Original Article
DETERMINATION OF 2-CYANO-4’-BROMOMETHYL BIPHENYL GENOTOXIC IMPURITY IN
IRBESARTAN DRUG SUBSTANCES USING HPLC TECHNIQUE
S. SENTHIL KUMAR
a*
, RITESH KUMAR SRIVASTAVA
b
,V. SRINIVAS RAO
a
a
Faculty of Pharmacy, Pacific Academy of Higher Education and Research University, Udaipur 313004, Rajasthan, India,
b
Analytical
Research and Development, Macleods Pharmaceuticals Limited, R and D Center, Mumbai 400059, India
Email: chensenk@gmail.com
Received: 12 Aug 2016 Revised and Accepted: 18 0ct 2016
ABSTRACT
Objective: The objective of present study was to develop and validate a specific and sensitive HPLC method for the quantitative determination of
genotoxic impurity 2-cyano-4’-bromomethyl biphenyl present in irbesartan drug substance.
Methods: The development activity was conducted by HPLC with UV as a detector. The impurity was separated on Kromasil C18 250 x 4.6 mm, 5 µm
analytical column with a mobile phase consisting of buffer pH 3.2 and acetonitrile in the ratio of 60:40 v/v at a flow rate 1.5 ml/min. The effluent was
monitored by UV detection at 258 nm with column temperature maintained at 40 °C and the injection volume 30 μl. Acetonitrile was selected as diluent.
Results: Validation activity was planned and completed based on the ICH guideline. The LOD and LOQ value were found to be 0.167 µg/g and 0.506 µg/g
and accuracy results were well in the range 98.34 to 103.46 %. The linearity curve showed the correlation coefficient of 0.9999 and method very sensitive.
Conclusion: From validation data, it was confirmed that the developed method is specific, sensitive, linear, precise and accurate for the
determination of 2-cyano-4’-bromomethyl biphenyl genotoxic impurity in irbesartan drug substances.
Keywords: Impurity, HPLC, TTC, Validation, ICH guidelines
© 2016 The Authors. Published by Innovare Academic Sciences Pvt Ltd. This is an open access article under the CC BY license (http://creativecommons.org/licenses/by/4. 0/)
DOI: http://dx.doi.org/10.22159/ijpps.2016v8i12.14682
INTRODUCTION
Irbesartan is a non-peptide tetrazole derivative drug, chemically
described as 2-butyl-3-({4-[2-(2H-1,2,3,4-tetrazol-5-yl)phenyl]
phenyl} methyl)-1,3diazaspiro [4.4] non-1-en-4-one [1]. Its molecular
formula is C25H28N6O and molecular weight 428.53 [2]. The drug is
used mainly for the treatment hypertension and commercially
available in 75 mg, 150 mg and 300 mg of tablet strength either
individually or combination with other antihypertensive drugs [3-5].
2-cyano-4’-bromomethyl biphenyl is the most important
intermediate used in the synthesis of irbesartan [6, 7]. This is
identified as a genotoxic impurity in irbesartan according to the
guidelines [8, 9]. Based on the threshold of toxicological concern
(TTC) and the maximum daily dosage of irbesartan the evaluation
limit of its genotoxic impurity is calculated 5.00 µg/g [8]. The
chemical structures of irbesartan and 2-cyano-4’-bromomethyl
biphenyl are presented in fig. 1 [6, 7].
Fig. 1: Chemical structure of (a) Irbesartan and (b) 2-cyano-4’-
bromomethyl biphenyl
Detailed literature survey reveals that the many HPLC methods are
available for the determination of the drugs individually or in
combination with other drugs [10-13]. However, very few analytical
methods are available for the determination of genotoxic impurity in
irbesartan drug by LC-MS/MS [14] and UPLC [15] technique. There
was no HPLC method available for quantitative determination of 2-
cyano-4’-bromomethyl biphenyl in irbesartan.
Because of literature gap for the determination of 2-cyano-4’-
bromomethyl biphenyl genotoxic impurity, we have reported here in
a specific and sensitive HPLC analytical method, which separates the
impurity from the drug substances and also could quantify the
impurity at less than 50 % to the evaluation limit.
MATERIALS AND METHODS
Chemicals and reagents
HPLC grade of water, orthophosphoric acid, methanol,
triethylamine, and acetonitrile were purchased from Merck, Mumbai
India. All pure drug substances and impurities are used for research
purpose were procured in-house Macleods pharmaceutical LTD.
Instrumentation
The HPLC system consisted of Shimadzu model LC 2010 CHT, UV and
PDA detector. The output signals were monitored and integrated
using LC solution software. Sartorius analytical balance and Pico
+
pH
meter were used.
Chromatographic conditions
The chromatographic separation was achieved on Kromasil C18
(250 x 4.6 mm, 5 µm) column using mobile phase consisting of
buffer pH 3.2 and acetonitrile in the ratio of 60:40 v/v. The flow rate
of the mobile phase was 1.5 ml/min and isocratic program run time
was 60 min. The column temperature was maintained at 40 °C and
the detection was monitored at 258 nm. The injection volume was
30 µl and acetonitrile used as diluent.
Preparation of Buffer pH 3.2: Transferred 5.5 ml of orthophosphoric
acid in 1000 ml of water, pH is adjusted to 3.2 with triethylamine.
Preparation of standard and sample solutions
A stock solution of 2-cyano-4’-bromomethyl biphenyl impurity was
prepared by dissolving the appropriate amount of 2-cyano-4’-
International Journal of Pharmacy and Pharmaceutical Sciences
ISSN- 0975-1491 Vol 8, Issue 12, 2016