IUPAC Name	methyl N-(6-propylsulfanyl-1H-benzimidazol-2-yl)carbamate	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

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)	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

InChI Key	HXHWSAZORRCQMX-UHFFFAOYSA-N	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Canonical SMILES	CCCSC1=CC2=C(C=C1)N=C(N2)NC(=O)OC	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Molecular Formula	C12H15N3O2S	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

DSSTOX Substance ID	DTXSID0022563	Source
Record name	Albendazole
Source	EPA DSSTox
URL	https://comptox.epa.gov/dashboard/DTXSID0022563
Description	DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology.

Molecular Weight	265.33 g/mol	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Physical Description	Solid	Source
Record name	Albendazole
Source	Human Metabolome Database (HMDB)
URL	http://www.hmdb.ca/metabolites/HMDB0014659
Description	The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body.
Explanation	HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.

Solubility	1.4 [ug/mL] (The mean of the results at pH 7.4), Practically insoluble, 2.28e-02 g/L	Source
Record name	SID855809
Source	Burnham Center for Chemical Genomics
URL	https://pubchem.ncbi.nlm.nih.gov/bioassay/1996#section=Data-Table
Description	Aqueous solubility in buffer at pH 7.4

Record name	Albendazole
Source	DrugBank
URL	https://www.drugbank.ca/drugs/DB00518
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Record name	Albendazole
Source	Human Metabolome Database (HMDB)
URL	http://www.hmdb.ca/metabolites/HMDB0014659
Description	The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body.
Explanation	HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.

Mechanism of Action	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. It works by binding to the colchicine-sensitive site of tubulin, thus inhibiting its polymerization or assembly into microtubules. As cytoplasmic microtubules are critical in promoting glucose uptake in larval and adult stages of the susceptible parasites, the glycogen stores of the parasites are depleted. 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., Benzimidazoles produce many biochemical changes in susceptible nematodes, eg, inhibition of mitochondrial fumarate reductase, reduced glucose transport, and uncoupling of oxidative phosphorylation ... /but/ the primary action ... /should be/ to inhibit microtubule polymerization by binding to beta-tubulin. The selective toxicity of these agents derives from the fact that specific, high-affinity binding to parasite beta-tubulin occurs at much lower concn than does binding to the mammalian protein ... Benzimidazole-resistant Haemonchus contortus display reduced high-affinity drug binding to beta-tubulin and alterations in beta-tubulin isotype gene expression that correlate with drug resistance ... Two identified mechanisms of drug resistance in nematodes involve both a progressive loss of "susceptible" beta-tubulin gene isotypes together with emergence of a "resistant" isotype with a conserved point mutation that encodes a tyrosine instead of phenylalanine at position 200 of beta-tubulin. While this mutation may not be required for benzimidazole resistance in all parasites, eg, Giardia lamblia, benzimidazole resistance in parasitic nematodes is unlikely to be overcome by novel benzimidazole analogs, because tyrosine also is present at position 200 of human beta-tubulin. /Benzimidazoles/, Although the exact mechanism of action of albendazole has not been fully elucidated, the principal anthelmintic effect of benzimidazoles, including albendazole, appears to be the specific, high-affinity binding of the drug to free beta-tubulin in parasite cells, resulting in selective inhibition of parasite microtubule polymerization, and inhibition of microtubule-dependent uptake of glucose. Benzimidazole drugs bind to the beta-tubulin of parasites at much lower concentrations than to mammalian beta-tubulin protein; the drugs do not inhibit glucose uptake in mammals, and do not appear to have any effect on blood glucose concentrations in humans, The mode of action of albendazole is by binding strongly with the tubulin in the cells of nematodes. The intestinal cells of the nematode are particularly affected, resulting in a loss of absorptive function which causes the nematodes to starve to death.	Source
Record name	Albendazole
Source	DrugBank
URL	https://www.drugbank.ca/drugs/DB00518
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Record name	ALBENDAZOLE
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Color/Form	Colorless crystals
CAS No.	54965-21-8	Source
Record name	Albendazole
Source	CAS Common Chemistry
URL	https://commonchemistry.cas.org/detail?cas_rn=54965-21-8
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Record name	Albendazole [USAN:USP:INN:BAN:JAN]
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Record name	Albendazole
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Record name	albendazole
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Record name	albendazole
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Record name	Albendazole
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Record name	Albendazole
Source	European Chemicals Agency (ECHA)
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Record name	ALBENDAZOLE
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Record name	ALBENDAZOLE
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Record name	Albendazole
Source	Human Metabolome Database (HMDB)
URL	http://www.hmdb.ca/metabolites/HMDB0014659
Description	The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body.
Explanation	HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.

Melting Point	208-210, 208-210 °C, Mol wt: 281.34. Active metabolite of albendazole. MP: 226-228 °C (decomposes) /Sulfoxide/, 209 °C	Source
Record name	Albendazole
Source	DrugBank
URL	https://www.drugbank.ca/drugs/DB00518
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Record name	ALBENDAZOLE
Source	Hazardous Substances Data Bank (HSDB)
URL	https://pubchem.ncbi.nlm.nih.gov/source/hsdb/7444
Description	The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel.

Record name	Albendazole
Source	Human Metabolome Database (HMDB)
URL	http://www.hmdb.ca/metabolites/HMDB0014659
Description	The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body.
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Synthesis routes and methods I

Procedure details

Preparation of methyl 5-propylthio-2-benzimidazole carbamate--A 1.82 g portion of cyanamide was dissolved in 10 ml of water. Methyl chloroformate, 4.64 g, and 6.34 g of 50% aqueous sodium hydroxide in 6 ml of water were added simultaneously so as to maintain the pH at approximately 7 as determined by a pH meter. The reaction mixture was stirred at 50° C. for one hour. A portion of 7.4 g of concentrated hydrochloric acid in 7 ml of water was added until the pH was 4. The methanol solution of 4-propylthio-o-phenylenediamine from Example IV was added at once. More of the hydrochloric acid solution was added to adjust the pH to 4. The reaction mixture was heated to distill the methanol. As methanol was nearly removed more hydrochloric acid solution was added to keep the pH at 4. Water was added from time to time to keep the slurry from becoming too thick. The reaction slurry was heated at 100° C. for one hour after the methanol had been removed. The reaction slurry was cooled, filtered and washed liberally with water. The solids were air dried to produce 8.77 g of crude methyl 5-propylthio-2-benzimidazole carbamate. The crude solids were washed 3 times with cold acetone and dried to produce 7.52 g of product assaying 97% methyl-5-propylthio-2-benzimidazole carbamate by HPLC, 73% yield from the 4-propylthio-2-nitroaniline employed in Example IV.

Name

4-propylthio-o-phenylenediamine

Quantity

0 (± 1) mol

Type

reactant

Reaction Step One

Name

methanol

Quantity

0 (± 1) mol

Type

solvent

Reaction Step One

[Compound]

Name

methyl 5-propylthio-2-benzimidazole carbamate--A

Quantity

1.82 g

Type

reactant

Reaction Step Two

Name

cyanamide

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Two

Name

Methyl chloroformate

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Three

Name

sodium hydroxide

Quantity

6.34 g

Type

reactant

Reaction Step Three

Name

water

Quantity

6 mL

Type

solvent

Reaction Step Three

Name

hydrochloric acid

Quantity

7.4 g

Type

reactant

Reaction Step Four

Name

water

Quantity

7 mL

Type

solvent

Reaction Step Four

Name

hydrochloric acid

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Five

Name

water

Quantity

10 mL

Type

solvent

Reaction Step Six

Name

methyl 5-propylthio-2-benzimidazole carbamate

Details

Synthesis routes and methods II

Procedure details

SKOV-3 human cystadenocarcinoma cell line, obtained from the American Type Culture Collection (ATCC Accession No. HTB 77) were grown in McCoy's 5a medium with 1.5 mM L-glutamine, 100 units/ml penicillin, and 100 μg/ml streptomycin, supplemented with 10% FCS. Cells were grown to confluence and harvested by trypsinization with 0.25 mg/ml trypsin/EDTA and suspended in the medium before plating. These were then seeded (2×105) on plastic 6-well Corning culture plates. Cultures were maintained in a 37° C. incubator in a humidified atmosphere of 95% O2/5% CO2. Twenty-four hours later, the medium was removed. Subconfluent cultures were washed three times with phosphate buffer followed by incubation for 6 hours with culture medium containing various concentrations of albendazole (0, 0.1, 0.25 and 1.0 μM) dissolved in 1% ethanol. After completion of the treatment period, medium from the wells were individually collected and analysed for the VEGF concentration using an enzyme-linked immunosorbant assay (ELISA) that detects soluble VEGF121 and VEGF165 isoforms (Quantikine R&D systems, Minneapolis, USA).

[Compound]

Name

Quantity

0 (± 1) mol

Type

reactant

Reaction Step One

Name

L-glutamine

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Two

Name

penicillin

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Three

Name

streptomycin

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Four

Name

EDTA

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Five

Name

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Six

Name

Albendazole

Details

Retrosynthesis Analysis

AI-Powered Synthesis Planning: Our tool employs the Template_relevance Pistachio, Template_relevance Bkms_metabolic, Template_relevance Pistachio_ringbreaker, Template_relevance Reaxys, Template_relevance Reaxys_biocatalysis model, leveraging a vast database of chemical reactions to predict feasible synthetic routes.

One-Step Synthesis Focus: Specifically designed for one-step synthesis, it provides concise and direct routes for your target compounds, streamlining the synthesis process.

Accurate Predictions: Utilizing the extensive PISTACHIO, BKMS_METABOLIC, PISTACHIO_RINGBREAKER, REAXYS, REAXYS_BIOCATALYSIS database, our tool offers high-accuracy predictions, reflecting the latest in chemical research and data.

Strategy Settings

Precursor scoring	Relevance Heuristic
Min. plausibility	0.01
Model	Template_relevance
Template Set	Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis
Top-N result to add to graph	6

Feasible Synthetic Routes

Reactant of Route 1

Albendazole

Reactant of Route 2

Albendazole

Reactant of Route 3

Albendazole

Reactant of Route 4

Albendazole

Reactant of Route 5

Albendazole

Reactant of Route 6

Albendazole

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