined with Atomoxetine.Approved
AzithromycinThe metabolism of Albendazole can be decreased when combined with Azithromycin.Approved
BevacizumabBevacizumab may increase the cardiotoxic activities of Albendazole.Approved, Investigational
BoceprevirThe metabolism of Albendazole can be decreased when combined with Boceprevir.Approved, Withdrawn
BortezomibThe metabolism of Albendazole can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Albendazole can be decreased when it is combined with Bosentan.Approved, Investigational
BosutinibThe serum concentration of Bosutinib can be increased when it is combined with Albendazole.Approved
Brentuximab vedotinThe serum concentration of Brentuximab vedotin can be increased when it is combined with Albendazole.Approved, Investigational
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Albendazole.Approved
CaffeineThe metabolism of Albendazole can be decreased when combined with Caffeine.Approved
CarbamazepineThe serum concentration of the active metabolites of Albendazole can be reduced when Albendazole is used in combination with Carbamazepine resulting in a loss in efficacy.Approved, Investigational
CeritinibThe serum concentration of Albendazole can be increased when it is combined with Ceritinib.Approved
ChloroquineThe serum concentration of Albendazole can be decreased when it is combined with Chloroquine.Approved, Investigational, Vet Approved
CitalopramThe metabolism of Albendazole can be decreased when combined with Citalopram.Approved
ClarithromycinThe metabolism of Albendazole can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Albendazole can be decreased when combined with Clemastine.Approved, Investigational
ClotrimazoleThe metabolism of Albendazole can be decreased when combined with Clotrimazole.Approved, Vet Approved
CobicistatThe metabolism of Albendazole can be decreased when combined with Cobicistat.Approved
ColchicineThe serum concentration of Colchicine can be increased when it is combined with Albendazole.Approved
ConivaptanThe serum concentration of Conivaptan can be increased when it is combined with Albendazole.Approved, Investigational
CrizotinibThe metabolism of Albendazole can be decreased when combined with Crizotinib.Approved
CurcuminThe metabolism of Albendazole can be decreased when combined with Curcumin.Approved, Investigational
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Albendazole.Approved, Investigational
CyclosporineThe metabolism of Albendazole can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
CymarinCymarin may decrease the cardiotoxic activities of Albendazole.Experimental
Cyproterone acetateThe serum concentration of Albendazole can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
Dabigatran etexilateThe serum concentration of the active metabolites of Dabigatran etexilate can be increased when Dabigatran etexilate is used in combination with Albendazole.Approved
DabrafenibThe serum concentration of Albendazole can be decreased when it is combined with Dabrafenib.Approved, Investigational
DarunavirThe metabolism of Albendazole can be decreased when combined with Darunavir.Approved
DasatinibThe serum concentration of Albendazole can be increased when it is combined with Dasatinib.Approved, Investigational
DeferasiroxThe serum concentration of Albendazole can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe metabolism of Albendazole can be decreased when combined with Delavirdine.Approved
DeslanosideDeslanoside may decrease the cardiotoxic activities of Albendazole.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Albendazole.Approved, Investigational
DigoxinDigoxin may decrease the cardiotoxic activities of Albendazole.Approved
Digoxin Immune Fab (Ovine)Digoxin Immune Fab (Ovine) may decrease the cardiotoxic activities of Albendazole.Approved
DihydroergotamineThe metabolism of Albendazole can be decreased when combined with Dihydroergotamine.Approved, Investigational
DiltiazemThe metabolism of Albendazole can be decreased when combined with Diltiazem.Approved, Investigational
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Albendazole.Approved, Investigational
DosulepinThe metabolism of Albendazole can be decreased when combined with Dosulepin.Approved
DoxorubicinThe serum concentration of Doxorubicin can be increased when it is combined with Albendazole.Approved, Investigational
DoxycyclineThe metabolism of Albendazole can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe metabolism of Albendazole can be decreased when combined with Dronedarone.Approved
EdoxabanThe serum concentration of Edoxaban can be increased when it is combined with Albendazole.Approved
EnzalutamideThe serum concentration of Albendazole can be decreased when it is combined with Enzalutamide.Approved
ErythromycinThe metabolism of Albendazole can be decreased when combined with Erythromycin.Approved, Investigational, Vet Approved
EverolimusThe serum concentration of Everolimus can be increased when it is combined with Albendazole.Approved
FluconazoleThe metabolism of Albendazole can be decreased when combined with Fluconazole.Approved, Investigational
FluvoxamineThe metabolism of Albendazole can be decreased when combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe metabolism of Albendazole can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Albendazole can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe metabolism of Albendazole can be increased when combined with Fosphenytoin.Approved, Investigational
Fusidic AcidThe serum concentration of Albendazole can be increased when it is combined with Fusidic Acid.Approved, Investigational
GitoformateGitoformate may decrease the cardiotoxic activities of Albendazole.Experimental
HydroxychloroquineThe serum concentration of Albendazole can be decreased when it is combined with Hydroxychloroquine.Approved
IdelalisibThe metabolism of Albendazole can be decreased when combined with Idelalisib.Approved
ImatinibThe metabolism of Albendazole can be decreased when combined with Imatinib.Approved
IndinavirThe metabolism of Albendazole can be decreased when combined with Indinavir.Approved
IsavuconazoleThe serum concentration of Albendazole can be increased when it is combined with Isavuconazole.Approved, Investigational
IsavuconazoniumThe metabolism of Albendazole can be decreased when combined with Isavuconazonium.Approved, Investigational
IsradipineThe metabolism of Albendazole can be decreased when combined with Isradipine.Approved, Investigational
ItraconazoleThe metabolism of Albendazole can be decreased when combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Albendazole can be increased when it is combined with Ivacaftor.Approved
KetoconazoleThe metabolism of Albendazole can be decreased when combined with Ketoconazole.Approved, Investigational
Lanatoside CLanatoside C may decrease the cardiotoxic activities of Albendazole.Experimental
LedipasvirThe serum concentration of Ledipasvir can be increased when it is combined with Albendazole.Approved
LidocaineThe metabolism of Albendazole can be decreased when combined with Lidocaine.Approved, Vet Approved
LobeglitazoneThe metabolism of Albendazole can be decreased when combined with Lobeglitazone.Approved, Investigational
LopinavirThe metabolism of Albendazole can be decreased when combined with Lopinavir.Approved
LorpiprazoleThe serum concentration of Albendazole can be increased when it is combined with Lorpiprazole.Approved
LovastatinThe metabolism of Albendazole can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Albendazole can be increased when it is combined with Luliconazole.Approved
LumacaftorThe metabolism of Albendazole can be increased when combined with Lumacaftor.Approved
MetildigoxinMetildigoxin may decrease the cardiotoxic activities of Albendazole.Experimental
MexiletineThe metabolism of Albendazole can be decreased when combined with Mexiletine.Approved, Investigational
MidostaurinThe metabolism of Albendazole can be decreased when combined with Midostaurin.Approved, Investigational
MifepristoneThe serum concentration of Albendazole can be increased when it is combined with Mifepristone.Approved, Investigational
MitotaneThe serum concentration of Albendazole can be decreased when it is combined with Mitotane.Approved
NaloxegolThe serum concentration of Naloxegol can be increased when it is combined with Albendazole.Approved
NefazodoneThe metabolism of Albendazole can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Albendazole can be decreased when combined with Nelfinavir.Approved
NetupitantThe serum concentration of Albendazole can be increased when it is combined with Netupitant.Approved, Investigational
NevirapineThe metabolism of Albendazole can be increased when combined with Nevirapine.Approved
NilotinibThe metabolism of Albendazole can be decreased when combined with Nilotinib.Approved, Investigational
OlaparibThe metabolism of Albendazole can be decreased when combined with Olaparib.Approved
OleandrinOleandrin may decrease the cardiotoxic activities of Albendazole.Experimental, Investigational
OsimertinibThe serum concentration of Albendazole can be increased when it is combined with Osimertinib.Approved
OuabainOuabain may decrease the cardiotoxic activities of Albendazole.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Albendazole.Approved, Vet Approved
PalbociclibThe serum concentration of Albendazole can be increased when it is combined with Palbociclib.Approved, Investigational
PazopanibThe serum concentration of Pazopanib can be increased when it is combined with Albendazole.Approved
Peginterferon alfa-2bThe serum concentration of Albendazole can be increased when it is combined with Peginterferon alfa-2b.Approved
PentobarbitalThe metabolism of Albendazole can be increased when combined with Pentobarbital.Approved, Investigational, Vet Approved
PeruvosidePeruvoside may decrease the cardiotoxic activities of Albendazole.Experimental
PhenobarbitalThe serum concentration of the active metabolites of Albendazole can be reduced when Albendazole is used in combination with Phenobarbital resulting in a loss in efficacy.Approved, Investigational
PhenytoinThe serum concentration of the active metabolites of Albendazole can be reduced when Albendazole is used in combination with Phenytoin resulting in a loss in efficacy.Approved, Vet Approved
PitolisantThe serum concentration of Albendazole can be decreased when it is combined with Pitolisant.Approved, Investigational
PosaconazoleThe metabolism of Albendazole can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PrimaquineThe serum concentration of Albendazole can be decreased when it is combined with Primaquine.Approved
PrimidoneThe metabolism of Albendazole can be increased when combined with Primidone.Approved, Vet Approved
ProscillaridinProscillaridin may decrease the cardiotoxic activities of Albendazole.Experimental
PrucaloprideThe serum concentration of Prucalopride can be increased when it is combined with Albendazole.Approved
RanolazineThe serum concentration of Ranolazine can be increased when it is combined with Albendazole.Approved, Investigational
RifabutinThe metabolism of Albendazole can be increased when combined with Rifabutin.Approved, Investigational
RifampicinThe metabolism of Albendazole can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Albendazole can be increased when combined with Rifapentine.Approved, Investigational
RifaximinThe serum concentration of Rifaximin can be increased when it is combined with Albendazole.Approved, Investigational
RopiniroleThe metabolism of Albendazole can be decreased when combined with Ropinirole.Approved, Investigational
RucaparibThe metabolism of Albendazole can be decreased when combined with Rucaparib.Approved, Investigational
SaquinavirThe metabolism of Albendazole can be decreased when combined with Saquinavir.Approved, Investigational
SarilumabThe therapeutic efficacy of Albendazole can be decreased when used in combination with Sarilumab.Approved, Investigational
SildenafilThe metabolism of Albendazole can be decreased when combined with Sildenafil.Approved, Investigational
SilodosinThe serum concentration of Silodosin can be increased when it is combined with Albendazole.Approved
SiltuximabThe serum concentration of Albendazole can be decreased when it is combined with Siltuximab.Approved, Investigational
SimeprevirThe serum concentration of Albendazole can be increased when it is combined with Simeprevir.Approved
St. John's WortThe serum concentration of Albendazole can be decreased when it is combined with St. John's Wort.Approved, Investigational, Nutraceutical
StiripentolThe serum concentration of Albendazole can be increased when it is combined with Stiripentol.Approved
SulfisoxazoleThe metabolism of Albendazole can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
TafenoquineThe serum concentration of Albendazole can be decreased when it is combined with Tafenoquine.Approved, Investigational
TelaprevirThe metabolism of Albendazole can be decreased when combined with Telaprevir.Approved, Withdrawn
TelithromycinThe metabolism of Albendazole can be decreased when combined with Telithromycin.Approved
Tenofovir disoproxilThe metabolism of Albendazole can be decreased when combined with Tenofovir disoproxil.Approved, Investigational
TeriflunomideThe serum concentration of Albendazole can be decreased when it is combined with Teriflunomide.Approved
TheophyllineThe metabolism of Albendazole can be decreased when combined with Theophylline.Approved
TiclopidineThe metabolism of Albendazole can be decreased when combined with Ticlopidine.Approved
TocilizumabThe serum concentration of Albendazole can be decreased when it is combined with Tocilizumab.Approved
TopotecanThe serum concentration of Topotecan can be increased when it is combined with Albendazole.Approved, Investigational
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Albendazole.Approved, Investigational
VemurafenibThe serum concentration of Albendazole can be increased when it is combined with Vemurafenib.Approved
VenlafaxineThe metabolism of Albendazole can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Albendazole can be decreased when combined with Verapamil.Approved
VincristineThe excretion of Vincristine can be decreased when combined with Albendazole.Approved, Investigational
VoriconazoleThe metabolism of Albendazole can be decreased when combined with Voriconazole.Approved, Investigational
ZiprasidoneThe metabolism of Albendazole can be decreased when combined with Ziprasidone.Approved
ZucapsaicinThe metabolism of Albendazole can be decreased when combined with Zucapsaicin.Approved, Investigational
Food Interactions
Not 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 References
  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:17350811]
  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:11110097]
  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:11343808]
  4. Haque A, Hollister WS, Willcox A, Canning EU: The antimicrosporidial activity of albendazole. J Invertebr Pathol. 1993 Sep;62(2):171-7. [PubMed:8228321]
External Links
Human Metabolome Database
HMDB0014659
KEGG Drug
D00134
KEGG Compound
C01779
PubChem Compound
2082
PubChem Substance
46506472
ChemSpider
1998
BindingDB
50241293
ChEBI
16664
ChEMBL
CHEMBL1483
Therapeutic Targets Database
DAP000951
PharmGKB
PA164746058
HET
ALW
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Albendazole
ATC Codes
P02CA03 — Albendazole
MSDS
Download (74.4 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentHelminthiasis1
1, 2CompletedBasic ScienceCholera / Salmonella Typhi Infection1
2Active Not RecruitingTreatmentLymphatic Filariasis1
2CompletedTreatmentLymphatic Filariasis2
2CompletedTreatmentLymphatic Filariasis / Wuchereria Bancrofti Infection1
2Not Yet RecruitingTreatmentHelminthiasis1
2Not Yet RecruitingTreatmentHookworm Infections / Trichuriasis1
2Not Yet RecruitingTreatmentTrichuris Infection1
2RecruitingPreventionHookworm Infections1
2, 3CompletedTreatmentAnemias / Helminthiasis / Tinea Capitis1
2, 3CompletedTreatmentEpilepsies / Neurocysticercosis1
2, 3CompletedTreatmentLymphatic Filariasis / Plasmodium Infections1
2, 3Not Yet RecruitingTreatmentTrichuriasis1
3Active Not RecruitingTreatmentToxocariasis1
3CompletedPreventionHealthy Volunteers1
3CompletedPreventionOnchocerciasis1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV)1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Protozoan Infections1
3CompletedTreatmentNeurocysticercosis3
3RecruitingTreatmentModerate Acute Malnutrition (MAM)1
3RecruitingTreatmentNeurocysticercosis1
3Unknown StatusTreatmentChronic Strongyloidiasis1
3WithdrawnTreatmentSubarachnoid Cysticercosis1
4CompletedPreventionIntestinal Diseases, Parasitic1
4CompletedPreventionVillage Children1
4CompletedTreatmentAnemias / Worm Infections1
4CompletedTreatmentAscariasis / Trichuriasis1
4CompletedTreatmentFilarial; Infestation1
4CompletedTreatmentHelminthiasis / Intestinal Diseases1
4CompletedTreatmentHookworm Infection1
4CompletedTreatmentInfection by Trichuris Trichiura1
4CompletedTreatmentInfections With Soil-Transmitted Helminths (STH)1
4CompletedTreatmentLymphatic Filariasis1
4CompletedTreatmentPeriodontitis, Chronic1
4Not Yet RecruitingDiagnosticHelminth Infection1
4Not Yet RecruitingTreatmentFilariasis / Helminthiasis1
4RecruitingPreventionTrachoma1
4RecruitingTreatmentDisease Transmission, Infectious / Helminthiasis / Nematode Infection1
4WithdrawnNot AvailableLymphatic Filariasis / Trachoma1
4WithdrawnTreatmentDiarrhea / Intestinal Helminthiasis1
Not AvailableActive Not RecruitingPreventionLymphatic Filariasis1
Not AvailableCompletedNot AvailableLymphatic Filariasis / Soil Transmitted Helminth Infections1
Not AvailableCompletedPreventionAnemias / Hepatosplenomegaly / Plasmodium Infections1
Not AvailableCompletedPreventionSoil Transmitted Helminths1
Not AvailableCompletedPreventionVisceral Leishmaniasis1
Not AvailableCompletedSupportive CareTuberculosis1
Not AvailableCompletedTreatmentAbdominal Pain (AP) / Lymphoedema / Mansonelliasis / Pruritus1
Not AvailableCompletedTreatmentAscariasis / Hookworm / Intestinal Helminthiasis / Plasmodium Infections1
Not AvailableCompletedTreatmentBacterial Diseases / Parasitic Diseases1
Not AvailableCompletedTreatmentCysticercosis / Epilepsies1
Not AvailableCompletedTreatmentEnteropathy1
Not AvailableCompletedTreatmentEnvironmental Enteropathy1
Not AvailableCompletedTreatmentHelminthiasis1
Not AvailableCompletedTreatmentHelminthiasis / Human Immunodeficiency Virus (HIV) Infections2
Not AvailableCompletedTreatmentMalnutrition1
Not AvailableCompletedTreatmentParasitic Diseases3
Not AvailableRecruitingTreatmentMalnutrition in Pregnancy / Nutrition Disorders / Pregnancy / Stunting1
Not AvailableTerminatedTreatmentHelminthiasis / Human Immunodeficiency Virus (HIV) Infections1
Not AvailableTerminatedTreatmentLymphatic Filariasis1
Not AvailableUnknown StatusPreventionAnemias / Hematologic Diseases / Infection, Human Immunodeficiency Virus I / Intestinal Helminthiasis / Intestinal Schistosomiasis / Opportunistic Infections1
Not AvailableUnknown StatusTreatmentAbdominal Pain (AP) / Bloating / Chronic Functional Diarrhea1
Not AvailableUnknown StatusTreatmentAnemias / Exercise Tolerance / Hookworm Stool Burden1
Not AvailableUnknown StatusTreatmentHelminthiasis / Strongyloides Stercoralis Infection1
Not AvailableWithdrawnTreatmentKwashiorkor / Marasmus1

Pharmacoeconomics

Manufacturers
  • Glaxosmithkline llc
Packagers
  • GlaxoSmithKline Inc.
  • Medisca Inc.
  • Southwood Pharmaceuticals
Dosage forms
FormRouteStrength
Tablet, film coatedOral200 mg/1
Prices
Unit descriptionCostUnit
Albenza 200 mg tablet1.91USD tablet
Albendazole powder0.41USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)208-210Gyurik, 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 Solubility0.0228 mg/mLALOGPS
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
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9944
Blood Brain Barrier+0.9381
Caco-2 permeable-0.8957
P-glycoprotein substrateNon-substrate0.6637
P-glycoprotein inhibitor INon-inhibitor0.6928
P-glycoprotein inhibitor IINon-inhibitor0.6089
Renal organic cation transporterNon-inhibitor0.8433
CYP450 2C9 substrateNon-substrate0.7742
CYP450 2D6 substrateSubstrate0.8918
CYP450 3A4 substrateNon-substrate0.6147
CYP450 1A2 substrateInhibitor0.9106
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8347
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8037
Ames testNon AMES toxic0.7894
CarcinogenicityNon-carcinogens0.9334
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.0752 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9707
hERG inhibition (predictor II)Non-inhibitor0.8549
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0zg0-1469000000-46c2b274ef14c131df22
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00dl-2920000000-8bfa1e52a364c2e1f3ac
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-01q9-0090000000-672ce5296af7aee8b705
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-001i-0390000000-5714d326ce05257dd82d
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-000i-0910000000-e659044fe535a4187c4c
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-000i-0900000000-a1c7141f3f860d69dca2
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-000i-0900000000-96ae063a35ee4fe53390
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-052r-2900000000-6103a7173b7b7689ee52
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0a4i-9600000000-7a4cee3070ee6f08b2cb
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0a4i-9200000000-109010056dd851a50ae4
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0a4i-9000000000-9f06e0952a63ae1312b3
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-001r-0790000000-8ba2b09e2eefe111496f
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-001i-0290000000-db0e07ed437380dd7f56
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0006-0910000000-80dd825626a5009e8924
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-052f-0900000000-ea3849a4ab993b24b4f0
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-014i-0090000000-fe82219d2c01efc3494d
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00lr-0090000000-6d1f652e7ecf943d7400
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-001i-0190000000-ab8f5993bbc5ebfcb04c
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-000x-0950000000-0c5ca5956802aa312e11
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0006-0900000000-02e757b669a99db25608
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-052f-0900000000-bef5aa7a328477b1c279
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a59-1900000000-e6bb8973c619c5c8931f
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0kx3-7900000000-1fd9a63d8e217dc205d8
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-004i-9300000000-d2ee5fa2f7585c731f11
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-001i-0090000000-d55bfd9a35890c748e63
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00lu-1590000000-c9fb90d6fb5c5eef928a
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0006-2920000000-16dde7ebb8b5e3dc144e
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00lr-0190000000-e151fe2dd28c96284d59
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as 2-benzimidazolylcarbamic acid esters. These are aromatic heteropolycyclic compounds that contain a carbamic acid ester group, which is N-linked to the C2-atom of a benzimidazole moiety.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzimidazoles
Sub Class
2-benzimidazolylcarbamic acid esters
Direct Parent
2-benzimidazolylcarbamic acid esters
Alternative Parents
Thiophenol ethers / Alkylarylthioethers / Imidazoles / Heteroaromatic compounds / Carbamate esters / Organic carbonic acids and derivatives / Sulfenyl compounds / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds
show 3 more
Substituents
2-benzimidazolylcarbamic acid ester / Aryl thioether / Thiophenol ether / Alkylarylthioether / Benzenoid / Azole / Imidazole / Carbamic acid ester / Heteroaromatic compound / Carbonic acid derivative
show 13 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
carbamate ester, benzimidazoles, benzimidazolylcarbamate fungicide (CHEBI:16664) / a small molecule (ALBENDAZOLE)

Targets

Kind
Protein
Organism
Pig roundworm
Pharmacological action
Yes
Actions
Inhibitor
General Function
Structural constituent of cytoskeleton
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.
Gene Name
Not Available
Uniprot ID
F1L7U3
Uniprot Name
Tubulin beta-2 chain
Molecular Weight
51336.46 Da
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:11980387]
Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Inhibitor
General 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.
Specific Function
Gtp binding
Gene Name
TUBA1A
Uniprot ID
Q71U36
Uniprot Name
Tubulin alpha-1A chain
Molecular Weight
50135.25 Da
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:11343808]
  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:19846910]
  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:10592235]
Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Inhibitor
General Function
Unfolded protein binding
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.
Gene Name
TUBB4B
Uniprot ID
P68371
Uniprot Name
Tubulin beta-4B chain
Molecular Weight
49830.72 Da
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:11980387]
  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:19846910]
  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:10592235]
Kind
Protein
Organism
Shewanella oneidensis (strain MR-1)
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Succinate dehydrogenase activity
Specific Function
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...
Gene Name
Not Available
Uniprot ID
P83223
Uniprot Name
Fumarate reductase flavoprotein subunit
Molecular Weight
62447.475 Da
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:6518278]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
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 react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Vitamin d 24-hydroxylase activity
Specific Function
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 un...
Gene Name
CYP1A1
Uniprot ID
P04798
Uniprot Name
Cytochrome P450 1A1
Molecular Weight
58164.815 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
Inducer
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
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 un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
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:11901088]

Drug created on June 13, 2005 07:24 / Updated on August 02, 2018 04:22