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 ...

基本信息

化学结构

分子式

C₁₂H₁₅N₃O₂S

分子量

265.3314

精确质量

265.08849774

电荷

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

计算属性

JChem

LogD (pH = 7.4)

3.20

LogD (pH = 5.5)

3.18

Log P

3.20

可自由旋转的化学键

质子供体

质子受体

里宾斯基五规则

true

Acid pKa

9.68

极化表面积

67.01

极化性

29.11

摩尔折射率

73.01

LOG S

-4.38

数据来源

名称和标识

IUPAC标准名

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

别名

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传统名

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

商标名

ZentelAlbenzaEskazoleValbazen

API名称

Albendazole

名称和标识

数据登录号

PubChem CID

2082

PubChem SID

16096386346506472248908948144956

Medline Plus

DrugBank ID

CHEMBL

ATC码

EC号

Chemspider ID

维基百科标题

CHEBI ID

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

CAS号

美国药典/FDA物质标识码

KEGG ID

MDL号

默克索引号

PubMed文献链接

244037072441109422152396

BRENDA数据库

1.13.12.51.14.14.741.14.14.731.14.13.321.14.13.82.5.1.182.7.4.92.7.2.3

专利号

US2006222684US2004254182US2008194694US2008255073WO2006134466US2003105066US2007208134

KEGG DRUG Database

ACToR数据库

BKMS React数据库

VSDB Database

UniProt数据库

P9WLT1P08684P9WKX7P9WFJ5P9WKW5

Rhea数据库

RHEA:10796RHEA:56288RHEA:55924

MetaboLights数据库

MTBLS2291MTBLS1455MTBLS379

Drug Central Database

Beilstein号

Reaxys Registry

SABIO-RK数据库

IntEnz数据库

EC 1.14.13.32EC 1.14.14.74EC 1.14.14.73

EnzymePortal数据库

CompTox数据库

SureChEMBL数据库

Pesticides数据库

BindingDB数据库

LINCS数据库

MetaCyc数据库

BRENDA Ligand数据库

HMDB数据库

NMRShiftDB数据库

数据登录号

化合物性质

分子相关蛋白质

暂无数据

点击上传数据

分子图谱

暂无数据

点击上传数据

描述信息

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
结合微管蛋白并抑制微管的聚合。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.

描述信息

参考文献

PubChem文献

数据源提供

• 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)

• Delatour, P. et al., Xenobiotica, 1991, 21, 217, (metab)

• U.S. Pat., 1975, SmithKline, 3 915 986; CA, 84, 31074r, (synth, pharmacol)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 2970, (synonyms)

• Gyurik, R.J. et al., Drug Metab. Dispos., 1981, 9, 503, (metab)

• Theodorides, V.J. et al., Experientia, 1976, 32, 702, (pharmacol)

• 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)

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

• Oldfield, E.C., Am. J. Gastroenterol., 1995, 90, 159, (use)

• 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

• Bogan, J.A., Drugs of Today (Barcelona), 1979, 15, 87, (rev)

参考文献

生物活性

PubChem BioAssay

生物活性