Bovine Metabolome Database: Showing metabocard for Albendazole (BMDB0109650)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2020-05-05 15:49:08 UTC

Update Date

2020-05-05 18:38:56 UTC

BMDB ID

BMDB0109650

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Albendazole

Description

Albendazole, also known as albenza or SK and F62979, 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. Albendazole is a drug which is used 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. Albendazole is a strong basic compound (based on its pKa). Albendazole exists in all living organisms, ranging from bacteria to humans. In humans, albendazole is involved in tamoxifen metabolism pathway. Albendazole is a potentially toxic compound. Symptoms of overdose include elevated liver enzymes, headaches, hair loss, low levels of white blood cells (neutropenia), fever, and itching. Albendazole causes degenerative alterations in the tegument and intestinal cells of the worm by diminishing its energy production, ultimately leading to immobilization and death of the parasite. 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. 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.

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 Weight

265.331

Monoisotopic Molecular Weight

265.088497429

IUPAC Name

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

Traditional Name

albendazol

CAS Registry Number

Not Available

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 )

Ontology

Status

Detected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0zg0-1469000000-46c2b274ef14c131df22	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00dl-2920000000-8bfa1e52a364c2e1f3ac	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0zg0-1469000000-46c2b274ef14c131df22	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00dl-2920000000-8bfa1e52a364c2e1f3ac	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00vl-3960000000-6405beb97aaf7baeef1e	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-01q9-0090000000-672ce5296af7aee8b705	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-001i-0390000000-5714d326ce05257dd82d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-000i-0910000000-e659044fe535a4187c4c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-000i-0900000000-a1c7141f3f860d69dca2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-000i-0900000000-96ae063a35ee4fe53390	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-052r-2900000000-6103a7173b7b7689ee52	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0a4i-9600000000-7a4cee3070ee6f08b2cb	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0a4i-9200000000-109010056dd851a50ae4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0a4i-9000000000-9f06e0952a63ae1312b3	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-001r-0790000000-8ba2b09e2eefe111496f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-001i-0290000000-db0e07ed437380dd7f56	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0006-0910000000-80dd825626a5009e8924	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-052f-0900000000-ea3849a4ab993b24b4f0	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-014i-0090000000-fe82219d2c01efc3494d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-00lr-0090000000-6d1f652e7ecf943d7400	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-001i-0190000000-ab8f5993bbc5ebfcb04c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-000x-0950000000-0c5ca5956802aa312e11	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0006-0900000000-02e757b669a99db25608	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-052f-0900000000-bef5aa7a328477b1c279	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0uxr-1190000000-b3b5e0c1c81c186e0323	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a6u-6390000000-49710f98d2607932e74d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01vo-6920000000-f7a76ee929303af68012	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-06si-5390000000-662c83573e8207d72065	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-5960000000-7fffbfea1f1e67fdbb9c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01rx-9610000000-014e3ec45924170b49d0	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100.40 MHz, DMSO-d6, experimental)	Not Available	View in JSpectraViewer