CAS 54965-21-8|methyl N-[5-(propylsulfanyl)-1H-1,3-benzodiazol-2-yl]carbamate|Methyl-5-[propylthio]-2-benzimidazole carbamate|albendazole|Albendazole|Zentel|Albenza|Eskazole|Albenza|Eskazole|methyl ...

General Information

Structure

Molecular Formula

C₁₂H₁₅N₃O₂S

Molecular Mass

265.3314

Exact Mass

265.08849774

Charge

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)

InChIKey

HXHWSAZORRCQMX-UHFFFAOYSA-N

Canonic Smiles

CCCSc1ccc2c(c1)[nH]c(n2)NC(=O)OC

Isomeric Smiles

S(c1cc2[nH]c(nc2cc1)NC(=O)OC)CCC

Calculated Properties

JChem

LogD (pH = 7.4)

3.20

LogD (pH = 5.5)

3.18

Log P

3.20

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

9.68

Polar Surface Area

67.01

Polarizability

29.11

Molar Refractivity

73.01

LOG S

-4.38

Data Source

Names and Identifiers

IUPAC name

methyl N-[5-(propylsulfanyl)-1H-1,3-benzodiazol-2-yl]carbamate methyl N-[6-(propylsulfanyl)-1H-1,3-benzodiazol-2-yl]carbamate

Synonyms

Methyl-5-[propylthio]-2-benzimidazole carbamateAlbendazoleAlbenzaEskazoleZentelAndazol)methyl (5-(propylthio)-1H-benzo[d]imidazol-2-yl)carbamateVermisenNSC 220008TobendBruzolVermizoleAndazolLoveralN-[6-(Propylthio)-1H-benzimidazol-2-yl]carbamic Acid Methyl EsterAtasolVermitanAshialbenValbazenProftril[5-(Propylthio)-1H-benzimidazol-2-yl]carbamic Acid Methyl EsterLurdex5-(丙硫基)-2-苯并咪唑氨基甲酸甲酯methyl N-[6-(propylsulfanyl)-1H-1,3-benzodiazol-2-yl]carbamateMethyl 5-(propylthio)-2-benzimidazolecarbamateAlbendazole阿苯达唑HelmintalBermosolAlbenMethyl 5-n-propylthio-2-benzimidazolecarbamatemethyl 5-propylthio-2-benzimidazolecarbamate(5-(propylthio)-1H-benzimidazol-2-yl)carbamic acid methyl esterProftrilO-methyl N-(5-(propylthio)-2-benzimidazolyl)carbamatealbendazolealbendazole5-(propylthio)-2-carbomethoxyaminobenzimidazoleZentelAlbendazoleValbazenAlbenzaEskazole

IUPAC Traditional name

albendazole albendazol methyl N-[5-(propylsulfanyl)-1H-1,3-benzodiazol-2-yl]carbamate albenza

Brand Name

ZentelAlbenzaEskazoleValbazen

API Name

Albendazole

Names and Identifiers

Registration numbers

PubChem CID

2082

PubChem SID

16096386346506472248908948144956

Medline Plus

DrugBank ID

CHEMBL

ATC CODE

EC Number

Chemspider ID

Wikipedia Title

CHEBI ID

16664CHEBI:2545CHEBI:16664CHEBI:13751CHEBI:22286

CAS Number

54965-21-8

Unique Ingredient Identifier

MDL Number

Merck Index

KEGG ID

MetaboLights Database

MTBLS2291MTBLS1455MTBLS379

EnzymePortal Database

P08684

UniProt Database

P9WLT1P9WFJ5P9WKW5P08684P9WKX7

MetaCyc Database

ALBENDAZOLE

Patent number

WO2006134466US2008255073US2008194694US2006222684US2004254182US2003105066US2007208134

NMRShiftDB Database

20207369

CompTox Database

DTXSID0022563

IntEnz Database

EC 1.14.14.74EC 1.14.13.32EC 1.14.14.73

BRENDA Database

2.7.2.31.14.13.322.5.1.182.7.4.91.14.14.731.14.14.741.13.12.51.14.13.8

Pesticides Database

albendazole

BindingDB Database

50241293

Rhea Database

RHEA:55924RHEA:10796RHEA:56288

BKMS React Database

SureChEMBL Database

Reaxys Registry

VSDB Database

PubMed Citation Links

221523962440370724411094

ACToR Database

54965-21-8

LINCS Database

LSM-3782

BRENDA Ligand Database

1438353447

SABIO-RK Database

3475

Drug Central Database

Beilstein Number

KEGG DRUG Database

HMDB Database

Registration numbers

Properties

Pharmacology Properties

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

DrugBank

DB00518

Drug Groups

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)

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.

Pharmacology

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.

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

Biotransformation

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.

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)

Half Life

Terminal elimination half-life ranges from 8 to 12 hours (single dose, 400mg).

Protein Binding

70% bound to plasma protein

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.

References

• 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]

• 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]

• 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]

• 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

• [Wikipedia]

• [RxList]

• [Drugs.com]

Selleck Chemicals

S1640

Research Area: Infection
Biological Activity:
Albendazole(Albenza) is a member of the benzimidazole compounds used as a drug indicated for the treatment of a variety of worm infestations. 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. [1]

MP Biomedicals

02193912

(Methyl-5-[propylthio]-2-benzimidazole carbamate)

Wikipedia

Albendazole

Sigma Aldrich

A4673

Biochem/physiol Actions
Binds to tubulin and inhibits microtubule assembly.1
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. A4673.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

TRC

A511610

An anthelmintic.

ChEBI

CHEBI:16664

A carbamate ester that is methyl 1H-benzimidazol-2-ylcarbamate substituted by a propylsulfanyl group at position 5. It is commonly used in the treatment of parasitic worm infestations.

Molecule Details

References

PubChem Literature

From Data Sources

• 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

• Haque A, Hollister WS, Willcox A, Canning EU: The antimicrosporidial activity of albendazole. J Invertebr Pathol. 1993 Sep;62(2):171-7. Pubmed

• http://en.wikipedia.org/wiki/Albendazole

• Sanderson, H., et al.: Toxicol. Lett., 187, 84 (2008)

• Zhao, Y., et al.: Org. Biomol. Chem., 6, 4509 (2008)

• Bochis, R.J. et al., J. Med. Chem., 1981, 24, 1518, (props)

• Firth, M., Int. Congr. Symp. Ser. R. Soc. Med., (Ed.), No. 61, 1984, (book)

• Archibald, L.K. et al., Quart. J. Med., 1993, 86, 191, (use)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, VAD000

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 38

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC name

methyl N-[5-(propylsulfanyl)-1H-1,3-benzodiazol-2-yl]carbamate methyl N-[6-(propylsulfanyl)-1H-1,3-benzodiazol-2-yl]carbamate

Synonyms

IUPAC Traditional name

albendazole albendazol methyl N-[5-(propylsulfanyl)-1H-1,3-benzodiazol-2-yl]carbamate albenza

Brand Name

ZentelAlbenzaEskazoleValbazen

API Name

Albendazole

Registration numbers

PubChem CID

2082

PubChem SID

16096386346506472248908948144956

Medline Plus

DrugBank ID

CHEMBL

ATC CODE

EC Number

Chemspider ID

Wikipedia Title

CHEBI ID

16664CHEBI:2545CHEBI:16664CHEBI:13751CHEBI:22286

CAS Number

54965-21-8

Unique Ingredient Identifier

MDL Number

Merck Index

KEGG ID

MetaboLights Database

MTBLS2291MTBLS1455MTBLS379

EnzymePortal Database

P08684

UniProt Database

P9WLT1P9WFJ5P9WKW5P08684P9WKX7

MetaCyc Database

ALBENDAZOLE

Patent number

WO2006134466US2008255073US2008194694US2006222684US2004254182US2003105066US2007208134

NMRShiftDB Database

20207369

CompTox Database

DTXSID0022563

IntEnz Database

EC 1.14.14.74EC 1.14.13.32EC 1.14.14.73

BRENDA Database

2.7.2.31.14.13.322.5.1.182.7.4.91.14.14.731.14.14.741.13.12.51.14.13.8

Pesticides Database

albendazole

BindingDB Database

50241293

Rhea Database

RHEA:55924RHEA:10796RHEA:56288

BKMS React Database

SureChEMBL Database

Reaxys Registry

VSDB Database

PubMed Citation Links

221523962440370724411094

ACToR Database

54965-21-8

LINCS Database

LSM-3782

BRENDA Ligand Database

1438353447

SABIO-RK Database

3475

Drug Central Database

Beilstein Number

KEGG DRUG Database

HMDB Database

Molecule Details

DB00518

Drug Groups

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)

Indication

Pharmacology

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.

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

Biotransformation

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)

Half Life

Terminal elimination half-life ranges from 8 to 12 hours (single dose, 400mg).

Protein Binding

70% bound to plasma protein

Elimination

References

• 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]

• 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

• [Wikipedia]

• [RxList]

• [Drugs.com]

Selleck Chemicals

S1640

MP Biomedicals

02193912

(Methyl-5-[propylthio]-2-benzimidazole carbamate)

A4673

A511610

An anthelmintic.

ChEBI

CHEBI:16664

A carbamate ester that is methyl 1H-benzimidazol-2-ylcarbamate substituted by a propylsulfanyl group at position 5. It is commonly used in the treatment of parasitic worm infestations.

Bioactivity

PubChem BioAssay

Properties

Pharmacology Properties

References

PubChem Literature

From Data Sources

• 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

• Haque A, Hollister WS, Willcox A, Canning EU: The antimicrosporidial activity of albendazole. J Invertebr Pathol. 1993 Sep;62(2):171-7. Pubmed

• http://en.wikipedia.org/wiki/Albendazole

• Sanderson, H., et al.: Toxicol. Lett., 187, 84 (2008)

• Zhao, Y., et al.: Org. Biomol. Chem., 6, 4509 (2008)

• Bochis, R.J. et al., J. Med. Chem., 1981, 24, 1518, (props)

• Firth, M., Int. Congr. Symp. Ser. R. Soc. Med., (Ed.), No. 61, 1984, (book)

• Archibald, L.K. et al., Quart. J. Med., 1993, 86, 191, (use)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, VAD000

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 38

Molecule

ID:400