CHAPTER – VI

References and summary

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SUMMARY

Page 225

SUMMARY

Any substance that is carefully used for diagnosis, cure and

prevention for altering the structure and function of the body is called drug. In

the modern era, drugs play an important role in the progress of human

civilization. While primitive man depended mainly on plant product and metal

salts to cure diseases, modern man uses a wide range of synthetic organic

compounds and biotechnology- derived antibiotics, vaccines, etc. There are

many important stages before a compound is used as a drug. The three

important stages in the use of a drug as a medicine, i.e., the conversion of a

drug into a formulation are i. The discovery of the drug. ii. The

manufacture of the drug in bulk form. iii. The formulation of a drug into

different dosage forms like tablet, capsule, injection, syrup etc. First

stage is the drug discovery, where the compounds are screened for biological

activities. Second stage is the manufacture of the drug using well understood

chemistry and adapting safe and proper manufacturing and analytical

practices and the third stage is the formulation of the drug in a convenient

dosage. Chemists play an important role in pharmaceutical research, as they

synthesize, purify and analyze the drugs. The study of conversion of drugs

into medicine and its manufacture, stability and the effectiveness of the drug

dosage form is termed as pharmaceutics. The preparation, chemical and

physical composition, reactive nature, geometry, influence on an organism,

quality control methods, storage conditions and like which are pre-requisites

in the study of drugs fall under pharmaceutical chemistry, a potential field,

based on the general laws of chemistry.

Page 226

Pharmaceutical analysis deals not only with drugs and their

formulations but also with their precursors. However, degree of purity and the

quality of medicament is a must. The quality of a drug is decided only after its

authenticity is tested, that too in the drug and its formulations. Whatever may

be the application, quality is paramount as it is more vital in the field of

medicine as the target is life. The growth of pharmaceutical industry, increase

in the number and variety of drugs and availability of sophisticated

instruments has paved way for rapid progress in providing simple analytical

procedures for the analysis of complex formulations also. The time tested

assays of medicinal products are no doubt still dependable. The availability of

new techniques with improved equipments has made the latest techniques

attractive.

Several methods for the estimation of drugs are classified into

physical, chemical, physico-chemical and biological ones. Physical methods

involve the study of the physical properties such as solubility, transparency or

degree of turbidity, color density, specific gravity etc. Physico-chemical

methods involve the study of the physical phenomena that occurs as a result

of chemical reactions [16-18]. These include optical and chromatographic

methods. The combination of mass spectroscopy with gas chromatography is

one of the most powerful tools available. The chemical methods include the

gravimetric and volumetric procedures which are based on complex

formation, redox reactions etc. Titration in non-aqueous media and

complexometry are also being used in pharmaceutical analysis. The

continuous growth of new drugs needs new methods for controlling the

Page 227

quality. Modern pharmaceutical analytical techniques need the following

requirements.

i. Minimal time for analysis

ii. Analysis accuracy should satisfy the demands of pharmacopoeia

iii. Analysis should be economical

iv. The selected method should be precise and selective

v. The above requirements are met by the physico-chemical methods of

analysis. An advantage is their universal nature that can be employed for

analyzing organic compounds with any diverse structure. Visible

spectrophotometry is generally preferred especially by small scale industries

as the cost of the equipment is less and the maintenance problems are

minimal.

Visible spectrophotometry and HPLC techniques have been

used in the present thesis work. Using visible spectrophotometry, seventeen

new analytical methods are developed for the assay of three selected drugs {

Saquinavir [SQVR], Atomoxetine [ATXT], Duloxetine [DLXT]} (Table A,

Page 181) by exploiting their functional groups present in them with the use of

appropriate chromogenic reagents in pure form and pharmaceutical

formulations (Table B, Page 182 & 183). In addition to visible

spectrophotometric methods, the author has developed one new HPLC

procedures for the assay of the selected drugs {Oseltamivir [OTVR]} in

pharmaceutical formulations (Table C, Page 184).

The content of the thesis has been divided into five chapters and

appropriate references have been placed at the end.

Page 228

Chapter-I starts with an introduction giving a brief account of various

aspects considered for the development of new visible spectrophotometric

(Part-A) and HPLC (Part-B) methods for the assay of four selected drugs.

The information given under Part-A, the chemistry of chromogenic reagents,

and the reactions used in the present investigation, and the general

methodology for developing new visible spectrophotometric methods (spectral

characteristics of the colored species) optimization of experimental conditions

(effect of pH, reagent concentration and order of addition, keeping time and

temperature during each addition, effect of solvent, color development and

stability) optical characteristics (Beer’s law limits, Sandell’s sensitivity,

optimum photometric range and molar absorptivity useful for sensitivity),

selectivity, precision, standard deviation, percent range of error, testing of

significance by F-test, accuracy( comparison of the proposed and reference

methods of pharmaceutical formulation, testing of significance by t-test and

recovery experiments in the present investigations.

The information given under Part-B, includes HPLC system

components (solvent delivery systems, solvent degassing systems, gradient

elution devices, sample introduction systems liquid chromatography detectors,

column packing materials inclusive of bonded phase, derivatization, gradient

elution), performance calculations (relative retention, theoretical plates, plates

per meter, height equivalent to theoretical plate, capacity factor, resolution,

peak asymmetry), linear fit properties of solvents used in chromatography and

Page 229

validation of analytical methods(recovery, response function, sensitivity,

precision and accuracy) in the present investigations.

Chapter - II, begins with the introduction giving brief account of

chemical name, structure, and mode of action, characteristics, analytically

useful functional groups, commercially available formulations and literature on

physicochemical methods reported for Saquinavir [SQVR]. Yet no visible

spectrophotometric method has been developed for the assay of SQVR in

pharmaceutical formulations. The chemical features of analytically useful

functional groups in SQVR offer a lot of scope for the development of new

methods, hopefully with better sensitivity precision and accuracy, which

prompted the author to carry out investigations in this accord. The author has

developed nine versatile visible spectrophotometric methods for the assay of

SQVR in pure and Pharmaceutical dosage forms

Saquinavir [SQVR] possesses different functional groups such as

aromatic primary amine and keto groups of varied reactivity. The primary

amine in Saquinavir [SQVR] was responsible for the development of ion-

association complex formation with acid dyes such as Bromo thymol

blue (BTBP) [M1a] and Bromo phenol blue (BPB) [M1b], condensation

reaction with Isatin - H2SO4 [M2]; Xanthydrol-H2SO4 [M3] and Vanillin-

H2SO4 [M4]; PDAB [M6]; PDAC [M6]; Ninhydrin in presence of ascorbic

acid [M7]; and diazo coupling product with Phloroglucinol and Resorcinol

[M8 and M9].

Page 230

Chapter - III, opens with the introduction giving or brief account of

chemical name, structure, therapeutic importance, analytically useful

functional groups, commercially available formulations and the literature on

the physicochemical methods reported so far for Atomoxetine [ATXT]. This

chapter describes the author’s attempts in developing visible

spectrophotometric methods as there is only one visible spectrophotometric

method for the assay of Atomoxetine [ATXT] in the literature survey and

hence, there is a need to develop few more visible spectrophotometric

methods for its determination in pharmaceutical dosage forms. Based on this

the author proposed five visible spectrophotimetric methods by exploiting the

functional groups present in it.

Atomoxetine [ATXT] possesses secondary amine group. The five

methods proposed by the author are based on reactivity of secondary amine

with various reagents. Oxidative coupling reactions with MBTH in presence

of IO4- / Fe (III) oxidant [M10 and M11], with Brucine in the presence of IO4

-

oxidant [M12] and redox reaction with Fe (III) in the presence of [Fe(CN)6]-3

[M14] and with AV [M15].

Chapter - IV of this chapter is focused on the author attempts in

developing suitable visible spectrophotometric methods with better sensitivity,

selectivity, precision and accuracy by exploiting the analytically useful groups

in Duloxetine [DLXT], the author developed four visible spectrophotometric

methods for Duloxetine [DLXT].

Page 231

The secondary amine of Duloxetine [DLXT] forms Oxidative

coupling reactions with Brucine in the presence of IO4 - oxidant [M12] and

with DCQC [M13]; charge transfer complex formation with DDQ [M16] and

DHQ [M17].

Chapter - V, reveals a brief note on the chemical properties and the

literature survey of the HPLC methods on Oseltamivir [OTVR]. As there are

very few HPLC (especially in pharmaceutical formulations) methods for the

assay of Oseltamivir [OTVR] were reported in the literature and therefore the

author has attempted to developed a simple HPLC method for the

quantitative estimation of Oseltamivir [OTVR] with a better sensitivity by

using stationary phase [YMC Pack Pro C18 RS, 250mm x 4.6 mm, 5m]

and mobile phase combination of [solution A and solution B in the ratio of

75:25 v/v], where solution A is Phosphate buffer solution, solution B is

Acetonitrile. The detection was carried at 220nm. The results of this

investigation are incorporated in this part of this chapter

The data and information of selected drugs, reagents and techniques

given in chapters [II-V] (Table - B & C, Page 182-184) reveals that the

proposed methods are simple, selective, sensitive (some are superior to most

of the reported visible spectrophotometric methods) and accurate with

reasonable precision and accuracy. In addition, selectivity to each selected

drug and its formulations was achieved by selecting the appropriate

combination of solvent systems in the sample solution preparation and

Page 232

exploring specific functional groups exclusively present in the drug. The

proposed methods can be used as alternative methods to reported ones and

provide wide choice for the routine determination of the above mentioned

drugs depending upon the availability of chemicals and situation arising due

to the presence of concomitants. Three papers were in press for publication

and much of the work has been communicated to reputed national and

international journals.

Page 233

TABLE - A

STRUCTURAL FEATURES OF SELECTED DRUGS

SI. No

Generic Name Structure

Drug Category

Chemical Name, Molecular formula& Molecular

weight

Analytical important

moieties/functional groups

1 Saquinavir

Antiviral N-tert-butyl-decahydro-2-[2(R)-hydroxy-4-phenyl-

3(S)-[[N-(2quinolylcarbonyl)-L-

asparaginyl]amino]butyl]-(4aS,8aS)-isoquinoline-

3(S)-carboxamide

Molecular Formula: C38H50N6O5

Molecular weight: 670.86 g mol−1

Primary, Tertiary nitrogen and

keto group

2 Atomoxetine

Antideptrssive N-methyl-3-phenyl-3-(o-tolyloxy)-propylamine

hydrochloride

Molecular Formula: C16H13Cl2NO4 .

Molecular weight: 291.82 g mol−1

secondary nitrogen group

3 Duloxetine

Antidepressive (+)-(S)-N-methyl-(1-naphthyloxy)-2-

thiophenepropylamine hydrochloride[

Chemical Formula: C18H19NOS,

Molecular weight: 297.41

secondary nitrogen group

4

Oseltamivir

phosphate

Antiviral (3R,4R,5S)-4-acetylamino-5-amino-3-(1-

ethylpropoxy)-1-cyclohexene-1-carboxylic acid,

ethyl ester

Chemical Formula: C16H31N2O8P

Molecular weight: 538.13

Carboxylic and secondary

nitrogen group

Page 234

TABLE - B LIST OF PROPOSED VISIBLE SPECTROPHOTOMETRIC METHODS

Type of Reaction Reagent used for the

exploitation of functional

group/ moiety

Method

proposed in

the thesis

Drug responded max nm max

L.mole-1 cm-1

Beer’s law limits

g ml-1 References

Ion association

complex

BTB M1 a SQVR 465 1.811 x 104 3.0 – 15.0 Chapter II, present work

Ion association

complex

BPB M1b

SQVR 615 1.077 x 104 3.0 – 15.0 Chapter II, present work

Condensation Isatin - H2SO4 M2

SQVR 630 3.045 x 104 2.0 – 10.0 Chapter II, present work

Condensation Xanthydrol - H2SO4 M3

SQVR 660 5.890 x 104 2.5 – 12.5 Chapter II, present work

Condensation Vanillin M4

SQVR 535 1.650 x 105 2.0 – 10.0 Chapter II, present work

Condensation PDAB M5

SQVR 540 4.243 x 104 2.0 – 10.0 Chapter II, present work

Condensation PDAC M6

SQVR 470 5.172 x 104 2.0 – 10.0 Chapter II, present work

Condensation Ninhydrin – Acsorbic acid M7

SQVR 560 1.224 x 104

4.0 – 20.0 Chapter II, present work

Diazo coupling NaNO2-phloroglucinol M8 SQVR 520 8.153 x 105

4.0 – 20.0 Chapter II, present work

Diazo coupling NaNO2-resorcinol M9

SQVR 625 9.397 x 105 4.0 – 20.0 Chapter II, present work

Page 235

TABLE - B

LIST OF PROPOSED VISIBLE SPECTROPHOTOMETRIC METHODS

Type of Reaction

Reagent used for the

exploitation of functional

group/ moiety

Method

proposed in

the thesis

Drug responded max nm max

L.mole-1 cm-1

Beer’s law limits

g ml-1 References

Oxidative Coupling MBTH - NaIO4 M10 ATXT 585 5.132 x 105 4.0 – 20.0 Chapter III, present work

Oxidative Coupling MBTH - Fe(III) M11 ATXT 625 3.600 x 105 2.0 – 10.0 Chapter III, present work

Oxidative Coupling Brucine - IO4- M12 ATXT 520 1.264 x 104 2.5 – 12.5 Chapter III, present work

Oxidative Coupling Brucine - IO4- M12 DLXT 520 1.683 x 104 2.5 – 12.5 Chapter IV, present work

Oxidative Coupling DCQC M13 DLXT 470 4.297 x 105 4.0 – 16.0 Chapter IV, present work

Redox Reaction Fe(III)/[Fe(CN)6]-3 M14 ATXT 650 5.694 x 105 5.0 – 25.0 Chapter III, present work

Redox Reaction AV-H2SO4 M15 ATXT 740 5.321 x 105 5.0 – 25.0 Chapter III, present work

Charge Transfer

reaction

DDQ M16 DLXT 480 6.632 x 105 2.5 – 12.5 Chapter IV, present work

Charge Transfer

reaction

CA –M eOH M17 DLXT 490 1.549 x 104 2.5 – 12.5 Chapter IV, present work

Page 236

TABLE - C

RP-HPLC METHODS

Drug responded Chromatographic column

used Mobile phase composition Detection limit Linearity range Reference

Oseltamivir phosphate

YMC Pack Pro C18 RS,

250mm x 4.6 mm, 5m

Combination of phosphate buffer

of pH 2.5 and acetonitrile in the

ratio of 75:25 v/v

220 0.08 -0.12mg.ml-1

Chapter - V