SynCED: Albendazole

Record Information

Version

1.0

Creation Date

2009-07-30 17:58:36 UTC

Update Date

2026-05-14 16:41:00 UTC

Accession Number

CHEM002502

Identification

Common Name

Albendazole

Class

Small Molecule

Description

Albendazole is only found in individuals that have used or taken this drug. It is a benzimidazole broad-spectrum anthelmintic structurally related to mebendazole that is effective against many diseases. (From Martindale, The Extra Pharmacopoeia, 30th ed, p38). 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.

Contaminant Sources

EAFUS Chemicals
HMDB Contaminants - Urine
STOFF IDENT Compounds
Suspected Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amine
Anthelmintic
Anticestodal Agent
Antiprotozoal Agent
Drug
Ester
Ether
Human Neurotoxin
Metabolite
Organic Compound
Synthetic Compound
Tubulin Modulator

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(5-(Propylthio)-1H-benzimidazol-2-yl)carbamic acid methyl ester	ChEBI
5-(Propylthio)-2-carbomethoxyaminobenzimidazole	ChEBI
Albenza	ChEBI
Eskazole	ChEBI
O-Methyl N-(5-(propylthio)-2-benzimidazolyl)carbamate	ChEBI
Proftril	ChEBI
Valbazen	ChEBI
Zentel	ChEBI
(5-(Propylthio)-1H-benzimidazol-2-yl)carbamate methyl ester	Generator
O-Methyl N-(5-(propylthio)-2-benzimidazolyl)carbamic acid	Generator
Albendazole armstrong brand	HMDB
Albendazole diba brand	HMDB
Albendazole pfizer brand	HMDB
Albendoral	HMDB
Armstrong brand OF albendazole	HMDB
SK And F62979	HMDB
Albendazole sanicoopa brand	HMDB
Albendazole valdecasas brand	HMDB
Bendapar	HMDB
Digezanol	HMDB
Endoplus	HMDB
Fustery brand OF albendazole	HMDB
Hormona brand OF albendazole	HMDB
Liferpal brand OF albendazole	HMDB
Lurdex	HMDB
Mediamix V disthelm	HMDB
Metiazol	HMDB
Monohydrochloride, albendazole	HMDB
SK And F-62979	HMDB
Sanicoopa brand OF albendazole	HMDB
Albendazole fustery brand	HMDB
Gascop	HMDB
Noé-socopharm brand OF albendazole	HMDB
Pfizer brand OF albendazole	HMDB
SmithKline beecham brand OF albendazole	HMDB
V Disthelm, mediamix	HMDB
Albendazole hormona brand	HMDB
Albendazole liferpal brand	HMDB
Albendazole monohydrochloride	HMDB
Albendazole noé-socopharm brand	HMDB
Bilutac	HMDB
Diba brand OF albendazole	HMDB
Disthelm	HMDB
Disthelm, mediamix V	HMDB
Noé socopharm brand OF albendazole	HMDB
SK And F 62979	HMDB
Valdecasas brand OF albendazole	HMDB
Andazol	MeSH

Chemical Formula

C₁₂H₁₅N₃O₂S

Average Molecular Mass

265.331 g/mol

Monoisotopic Mass

265.088 g/mol

CAS Registry Number

54965-21-8

IUPAC Name

methyl N-[6-(propylsulfanyl)-1H-1,3-benzodiazol-2-yl]carbamate

Traditional Name

albendazol

SMILES

CCCSC1=CC2=C(C=C1)N=C(NC(=O)OC)N2

InChI Identifier

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)

InChI Key

HXHWSAZORRCQMX-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Substituents

2-benzimidazolylcarbamic acid ester
Aryl thioether
Thiophenol ether
Alkylarylthioether
Benzenoid
Azole
Imidazole
Carbamic acid ester
Heteroaromatic compound
Carbonic acid derivative
Thioether
Azacycle
Sulfenyl compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

carbamate ester (CHEBI:16664 )
benzimidazoles (CHEBI:16664 )
benzimidazolylcarbamate fungicide (CHEBI:16664 )
a small molecule (ALBENDAZOLE )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

anthelminthic drug

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White to off-white.

Experimental Properties

Property	Value
Melting Point	208-210°C
Boiling Point	Not Available
Solubility	Practically insoluble

Predicted Properties

Property	Value	Source
Water Solubility	0.023 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 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	73.01 m³·mol⁻¹	ChemAxon
Polarizability	29.3 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Toxicity Profile

Route of Exposure

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)

Mechanism of Toxicity

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.

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).

Toxicity Values

LD50: 1500 mg/kg (oral,mouse). [MSDS]

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

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.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Symptoms of overdose include elevated liver enzymes, headaches, hair loss, low levels of white blood cells (neutropenia), fever, and itching.

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID