Currents in Pharmacy Teaching and Learning xxx (xxxx) xxx–xxx

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Currents in Pharmacy Teaching and Learning

journal homepage: www.elsevier.com/locate/cptl

Experiences in Teaching and Learning

Structure activity relationship (SAR) maps: A student-friendly tool

to teach medicinal chemistry in integrated pharmacotherapy
courses
Kathleen M. Frey
Pharmaceutical Sciences, Fairleigh Dickinson University School of Pharmacy and Health Sciences, 230 Park Avenue, M-SP1-01, Florham Park, NJ
07932, United States

ARTICLE INFO ABSTRACT

Keywords: Background and purpose: Courses that integrate pharmacology, medicinal chemistry, and phar-
Medicinal chemistry macotherapy are widely implemented in pharmacy curriculums. The integration of medicinal
Integrated pharmacy curriculum chemistry is often challenging given the difficulty of material and time constraints. The objective
Pharmacotherapy of this pedagogical approach is to utilize structure activity relationship (SAR) maps as visual aids
Structure activity relationships (SAR)
to teach students medicinal chemistry in an integrated course.
Educational setting: SAR maps were designed and implemented within an integrated course fo-
cusing on cardiopulmonary diseases. Specific SAR maps used in lecture and class activities in-
cluded phenylethylamines (adrenergic agonists (i.e. bronchodilators)) and arylox-
ypropanolamines (beta blockers). Students were assessed in class activities (formative) and
exams (high stakes) for specific information surrounding drug structure and the SAR map. Drug
properties assessed included essential pharmacophores, pharmacodynamics, physiochemical
properties, metabolism, duration of action, and decision-making.
Findings: Results from assessment item analysis reveal that students performed well on medicinal
chemistry questions related to the SAR maps (~90% correct on first exam). Students revealed in a
survey that the SAR maps enhanced their understanding of medicinal chemistry concepts.
Summary: SAR maps are effective tools that visually teach students key concepts in medicinal
chemistry. This millennial student-friendly tool is time-effective and promotes learning as op-
posed to drug structure memorization. The SAR map can be easily implemented in other in-
tegrated courses focused on various disease states.

Background and purpose

Current trends in healthcare education focus on integrating basic and clinical sciences. In pharmacy education, most colleges accredited
by the Accreditation Council for Pharmacy Education (ACPE) have adopted integrated curriculums combining sciences such as pharmacology
and medicinal chemistry with clinical pharmacotherapy.1,2 Based on a survey in 2016, Islam et al.3 reported that the majority of pharmacy
curriculums in the United States (US) use coordinated, sequential delivery of disciplines for integrated courses. Commonly integrated dis-
ciplines include pharmacotherapy, pharmacology, physiology/pathophysiology, and medicinal chemistry within a focused course series.1–3
Several articles on healthcare education delineate the benefits of integrated courses4,5; however, there are several limitations in
successfully implementing truly integrated material. Such limitations include the amount of material covered by multiple disciplines,
extreme efforts to plan and implement integrated courses, and the fast-paced style of learning.2,4 Additional time constraints exist in

E-mail address: [email protected].

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Please cite this article as: Kathleen M. Frey, Currents in Pharmacy Teaching and Learning,
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K.M. Frey Currents in Pharmacy Teaching and Learning xxx (xxxx) xxx–xxx

integrated courses when several disciplines must share limited contact hours.6

Impetus for change

The majority of pharmacy curriculums integrate medicinal chemistry within pharmacotherapy courses allocating only a few
contact hours to this discipline.6 Poor delivery of medicinal chemistry content, given the time constraints in integrated courses, can
depreciate student enthusiasm for the discipline. In addition, this pharmaceutical science is often challenging for students in the first
professional year. For many students, the clear connection between drug structure and clinical pharmacy practice is unclear.7
Without a clear connection, students may lose interest and prioritize pharmacotherapy and pharmacology over medicinal chemistry.
The purpose of this communication is to describe the utility of structure activity relationship (SAR) maps as visual aids (and study
tools) to teach medicinal chemistry in an integrated pharmacotherapy course. The pedagogical approach was implemented in an
integrated course to promote student learning in medicinal chemistry. SAR maps were designed to achieve learning objectives
outlined in the Pharmacy Curriculum Outcome Assessment (PCOA) blueprint8 and topics recommended in ACPE Appendix 1.9 The
effectiveness of SAR maps were evaluated in assessments (formative in-class activity and exam) and a student survey.

Educational activity and setting

SAR maps were used as an educational tool specifically in an integrated pharmacotherapy course at ACPE-accredited Fairleigh
Dickinson University School of Pharmacy and Health Sciences. SAR maps were implemented in PHRM 6104: Cardiopulmonary I. This
course integrates pharmacology, medicinal chemistry, and pharmacotherapy for disease states such as hypertension, asthma/chronic
obstructive pulmonary disease (COPD), and heart failure. The course is offered to first professional year (P1) students during the
spring semester and students meet two and one-half hours per week (three credits). Students have already completed foundational
courses in pharmacology/medicinal chemistry/pharmacokinetics, pharmacy calculations, medical communications, pharmaceutics,
pathophysiology, and pharmacy practice. During the spring semester, students are first introduced to integrated pharmacotherapy
courses. Students are enrolled in two additional integrated pharmacotherapy courses concurrently with PHRM 6104.
SAR maps were introduced to students in a lecture covering drugs acting on the sympathetic division of the autonomic nervous
system. Example SAR maps were drawn using Chemdraw (PerkinElmer) and Microsoft PowerPoint (Fig. 1). SAR maps were con-
structed by drawing essential pharmacophores for a drug class such as alpha agonists or beta blockers (Fig. 1A and 1B, respectively).
Variable functional groups (i.e. R1, R2 groups) were added to the pharmacophore; these designations reminded students that mod-
ification of variable groups lead to different activities (structure activity relationships, or SAR). Important concepts related to drug
activity were mapped to the pharmacophore or variable functional groups using arrows and highlighted text. Students were given
instructions in class on how to generally interpret the SAR maps. This same SAR map template was used for all major drug classes that
had common pharmacophores or scaffolds. Additional SAR maps used in the course are included in Appendix 1.
Before examining the map, the drug pharmacophore concept was reviewed so that students understand that these structural
elements in drugs are essential for a particular activity. Allotted time (approximately two to three minutes per map) during each
lecture focused on reviewing the map for each drug class followed by an activity examining the specific drugs, pharmacophores, and
SAR. For example, Fig. 1A depicts the SAR map for adrenergic agonists. The map is first introduced as a common pharmacophore for
phenylethylamine adrenergic agonists with important concepts highlighted such as receptor selectivity, central nervous system (CNS)
activity, and metabolism/duration of action (DOA). After reviewing the map, students are then shown structures of specific drugs that
share the phenylethylamine pharmacophore. Applied SAR activities were used to review content throughout a specific lecture or used
in formative assessments such as medicinal chemistry trivia (Fig. 1C).
Using salmeterol as an example (Fig. 1C-C), students are shown the structure with an explanation of how the SAR map relates to
activity. Salmeterol has a large bulky R1 substitution off the amine; this group makes salmeterol selective for beta receptors (beta2 agonist).
The large bulky ether-linked phenyl group also protects the terminal amine from rapid monoamine oxidase (MAO) metabolism. This
protection extends the half-life for salmeterol, which is known as a long acting beta2 agonist (LABA). Using the SAR map, students can also
identify that metabolism for salmeterol by catechol O-methyl transferase (COMT) will be reduced since R4 is not a catechol hydroxyl (OH).
To reinforce these concepts, students were asked to use the maps as study tools for exams and homework assignments.
Assessments in the form of class activities, homework assignments, and exams were used to evaluate student performance in medicinal
chemistry. For class activities, students worked individually (for trivia) or in small groups of two to three students (other games). In
addition, students were asked to complete a survey on the SAR maps administered on the course Blackboard page. The survey asked
specific questions regarding SAR maps and their utility in learning medicinal chemistry. The survey was administered one month after the
first exam. Students had a week to respond to the survey on Blackboard online outside of class time. Students already had knowledge of
their first exam grades and post-exam reviews already took place. Reminders were sent to students about the survey and there were no
incentives for the students to complete the survey within the week. Student responses to the survey questions were on a Likert scale
(1 = Strongly agree; 2 = Agree; 3 = Neither agree or disagree; 4 = Disagree; 5 = Strongly disagree; 6 = not applicable).

Findings

Assessment data: formative assessment and exams

During in-class activities, students were able to examine a specific drug and identify an activity or physiochemical property based

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 K.M. Frey

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Fig. 1. SAR maps used to teach medicinal chemistry in an integrated pharmacotherapy course. A) Example SAR map for adrenergic agonists; B) example SAR map for beta blockers; C) medicinal
chemistry trivia activity asking students information directly related to adrenergic agonist SAR map depicted in 1A. SAR = structure activity relationship; CNS = central nervous system; Asp = aspartic
acid; MAO = monoamine oxidase; COMT = catechol-O-methyltransferase; BBB = blood brain barrier.
Currents in Pharmacy Teaching and Learning xxx (xxxx) xxx–xxx
K.M. Frey Currents in Pharmacy Teaching and Learning xxx (xxxx) xxx–xxx

Table 1
Sample exam questions based on foundational knowledge or application of content from SAR maps.

1. Which beta blocker is unlikely to cause bronchoconstriction?

A) Beta Blocker A*
B) Beta Blocker B
C) Beta Blocker C
D) Beta Blocker D

2. Which drug (A-D) will be most resistant to MAO metabolism?

A) Drug A
B) Drug B
C) Drug C
D) Drug D*

3. Which beta blocker is selective for β1 receptors?

A) Beta blocker A
B) Beta blocker B
C) Beta blocker C*
D) Beta blocker D

4. Which alpha blocker will have the longest half-life and duration of action?
A) Alpha blocker A
B) Alpha blocker B
C) Alpha blocker C*

5. Identify the common pharmacophore for all of the above agents.

A) Aryloxypropanolamine
B) Arylimidazoline
C) Catecholamine
D) Phenylethylamine*

SAR = structure activity relationship; MAO = monoamine oxidase.

on the SAR maps. Formative “low stakes” in-class activities included medicinal chemistry review trivia (Fig. 1C) and “identify the
metabolite” game to allow students to apply their knowledge from the SAR maps. Based on student participation, these activities
provided general feedback to the instructor on student interpretation of SAR maps and how to apply such knowledge to specific
drugs. Overall, students actively participated in the activities and appeared to retain knowledge from the SAR maps.
The first exam evaluated medicinal chemistry student knowledge or application of content from the SAR maps. Table 1 provides
sample exam questions used to assess student knowledge of medicinal chemistry for drugs acting on the sympathetic division of the
autonomic nervous system. There were 50 questions total with the following exam blueprint: 30% medicinal chemistry (15 questions)
and 70% pharmacology (35 questions). All questions focused on drugs used for hypertension (including agents acting on the sym-
pathetic system). The exam was administered through Examsoft and included multiple choice (MC) and fill in the blank (FITB) style
questions. Medicinal chemistry questions with drug structures were drawn in the same common orientation as the SAR maps. These
figures were embedded in the exam question and also provided as an attachment.
General statistics for student exam grades were the following: mean approximately 83%, standard deviation approximately 11%,
and median of 86 (n = 71 exam takers). Category performance reports from Examsoft indicate that students selected the correct

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Table 2
Exam questions from Table 1, the relevant SAR map, and content mapping to ACPE Accreditation Standards Appendix 1 topics and PCOA blueprint
content.
Exam question % correct SAR map ACPE standards, Appendix 1 topic PCOA blueprint content
#

1 89% Beta blockers (aryloxypropanolamine) Therapeutic decision-making; SAR 2.1.6 Applicability to making drug
(63/71) therapy decisions
2 94% Adrenergic agonists (phenylethylamine) Drug metabolism; SAR 2.1.5 Chemical pathways of drug
(67/71) metabolism
3 97% Beta blockers (aryloxypropanolamine) Drug action behavior in vivo and in 2.1.2 Chemical basis for drug action
(69/71) vitro; SAR
4 99% Alpha blockers Therapeutic decision-making 2.1.6 Applicability to making drug
(70/71) (aminodimethoxyquinazoline) (dosing); metabolism; SAR therapy decisions
2.1.5 Chemical pathways of drug
metabolism
5 94% Adrenergic agonists (phenylethylamine) Pharmacophore recognition 2.1.3 Fundamental pharmacophores for
(67/71) drugs used to treat diseases

SAR = structure activity relationship; ACPE = Accreditation Council for Pharmacy Education; PCOA = Pharmacy Curriculum Outcomes
Assessment.

answer for approximately 90% of the medicinal chemistry questions on the exam. Table 2 also shows the specific exam question from
Table 1 (# 1–5), % of correct responses (% correct), relevant SAR map, and content mapping to ACPE Appendix 1 topics and the
PCOA blueprint. Overall, students performed well on these sample questions with percent correct responses ranging from 89 to 99%
for the five sample questions. Students also performed well on the other 10 medicinal chemistry exam questions (not shown) as
reflected in the category performance (approximately 90% correct).
This is the first integrated pharmacotherapy course at Fairleigh Dickinson University School of Pharmacy and Health Sciences to use SAR
maps regularly in teaching medicinal chemistry. In a previous foundations course (PHRM 6100) that integrated medicinal chemistry,
pharmacology, and pharmacokinetics, SAR maps were not used regularly. Upon examining the assessment data from previous years,
medicinal chemistry was taught as one module with one major exam. The exam averages for the medicinal chemistry exam for the last three
years were the following: 66.8% (2016); 68.5% (2017); and 69.9% (2018). It should also be disclosed that different instructors taught
medicinal chemistry in the foundations course. While there are several variables, and the foundations course is not the best comparison for
integrated pharmacotherapy courses, the SAR maps appear to improve overall student performance on medicinal chemistry exam questions.

Student survey

The majority of students (56/71 or approximately 79% of students) in the course participated in the survey. Student survey results
indicate an overall positive view of the SAR maps. Student responses (Table 3) indicate that the SAR maps helped them visually learn
medicinal chemistry better (approximately 66% strongly agree; approximately 32% agree), understand structure modifications that
affect DOA, absorption, metabolism, efficacy, and toxicity (approximately 70% strongly agree; approximately 23% agree), and un-
derstand drug pharmacophores (approximately 66% strongly agree; 28.6% agree). Interestingly, the majority of students in the class

Table 3
Student survey responses (n = 56).
Survey questiona 1 2 3 4 5 6

The SAR maps used in PHRM 6104 help me understand medicinal chemistry better. 66.1% 32.1% 1.8% 0 0 0
(37/56) (18/56) (1/56)
SAR maps help me visually understand how a drug can be modified and have different activities (such as 69.6% 23.2% 7.1% 0 0 0
duration of action, absorption, metabolism, efficacy, or toxicity). (39/56) (13/56) (4/56)
I now have a better understanding of a drug pharmacophore based on visualizing SAR maps and 66.1% 28.6% 5.3% 0 0 0
completing related class activities. (37/56) (16/56) (3/56)
I feel that I have a strong background in organic chemistry. 17.9% 19.6% 42.9% 19.6% 0 0
(10/56) (11/56) (24/56) (11/56)
I feel that I have a strong background in biological sciences. 21.4% 53.6% 21.4% 1.8% 1.8% 0
(12/56) (30/56) (12/56) (1/56) (1/56)
I feel that I am a visual learner. 51.8% 35.7% 12.5% 0 0 0
(29/56) (20/56) (3/56)
SAR maps help me learn about drug structures as opposed to just memorizing them for the exams. 69.6% 25% 5.4% 0 0 0
(39/56) (14/56) (3/56)

SAR = structure activity relationship.

Bold in the table represents greatest % responses.
a
Likert responses of: strongly agree = 1, agree = 2, neither agree or disagree = 3, disagree = 4, strongly disagree = 5, and not applicable = 6.

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felt that they had a stronger biology background than chemistry (75% agree/strongly agreed that had a strong biological sciences
background). This question was specifically asked in order to gauge the incoming academic background of students in the class. Most
significantly, the majority of students feel that they are visual learners (approximately 88% strongly agree/agree) and that the SAR
maps helped them learn and not memorize drug structures for the exams (approximately 95% strongly agree/agree).

Discussion

Medicinal chemistry is a challenging discipline that requires careful, yet effective integration with pharmacology and pharma-
cotherapeutics. Pharmacy education literature presents several examples where pharmacy schools are implementing innovative ways to
teach medicinal chemistry in integrated courses. Alsharif et al.10 developed a standardized instructional model for teaching clinically
relevant medicinal chemistry on beta adrenergic antagonists. This instructional model focused on using medicinal chemistry knowledge,
such as pharmacophores and SAR, to make clinical decisions.10,11 Other pharmacy schools have used case-based studies, active learning,
test-enhanced learning, online modules, and process-oriented guided inquiry approaches to teach medicinal chemistry.12–14 All of these
novel teaching methods for medicinal chemistry can be easily combined with the SAR maps proposed in this study.
The approach described here demonstrates the utility of visual SAR maps to teach major concepts in medicinal chemistry. This
one-figure visual aid can help pharmacy students learn pharmacophores, SAR, and drug properties for all major drug classes. Previous
pedagogical approaches to teach medicinal chemistry often included drug structures followed by textual support as depicted in Foye's
Medicinal Chemistry.15 The use of SAR maps can help students recognize the importance of drug structure, its influence on me-
chanism of action, DOA, absorption, metabolism, efficacy, and toxicity. As identified in the survey responses, approximately 88% of
students claim they are visual learners. This finding is similar to a recent study in 2018 that revealed student exam performance was
better when visualization technologies were incorporated into pharmacy courses.16 Thus, visual aids such as SAR maps are effective
tools for learning medicinal chemistry.
From the instructor point of view, SAR maps are time-effective, easy to explain, and can easily interface with class activities. The
SAR map also allows the instructor to cover several medicinal chemistry topics, including topics covered in the PCOA blueprint and
ACPE Appendix 1 topics, for a given drug class in a limited amount of time. Content heavy courses, such as integrated pharma-
cotherapy for cardiopulmonary diseases, require coverage of several drugs and drug classes. The SAR maps specifically used in this
study were included for effective coverage of more than 60 drugs used for hypertension.
In integrated pharmacotherapy courses, it is often difficult to specifically integrate medicinal chemistry with pharmacotherapy.
The SAR maps can be used to explain clinical implications of certain drug classes. For example, in an integrated pharmacotherapy
course, the pharmacist will explain why a LABA is best for a patient with asthma based on the current clinical studies. Using SAR
maps, the connection between medicinal chemistry, pharmacology, and pharmacotherapy can be established. The LABA structure is
modified to protect against metabolism (SAR map; medicinal chemistry), this influences its mechanism of action (pharmacology) and
utility in asthma patients (pharmacotherapy). Future iterations of the SAR map can incorporate more connections between phar-
macology and pharmacotherapy.
SAR maps appear to promote student learning; however, there are limitations to this report and the overall pedagogical approach.
The SAR maps and related activities were used in a large group lecture setting. In this environment, it is often difficult to observe
student engagement in the activities compared to a small group setting. In addition, the assessment data (one exam and one survey) is
insufficient to make major claims that this approach is completely effective in improving performance in medicinal chemistry. Based
on the limited assessment data and survey, it appears that students retain major medicinal chemistry concepts in challenging in-
tegrated courses.

Summary

SAR maps appear to be effective tools for learning major foundations in medicinal chemistry. Results from this study reveal that
SAR maps can help students understand complex concepts regarding drug structure and apply such knowledge to make clinical
decisions. Most significantly, the SAR maps have utility in teaching medicinal chemistry in integrated pharmacotherapy courses with
limited contact hours. In future work, the use of SAR maps may be incorporated into medicinal chemistry taught in more complex
pharmacotherapy courses focusing on chemotherapy for infectious diseases and oncology.

Conflict of interest

None.

Disclosures

None.

Author statement

Author verification occurred prior to implementation of requiring an Author statement.

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K.M. Frey Currents in Pharmacy Teaching and Learning xxx (xxxx) xxx–xxx

Appendix 1. Additional SAR maps and general lesson plan used in integrated pharmacotherapy course

1. SAR map for alpha blockers.

2. SAR map for dihydropyridine (DHP) calcium channel blockers (CCBs).

3. General lesson plan using SAR maps in medicinal chemistry and pharmacology lecture.

Class duration Topic covered Activities

75 min

10 minutes Introduction of disease state including review of pathophysiology and Normal, wrong, fixed Activity to help students understand basis for
drugs pharmacological treatment.
5–10 minutes Discussion of pharmacological treatment and drug classes Student reflection: discuss with students why these drug classes are
effective for treating the disease state.
5–10 minutes/ For each drug class: discussion of pharmacology (mechanism of action, After SAR map is introduced, show all individual drug structures in
drug class specific drugs) and medicinal chemistry (presentation of pharmacophore that class to establish “similar pharmacophore” and groups that
in relation to target, SAR map, and SAR map activity). contribute to the SAR.
5 minutes/drug Active learning exercise to help students use SAR map in understanding Trivia: questions about drug structure and concept map.
class drug chemistry or action.
Classes are 75 min long and cover the sciences (pharmacology and medicinal chemistry together) or pharmacotherapy (clinical science/pharmacy practice).

SAR = Structure activity relationship.

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