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Rapid, Simultaneous Determination of Levamisole

and Abamectin in Liquid Formulations Using HPLC
a b a
Peyami Sari , Majid Razzak & Ian G. Tucker
a
School of Pharmacy , University of Otago , 7th Floor, Adams Building, 18 Frederick
Street, Dunedin, 9001, New Zealand
b
Ancare New Zealand Ltd. , Auckland, New Zealand
Published online: 23 Aug 2007.

To cite this article: Peyami Sari , Majid Razzak & Ian G. Tucker (2005) Rapid, Simultaneous Determination of Levamisole
and Abamectin in Liquid Formulations Using HPLC, Journal of Liquid Chromatography & Related Technologies, 27:2,
351-364, DOI: 10.1081/JLC-120027105

To link to this article: http://dx.doi.org/10.1081/JLC-120027105

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 JOURNAL OF LIQUID CHROMATOGRAPHY & RELATED TECHNOLOGIESw
Vol. 27, No. 2, pp. 351–364, 2004
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Rapid, Simultaneous Determination of

Levamisole and Abamectin in Liquid
Formulations Using HPLC

Peyami Sari,1 Majid Razzak,2 and Ian G. Tucker1, *

1
School of Pharmacy, University of Otago, Dunedin, New Zealand
2
Ancare New Zealand Ltd., Auckland, New Zealand

ABSTRACT

The aim of the study was to develop a high performance liquid

chromatography (HPLC) assay for the rapid, simultaneous determination
of levamisole phosphate and abamectin in liquid formulations containing
mixtures of solvents and medium chain mono- and diglycerides and
triglycerides. The experimental procedure involved reversed-phase-HPLC
with a Zorbax ODS column (7 mm particle size, 4.6 ID  250 mm),
acetonitrile-water- and ammonia 1.0N volumetric solution (80 : 20 : 0.1,
v/v/v) mobile phase, UV detection at 253 nm for both levamisole
phosphate and abamectin. The flow rate of the mobile phase was
2 mL/min. The retention times of levamisole phosphate and abamectin
varied from 2.45–2.46 min and 5.78–5.82 min, respectively. Formulation

*Correspondence: Ian G. Tucker, School of Pharmacy, University of Otago, 7th Floor,

Adams Building, 18 Frederick Street, Dunedin 9001, New Zealand; E-mail:
ian.tucker@stonebow.otago.ac.nz.

351

DOI: 10.1081/JLC-120027105 1082-6076 (Print); 1520-572X (Online)

Copyright # 2004 by Marcel Dekker, Inc. www.dekker.com
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352 Sari, Razzak, and Tucker

components did not give rise to any interfering peaks. Calibration curves
were linear over the range 13.5–270 mg/mL for levamisole phosphate and
0.5–10 mg/mL for abamectin. The maximum intraday and interday
coefficients of variation were 0.7% and 1% at 13.5 mg/mL for levamisole
phosphate, and 2.2% and 5.8% at 0.5 mg/mL for abamectin, respectively.
Accuracies were 98.9 + 5.2% and 96.2 + 3.1% (Mean + SD, n ¼ 14)
for levamisole phosphate and abamectin, respectively, at concentrations of
27.3 mg/mL of levamisole phosphate and 1 mg/mL of abamectin. The
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assay was used to evaluate the stability of these drugs in the liquid
formulations. A simple and accurate liquid chromatographic method was
developed and validated for simultaneous determination of levamisole and
abamectin in liquid formulations. Due to its simplicity and accuracy, the
assay method is suitable for routine analysis of both drugs in liquid
formulations.

Key Words: High performance liquid chromatography; Levamisole

phosphate; Abamectin; Validation; Liquid formulation.

INTRODUCTION

Levamisole (2,3,5,6-tetrahydro-6-phenylimidazole[2,1-b]thiazole) is an
imidazothiazole derivative and used as an anthelmintic (Fig. 1A). It is the
levo-rotatory (laevo) isomer of tetramisole, an anthelmintic described in
1966.[1] The dextro isomer contributes to the toxicity, but not the therapeutic
effect, so it has been removed in marketed preparations.[2]
Abamectin (avermectin B1a) was presented as an animal endoctocide in
1985, in Australia.[3] It was marketed as an injectable formulation in the same
excipient as the injectable ivermectin for use in cattle, and was administered at
the same dose level of 200 mg/kg. The basic structure of the avermectins is
a 16-membered lactone ring, with three main substituent groups: a hexahydro-
benzofuran group, a disaccharide group at C-13, and a spiroketal ring (C-17 to
C-28) (Fig. 1B). Abamectin is at least 80% avermectin B1a and not more than
20% avermectin B1b. The b series are minor components. The biological
activity of the a- and b- series are so similar that they are not separated for
commercial use (Fisher and Mrozik, 1989).[4]
HPLC methods for the determination of levamisole[5,6] and abamectin[7,8]
in tablet dosage forms are available. However, no reports have been found for
determination of levamisole or abamectin combinations in pharmaceutical
dosage forms, or for the simultaneous HPLC determination of these two drugs
in compounded preparations. There is, therefore, need of a simple HPLC
technique for control procedures aimed at ensuring the quality of combination
preparations, which are available for clinical use.
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Determination of Levamisole and Abamectin 353

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Figure 1. Chemical structure of levamisole (A) and abamectin (avermectin B1a) (B).

The aim of this study was to develop a HPLC assay method with fast
sample analysis for simultaneous determination of levamisole and abamectin
in liquid pharmaceutical formulations with an optimized separation and
acceptable elution times.

EXPERIMENTAL

Chemical Reagents

Acetonitrile (HPLC grade) (BHD Laboratory Supplies, England) and

distilled and MilliQ filtered water were used for the preparation of the mobile
phase. Ammonia 1.0N volumetric solution was obtained from Pouling
Industries Ltd., Auckland. Sesame oil (SO) was obtained from Bronson and
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354 Sari, Razzak, and Tucker

Jacobs Pty Ltd. (Auckland). Medium chain mono- and diglyceride (MCMDG)
(Capmul MCM) was supplied by Abitec, Columbus, OH. Propylene glycol
(PG) and glycerol formal (GF) were obtained from Bomac Laboratories,
Auckland and were of pharmaceutical grade, and used without further
treatment. Levamisole phosphate, which is a hydrophilic drug, was supplied
by Ancare, Auckland. Abamectin, which is a highly lipophilic drug, was
purchased from Zhejiang Hisun Pharmaceutical, China.
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Chromatographic System and Conditions

The HPLC system consisted of a model Shimadzu LC 6A pump (Japan), a

SPD-6A variable-wavelength UV absorbance detector (Shimazdu, Japan), a
Rheodyne 7125 injector (Rheodyne Incorporated, CA), 20 mL injection loop,
and a Hitachi D-2500 integrator (Hitachi, Tokyo, Japan). A Zorbax ODS
column, 7 mm particle size, 4.6 ID  250 mm (Phenomenex, Torrance, CA)
was used.
For simultaneous determination, both levamisole phosphate and
abamectin in the liquid formulations containing MCMDG, sesame oil,
propylene glycol, glycerol formal, ethyl alcohol, and water, the mobile
phase consisted of acetonitrile-water-ammonia 1.0N volumetric solution
(80 : 20 : 0.1, v/v/v) (pH 8.91). The mobile phase was filtered through a
0.45 mm Millipore membrane filter (Alltech, USA), and degassed by
ultrasonication (Sonorex, Germany) before use. The flow rate of the mobile
phase was 2 mL/min. The wavelength for detection was 253 nm. The HPLC
system was operated at ambient temperature. An aliquot of 20 mL was injected
onto the column.

Preparation of Stock and Standard Solutions

Stock solutions were prepared by weighing drugs (0.675 g levamisole

phosphate and 0.025 g abamectin) and appropriate amounts of formulation
components (oils, MCMDG, solvents, and water), dependent on their ratios
in formulations, and adjusting to 50 mL with mobile phase. Standard
solutions of appropriate concentrations were made by dilution of the stocks
using the mobile phase. The concentrations of standard solutions were
13.5/0.5, 27/1, 54/2, 135/5, and 270/10 mg/mL of levamisole phosphate/
abamectin. The stock and standard solutions were stored at 48C protected
from light.
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Determination of Levamisole and Abamectin 355

HPLC Assay Validation

Calibration Curves and Linearity

Duplicate injections were used. The mean peak areas and mean peak
heights of standard concentrations were used to construct calibration curves,
and data were analysed by least-squares linear regression analysis using
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Excel 7.0. This was done once daily for five days and twice daily for one day.
Since peak areas gave a better fit (higher correlation coefficient) for levamisole
phosphate than peak heights, areas were used thereafter. Conversely, peak
heights were used for abamectin.

Precision and Accuracy

Three working solutions of levamisole phosphate and abamectin (13.5/0.5,

135/5, and 270/10 mg/mL) were prepared using mobile phase. Five replicate
injections of the working solutions were used each day, for 5 days, to determine
intra and interday variability. Precision was also evaluated over 10 months.
Liquid formulations containing both levamisole phosphate and abamectin
were prepared in mixtures of MCMDG, oils, solvents, and water. The contents
of levamisole phosphate and abamectin in formulations were 136.5 and
5 mg/mL (27.3 : 1), respectively. Recovery studies of both drugs were
performed after preparation of formulations.

Assessment of Stability

The stability-indicating studies of formulations were carried out at 4 and

608C for 10 days. Formulations were stored in sealed, amber glass bottles,
away from light at 48C and 608C (Contherm incubator). After 10 days, the
levels of levamisole phosphate and abamectin were determined.

RESULTS

Chromatographic Procedure and Linearity

There were no interfering compounds in the chromatographic determi-

nations. The HPLC method achieved good baseline separation of levamisole
phosphate and abamectin, and at retention times less than 6 min (Fig. 2).
Calibration curves for levamisole phosphate/abamectin combination were
linear over the range 13.5 –270 mg/mL for levamisole phosphate and 0.5–
10 mg/mL for abamectin with the correlation coefficients for both drugs
exceeding R2 . 0.999.
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356
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Figure 2. Chromatograms of levamisole phosphate and abamectin. A) blank drug-free sample containing
components of formulations, B) 54 mg/mL levamisole phosphate, C) 2 mg/mL abamectin, and D) 54 mg/mL of
levamisole phosphate/2 mg/mL of abamectin. Retention times of levamisole phosphate and abamectin were 2.45
and 5.80 min, respectively.
Sari, Razzak, and Tucker
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Determination of Levamisole and Abamectin 357

Precision and Accuracy

Table 1 summarizes the intraday and interday coefficients of variation.

Intraday and interday precision was less than 1%, except for 0.5 mg/mL
abamectin. Abamectin RSD was 2.2% and 5.8% at the lowest concentration
(0.5 g/mL) in intraday and interday applications, respectively. Intraday and
interday relative standard deviation (RSD) of levamisole phosphate was 0.7%
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and 1.0% at the lowest concentration (13.5 mg/mL), respectively (Table 1).
RSD of levamisole phosphate and abamectin were 3.4% and 6.0%, respectively,
at the lowest concentrations over 10 months. Table 2 shows the RSD of
levamisole phosphate and abamectin determination over a period of several
months. Recoveries of levamisole phosphate and abamectin were 98.9+5.2%
and 96.2+3.1% (n ¼ 14, Mean+SD), respectively, in different liquid
formulations containing MCMDG, sesame oil, solvents (propylene glycol and
glycerol formal, ethyl alcohol) or solvent mixtures (Table 3).

Applicability of the Method: Stability Study

Figure 3 presents sample chromatograms of formulations after storage at

4 and 608C for 10 days. A good baseline separation of both drugs was
achieved. The results (Table 4) showed that concentrations of both drugs in
formulation C, D, and E, which contained 5% water, were higher than in

Table 1. Intraday and interday RSD of levamisole phosphate and abamectin assays
for 5 day applications (mean+SD) (n ¼ 5).

Levamisole phosphate Abamectin

Added Assayed
Added conc. Assayed conc. RSD conc. conc. RSD
(mg/mL) (mg/mL) (%) (mg/mL) (mg/mL) (%)

Intraday
13.5 13.1+0.09 0.7 0.5 0.46+0.01 2.2
135 134.6+0.63 0.5 5 4.97+0.02 0.4
270 256.3+1.84 0.7 10 9.48+0.09 0.9
Interday
13.5 13.0+0.13 1.0 0.5 0.52+0.03 5.8
135 134.7+0.78 0.6 5 5.01+0.04 0.8
270 269.4+0.72 0.3 10 10.02+0.05 0.5

Note: RSD: relative standard deviation; Conc.: concentration.

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358

Table 2. The RSD of levamisole phosphate and abamectin over 10 months.

Concentration assayed (mg/mL)

Added conc. 2 3 4 5 9 10 RSD

(mg/mL) Initial months months months months months months Mean+SD (%)
ORDER

Levamisole phosphate
13.5 12.1 12.6 12.6 12.3 12.1 13.1 13.1 12.5+0.42 3.4
135 135.4 133.5 134.2 135.2 135.5 136.3 136.2 135.2+1.00 0.7
270 269.9 270.8 270.3 269.7 269.7 269.0 269.0 269.8+0.64 0.2
Abamectin
REPRINTS

0.5 0.48 0.46 0.50 0.47 0.49 0.54 0.54 0.50+0.03 6.0
5 4.99 5.01 4.98 5.01 5.00 4.84 4.86 4.96+0.07 1.4
10 10.0 10.0 10.01 9.99 9.99 10.07 10.07 10.02+0.04 0.4

Note: RSD: Relative standard deviation; Conc.: concentration.

Sari, Razzak, and Tucker
 ORDER REPRINTS

Determination of Levamisole and Abamectin 359

Table 3. Recovery studies of both levamisole phosphate and abamectin in different

liquid formulations.

Levamisole phosphate
(concentration added: Abamectin (concentration
136.5 mg/mL) added: 5 mg/mL)

Concentration Recovery Concentration Recovery

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Formulationa assayed (mg/mL) (%) assayed (mg/mL) (%)

1 126.0 92.3 4.54 90.8

2 125.3 91.8 4.61 92.2
3 142.7 104.5 4.85 97.0
4 147.2 107.9 5.00 100.0
5 134.8 98.8 4.75 95.0
6 132.9 97.4 4.79 95.8
7 135.7 99.4 4.74 94.8
8 143.6 105.2 5.00 100.0
9 142.0 104.0 5.10 102.0
10 133.1 97.5 4.90 98.0
11 133.1 97.5 4.87 97.4
12 138.7 101.6 4.74 94.8
13 128.5 94.2 4.78 95.6
14 126.0 92.3 4.67 93.4
Mean 135.0 98.9 4.81 96.2
SD 7.1 5.2 0.2 3.1
a
Formulations 1 – 2 and 3 – 4 contain water 10% and 5% respectively and are
combinations of solvent/solvent mixture and MCMDG. Formulations 5 – 14 are non-
aqueous systems. Formulations 5 – 8 are only solvent mixtures and 9 –14 are
combinations of MCMDG and solvents/solvent mixture.

formulation A and B, which contained 10% of water. Concentrations of both

drugs were more in non-aqueous formulations (F–J) than aqueous formulations
(A–E) at 608C after 10 days (Table 4). Both drugs in non-aqueous formulations
were more stable compared with those in aqueous formulations.

DISCUSSION

Chromatographic Procedure

In this study, the retention times of levamisole phosphate and abamectin

varied from 2.45 to 2.70 and 5.68, 5.81 min across all samples. The retention
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360
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REPRINTS

Figure 3. Sample chromatograms of HPLC showing separation of levamisole phosphate and abamectin at 48C and 608C. Retention times
of levamisole phosphate and abamectin varied from 2.58 to 2.60 and 5.72 to 5.77 min, respectively. Chromatograms 1, 2, 3, and 4 represent
formulation C, D, H, and J, respectively in Table 4.
Sari, Razzak, and Tucker
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Table 4. Stability-indicating test studies of levamisole phosphate and abamectin in aqueous and non-aqueous liquid formulations at 4 and
608C for 10 days (mean + SD).

Levamisole phosphate (conc. added: 136.5 mg/mL) Abamectin (conc. added: 5 mg/mL)

48C 608C 48C 608C

Formulations Conc. assayed Recovery Conc. assayed Recovery Conc. assayed Recovery Conc. assayed Recovery
(% w/w) (mg/ml) (%) (mg/ml) (%) (mg/ml) (%) (mg/ml) (%)

Aqueous
ORDER

A 127.4 93.3 67.9 49.7 4.12 82.5 2.11 42.2

B 128.6 94.2 68.9 50.5 4.17 83.4 2.19 43.8
C (n ¼ 3) 135.5 + 7.6 99.3 + 5.6 90.8 + 3.0 66.5 + 2.2 4.70 + 0.7 94.1 + 14.7 3.84 + 0.7 76.9 + 13.3
D (n ¼ 3) 137.8 + 10.5 100.9 + 7.7 94.1 + 2.4 68.9 + 1.8 4.36 + 0.6 87.2 + 11.2 3.72 + 0.3 74.4 + 6.7
Determination of Levamisole and Abamectin

E (n ¼ 3) 142.2 + 8.6 104.2 + 6.3 92.6 + 5.4 67.9 + 4.0 4.75 + 0.3 94.9 + 5.2 3.98 + 0.2 79.6 + 4.7
REPRINTS

Non-aqueous
F 137.2 100.5 89.2 65.3 4.88 97.6 3.88 77.6
G 129.7 95.0 89.4 65.5 4.64 92.8 4.02 80.4
H (n ¼ 4) 142.5 + 9.5 104.4 + 7.0 109.0 + 3.1 79.8 + 2.3 4.84 + 0.1 96.9 + 1.8 4.11 + 0.2 82.2 + 4
I (n ¼ 4) 145.7 + 7.4 106.7 + 5.4 111.0 + 2.9 81.3 + 2.1 4.84 + 0.2 96.7 + 4.0 4.32 + 0.3 86.4 + 5.1
J (n ¼ 6) 144.0 + 6.8 105.5 + 5.0 111.0 + 4.7 81.3 + 3.5 4.78 + 0.3 95.7 + 6.1 4.37 + 0.3 87.3 + 5.7
J (n ¼ 4)a 148.3 + 6.6 108.6 + 4.9 113.3 + 4.1 83.0 + 3.0
J (n ¼ 4)a 4.88 + 0.4 97.6 + 7.7 4.82 + 0.4 96.4 + 6.9
a
Formulations contain levamisole phosphate or abamectin alone.
Conc.: concentration.
361
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362 Sari, Razzak, and Tucker

time of abamectin was greater than that of levamisole because of solute

hydrophobicity. The 1-octanol/water partition coefficient (log P) has been
proposed as a useful predictor of retention in the liquid chromatography.[9]
The experimental log P of levamisole is 1.84 and calculated log P is
2.87.[10] The log P of ivermectin, which is structurally similar to abamectin,
is 3.35,[11] and both are members of the avermectin group.
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Precision and Accuracy

The assay showed good intraday and interday precisions, as indicated by

the RSD except for the lowest concentrations. The mean recoveries of
levamisole phosphate and abamectin were within 1% and 4% with the RSD
5.3% and 3.2%, respectively in this study.
Youchang et al.[5] determined the contents of mebendazole and
levamisole in tablets by reversed-phase HPLC with a C18 Hypersil column
(100 mm, 4.6 mm, 5 mm). Phosphate buffer (pH 3.0), methanol – diethylamine
(50 : 50 : 0.1, v/v/v) mobile phase, UV detection at 230 nm, and diclofenac
sodium as internal standard, were used. The recovery was 100.7% for
mebendazole and 99.20% for levamisole, and RSD 1.8%.
A reversed-phase HPLC method for the determination of mebendazole
and levamisole in tablets was developed by Yingzheng et al.[6] A reversed-
phase C8 (5 mm) stainless steel column (220 mm  2.1 mm) with methanol –
5% ammonium acetate solution (pH 5.0) (53 : 47, v/v) as the mobile phase,
and detection at 220 nm were used. The recovery rates of mebendazole and
levamisole were 99.21% and 99.71% with the RSD 1.2% and 0.53%,
respectively. The assay data obtained from the 10 batches of samples showed
consistency with that published in the China Pharmacopeia.[6]
A method was developed for the separation and determination of
avermectin in avermectin tablets by reversed-phase HPLC by Yun et al.[7]
Operating conditions were as follows: TSK-GEL C18 column (250 mm,
4.6 mm ID), methanol-water (75 : 25, v/v) mobile phase with a flow rate of
1.0 mL/min, and UV detection at 245 nm. The results showed that the
active constituents avermectin B1a and B1b can be separated effectively. The
RSD were 2.56% and 1.31%, respectively (n ¼ 6). The method might
provide a rapid and simple, scientific basis for recovery of avermectin in
tablets.
In another study, Dashui described the quantification analysis of
abamectin by HPLC with a kromasil C18 column at UV 254 nm. RSD,
linear correlation, and the average recovery of abamectin were 1.9%, 0.9978,
and 99.7%, respectively.[8]
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Determination of Levamisole and Abamectin 363

CONCLUSIONS

A rapid reversed-phase HPLC assay method was developed for

simultaneous determination of levamisole and abamectin in liquid formulations
containing markedly different concentrations of the drugs. The assay can be
used to assess stability of the liquid formulations. Chromatography was
conducted on a Zorbax 7 mm ODS column, using a mixture of acetonitrile-
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water- and ammonia 1.0N volumetric solution (80 : 20 : 0.1 v/v/v) as the
mobile phase. Detection was scheduled at 253 nm. This method is suitable for
routine analysis with satisfactory recovery and precision.

REFERENCES

1. Thienpont, D.; Vanparijs, O.G.J.; Raeymaekers, A.H.M.; Vandenberk, J.;

Demoen, P.J.A.; Allewinjn, F.T.N.; Marsboom, R.P.H.; Nie-
megeers, C.J.E.; Schellekens, K.H.L.; Janssen, P.A.J. Tetramisole
(R 8299), a new potent broad spectrum anthelmintic. Nature 1996, 209,
1084 – 1086.
2. Campbell, N.J.; Hall, L.A.; Kelly, J.D.; Martin, L. The anthelmintic
efficacy of non-benzimidazole anthelmintics against benzimidazole
resistant strains of Haemonchus contortus and Trichostrongylus colubri-
formis in sheep. Aust. Vet. J. 1978, 54 (1), 23– 25.
3. Tahir, M.S.; Holroyd, G.; Copeman, D.B. Treatment of beef calves with
ivermectin and avermectin B1 in dry tropical Australia. In Parasitology-
Quo Vadit, 6th International Congress of Parasitology; Howell, M.J.,
Ed.; Australian Academy of Science: Canberra, 1986; 240.
4. Fisher, M.; Mrozik, H. Chemistry. In Ivermectin and Abamectin;
Campbell, W., Ed.; Springer-Verlag: New York, 1989; 1– 23.
5. Youchang, S.; Yingxiang, D.; Jing, W. RP-HPLC determination of
mebendazole and levamisole in compound mebendazole tablets.
Zhongguo Yaoke Daxue Xuebao (Acta of China Pharmaceutical
University) 1995, 26 (4), 213 –216.
6. Yingzheng, X.; Mingshui, C.; Jing, X.; Hai, G.; Wenji, G. Determination
of mebendazole and levamisole in tablets by RP-HPLC. Yaowu Fenxi
Zazhi (Journal of Pharmaceutical Analysis) 1999, 19 (5), 331– 334.
7. Yun, S.; Fengzu, H.; Zhixian, S. Determination of avermectin in
avermectin tablets by high-performance liquid chromatography, North- EQ1
west Plateau Institute Biology, Chinese Academy Sciences, Xining. Peop.
Rep. China. Sepu. 1998, 16 (1), 87– 88.

EQ1: Journal name for Ref. 7?

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364 Sari, Razzak, and Tucker

8. Dashui, S. Determination of abamectin by HPLC. Zhejiang Institute

Control Agrochemicals, Hangzhou, Peop. Rep. China. Nongyao 1998,
37 (4), 19– 20.
9. Karger, B.L.; Gant, J.R.; Hartkopf, A. Hydrophobic effects in reversed-
phase liquid chromatography. J. Chromatogr. 1976, 128, 65 – 78.
10. Meylan, W.M.; Howard, P.H. Atom/fragment contribution method for
estimating octanol-water partition coefficients. J. Pharm. Sci. 1995, 84 (1),
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83– 92.
11. Ho, N.F.; Geary, T.G.; Raub, T.J.; Barsuhn, C.L.; Thompson, D.P.
Biophysical transport properties of the cuticle of Ascaris suum. Mol.
Biochem. Parasitol. 1990, 41 (2), 153 – 165.

Received August 15, 2003

Accepted September 5, 2003
Manuscript 6208
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