Benzimidazole and Imidazole Derivatives

<p>Applications 4,9-Diisobutyl-1,6-diazecane-2,7-dione is in impurity of rac-Pregabalin (P704800) which is a GABA analogue used as an anticonvulsant.<br>References Taylor, C.P., at al.: Epilepsy Res., 14, 11 (1993), Field, M.J., et al.: Pain, 80, 391 (1999)<br></p>

<p>Applications 4,4'-(1-Bromomethyl)bis-benzonitrile (CAS# 69545-39-7) is a useful research chemical compound.<br></p>

<p>Applications: 2-Cyclopropylmethylamino-5-chlorobenzophenone is a benzodiazepine derivative.<br>References Japp, M. et al.: J. Chrom., 439, 317 (1988); Guan, F. et al.: J. Anal Toxicol., 23, 54 (1999);<br></p>

<p>Applications Lurasidone Opened Imide is an impurity in the synthesis of Lurasidone (L474920) which is antipsychotic used for treatment of schizophrenia.<br>References Ishiyama, T., et al.: Eur. J. Pharmacol., 572, 160 (2007); Cole, P., et al.: Drugs of the Fut., 33, 316 (2008);<br></p>

<p>Applications 2,5-Dichlorobenzoyl Cyanide is a reagent applied for research purposes<br>References Veerareddy, A., et al.: J. Heterocyclic Chem., 51, 1311 (2014)<br></p>

<p>Stability Hygroscopic<br>Applications A metabolite of Atropine (A794625). Two metabolites of Atropine (apoatropine and noratropine) were found in rat urine.<br>References Xu, A., et al.: J. Pharm. Biomed. Anal., 14, 33 (1995), Cherkaoui, S., et al.: J. Pharm. Biomed. Anal., 17, 1167 (1998),<br></p>

<p>Applications Nitroguanidine is used in the prediction of heats of detonation of energetic compounds from their molecular structure. It is also used in the synthetic preparation of imidacloprid-d4 (I274992), which is a neonicotinoid.<br> E0<br>References Keshavarz, M.H., et al.: Propellant, Explosives, Pyrotechnics, 37, 93 (2012); Chauzat, M., et al.: Env. Entomol., 38, 514 (2009), Patial, A., et al.: Env. Ecol., 27, 320 (2009), Fernandez-Bayo, J., et al.: J. Agric., Food Chem., 57, 5435 (2009), Tomizawa, M., et al.: J. Med. Chem., 52, 3735 (2009), Chem. and Eng. News 90: 10 (2012)<br></p>

<p>Applications 9-Acridinecarboxylic acid is used in the synthesis of short DNA-binding peptides.<br></p>

<p>Applications (R)-4,5-Dehydro Pregabalin is derived from rac 4,5-Dehydro Pregabalin (D230050), which is an impurity of the anti-convulsnat, Pregabalin.<br>References Dousa, M, et al.: J. Pharmac. Biomed. Anal., 53, 717 (2010);<br></p>

<p>Applications Temazepam is a pharmacologically active metabolite of Diazepam. It is used as a sedative and hypnotic drug.<br>References Sarteschi, P., et al.: Arzneim.-Forsch., 22, 93 (1972), Schwandt, H.J., et al.: Xenobiotica, 4, 733 (1974), Curry, S.H., et al.: Br. J. Pharmacol., 57, 427 (1976), Heel, R.C., et al.: Drugs, 21, 321 (1981),<br></p>

<p>Applications (αS)-N,N,α-Trimethyl-3-(4-nitrophenoxy)benzenemethanamine is an impurity of Rivastigmine Tartrate (R541000). Rivastigmine Tartrate is a brain selective acetylcholinesterase inhibitor.<br>References Rosler, M., et al.: Brit. Med. J., 318, 633 (1999); Enz, A., et al.: Prog. Brain Res., 98, 431 (1993)<br></p>

<p>Applications Trimebutine-d9 Maleate Salt, is the labeled analogue of Trimebutine Maleate Salt (T795605), acting as an opioid receptor agonist. Antispasmodic.<br>References Delvaux, M., et al.: J. Int. Med. Res., 25, 225 (1997), Lavit, M., et al.: Arzneim.-Forsch., 50, 640 (2000),<br></p>

<p>Applications Isometronidazole-D4 is a labelled analogue of Isometronidazole (I821342). Isometronidazole is an impurity of Metronidazole (M338880), a chemotherapeutic agent that is used as a first line defense against Clostridium difficile (C.diff). Isometronidazole is also a hypoxic cell sensitizer in humans and mice.<br>References Hentschel, M. &amp; Schmidt, W.: Die Pharm., 47, 221 (1992); Musher, D., et al.: Clin. Inf. Dis., 40, 1586 (2005); Rosenkranz, H. &amp; Speck, W.: Biochem. Biophys. Res. Comm., 66, 520 (1975)<br></p>

<p>Impurity Itraconazole EP Impurity A<br>Applications 2-(2-Butyl)-4-{4-[4-(4-methyloxy-phenyl)-piperazin-1-yl]-phenyl}-2,4-dihydro-[1,2,4]-triazol-3-one (Itraconazole EP Impurity A) is an intermediate of Itraconazole.<br></p>

<p>Applications Mebendazole (M200500) thermal decomposition product. Mebendazole impurity.<br>References Himmelreich, M., et al.: Aus. J. Pharmaceut. Sci., 6, 123 (1977),<br></p>

<p>Applications Solifenacin (S676700) metabolite.<br></p>

<p>Applications A labelled metabolite of Midazolam (M343000).<br>References Ha, H., et al.: Ther. Drug Monit., 15, 338 (1993), Thummel, K., et al.: J. Pharmacol. Exp. Ther., 271, 557 (1994), Kim, R., et al.: Pharm. Res., 16, 408 (1999), Maurer, H., et al.: Anal. Bioanal. Chem., 381, 110 (2005), Smink, B., et al.: J. Anal. Toxicol., 30, 478 (2006),<br></p>

<p>Applications A promethazine (P757000) metabolite.<br>References Clement, B. A. &amp; Beckett, A. H.; Xenobiotica 11, 609 (1981)<br></p>

<p>Applications A metabolite of Midazolam (M343000).<br>References Soucek, P., et al.: Xenobiotica, 22, 83 (1992), Ghosal, A., et al.: Drug Metab. Dispos., 24, 940 (1996), Kobayashi, K., et al.: Biochem. Pharmacol., 63, 889 (2002),<br></p>

<p>Applications (S)-Aclidinium Bromide is an isomer of Aclidinium Bromide (A190180) a novel long-acting antimuscarinic bronchodilator in phase II clinical trials for the treatment of chronic obstructive pulmonary disease (1,2).<br>References (1) Gupta, V. and Singh, D.: Expert Rev Respir Med. 6, 581 (2012)(2) De La Motte, S., et al.: Int. J. Clin. Pharmacol. Therap., 50,403 (2012)<br></p>

<p>Applications Labelled Propantheline (P760900). Propantheline is an antimuscarinic agent used in the treatment of hyperhidrosis (excessive sweating), enuresis (involuntary urination) as well as cramps or spasms of the stomach, intestine and bladder.<br>References Levin, R. et al.: Neurol. Urodyn., 1, 221 (1982); Daniotti, S. et al.: Br. J. Pharmacol., 82, 305 (1984); Moller, J. et al .: Acta Med. Scand., 184, 201 (1968);<br></p>

<p>Applications 4,4'-Dibromobenzophenone is a reagent used in the synthesis of polyelectrolytes which serve as fluorescent visualizers for intracellular imaging with good biocompatibility.<br>References Hu, R., et al.: Chem. Asian J., 8, 2436-2445 (2013)<br></p>

<p>Applications Labelled Triazolam (T767380(M)). Triazolam in an hypnotic drug used in the short term treatment of insomnia.<br>References Lomen, P., et al.: J. Int. Med. Res., 4, 55 (1976), Allens, G.S., et al.: J. Int. Med. Res., 6, 343 (1978), Pakes, G.E., et al.: Drugs, 22, 81 (1981).<br></p>

<p>Impurity Pregabalin Impurity 17<br>Applications (3S)​-3-​(2-Methylpropyl)​-pentanedioic Acid 1-Methyl Ester (Pregabalin Impurity 17) is an impurity of Pregabalin (P704800), a GABA analogue used as an anticonvulsant.<br>References Taylor, C.P., at al.: Epilepsy Res., 14, 11 (1993); Field, M.J., et al.: Pain, 80, 391 (1999)<br></p>

<p>Desdifluoromethoxy hydroxy pantoprazole is a synthetic compound that is used as an impurity standard for the drug product Pantoprazole. It has a purity of ≥98% and is stable under ambient conditions. Desdifluoromethoxy hydroxy pantoprazole is not active on its own, but it is a metabolite of pantoprazole. It can be used to study the metabolism of pantoprazole.</p>

<p>Tiotropium Bromide EP Impurity G is an anticholinergic bronchodilator that is used in the treatment of asthma. Tiotropium Bromide EP Impurity G has been shown to have long-acting properties, with a half-life of about 20 hours. It has a high affinity for the muscarinic receptor and acts as a competitive antagonist at this site. Tiotropium Bromide EP Impurity G also has a cavity, which may be necessary for its activity.</p>

<p>Solifenacin impurity C is an impurity that is found in the drug product Solifenacin. It has been shown to be a natural metabolite and has been detected in human urine. Solifenacin impurity C is used as an analytical standard for HPLC analyses of solifenacin, and can also be used as a reference material for pharmacopoeia. The purity of this compound is 99%.</p>

<p>Pantoprazole sulfone N-oxide is a prodrug that is converted to the active form pantoprazole in the stomach where it inhibits gastric acid secretion. Pantoprazole sulfone N-oxide has been shown to be genotoxic, and can cause polyvinyl chloride to degrade when stored together. Reconstituted solution of this drug should be used within 24 hours after reconstitution, as the chemical stability of this drug decreases rapidly. Validation studies have been conducted on different analytical methods for determining pantoprazole concentrations in reconstituted solutions, and these methods have been harmonized with those published by the United States Pharmacopeia (USP). The pump inhibitor activity of pantoprazole sulfone N-oxide has been demonstrated in dogs, and it is also useful for treating acid reflux disease in humans. Pantoprazole sulfone N-oxide is unstable at high temperatures (&gt;25°C), so should not be refrigerated or</p>

<p>7-Hydroxyhyoscyamine is an antibacterial agent that is used in the treatment of bacterial infections. It has been shown to inhibit the growth of a number of bacteria including Staphylococcus aureus, Streptococcus pyogenes, and Escherichia coli. 7-Hydroxyhyoscyamine has been shown to be more potent than 6-hydroxyhyoscyamine (6-OH Hya) for inhibiting protein synthesis in the bacteria. The compound does not have any psychoactive effects, unlike atropine sulfate, which is also an alkaloid found in plants from the Solanaceae family. 7-Hydroxyhyoscyamine can be synthesized by reacting atropine with nitrous acid or hydrochloric acid. This synthetic process leads to n-oxides as impurities, which can be removed by using a reversed phase high performance liquid chromatography (RP HPLC). Validation of this</p>

<p>Oxybutynin EP impurity B is a metabolite of oxybutynin and is a natural product. It is used as an analytical reference substance, to develop new drugs, and in pharmacopoeia in order to measure the purity of oxybutynin. The compound is synthesized by chemical synthesis and can be used as a standard for HPLC analysis.</p>

<p>N,N-Dimethylaminoethyl-a-(1-Hydroxycyclopentyl)phenylacetate hydrochloride (DMAEA) is a drug that is used as an ophthalmic. It has been shown to be safe and effective in patients with chronic open angle glaucoma, and it may also have some efficacy for the treatment of other conditions such as uveitis and retinal detachment. DMAEA is thought to work by binding to the DNA in the eye’s optic nerve cells and blocking the production of leukotrienes. This drug has also been shown to have anti-inflammatory properties.</p>

<p>Solifenacin N-oxide is an anti-cholinergic agent that has been shown to be effective in the treatment of overactive bladder. Solifenacin N-oxide is a prodrug that is hydrolyzed in vivo to solifenacin, its active form. The compound reversibly binds to muscarinic receptors and inhibits the release of acetylcholine. Solifenacin N-oxide has been shown to have low levels of impurities and is highly soluble in water. It was also found to be stable when stored at room temperature for two months. This drug has a high flow rate and moderate retention time, which makes it suitable for reversed-phase liquid chromatography (RPLC). RPLC is a chromatographic technique that separates compounds by size, hydrophobicity, or charge.</p>

<p>2-Hydroxy-5-methylphenylbenzenepropanol is an aliphatic phenol that is used as a treatment for benzene poisoning. It is also used as a precursor to other compounds, such as the chlorides and alkylates of 2-hydroxy-5-methylphenylbenzenepropanol. This compound can be synthesized by reacting ethyl benzoylacetate with diisopropylamine in the presence of oxygen and chlorine gas. It is often immobilized using nutrients, l-tartaric acid, or cinnamic acid.</p>

<p>1-[[4-(3-Methoxypropoxy)-3-methyl-2-pyridinyl]methyl]-2-[(4-(3-methoxypropoxy)-3-methyl-2-pyridinyl)methylsulfonyl]-1H-benzimidazole (MKC1807) is a synthetic drug product. MKC1807 is an analytical standard in the HPLC assay for the determination of Epiandrosterone sulfate and its metabolites. 1-[4-(3-Methoxypropoxy)-3,5,6,7,8 -pentamethylcyclohexyl]methyl 2-[(4-(3 -methoxypropoxy) 3,5,6,7,8 -pentamethylcyclohexyl)methylsulfonyl]-1H benzimidazole has been shown to be a natural metabolite of Epiandrosterone sulfate. This compound</p>

<p>1-[[4-(3-Methoxypropoxy)-3-methyl-2-pyridinyl]methyl]-2-[[[4-(3-methoxypropoxy)-3-methyl-2-pyridinyl]methyl]thio]-1H-benzimidazole is a drug product with analytical applications. It has been shown to have natural and synthetic origins, as well as impurities of its own. It is a custom synthesis and research and development compound that is used for HPLC standardization. The compound has been synthesized for the purpose of drug development and it is intended for niche use.</p>

<p>Dehydrodeoxy donepezil is an analytical standard that is used in the manufacture of pharmaceuticals. It is a synthetic drug impurity, and its CAS number is 120013-45-8. Dehydrodeoxy donepezil can be found in the API impurity grade of various drugs, including those that are manufactured by Custom synthesis and natural synthesis. The pharmacopoeia states that dehydrodeoxy donepezil has a purity level of 98% or greater. This product can also be found as a metabolite in humans, with its half-life being approximately 40 minutes.</p>

<p>Lansoprazole impurity H is a metabolite of lansoprazole, a proton pump inhibitor that inhibits the production of stomach acid. Lansoprazole impurity H is used in research and development as an analytical standard to measure lansoprazole concentrations in drug products. It is also used as an impurity standard for pharmacopoeia purposes. Lansoprazole impurity H is not known to be toxic, but it has not been evaluated for carcinogenicity or reproductive toxicity.</p>

<p>1-[[3-Methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]methyl]-2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]methyl]sulfinyl]-1H-b enzimidazole is an impurity of a drug product. It is a metabolite that has been shown to be present in human plasma and urine. This compound is synthetically produced and is not found in nature. It has been shown to have niche applications in both analytical chemistry and pharmacopoeia.</p>

<p>6-Methyl-4-phenyl-3,4-dihydro-1-benzopyran-2-one is an analog of the natural product zearalenone, which can be used as an acid catalyst for the synthesis of various pharmaceuticals. It has a linear range and is structurally similar to a number of other analogs. The chloride ion is involved in the optimization of the extraction parameters and can be replaced by other c1-4 alkyl groups. 6-Methyl-4-phenyl-3,4-dihydro-1 -benzopyran 2 one is typically prepared using a preparative high performance liquid chromatography technique that involves dehydration.</p>

<p>2-(3-(1-Benzylpiperidin-4-yl)-2-oxopropyl)-4,5-dimethoxybenzoic acid is a synthetic compound that is being researched as a potential drug product. It is an impurity standard for HPLC and has been used in the past to develop drugs. The chemical structure of this compound closely resembles that of the natural metabolite 4,5-dimethoxybenzoic acid, which is found in plants such as thyme. 2-(3-(1-Benzylpiperidin-4-yl)-2-oxopropyl)-4,5-dimethoxybenzoic acid has shown to inhibit human cytochrome P450 enzymes, which may lead to serious side effects when taken orally.</p>

<p>N-Desalkyl itraconazole is a triazole antifungal drug that belongs to the group of medicines. It is used in the treatment of systemic mycoses, including blastomycosis and histoplasmosis. N-Desalkyl itraconazole has been shown to inhibit the growth of fungi by interfering with their cell membranes and inhibiting their production of ergosterol. Calibration studies have shown that this drug binds to human liver microsomes and plasma proteins, as well as transporters such as P-glycoprotein. These interactions may influence its pharmacokinetics, which can be determined using a bioanalytical method.</p>

<p>2,12-Dihydro-1,3-dimethyl-9-methoxy-12-thioxobenzo [4,5] pyrido [1,2-c] imidazo [1,2-a] imidazol-2-one is a synthetic compound that has not been evaluated in humans. This compound is an impurity standard for the synthesis of an API. The purity of this compound is &gt;98% and it has been shown to be stable under acidic conditions.</p>

<p>2-[[(4-Chloro-3-methyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole (CAS No. 168167-42-8) is a synthetic compound that is used as an analytical reference standard for HPLC. It is also used in the study of drug metabolism, and it has been shown to induce natural oxidation in vitro. 2-[(4-Chloro-3-methylpyridinium)methylsulfinyl]-1Hbenzimidazole is an impurity found in pharmaceutical products that are synthesized from 1-(2,4,6trichlorophenyl)-3-[(4chloromethyl)phenyl]urea.</p>

<p>Oxybutynin EP Impurity E is a research and development impurity standard that is used in the synthesis of Oxybutynin. It can be synthesized by reacting 2-chloro-4-nitroaniline with potassium tert-butoxide, followed by acetylation with acetic anhydride. The purity and structure of this compound have been verified by gas chromatography, mass spectrometry, and melting point analysis. This impurity standard has a CAS number of 1215677-72-7.<br>Oxybutynin EP Impurity E is used as a drug product for the treatment of overactive bladder, urinary incontinence, and painful bladder syndrome/interstitial cystitis. It also helps to reduce pain due to spinal cord injury or multiple sclerosis. <br>The pharmacopoeia name for this compound is 4-(2-Chloroethyl)-1H-imidazoleacetic acid. It has been found to be</p>

<p>Albendazole is an anti-helminthic drug that is structurally classified as a benzimidazole. It has been shown to be effective against a variety of helminths, including roundworms, pinworms, hookworms, and tapeworms. Albendazole impurity F is an analytical standard for the determination of albendazole in pharmaceutical products by HPLC. It also serves as a reference substance to establish the purity of drug products containing albendazole and its metabolites. Albendazole impurity F is not considered to be a metabolite of albendazole because it has been shown to be stable under acidic conditions and can be synthesized from other starting materials.</p>