Comparison of Enalapril and Atenolol Hypertension Drugs’ Principle

Zhengkai Li

Bishops College School, Sherbrooke, Quebec, J1M 1Z8, Canada

Keywords:

Hypertension, Atenolol Mechanism, Enalapril Mechanism, Comparison, Drug Principle.

Abstract:

This essay investigates two drugs that are both treatments for Hypertension, Enalapril and Atenolol, by

researching and comparing their structures, mechanisms, cost, and side effects. As a result, it was found that

even their mechanisms of action are different. What they do is a duplicate, simple thing. Enalapril and

Atenolol inhibits something that is producing in the body, which can lead to Hypertension. Therefore, it can

reduce blood pressure to the average level. In conclusion, Medicine is not as arcane as it looks. To be

straightforward, Medicine is just something that can affect mechanisms in the body and is used to make

various physical indicators to achieve usual standards. So that people won't have any health issues.

1 INTRODUCTION

Hypertension is a worldwide disease that leads to tons

of deaths. After a long working period,

Pharmacologists worldwide have discovered many

types of medicine for hypertension such as ACE

inhibitors, beta-blockers, Angiotensin II receptor

blockers, and Calcium channel blockers. The

following text talks about two drugs which count as

ACE inhibitors (Enalapril) and beta-blockers

(Atenolol). It tends to investigate drugs’ principles

and how the side effects cause the drugs’ popularity.

In the work, I introduced and compared these two

drugs’ structures, mechanisms, costs, side effects,

and popularity. I argued that side effects might be the

main reason for their popularity by stating two

research works done by other researchers. And at last,

I state how simple the drug principle is.

2 OVERVIEW OF DISEASE

Blood pressure, also known as Hypertension, It's the

pressure that blood gives to the wall of arteries

(https://www.who.int/china/health-

topics/hypertension). There are no specific symptoms

for high blood pressure, but in the long-term having

it, it may lead to other issues such as kidneys failure

and heart diseases. The only way patients will know

if they are weather-affected is to see a doctor for a

physical examination.

There is used to have two numbers doctor will

give as a result. For example 140/60. The first number

is systolic blood pressure. It is the pressure when the

heart is pushing or contracting blood. And the second

number represents the pressure heart is relaxed and

filled up with blood. It's called diastolic blood

pressure.

Typically, healthy blood pressure for an adult is

under 120/80. The first number is always higher than

the second one. It's not a health concern. Here is a list

of Hypertension and how're their numbers look.

Table 1 shows different categories of blood pressure

at different systolic and diastolic number.

- If the systolic number is higher than 140 and the

diastolic number is higher than 90, this is just

commonly Hypertension with no other heart risk

factors

- If the systolic number is higher than 130 and the

diastolic number is higher than 80, patients may have

Hypertension with other heart risk factors, according

to some providers

- If the systolic number is higher than 180 and the

diastolic number is higher than 120. It's better to see

medical care immediately.

490

Li, Z.

Comparison of Enalapril and Atenolol Hypertension Drugs’ Principle.

DOI: 10.5220/0011218500003443

In Proceedings of the 4th International Conference on Biomedical Engineering and Bioinformatics (ICBEB 2022), pages 490-500

ISBN: 978-989-758-595-1

Table 1: Blood Pressure Categories (U.S. National Library of Medicine, 2021).

Pressure Category

Systolic Blood

Pressure

Diastolic Blood

Pressure

Normal Less than 120 and Less than 80

High Blood Pressure (no other heart risk factors) 140 or higher or 90 or higher

High Blood Pressure (with other heart risk factors,

according to some providers)

130 or higher or 80 or higher

Dangerously high blood pressure - seek medical care

right away

180 or higher and 120 or higher

There are about 1.13 billion people affected by

high blood pressure, and 2/3 of them live in a low,

mid-income country. In 2015, one in four men and

one in five women had Hypertension. There are about

270-million-people have high blood pressure in

China. And only 13.8% is under control. Not

everyone who has Hypertension can access treatment.

Some primary care services are in the hard-to-reach

area. They are not empowered to diagnose and treat

high blood pressure to prevent life-threatening

conditions (https://www.who.int/china/health-

topics/hypertension); (https://www.who.int/news-

room/fact-sheets/detail/hypertension).

There are many drugs used to treat Hypertension.

Enalapril, Atenolol, Trandolapril, Ramipril,

Lisinopril... In the following articles, Enalapril and

Atenolol will be detailedly introduced.

3 DESCRIPTION OF DRUGS

Enalapril was patented in 1978, and it started to be

used as Medicine in 1984. Its condensed chemical

formula is C20H28N2O5. It's IUPAC name is (2S)-1-

[(2S)-2-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]

amino] propanoyl] pyrrolidine-2-carboxylic acid

(https://pubchem.ncbi.nlm.nih.gov/compound/Enala

pril). It belongs to the ACE inhibitor drug class.

Figure 1 and figure 2 shows Enalapril’s 2D and 3D

structure.

Figure 1: 2D Structure of Enalapril (https://pubchem.ncbi.nlm.nih.gov/compound/Enalapril).

Comparison of Enalapril and Atenolol Hypertension Drugs’ Principle

491

Figure 2: 3D structure of Enalapril (https://pubchem.ncbi.nlm.nih.gov/compound/Enalapril)

Enalapril is solid with a melting point around 143-

144.5°C

(https://pubchem.ncbi.nlm.nih.gov/compound/Enala

pril). It is slightly soluble in water. Under the room

temperature (25°C), 16.4g Enalapril can dissociate

with one litre of water. It has a molarity of 0.04 M.

It's stable under specific conditions. With the dilution

of enalaprilat injection in 5% dextrose, 0.9% sodium

chloride, 5% dextrose and 0.9% sodium chloride, 5%

dextrose in lactated Ringer's, or Isoyte (R) E,

Enalapril solution is stable for the next 24 hours at

room temperature (American Society of Health-

System Pharmacists, 2017). It's a dicarboxylic acid

monoester. Enalapril has a 𝑝𝐾𝑎1 = 2.3

(carboxylic acid), 𝑝𝐾𝑎2 = 3.4 (carboxylic acid)

and 𝑝𝐾𝑎3 = 8.0 (secondary amid) (Loftsson T,

2017). Table 2 shows its detailed properties.

Table 2: Enalapril chemical and physical properties (https://pubchem.ncbi.nlm.nih.gov/compound/Enalapril).

Property Name Property Value Reference

Molecular Weight 376.4 Computed by PubChem 2.1 (PubChem release 2021.05.07)

XLogP3 -0.1 Computed by XLogP3 3.0 (PubChem release 2021.05.07)

Hydrogen Bond Donor Count 2 Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)

Hydrogen Bond Acceptor Count 6 Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)

Rotatable Bond Count 10 Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)

Exact Mass 376.199822 Computed by PubChem 2.1 (PubChem release 2021.05.07)

Monoisotopic Mass 376.199822 Computed by PubChem 2.1 (PubChem release 2021.05.07)

Topological Polar Surface Area 95.9 Å² Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)

Heavy Atom Count 27 Computed by PubChem

Formal Charge 0 Computed by PubChem

Complexity 519 Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)

Isotope Atom Count 0 Computed by PubChem

Defined Atom Stereocenter Count 3 Computed by PubChem

Undefined Atom Stereocenter Count 0 Computed by PubChem

Defined Bond Stereocenter Count 0 Computed by PubChem

Undefined Bond Stereocenter Count 0 Computed by PubChem

Covalently-Bonded Unit Count 1 Computed by PubChem

Compound Is Canonicalized Yes Computed by PubChem (release 2021.05.07)

ICBEB 2022 - The International Conference on Biomedical Engineering and Bioinformatics

492

3.1 Atenolol

Atenolol was found out by a Scottish pharmacologist,

James Black. He is the first man who used the beta-

blocker for managing angina pectoris. He received

Nobel Prize in 1958. Since then, Beta-blocker has

quickly become popular. During the 1960s-1980s, It

was investigated soon to be used in different types of

cardiovascular diseases. It has a condensed molecular

formula, C14H22N2O3. It is a beta-blocker (Drug

Bank, 2021). Figure 3 and figure 4 shows its 2D and

3D structure.

Figure 3: Atenolol 2D structure (https://pubchem.ncbi.nlm.nih.gov/compound/Atenolol)

Figure 4: Atenolol 3D structure (https://pubchem.ncbi.nlm.nih.gov/compound/Atenolol).

It's a white crystalline powder worn at a melting

point around 158-160°C. It is also slightly soluble in

water. At 25°C, only 13.3g of Atenolol can be mixed

up with one litre of water. It has a molarity of 0.05M.

It is also a monocarboxylic acid. It has a 𝑝𝐾𝑎 = 9.6

(https://pubchem.ncbi.nlm.nih.gov/compound/Ateno

lol). Table 3 is a graph that shows other properties of

Atenolol.

Comparison of Enalapril and Atenolol Hypertension Drugs’ Principle

493

Table 3: Atenolol chemical and physical properties (https://pubchem.ncbi.nlm.nih.gov/compound/Atenolol).

Property Name

Property

Value

Reference

Molecular Weight 266.34

Computed by PubChem 2.1 (PubChem release

2021.05.07

)

XLogP3 0.2

Computed by XLogP3 3.0 (PubChem release

2021.05.07)

Hydrogen Bond Donor Count 3

Computed by Cactvs 3.4.8.18 (PubChem release

2021.05.07

)

Hydrogen Bond Acceptor Count 4

Computed by Cactvs 3.4.8.18 (PubChem release

2021.05.07)

Rotatable Bond Count 8

Computed by Cactvs 3.4.8.18 (PubChem release

2021.05.07

)

Exact Mass 266.16304257

Computed by PubChem 2.1 (PubChem release

2021.05.07)

Monoisotopic Mass 266.16304257

Computed by PubChem 2.1 (PubChem release

2021.05.07

)

Topological Polar Surface Area 84.6 Å²

Computed by Cactvs 3.4.8.18 (PubChem release

2021.05.07)

Heavy Ato

Count 19 Compute

yPubChe

Formal Charge 0 Compute

yPubChe

Complexity 263

Computed by Cactvs 3.4.8.18 (PubChem release

2021.05.07

)

Isotope Ato

Count 0 Compute

yPubChe

Defined Atom Stereocenter

Count

0 Computed by PubChem

Undefined Atom Stereocenter

Count

1 Computed by PubChem

Define

Bon

Stereocente

Count 0 Compute

yPubChe

Undefined Bond Stereocenter

Count

0 Computed by PubChem

Covalentl

-Bonde

Unit Count 1 Com

ute

PubChe

Com

oun

Is Canonicalize

Yes Com

ute

PubChem

(

release 2021.05.07

)

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494

3.2

Drug Pharmacology

If a doctor has prescribed Enalapril, the patient must

be affected by Hypertension, heart failure, or heart

attack.

Enalapril works as an ACE(Angiotensin-

converting-enzyme) inhibitor; it belongs to the ACE

inhibitor drug class. It works by inhibiting the

mechanisms the body customarily used to maintain

blood pressure. Angiotensin 1 is officially called

angiotensin. It's an enzyme that is contained in a

human's bloodstream. Its chemical formula is

C62H89N17O14

(https://pubchem.ncbi.nlm.nih.gov/compound/Angio

tensin-I). Figure 8 shows it’s structure. It is formed

by an enzyme called "renin" produced by the kidney

on a protein called "angiotensinogen" produced by

the liver. It has no direct biological activity. It just

exists as a precursor of angiotensin 2.

Figure 5: Structure of Angiotensin 1 (https://pubchem.ncbi.nlm.nih.gov/compound/Angiotensin-I).

Figure 6: Structure of Angiotensin converting enzyme (Proteopedia. 2021).

ACE (Angiotensin-converting enzyme) is an

enzyme that converts Angiotensin 1 to Angiotensin 2.

The Figure 9 shows how its structure looks.

Angiotensin 2 is an enzyme that narrows our

blood vessels and releases hormones to increase our

blood pressure. It has a chemical formula

C50H71N13O12. Figure 10 shows its structure.

Comparison of Enalapril and Atenolol Hypertension Drugs’ Principle

495

Figure 7: Angiotensin 2 structure (https://pubchem.ncbi.nlm.nih.gov/compound/Angiotensin-II).

Enalapril (ACE inhibitor) stops this conversion to

reduce the Angiotensin two in our body. Usually,

Angiotensin-Converting Enzyme will cut

Angiotensin 1 as a protease (an enzyme that cuts

other peptides) and form Angiotensin 2. What

Enalapril does is bind with Angiotensin-Converting

Enzyme before it binds with Angiotensin 1. That

makes it can't attach to Angiotensin 1 anymore. Like

if a boy (ACE) wanna eat an apple (Angiotensin 1),

but someone has put a baseball (Enalapril) in his

mouth. So he can't eat the apple (Angiotensin 1)

anymore, it means there is no Angiotensin 2 produced

anymore. Therefore, it can reduce our blood pressure

to the average level. This means that more salt is

going to pass through our kidneys in an aqueous

solution.

At last, it will be mixed into our urine for us to pee

it out. With the reduction of fluid in our body, there

is going to be a smaller volume of blood for our hearts

to pump. All in all, by relaxing our blood vessels and

reducing the amount of fluid in them, strain for the

heart is also decreasing. That's the reason why

Enalapril can be used in other two types of

cardiovascular disease rather than only blood

pressure.

Figure 8: A photo of Enalapril drug box (Prescriptiongiant. 2021).

Enalapril is always an oral tablet. Figure 11 shows

how is a Enalapril drug box looks like. It's typically

taken once or twice a day. Doctors may suggest

taking it before bed because it will make you dizzy.

The main reason doctors prescribed you Atenolol

probably you may have Hypertension, abnormal

rhythms, angina, heart failure or heart attack.

People heart pumps blood to their body through a

network of blood vessels, known as the circulatory

system. Then it supplies the cells in the body with the

oxygen and nutrient they need. Atenolol works as a

beta-blocker by blocking hormones. There is a group

of substances released in blood in responses to

physical and emotional stress. Adrenaline and

Noradrenaline.

Adrenaline, chemical structure shows in Figure

12, is a chemical produced by people’s body and

released during increased stress or sudden vigorous

ICBEB 2022 - The International Conference on Biomedical Engineering and Bioinformatics

496

activity. It has many uses in bodies. For example, It

can improve the strength of the heart; therefore, it can

deliver more blood to the muscles. It can also open

the airways of the lungs, which increases the oxygen

level in human’s blood.

Figure 9: Adrenaline structure (https://pubchem.ncbi.nlm.nih.gov/compound/Epinephrine).

Noradrenaline, shows is a neurotransmitter in

both the peripheral and central nervous systems. Its

structure is showed in Figure 13. It also produces

many effects on the body. The most notable is the

"flight or fight" response to perceived danger.

Figure 10: Noradrenaline structure (https://pubchem.ncbi.nlm.nih.gov/compound/Norepinephrine).

Like many other cell types, cardiac myocytes

possess membrane receptors that respond to

Noradrenaline and adrenaline, called adrenoceptors.

It makes up a vital part of the sympathetic nervous

system. There are two significant categories of

adrenoceptor, which is alpha and beta. There are

different subtypes for each of them. These vary in

their structure-function, ligand specificity, and

location of expression within the body. As for the

heart itself, the primary adrenoceptor is the beta one

receptor.

Comparison of Enalapril and Atenolol Hypertension Drugs’ Principle

497

Figure 11: Mechanism of Atenolol works in human’s body (Strong Medicine. 2017).

In Figure 15, there is a cardiac myocyte with a

beta 11 adrenoceptor sitting there. It is couple to

something called g-protein, a family of proteins that

switch molecules inside cells and are involved in

transmitting signals from various stimuli outside the

cell to the inside of the cell. As the figure shows, there

are three different subunits. Beta 1 adrenoceptor can

respond to either adrenaline or Noradrenaline. With

binding to either adrenaline or Noradrenaline, one of

the subunits of g-protein will be released. This

increased the Adenylyl cyclase activity, which

converts ATP (Adenosine triphosphate) to cyclic

AMP, a second messenger important in many

biological processes (Alberts, 2008). cAMP, in turn,

activates protein kinase A, then kinase A

phosphorylates a subtype of the calcium channel

called the "l-type" calcium channel. It increases the

calcium entry into the cell cytosol. As a result, it

increases the heart rate and cardiac contractility.

To this point, what beta-blocker does is quite

apparent. It decreases the heart rate and cardiac

contractility by blocking beta one adrenoceptor bind

to adrenaline or Noradrenaline.

Figure 12: Atenolol drug box (Christine Whitehead / Alamy Stock Photo. 2018).

Atenolol is both oral and intravenous. To treat

different types of cardiovascular diseases, there are

different kinds of ways to use them. Figure 16 shows

how’s Atenolol drug box looks like.

Always follow what doctors said before using it.

3.3 Drugs Economics

Enalapril is an inexpensive drug. It can be used alone,

or with other drugs. It is less popular than the similar

drug. It is available in branded and regular versions.

ICBEB 2022 - The International Conference on Biomedical Engineering and Bioinformatics

498

It is usually covered by health insurance, but some

drug coupons or cash prices may be lower. GoodRx's

most common version of Enalapril starts at about

$12.00, 69% off its average retail price of $39.14

(GoodRx contributors. (2011-2021) Enalapril.

https://www.goodrx.com/enalapril).

Atenolol is also an inexpensive drug used to treat

high blood pressure and to prevent chest pain. It is

also used to protect the heart during a heart attack. It's

slightly more popular than its peers. It comes in

generic and branded versions. Same as Enalapril, it is

also covered by health insurance and cheaper in some

drug coupons and cash prices. The most common

version of Atenolol, GoodRx, starts at about $1.77,

84% off the average retail price of $11.12 (GoodRx

contributors. (2011-2021) Atenolol.

https://www.goodrx.com/atenolol).

4 DISCUSSIONS

From the Drug pharmacology, how Enalapril works

are logical. But what makes it less popular than

similar drugs? Side effects are noteworthy.

Enalapril is the best option for facing stroke

volume, increased ejection fraction, and decreased

mean arterial pressure. But it was associated with the

highest incidence of cough, gastrointestinal

discomfort, and more significant deterioration in

renal function. By giving interventions and

comparisons to patients with chronic kidney diseases

and patients with chronic heart failure, they have

found that Trandolapril would be the best choice to

reduce diastolic and systolic blood pressure. Ramipril

was associated with the lowest incidence of all-cause

mortality. Lisinopril had the lowest efficiency on

lowering the diastolic and systolic blood pressure,

and was associated with the highest incidence of all-

cause mortality (Zhang, Dong, Sun, Zhang, Chen,

Ma, 2011).

Compare to Enalapril, Atenolol would be a better

choice for Hypertension. Atenolol was given to 20

patients in M M Ibrahim et al, 1981. Six of them had

cardiomegaly with recent exertional dyspnea, three

had accelerated Hypertension, and three were

diabetics. They were asking to take Atenolol once a

day (100-300 mg) for two weeks. It controlled both

standing blood pressure and the supine. Within two

weeks treatment, a significant hypotensive action has

developed. Even after a sudden interruption of

therapy, control of Hypertension was still maintained

for two weeks. No patient had postural or

postexercise hypotension. The drug appeared to exert

its maximum hypotensive effect at the 100-mg

dosage. Except for the impairment of glucose

tolerance in diabetic patients, Atenolol had minimal

side effects (M M Ibrahim, 1981).

By comparing with the different mechanisms of

action of both drugs. It's not hard to find that even

they have two completely different mechanisms,

what both of them are doing is inhibiting some

mechanisms used to act in human bodies to make

blood pressure to an average level. And one thing that

is valuable for mentioning is they both belong to their

drug classes. (Beta-blockers drug class and ACE

inhibitors drug class) With this means, other drugs

used in Hypertension follow the same ideas. Not only

beta-blockers drug class

5 CONCLUSIONS

In summary, medicine is not as arcane as people used

to think. It's just something that can affect original

out-controlled mechanisms in the human body and is

used to make people's various physical indicators to

a healthy level. So that people can keep healthy. The

side effect is a significant factor for doctors to be

concerned about whether prescribed a type of

medicine or not. Whether a drug is successful or not,

it is concerned with how well the medicine treats the

diseases and its few side effects. These two ideas help

discover new drugs with high popularity a lot.

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