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Various Analytical Methodologies for Determination of Selective α1A Receptor Blocker Tamsulosin Hydrochloride and Its Combinations in Different Matrices

Alankar Shrivastava*, Pratibha Aggrawal

Department of Pharmaceutical Analysis. Tifac-core Innovation square, B.R. Nahata College of Pharmacy, Mandsaur, India

Abstract: Tamsulosin is a more selective α1A subtype antagonist, which maintains the α-antagonist effect on the prostatic capsule and bladder neck but has less of an effect on the vascular system and blood pressure. It has a better side effect profile than earlier α-adrenergic-receptor antagonists, which were initially developed as antihypertensive agents. Tamsulosin hydrochloride is clinically important drug as far as benign prostatic hyperplasia is concerned. Thus in this review all of the analytical methods reported in the literature are summarized. Different spectrophotometric, chromatographic, electroanalytical and some other types of analytical methods were discussed here. Analytical methods were compared in terms of sensitivity, range, applications and economy. The presented review is helpful for the researchers involved in the development of new analytical methods or formulations of Tamsulosin hydrochloride.

Keywords: tamsulosin hydrochoride, spectrophotometry, chromatography, analytical methods for tamsulosin hydrochloride, electroanalytical method for tamsulosin hydrochloride

Received April 15, 2013; Revised May 16, 2013; Accepted July 18, 2013

Citation: Alankar Shrivastava, Pratibha Aggrawal, Various Analytical Methodologies for Determination of Selective α1A Receptor Blocker Tamsulosin Hydrochloride and Its Combinations in Different Matrices. World Journal of Analytical Chemistry, 1 (3). 37-48. January 2013. doi:10.12691/wjac-1-3-3

1. Introduction

Management of lower urinary tract symptoms (LUTS) and benign prostatic hyperplasia (BPH) has been central to urology for decades. The urologic community has increasingly come to realize that many men with LUTS do not have prostate enlargement and do not need their prostates debulked surgically [1].

Benign prostatic hyperplasia (BPH), a urological disorder which is highly prevalent in the aging male population affecting over 50% of men above the age of 60, leads to a variety of symptoms including increased frequency of urination, poor stream of urine flow, dribbling, nocturia, hesitancy in starting urine flow, and large residual volumes [2]. In benign prostatic hyperplasia (BPH) there will be a sudden impact on overall quality of life of patient. This disease occurs normally at the age of 40 or above and also is associated with sexual dysfunction [3].

The goal for BPH should be to relieve bothersome symptoms and to reduce the risk of progression to potentially serious outcomes such as acute urinary retention (AUR) and BPH-related surgery [4]. According to the EAU 2011 guidelines, alpha-blockers are currently the preferred first-line therapy for all men with moderate or severe LUTS/BPH. The amount of prescriptions for α-blockers has been increasing steadily in the last 10 years [5]. The α₁-blockers relieve the smooth muscle tension within the prostate and bladder neck approximately two weeks after their administration [6].

α₁-Adrenergic receptors are subdivided into α1A, α1B, and α1D subtypes, and antagonists include quinazoline based prazosin, doxazosin (dox), and terazosin and the sulfonamide derivative tamsulosin [7]. Among the currently available alpha-blockers, tamsulosin is selective to the alpha1A-adrenergic receptor subtype that is predominant in the human prostate, whereas other alpha-blockers do not discriminate among alpha-adrenergic receptor subtypes [8,9].

Figure 1. Chemical structure of Tamsulosin hydrochloride

Tamsulosin hydrochloride is the international non-proprietary name of (-)-(R)-5-[2-[[2-(o-ethoxyphenoxy) ethyl]amino]propyl]-2-methoxybenzenesulfonamide hydrochloride (Figure 1), was first developed by Yamanouchi Pharmaceuticals and is currently marketed as a single enantiomer [10]. Tamsulosin is a chiral molecule and its (R) enantiomer is used as a therapeutic active substance [11].

It has a better side effect profile than earlier α-adrenergic-receptor antagonists, which were initially developed as antihypertensive agents. Clinical trials of 1 year or longer with tamsulosin showed high tolerability for the 0.4mg dose and no significant interaction with other antihypertensive medications. Tamsulosin is a more selective α1A subtype antagonist, which maintains the α-antagonist effect on the prostatic capsule and bladder neck but has less of an effect on the vascular system and blood pressure. In fact, tamsulosin is ineffective and not indicated in the treatment of hypertension. Tamsulosin has a favorable side effect profile in regard to problems related to hypotension and dizziness compared to those of terazosin and doxazosin [12].

Combining α₁-ARAs and antimuscarinic agents [e.g Tolterodine Tartarate] in the treatment of BPH resulted in statistically significant benefits in QoL scores, patient satisfaction, urinary frequency, storage symptoms and IPSS scores. The combination of α1-ARAs with antimuscarinic agents is useful for relieving symptoms of bladder outlet obstruction (BOO) and detrusor overactivity (DO). Also the combination of α1-ARAs and 5 α- reductase inhibitors [e.g. Dutesteride and Finasteride] appears to prevent disease progression in patients [13].

Tamsulosin is absorbed from the gastro–intestinal tract; 90% following oral administration. The extent and rate of absorption is reduced in the presence of food. It is distributed into extracellular fluid in the body. The drug is metabolised slowly in the liver by hepatic metabolism while first-pass metabolism is negligible. It is mainly metabolised by the cytochrome P₄₅₀ CYP3A enzyme and less than 10% of the dose is excreted in urine unchanged. The metabolites of tamsulosin hydrochloride undergo extensive conjugation to glucuronide or sulfate prior to renal excretion. It is excreted mainly in urine as metabolites and some unchanged drug. The apparent half–life is approximately 9 to 13 h in healthy individuals and 14 to 15 h in the target population [14].

Thus there is no doubt that tamsulosin is clinically important alpha one blocker. This forms the background of our study. There is clear need to study all of the analytical methods available in different matrices. Different analytical methods such as spectrophotometry, chromatography and electroanalytical methods will be discussed here. The presented study provides substantial information to the researchers involved in the development of new analytical methods and formulation development.

Review of analytical methods for the determination of five alpha one blockers was published by Shrivastava et al [15]. In this review authors also described tamsulosin determination methods available during the preparation of manuscript. In this paper authors focused in the determination methods of tamsulosin because of its proved clinical advantages over other alpha one blockers. This review differs in advancement of technology by inclusion of 30 more references of analytical methods for Tamsulosin.

In search for analytical methods for the determination of tamsulosin hydrochloride database like Sciencedirect, Pubmed, Medknow, NCBI, Taylor and Francis and Google scholar were explored by using keywords “Analytical methods for tamsulosin”, “Determination of tamsulosin”, “Spectrophotometric method for tamsulosin determination, “Chromatographic method for tamsulosin determination”, “Electroanalytical methods for determination of tamsulosin”. Total 82 different analytical methods were found including 24 spectrophotometry, 46 chromatography, 11 electroanalytical (including pharmacopoeia references) and 1 redioreceptor methods for the determination of tamsulosin hydrochloride either alone or in combination in different matrices.

2. Analytical Methods

Tamsulosin hydrochloride 5-[(2R)-2[[2-(2-Ethoxyphenoxy) ethyl]amino]propyl]-2-methoxybenzenesulfonamide hydrochloride is white or almost white powder slightly soluble in water, freely soluble in formic acid, slightly soluble in anhydrous ethanol. [16] Drug is official in JP [17], Eu Ph [16], USP [18] and BP [19].

Analytical methods for the determination of TAM are divided into three main categories, spectrophotometry, chromatography and other electroanalytical methods. Summary of all of the spectrophotometric methods are given under Table 1 and Table 2. Chromatographic methods are summarized under Table 3 and Table 4 whereas in Table 5 all electroanalytical methods for TAM determination are presented.

2.1. Spectrophotometric Methods

During the 1980s, the introduction of miniature diode array detectors, combined with powerful microprocessors and state-of-the-art mathematical tools, led to a renaissance of ultraviolet visible (UV/vis) spectrometry that enabled the rapid spread of compact, relatively low-cost, yet still powerful, laboratory UV/vis machines [20]. One of the interesting aspects of UV spectrophotometry is its low cost and its ease of use, allowing many measurements in a short time [21]. Derivative spectrophotometry, which consists in the differentiation of a normal spectrum, offers a useful means for improving the resolution of mixtures, because it enhances the detectability of minor spectral features [22].

Total 25 different spectrophotometric methods for the determination of TAM in either bulk or formulations are available. There is no doubt on the fact that the spectroscopic methods are rapid and far more economical than chromatographic methods, but their destructive nature and lack of sensitivity is a huge disadvantage [23,24]. Morever, TAM has high potency (0.4mg/tab/cap) and may be this is one of the reason that spectrophotometric method or determination in biological matrices is not available. Analytical methods for the determination of tamsulosin alone is presented in Table 1 whereas Table 2 presents literatures related to combinations with other drugs.

Table 1. Summary of spectrophotometric methods for determination of Tamsulosin

Table 2. Summary of spectrophotometric methods of Tamsulosin HCl in combination with other drugs

Table 3. Summary of chromatographic procedures found in literature survey for the determination of Tamsulosin HCl in different matrices

Table 4. Summary of chromatographic methods for the determination of tamsulosin HCl in combination with other drugs

2.1.1. Comparison of Spectrophotometric Methods

Tamsulosin HCl is a potent drug [0.4/mg/cap/tab] and this is the reason there are attempts to enhance UV absorbance by addition of chromophore by some of the authors. [28,29,30,31,32]. Although UV spectrophotometric methods have advantage of simplicity and economy over chromatographic methods but it’s difficult to develop highly sensitive determinations in biological fluids. In this case there sensitivity is questionable. This may be the reason that no author till date attempted spectrophotometry method for complex matrices like biological fluids. High potency of the drug further enhances the difficulty to develop such kind of methods. However method using water for preparing dilution [26] seems to be most economical and simple method. Derivative spectrophotometry may be better option for resolving mixtures in simultaneous determinations. With LOD and LOQ of 0.003μg/ml 0.01μg/ml method developed by Shrivastava et al. [28]. is the most sensitive method available in the literature.

2.2. Chromatographic Methods

Analytical chemists have to analyze a variety of complex samples often originating in different matrices to answer questions about the quality and quantity of different analytes. These requirements are satisfied with HPLC especially if combined with an advanced detection technique such as diode array detection (DAD) or mass spectroscopy [40].

HPTLC allows fast and inexpensive method of analysis in the laboratory and in the field. The modern HPTLC technique, combined with automated sample application and densitometric scanning, is sensitive and completely reliable, suitable for use in qualitative and quantitative analysis. HPTLC is a valuable tool for reliable identification because it can provide chromatographic fingerprints that can be visualized and stored as electronic images [41,42]. HPTLC remains one step ahead when compared with other tools of chromatography [43].

Summary of all of the chromatographic methods found in the literature survey for Tamsulosin alone and in combinations are presented under Table 3 and Table 4 respectively.

Table 5. Summary of electroanalytical methods found in literature survey

2.2.1. Comparison of Chromatographic Methods

Overall 45 different chromatographic methods reported in the currently available literature for the determination of Tamsulosin either alone or in combinations with other drugs. Out of this 28 HPLC-UV, one UPLC-MS-MS, one TLC, three HPTLC, and rest of the methods reported with mass spectrometer as detector equipped with liquid chromatography. HPLC-UV methods are economical methods but are less sensitive in comparison to HPLC-MS.

Most sensitive chromatographic method reported is UPLC-MS-MS method [LOQ 0.10ng/ml]. Although with LOQ of 0.4ng/ml HPLC-F method is also one of the most sensitive method on records for tamsulosin determination. With LOQ of 0.02μg/ml Sudha and Dhomane [57] is most sensitive method among HPLC-UV method. However LOD and LOQ value also depends upon the noise of the detector and the matrix. S-isomer of the drug is available in the form of impurity and of not much therapeutic interest thus methods for separation of enantiomers [47,62,19,75,76,77] are also appreciable.

2.3. Electroanalytical Methods

Modern electrochemical methods are now sensitive, selective, rapid, and easy techniques applicable to analysis in the pharmaceutical fields, and indeed in most areas of analytical chemistry. They are probably the most versatile of all trace pharmaceutically active compound analysis [24]. Electroanalytical techniques can easily be adopted to solve many problems of pharmaceutical interest with a high degree of accuracy, precision, sensitivity and selectivity, often in a spectacularly reproducible way by employing this approach [86].

All of the electroanalytical methods found in literature available related to determination of tamsulosin HCl is presented under Table 5.

2.3.1. Conductometric

The conductometry is the analytical method used both in research laboratories as well as in industry [94]. Conductometry provide convenient mean for the determination of end point in the titration [95]. Since tamsulosin hydrochloride is able to form precipitates with heteropoly acids, phosphotungestic, silicotungestic, and sodium tetraphenylborate so the applicability of conductimetric titration of these drugs with the above mentioned reagents, was tested by Abdel-Moety et al. [92]. There was no effect in the shape of titration curve upto 50°C and titrant solutions lower than 10⁻²M are not suitable for conductimetric titrations because of unstable readings.

2.3.2. Voltammetric

Voltammetry encompasses a group of electrochemical technique in which potential is applied to an electrochemical cell with the simultaneous measurement of the resulting current. By varying potential in the electrodes, it is possible to oxidize or reduce analytes in the solution [96]. the method developed by Ozkan et al. [87] is one of the most sensitive analytical method reported for tamsulosin determination. Authors claim that procedures did not require sample pre-treatment or any time-consuming extraction step prior to drug assay. Another method developed by Lonappan et al. [93] using differential pulse voltammetric sensor for the determination of tamsulosin hydrochloride (TAM) using multiwalled carbon nanotubes (MWNTs)–Nafion-modified glassy carbon electrode (GCE).

2.3.3. Potentiometric

Potentiometry is a classical analytical technique with roots before the twentieth century. However, the rapid development of new selective electrodes and more sensitive and stable electronic components since 1970 has tremendously expanded the range of analytical applications of potentiometric measurements [97]. May be this is one of the reason that potentiometric measurements are official methods in all pharmacopeias [16,17,18,19] for determination of Tamsulosin HCl. In thses methods 0.1 N perchloric acid is used as titrant and end point was determined potentiometrically.

2.3.4. Capillary Electrophoresis

Capillary electrophoresis (CE) is a special case of using an electrical field to separate the components of a mixture [98]. CE is a powerful clinical diagnostic tool for profiling, screening, and detecting drugs, carbohydrates, lipids, enzymes, proteins, and nucleic acid [99]. Four capillary electrophoresis methods [88,89,90,91] were developed for chiral determination of drugs. Method developed by Maier et al. [88] is the most sensitive method among capillary electrophoresis methods.

2.4. Radioreceptor Assay

Radioreceptor analysis method was developed by Taguchi et al. [100]. This was performed by pharmacokinetic analysis of receptor binding following single, oral dose of tamsulosin (0.4mg) in a placebo-controlled, single-blind, randomized, three-way cross-over study. This technique is effectively independent of knowledge of the chemical identity of drug metabolites and evaluates the parent compound and all of its metabolites according to their relative contribution to receptor binding [100].

3. Conclusion

Metabolic and regulatory processes mediated by biological systems are sensitive to stereochemistry, and different responses can be often observed when comparing the activities of pair of enantiomers. Thus, regulatory authorities encourage the pharmaceutical industries to provide single enantiomer of drugs, although most of them were commercialized as racemates. Nowadays, the situation has definitely changed, as technical advances permit production of many single enentiomer on a commercial scale. Thus there is clear need for such kind of review of analytical methods of drugs as well as separation of isomers in different matrices [101].

In general, the LOD is taken as the lowest concentration of an analyte in a sample that can be detected, but not necessarily quantified, under the stated conditions of the test. The LOQ is the lowest concentration of an analyte in a sample that can be determined with acceptable precision and accuracy under the stated conditions of test. This is the reason here it is important to discuss about these parameters [102].

Reactions of both the isomers also vary and with post/pre column derivatization and using liquid chromatography the spectrum of analytical methods for separation of isomers can be further increased. In this way various analytical methods for the determination of tamsulosin and its isomers are discussed. The presented review can be useful for the researchers involved in the development of new analytical methods or formulations.

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