STEROIDS

AND
TERPENES
 STEROIDS

 The important class of lipids

 Sometimes called
corticosteroids
 Naturally produced in the
body
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 Made by the adrenal glands

It is the hormones
Secretion must be within
the optimal amount
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 Given along with
medicines
Control different functions in
our bodies
 Balance of salt and water in
our bodies
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Reduce inflammation
 Regulate our immune
system
 Help destroy cancer cells
 They have legitimate
medical uses
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 Similar to the male sex
hormone (testosterone)
 Help overcome stress
 Grow bigger during puberty
 Improve appetite
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• Commonly abused steroids Oral steroids
• Anadrol (oxymetholone)
• Oxandrin (oxandrolone)
• Dianabol (methandrostenolone)
• Winstrol (stanozolol)
• Injectable steroids
• Deca-Durabolin (nandrolone decanoate)
• Durabolin (nandrolone phenpropionate)
• Depo-Testosterone (testosterone cypionate)
• Equipoise (boldenone undecyclenate)
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Testosterone Viagra
Propionate

Testosterone
Cypionate
Anadrol
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Types:
• Androgenic Steroids
 growth or thickening of the body’s non-
reproductive tract tissues.
 decrease in body fat
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 Cortico Steroids
man-made steroids that
mimic the activity of
cortisone(regulating
inflammation)
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Anabolic Steroids
increase in muscle bulk and
strength
treat hypogonadism
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Anabolic-androgenic steroid
• It is illegal to sell
• May create growth related
problems in teens and kids
• Failure in the doping test
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Ergogenic uses for anabolic

steroids in sports and
bodybuilding is very
controversial….
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Effects – Women
– Men
•Enlargement
•Infertility
•Breast development of the clitoris
•Shrinking of the •Excessive
testicles growth of
body hair
(hirsutism)
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– Both sexes • Cardiovascular
•Male-pattern system
baldness – Heart attacks
• Musculoskeletal – Enlargement of
system the heart’s left
– Short stature ventricle
– Tendon rupture
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• Liver • Infection
– Cancer – HIV/AIDS
– Peliosis hepatis – Hepatitis
• Skin • Psychiatric effects
– Acne and cysts – Homicidal rage
– Oily scalp – Mania
– Delusions
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 How Do AAS Affect the Brain?
 binding to androgen and estrogen
receptors on the surface of a cell
 not “euphorigenic”, meaning they do not
trigger rapid increases in the
neurotransmitter dopamine
 affect mood and behavior in significant
ways.
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• AAS and Mental Health
 They contribute to psychiatric dysfunction
1.feels good but may have manic-like symptoms
that could lead to violence
2. suffer from paranoid jealousy, extreme
irritability, delusions, and impaired judgment
stemming from feelings of invincibility.
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• Addictive Potential
 Reinforcing
 Continues despite physical problems and
negative effects
 Spend time and money obtaining the drug
 Can experience withdrawal symptoms esp.
depression that can lead to suicide attempt
 AAS is taken before the typical adolescent
growth spurt
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• Steroid hormones
 Pregnenolone - produced directly from
cholesterol, the precursor molecule for all C18,
C19 and C21 steroids
 Progesterone - a progestagen, produced directly
from pregnenolone and secreted from the corpus
luteum, responsible for changes associated with
luteal phase of the menstrual cycle,
differentiation factor for mammary glands
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 Aldosterone - the principal mineralocorticoid,
produced from progesterone in the zona
glomerulosa of adrenal cortex, raises blood
pressure and fluid volume, increases Na+ uptake
 Testosterone - an androgen, male sex hormone
synthesized in the testes, responsible for
secondary male sex characteristics, produced
from progesterone
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 Estradiol - an estrogen, principal female sex
hormone, produced in the ovary, responsible for
secondary female sex characteristics
 Cortisol - dominant glucocorticoid in humans,
synthesized from progesterone in the zona
fasciculata of the adrenal cortex, involved in
stress adaptation, elevates blood pressure and
Na+ uptake, numerous effects on the immune
system
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Steroid Hormone Biosynthesis Reactions
Luteinizing Hormone (LH):
progesterone and testosterone
Adrenocorticotropic hormone (ACTH):
cortisol
Follicle Stimulating Hormone (FSH):
estradiol
Angiotensin II/III: aldosterone
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Steroids of the Adrenal Cortex
• 3 major classes:
1. glucocorticoids - regulate carbohydrate
metabolism & are immunosuppressive and anti-
inflammatory
2.Mineralocorticoids - regulate the body levels of
sodium and potassium
3. Androgens - actions are similar to that of
steroids produced by the male gonads
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• Adrenal insufficiency is known as Addison
disease
 3 main tissue regions:
 zona glomerulosa
 zona fasciculata
 zona reticularis
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• Regulation of Adrenal Steroid Synthesis
 Adrenocorticotropic hormone (ACTH), of the
hypothalamus, regulates the hormone
production of the zona fasciculata and zona
reticularis
 ACTH receptors in the plasma membrane of
the cells of these tissues activate adenylate
cyclase with production of the second
messenger, cAMP.
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 The effect of ACTH on the production of cortisol
is particularly important, with the result that a
classic feedback loop is prominent in regulating
the circulating levels of corticotropin releasing
hormone (CRH), ACTH, and cortisol.
 Mineralocorticoid secretion from the zona
glomerulosa is stimulated by an entirely
different mechanism.
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 Angiotensins II and III, derived from the
action of the kidney protease renin on liver-
derived angiotensinogen, stimulate zona
glomerulosa cells by binding a plasma
membrane receptor coupled to
phospholipase C.
 angiotensin II and III binding to their
receptor leads to the activation of PKC and
elevated intracellular Ca2+ levels
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 increased production of aldosterone
 In the kidney, aldosterone regulates
sodium retention by stimulating gene
expression of mRNA for the Na+/K+–ATPase
responsible for the reaccumulation of
sodium from the urine
 RAAS process using he ACE inhibitors
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Functions of the Adrenal Steroid Hormones
Cortisol - naturally occurring glucocorticoid
 cortisol is synthesized in the zona
fasciculata of the adrenal cortex
 It bounds to protein, albumin then
transcortin
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Clinical Significance of Adrenal
Steroidogenesis
 Defective synthesis can have profound
effects on human development and
homeostasis
 As with Addison disease, disorders that
manifest with adrenocortical hyperplasia
are referred to as Cushing syndrome
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 Adrenocortical hyperfunction and Virilism -
premature development of male secondary sex
characteristics
 Gonadal Steroid Hormones
 the two most important are testosterone and
estradiol
 regulate the secretion of follicle stimulating
hormone (FSH) and luteinizing hormone (LH) by the
pituitary and gonadotropin releasing hormone
(GnRH) by the hypothalamus
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 Low levels of circulating sex hormone
reduce feedback inhibition on GnRH
synthesis (the long loop), leading to
elevated FSH and LH
 The biosynthetic pathway to sex hormones
in male and female gonadal tissue includes
the production of the androgens,
androstenedione and
dehydroepiandrosterone
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 Testes and ovaries contain an additional enzyme, a
17β-hydroxysteroid dehydrogenase, that enables
androgens to be converted to testosterone.
 In males, LH binds to Leydig cells, stimulating
production of the principal Leydig cell hormone,
testosterone
 Testosterone is secreted to the plasma and also
carried to Sertoli cells by androgen binding protein
(ABP).
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 In Sertoli cells the Δ4 double bond of
testosterone is reduced, producing
dihydrotestosterone
 Testosterone and dihydrotestosterone are
carried in the plasma, and delivered to target
tissue, by a specific gonadal-steroid binding
globulin (GBG).
 In a number of target tissues, testosterone can
be converted to dihydrotestosterone (DHT).
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 DHT is the most potent of the male steroid
hormones, with an activity that is 10 times that of
testosterone. Because of its relatively lower
potency, testosterone is sometimes considered to
be a prohormone.
 Synthesis of the major female sex hormones in the
ovary
 Aromatase activity is also found in granulosa cells,
but in these cells the activity is stimulated by FSH
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 Nomally, thecal cell androgens produced in
response to LH diffuse to granulosa cells, where
granulosa cell aromatase converts these
androgens to estrogens
 . As granulosa cells mature they develop
competent large numbers of LH receptors in the
plasma membrane and become increasingly
responsive to LH, increasing the quantity of
estrogen produced from these cells.
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 Granulosa cell estrogens are largely, if not
all, secreted into follicular fluid. Thecal
cell estrogens are secreted largely into the
circulation, where they are delivered to
target tissue by the same globulin (GBG)
used to transport testosterone.
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Steroid Hormone Receptors
 The receptors to which steroid hormones
bind are ligand-activated proteins that
regulate transcription of selected genes
 steroid hormone receptors are found in the
cytosol and the nucleus
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 What Are the Common Street Names?
 Most people just say steroids
 On the street, steroids may be called roids
or juice
 The scientific name for this class of drugs is
anabolic-androgenic steroids
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How Are They Used?
 Some steroid users pop pills.
 Others use hypodermic needles to inject
steroids directly into muscles.
 When users take more and more of a drug
over and over again, they are called
"abusers.“
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 Abusers have been known to take doses 10 to
100 times higher than the amount prescribed
for medical reasons by a doctor.
 Many steroid users take two or more kinds of
steroids at once called stacking, this way of
taking steroids is supposed to get users bigger
faster.
 Some abusers pyramid their doses in 6-12-
week cycles.
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 At the beginning of the cycle, the steroid
user starts with low doses and slowly
increases to higher doses. In the second
half of the cycle, they gradually decrease
the amount of steroids. Neither of these
methods has been proven to work.
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How Many Teens Use Them?
 Most teens are smart and stay away from
steroids.
 As part of a 2002 NIDA-funded study, teens
were asked if they ever tried steroids - even
once.
 Only 2.5% of 8th graders ever tried steroids;
only 3.5% of 10th graders; and 4% of 12th
graders.
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What steroids look like
• Some are clear fluids for injection after being
dissolved from powder.
• Some steroids are available as tablets. The
colour and dose of the tablets depends on the
type of steroid used.
• Soluble tablets of prednisolone and a
dexamethasone syrup are available for people
who have difficulty swallowing.
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How they are given
• By injection into a muscle
(intramuscularly).
• Through a tube (cannula) that is inserted
into the vein, either as a quick injection,
or as a drip which takes about 30 minutes.
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• Through a central line, which is inserted
under the skin into a large vein near the
collar bone, or through a PICC line – a tube
inserted into a vein in the bend of your arm
near the elbow.
• As tablets, which are swallowed with plenty
of water. They may need to be taken at set
times each day and are often given in short
courses rather than continuously.
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Possible side effects
 Irritation of the stomach lining - Steroids
can irritate the lining of the stomach and
may cause a stomach ulcer, or make one
worse
 Indigestion or heartburn - you need to
take your tablets after a meal or with milk,
as they can irritate your stomach
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 Swollen hands, feet or ankles from water
retention - if you have swollen ankles,
avoid standing for long periods of time and
put your feet up when you are sitting down
 Temporary changes in blood-sugar level -
This may happen if you have high-dose or
long-term treatment. While you are having
your steroid therapy, your blood-sugar
levels may be checked by blood tests
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 Increased appetite - You may notice that
you want to eat more than usual while
taking steroids
 Increased chance of infection and
delayed healing - This happens mainly with
high dose or long-term treatment.
 Menstrual changes - Women may find that
their periods become irregular or stop
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 Hormone Imbalances - . When someone
abuses steroids, gender mix-ups happen.
• Using steroids, guys can experience
shrunken testicles and reduced sperm
count.
• They can also end up with breasts, a
condition called gynecomastia.
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• Using steroids, girls can become more
masculine.
• Their voices deepen.
• They grow excessive body hair(hirsuitism)
• Their breast size decreases.
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 Steroids can make pimples pop up and hair
fall out
 Steroids can cause livers to grow tumors
and hearts to clog up
 They can even send users on violent, angry
rampages
 Steroids throw a body way out of whack
 steroid use can shorten their lives.
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- For adolescents: growth halted
prematurely through premature skeletal
maturation and accelerated puberty
changes. This means that adolescents risk
remaining short for the remainder of their
lives if they take anabolic steroids before
the typical adolescent growth spurt.
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• Behavioral changes - You may notice mood
swings, difficulty in sleeping and perhaps
anxiety or irritability. These effects
happen mainly with high-dose or long-term
treatment and will stop when the steroid
therapy ends.
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• Difficulties with pregnancy -steroids may
be harmful to a baby that is developing in
your womb. It is not advisable to become
pregnant or father a child if you are on
steroids.
• Difficulty sleeping - taking your tablets
first thing in the morning may help
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Less common side effects
• Eye changes Cataracts or glaucoma may
develop with the long-term use of steroids.
• There is also an increased risk of eye
infections.
• Raised blood pressure - your blood
pressure should be checked regularly
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• Cushing’s syndrome This is usually caused
only by long-term use of steroids. It can
cause acne, puffiness of the face, facial
hair in women and dark marks on the skin.
• Osteoporosis (bone thinning) This may
happen with long term use of steroids
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• Muscle wasting With long-term use of
steroids your legs may feel weaker. When
the steroid use is stopped some people
have muscle cramps for a short time.
Additional information
• You will be given a steroid card if you have
to take the steroids at home so the doctor
will know you are having a treatment.
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Things to remember about steroid tablets
• Keep the tablets in a safe place where
children cannot reach them.
• If your doctor decides to stop the
treatment, return any remaining tablets to
the pharmacist. Do not flush them down
the toilet or throw them away.
 STEROIDS

• If you are sick just after taking a tablet,

tell your doctor, as you may need to take
another one.
• If you forget to take your tablet, do not
take a double dose. Let your doctor or
nurse know.
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Stopping steroid treatment
• You should only stop taking steroids if your
doctor tells you to. If you take steroids for
more than a few days, your body will
produce less steroids naturally. So when you
stop taking the steroids, your body has to
readjust. Your doctor will gradually reduce
your dose of steroids, rather than stopping
them suddenly.
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• There has been very little research on
treatment for AAS abuse. Current
knowledge derives largely from the
experiences of a small number of physicians
who have worked with patients undergoing
steroid withdrawal. They have learned that,
in general, supportive therapy combined
with education about possible withdrawal
symptoms is sufficient in some cases.
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• Sometimes, medications can be used to
restore the balance of the hormonal system
after its disruption by steroid abuse. If
symptoms are severe or prolonged,
symptomatic medications or hospitalization
may be needed.
STEROIDS
 TERPENES
 Are a large and varied class of
hydrocarbons, produced primarily by a
wide variety of plants, particularly conifers
, though also by some
insects such as termites
or swallowtail butterflies, which emit
terpenes from their osmeterium.
 TERPENES
 They are the major components of resin,
and of turpentine produced from resin. The
name "terpene" is derived from the word "
turpentine". In addition to their roles as
end-products in many organisms, terpenes
are major biosynthetic building blocks
within nearly every living creature.
Steroids, for example, are derivatives of
the triterpene squalene.
 TERPENES
 When terpenes are modified chemically,
such as by oxidation or rearrangement of
the carbon skeleton, the resulting
compounds are generally referred to as
terpenoids. Some authors will use the term
terpene to include all terpenoids.
Terpenoids are also known as Isoprenoids.
 TERPENES
 Terpenes and terpenoids are the primary
constituents of the essential oils of many
types of plants and flowers. Essential oils
are used widely as natural flavor additives
for food, as fragrances in perfumery, and
in traditional and alternative medicines
such as aromatherapy.
 TERPENES
 Synthetic variations and derivatives of
natural terpenes and terpenoids also
greatly expand the variety of aromas used
in perfumery and flavors used in food
additives. Vitamin A is an example of a
terpene.
 TERPENES

 Terpenes are released by trees more

actively in warmer weather, acting as a
natural form of cloud seeding. The clouds
reflect sunlight, allowing the forest to
regulate its temperature.
 TERPENES
Structure and biosynthesis
• Isoprene
 Terpenes are derived biosynthetically from
units of isoprene, which has the molecular
formula C5H8. The basic molecular formulae
of terpenes are multiples of that, (C5H8)n
where n is the number of linked isoprene
units.
 TERPENES
• This is called the isoprene rule or the C5
rule.
 TERPENES

 The isoprene units may be linked together

"head to tail" to form linear chains or they
may be arranged to form rings. One can
consider the isoprene unit as one of
nature's common building blocks.
 TERPENES
Isoprene itself does not • dimethylallyl pyrop
undergo the building hosphate
process, but rather are the
activated forms, components in the
isopentenyl pyrophosp
hate biosynthetic
and pathway
 TERPENES
 IPP is formed from  An alternative,
acetyl-CoA via the totally unrelated
intermediacy of biosynthesis
mevalonic acid in the
HMG-CoA reductase pa
pathway of IPP is
thway known in some
. bacterial groups
and the plastids of
plants,
 TERPENES
 the so-called MEP(2-
Methyl-D-erythritol-4- isopentenyl
phosphate)-pathway, pyrophosphate
which is initiated from isomerase.
C5-sugars. In both
pathways, IPP is
isomerized to DMAPP
by the enzyme
 TERPENES
TYPES
• Hemiterpenes
- consist of a single isoprene unit.
Isoprene itself is considered the only
hemiterpene, but oxygen-containing
derivatives such as prenol
and isovaleric acid
are hemiterpenoids.
 TERPENES
• Monoterpenes
- consist of two isoprene units and
have the molecular formula C10H16.
Examples of monoterpenes are: geraniol,
limonene and terpineol.
 TERPENES
• Sesquiterpenes
- consist of three isoprene units and
have the molecular formula C15H24.
Examples of sesquiterpenes are: farnesenes
, farnesol. The sesqui- prefix means one
and a half.
 TERPENES
• Diterpenes
- are composed for four isoprene units
and have the molecular formula C20H32.
They derive from
geranylgeranyl pyrophosphate. Examples of
diterpenes are cafestol, kahweol,
cembrene and taxadiene (precursor of
taxol).
 TERPENES

• Diterpenes also form the basis for

biologically important compounds such as
retinol, retinal, and phytol. They are
known to be antimicrobial and
antiinflammatory.
 TERPENES
• Sesterterpenes
- terpenes having 25 carbons and
five isoprene units, are rare relative to the
other sizes. The sester- prefix means half
to three, i.e. two and a half. Examples of
sesterterpenes are geranylfarnesol.
 TERPENES
• Triterpenes
- consist of six isoprene units and have the
molecular formula C30H48. The linear triterpene
squalene, the major constituent of shark liver
oil, is derived from the reductive coupling of
two molecules of farnesyl pyrophosphate.
Squalene is then processed biosynthetically to
generate either lanosterol or cycloartenol, the
structural precursors to all the steroids.
 TERPENES
• Tetraterpenes
- contain eight isoprene units and
have the molecular formula C40H64.
Biologically important tetraterpenes
include the acyclic lycopene, the
monocyclic gamma-carotene, and the
bicyclic alpha- and beta-carotenes.
 TERPENES
• Polyterpenes
- consist of long chains of many
isoprene units. Natural rubber consists of
polyisoprene in which the double bonds are
cis. Some plants produce a polyisoprene
with trans double bonds, known as gutta-
percha.
TERPENES