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Steroids: Pharmacognosy #6

This document discusses steroids, including their structure, functions, uses, and key examples. Steroids contain a cyclopentanoperhydrophenanthrene nucleus and function in development, reproduction, and molting. Examples discussed include sterols like cholesterol, ergosterol, and β-sitosterol; bile acids; and cardiac glycosides. Cardiac glycosides increase heart contraction and examples provided are digitalis, digoxin, and des lanoside. Other cardioactive drugs mentioned include convallaria and strophanthus.

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Arman Renz Paulo
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457 views23 pages

Steroids: Pharmacognosy #6

This document discusses steroids, including their structure, functions, uses, and key examples. Steroids contain a cyclopentanoperhydrophenanthrene nucleus and function in development, reproduction, and molting. Examples discussed include sterols like cholesterol, ergosterol, and β-sitosterol; bile acids; and cardiac glycosides. Cardiac glycosides increase heart contraction and examples provided are digitalis, digoxin, and des lanoside. Other cardioactive drugs mentioned include convallaria and strophanthus.

Uploaded by

Arman Renz Paulo
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© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Steroids

Pharmacognosy #6
Steroids
 Compounds that contain Cyclopentanoperhydrophenanthrene
(CPP) nucleus.
 FUNCTIONS OF STEROIDS:
• Development and control of reproductive tract in humans
• Molting of insects
• Induction of sexual reproduction in aquatic fungi
 Uses:
• Cardiotonic (Digitoxin)
• Vit D precursors
• Oral Contraceptive agents
• Anti-inflammatory
• Anabolic agents
Nomenclature of Steroids
 Any compound that contains CPPP nucleus
 The chemical nomenclature of steroids is based on this fundamental
carbocycle with adjacent side-chain carbon atoms.
 Steroids are numbered and rings are lettered
Nomenclature of Steroids
 If one or more of the carbon atoms shown in the structure of
cholesterol is not present, the numbering of the remainder is
undisturbed.
 When the rings of a steroid are denoted as projections onto the plane
of a paper, an atom or group attached to a ring is termed as:
•  (alpha)
 if it lies below the plane of the paper
 Bonds to atoms or groups attached in this configuration are
shown as broken lines.
• β (beta)
 If it lies above the plane of paper
 Shown as solid lines.
Principal Steroid Stereoparent
Hydrocarbons
ESTRANE ANDROSTANE

PREGNANE CHOLANE
Principal Steroid Stereoparent
Hydrocarbons
CHOLESTANE CARDANOLIDE

ERGOSTANE STIGMASTANE
Principal Steroid Stereoparent
Hydrocarbons BUFANOLIDE
A. Sterols
 The first steroids isolated from nature were found in lipid fractions of
many tissues.
 These compounds were solids and therefore named “Sterols” from
the Greek word stereos, meaning “solid”

1. Cholesterol
• Most widely occurring sterol
• First isolated from human gallstones
• Found in ALL animal tissue
• One of the chief constituents of lanolin
• Identified in animals, algae, fungi, bacteria (actinomycetes), ferns
and higher plants.
A. Sterols
2. Ergosterol
• Principal sterol in fungi
• Aka: Provitamin D2
 Upon ultraviolet radiation, a series of isomerizations with the
subsequent opening of ring B results in the formation of Vit D2.

3. β-sitosterol
• Common sterol in plants
• May be obtained from wheat germ oil, rye germ oil, corn oil,
cottonseed oil and other seed oils.
B. Bile Acids
 These are steroids collected in the bile
1. Primary Bile Acids
• Directly formed in the liver
 Cholic acid
 Chenodeoxycholic acid
2. Secondary Bile Acids
• From the fermentation of primary bile acids by intestinal bacteria
 Cholic acid Deoxycholic acid
 Chenodeoxycholic acid Lithocholic acid
B. Bile Acids
 Presence in the bile is attributed to enterohepatic circulation
 Generally, Bile acids do not exist in the free state but are conjugated
through a peptide bond to either glycine or taurine.
 The conjugated bile acids are discharge into the duodenum where
they act as emulsifying agents to aid in the intestinal absorption of
fats.

1. Ox Bile Extract
• Fresh ox bile was exposed to multiple processes until the filtrates
are dried at a temperature NMT 80oC
• Used as a laxative
2. Chenodiol
• Suppresses hepatic synthesis of both cholesterol and cholic acid
C. Cardiac Glycosides
 2 Types of Steroid aglycones:
1. Cardenolides
• C23 steroids
• More prevalent in nature
2. Bufaienolides
• C24 steroids
• Name is derived from the generic name for the toad Bufo
 Cardiac Glycosides increases the force of systolic contraction.
 An increase in contractility results to a more complete emptying of the
ventricle and a shortening in the length of systole.
C. Cardiac Glycosides
1. Digitalis or Foxglove
• Dried leaves of Digitalis purpurea
• Digitalis is from the Latin digitus, meaning “finger”
• purpurea is Latin and refers to the purple color of the flower
• To ensure potency, the leaves must be rapidly and gently dried at
50oC to 60oC as soon as the plants are harvested.
C. Cardiac Glycosides
1. Digitalis or Foxglove
• Contains a large number of glycosides, some of which are:
 Digitoxin
 Gitoxin
 Gitaloxin
• Uses and Dose:
 Used in form of tablets or capsules to treat Congestive Heart
Failure, Paroxysmal atrial tachycardia, atrial flutter, and atrial
fibrillation.
 NOTE: Dose must be reduced by 25% to 50% for the elderly,
patients with lean body mass, and for patients with metabolic or
electrolyte disorders.
C. Cardiac Glycosides
a. Digitoxin
• Cardiotonic glycosides obtained from Digitalis purpurea
• Upon Hydrolysis, it yields 1 molecule of digitoxigenin and 3 of
digitoxose.
• Occurs as a white or pale buff, odorless, microcrystalline powder.
• It is a bitter substance that is practically insoluble in water and
slightly soluble in alcohol.
• It is the most lipid soluble of the cardiac glycosides used in
therapeutics.
• Upon oral administration, its onset of action is 1 to 4 hours with a
peak at 8 to 14 hours.
C. Cardiac Glycosides
2. Digitalis Lanata or Grecian Foxglove
• From dried leaves of Digitalis lanata
• Source of Digoxin and Desacetyllanatoside C

• NOTE: Glycosides derived from aglycones of the C and D series


may be obtained only from D. lanata
C. Cardiac Glycosides
a. Digoxin
• Most widely used of the cardiotonic glycosides, obtained from the
leaves of D. lanata
• Upon hydrolysis, it yields 1 molecule of digoxigenin and 3 of
digitoxose.
• Digoxin tablets are 60 to 80% absorbed
• Upon oral administration, the onset of action is 30 minutes to 2
hours, with a peak at 2 to 6 hours.
• It is also administered parenterally for a more rapid effect.
C. Cardiac Glycosides
3. Deslanoside
• Is a desacetyllanatoside C, which on hydrolysis yields 1 molecule of
digoxigenin , 3 igitoxose, and 1 of glucose.
• Also occurs as a white, crystalline powder.
• It is hygroscopic, absorbing about 7% of moisture when exposed to
air
• Highly potent
• Frequently used to attain rapid initial loading by parenteral
administration
• Onset of Action is 10 to 30 minutes, maximal effect occurs in 2 to 3
hours, with dissipation in 3 to 6 days.
C. Cardiac Glycosides
4. Other Cardioactive Drugs:
a. Convallaria
• From dried rhizome and roots of
• Contains more than 20 cardioactive glycosides
• Principal constituent is Convallatoxin
 A monoglycoside composed of the genin K-strophantin
(strophanthidin) and sugar og G-strophanthin (rhamnose)
• Other minor glycosides includes:
b. Apocynum
• Dried rhizomes and roots of
• Chief constituent: Cymarin
C. Cardiac Glycosides
4. Other Cardioactive Drugs:
c. Adonis
• Dried overground portion of
• Cardioactive glycosides present are adonitoxin, cimarin, and K-
strophanthin.
d. Cactus Grandiflorus
• Consist of fresh, succulent stem of wild growing
e. Black Hellebore
• Dried rhizome and roots of
• Chief Constituent: Hellebrin
• Possesses cardiac stimulant properties in contrast to Green
Hellebore
C. Cardiac Glycosides
4. Other Cardioactive Drugs:
f. Nerium oriander
• Leaves are used to treat cardiac insuffieciency.
• Chief Constituent: Oleondrin
 3-glycoside-16-acetyl derivative of gitoxigenin
g. Strophantus
• Dried, ripe seed of
• Used by the native Africans in preparation of arrow poisons
• K-strophanthoside
 aka: Strophoside
C. Cardiac Glycosides
4. Other Cardioactive Drugs:
h. Ouabain / G-strophanthin
• Glycoside of ouabagenin and rhamnose
• Obtained from seeds of
• Or from the wood of
• It is extremely poisonous
i. Squill or Squill bulb
• Consist of the cut and dried fleshy, inner scales of the bulb of the
white variety of
• Contains about a dozen cardioactive glycosides
• Principal Constituent: Scillaren A
• Expectorant and has Emetic, Cardiotonic and Diuretic Properties
C. Cardiac Glycosides
j. Red Squill
• From the bulb or bulb scales of the red variety of
• Imported for use as a rat poison.

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