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

• ChemBase ID: 400
• Molecular Formular: C12H15N3O2S
• Molecular Mass: 265.3314
• Monoisotopic Mass: 265.08849774
• SMILES: S(c1cc2[nH]c(nc2cc1)NC(=O)OC)CCC
• Canonical SMILES: CCCSc1ccc2c(c1)[nH]c(n2)NC(=O)OC
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl N-[6-(propylsulfanyl)-1H-1,3-benzodiazol-2-yl]carbamate; methyl N-[5-(propylsulfanyl)-1H-1,3-benzodiazol-2-yl]carbamate
• IUPAC Traditional name: albendazol; albendazole; methyl N-[5-(propylsulfanyl)-1H-1,3-benzodiazol-2-yl]carbamate
• Brand Name: Albenza; Valbazen; Eskazole; Zentel
• Synonyms: Methyl 5-(propylthio)-2-benzimidazolecarbamate; Albendazole; Albendazole; Alben; Bermosol; Helmintal; methyl N-[6-(propylsulfanyl)-1H-1,3-benzodiazol-2-yl]carbamate; Methyl 5-n-propylthio-2-benzimidazolecarbamate; methyl 5-propylthio-2-benzimidazolecarbamate; Albenza; Eskazole; Zentel; Andazol); methyl (5-(propylthio)-1H-benzo[d]imidazol-2-yl)carbamate; Methyl-5-[propylthio]-2-benzimidazole carbamate; N-[6-(Propylthio)-1H-benzimidazol-2-yl]carbamic Acid Methyl Ester; [5-(Propylthio)-1H-benzimidazol-2-yl]carbamic Acid Methyl Ester; Andazol; Ashialben; Atasol; Bruzol; Loveral; Lurdex; Proftril; Valbazen; NSC 220008; Tobend; Vermisen; Vermitan; Vermizole; 5-(丙硫基)-2-苯并咪唑氨基甲酸甲酯; 阿苯达唑

Database IDs

• CAS Number: 54965-21-8
• EC Number: 259-414-7
• MDL Number: MFCD00083232
• Merck Index: 14210
• PubChem SID: 24890894; 160963863; 46506472
• PubChem CID: 2082
• CHEBI ID: 16664
• ATC CODE: P02CA03; QP52AC11
• CHEMBL: 1483
• Chemspider ID: 1998
• DrugBank ID: DB00518
• KEGG ID: D00134
• Unique Ingredient Identifier: F4216019LN
• Wikipedia Title: Albendazole
• Medline Plus: a610019

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.681593
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.183769
• LogD (pH = 7.4): 3.2022638
• Log P: 3.204525
• Molar Refractivity: 73.0091 cm^3
• Polarizability: 28.787241 Å^3
• Polar Surface Area: 67.01 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.22
• LOG S: -4.07
• Solubility (Water): 2.28e-02 g/l

PROPERTIES

Physical Property

• Solubility: DMSO; Practically insoluble
• Apperance: White Solid
• Melting Point: 208-210°C; 215 - 217°C
• Hydrophobicity(logP): 2.7; 3.461

Safety Information

• Storage Condition: -20°C; -20°C Freezer; Room Temperature (15-30°C)
• RTECS: FD1100000
• European Hazard Symbols: Toxic (T); Harmful (Xn)
• German water hazard class: 2
• Risk Statements: 48/22; 61
• Safety Statements: 53-20-36-45
• TSCA Listed: 否
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H360-H302; H373
• GHS Precautionary statements: P281-P264-P301+P312-P308+P313-P405-P501A
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Admin Routes: only oral route
• Half Life: About 8.5 h
• Metabolism: oxidation of sulfur atom to sulfoxide, the active metabolite
• Legal Status: prescription
• Pregnancy Category: D
• Mechanism of Action: Causes degenerative alterations in the tegument and intestinal cells of the worm by binding to the colchicine-sensitive site of tubulin,; 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),; Due to diminished energy production, the parasite is immobilized and eventually dies; 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.; thus inhibiting its polymerization or assembly into microtubules.; which is the energy required for the survival of the helminth.

Product Information

• Purity: ≥98%; 95%; 97%; 98+%
• Salt Data: Free Base
• Application(s): Anthelmintic.; Investigated for treatment of chronic stronglyoidiasis, and for microsporidiosis in AIDS patients
• Empirical Formula (Hill Notation): C12H15N3O2S

DETAILS

MP Biomedicals - 02193912

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

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]

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.

Toronto Research Chemicals - A511610

An anthelmintic.

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
• http://en.wikipedia.org/wiki/Albendazole
• Zhao, Y., et al.: Org. Biomol. Chem., 6, 4509 (2008)
• Sanderson, H., et al.: Toxicol. Lett., 187, 84 (2008)
• U.S. Pat., 1975, SmithKline, 3 915 986; CA, 84, 31074r, (synth, pharmacol)
• Theodorides, V.J. et al., Experientia, 1976, 32, 702, (pharmacol)
• Bogan, J.A., Drugs of Today (Barcelona), 1979, 15, 87, (rev)
• Gyurik, R.J. et al., Drug Metab. Dispos., 1981, 9, 503, (metab)
• 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)
• Delatour, P. et al., Xenobiotica, 1991, 21, 217, (metab)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 38
• Archibald, L.K. et al., Quart. J. Med., 1993, 86, 191, (use)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 2970, (synonyms)
• Oldfield, E.C., Am. J. Gastroenterol., 1995, 90, 159, (use)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, VAD000