It contains information about adrenocorticoids and chemistry of vitamin D.

1. PRESENTED BY
PABBA SUPRAJA
1008-21-884-018
M.PHARM 1ST SEMESTER
PHARMACEUTICAL CHEMISTRY
UNIVERSITY COLLEGE OF
TECHNOLOGY
OSMANIA UNIVERSITY
UNDER THE GUIDANCE OF
DR. S. ANITHA
FACULTY OF PHARMACY
UCT, OSMANIA UNIVERSITY
AND

2. •These are the hormones released from adrenal glands. The adrenal glands are flattened,
cap-like structures located above the kidneys. The inner core (medulla) of the gland
secretes Catecholamines, whereas the shell (cortex) of the gland synthesizes steroid
hormones known as Adrenocorticoids or Adrenocorticosteroids.
•The term adrenocorticosteroids (a-dree-noe-KOR-ti-KO-ster-oids) refers to a group of
agents secreted by the adrenal cortex.
•Also called as Adrenal corticosteroids or Corticosteroids.
•Adrenal cortex consists of three parts :
1. Zona reticulosa
2. Zona fasiculata
3. Zona glomerulosa

3. • Zona fasiculata :- Glucocorticoids
Zona glomerulosa :- mineralocorticoids.
The adrenal cortex Synthesizes two classes of steroids. they are as follows:
The word glucocorticoid was derived from “glucose + cortex + steroid” to
reflect their :
a) role in regulating glucose metabolism
b) adrenal cortex origin
c) steroidal structure
-Endogenous glucocorticoids are part of the feedback mechanism the body utilizes to
reduce immune activity (inflammation) .

4. -Exogenous glucocorticoids are used to treat diseases caused by an overactive immune
system (eg. allergies, asthma, autoimmune diseases and sepsis.
-Glucocorticoids are distinguished from mineralocorticoids and sex hormones that have
different receptors, target cells and effects.
A class of steroid hormones that cause retention of sodium and water.
Aldosterone is the most importment endogenous mineralocorticoid.
-Aldosterone’s physiological role is essential in maintenance of adequate fluid volume
needed for normal cardiac output and blood pressure.
-Without adequate levels of mineralocorticoids, diminished cardiac output can result in
fatal shock.

5. Based on duration of action , Glucocorticoids are further classified as :
1. Short acting :-
- t1/2 is less than 12 hours
Eg: Hydrocortisone, cortisone.
2. Intermediate acting :-
- t1/2 is betweenj 12-36 hours
Eg : Predisolone
Methyl predisolone
Triamcinolone
3. Long acting :-
-t1/2 is greter than 36 hours
Eg : Dexamethazone
Betamethasone
Glucocorticoids
Short
acting
Intermediate
acting Long
acting

6. －same as sex hormones. All are steroids, consequently the rules that define their
structures, chemistry, and nomenclature are the same.
－Adrenocorticoids consists of four fused rings ( A,B,C and D).
－Chemically these hydrocarbons are “cyclopentano perhydro phenanthrenes”.
－D ring- five-memebered cyclopentane
A,B,C rings- phenanthrene rings ( saturated derivative)
－The polycyclic hydrocarbon, known as 5 alpha- cholestane, is used to illustrate the
numbering system.

8. －Solid lines denote the groups above the plane of the nucleus (β- configuaration) and
dotted or broken lines denote groups below the plane ( ɑ- configuaration).
－If the configuaration of substituent is unknown, its bond to the nucleus is drawn as
a wavy line.
－The configuaration of the H at C-5 is always indicated in the name.
－When a methyl group is missing from the side chain, this is indicated by the
prefix ‘nor’ with the number of carbon atom, which has disaapeared.
－The symbol Δis often used to designate a C=C bond in a steroid. If C=C is in
between carbons 5and 4 the compound is referred to as a Δ4 steroid.

9. Structures of Adrenocorticoids :

13. - a C21-steroid that is pregn-4-ene substituted by hydroxy groups at positions 17 and 21 and
oxo group at positions 3, 11 and 20.
-IUPAC NAME : 17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-
1,2,6,7,8,9,12,14,15,16-decahydrocyclopenta[a]phenanthrene-3,11-dione.
-Molecular formula : C21H28O5

14. -White crystalline powder.
- Insoluble in water and soluble in alcohol.
- Naturally-occurring corticosteroid metabolite.
- Also used as a pharmaceutical prodrug.
-Cortisone is the inactive precursor molecule of the active hormone cortisol, which is the
hydroxylation product of cortisone by 11-beta-steroid dehydrogenase.
-It derives from a hydride of a pregnane.

15. MECHANISM OF ACTION OF CORTISONE :

16. -used to treat a variety of cancers, such as leukemia, lymphoma, and
multiple myeloma.
•used to treat nausea and vomiting associated with some chemotherapy
drugs.
-Cortisone is used to stimulate appetite in cancer patients with severe
appetite problems.
•The lotion (topical) is used in treatment of allergic skin reactions, and
relieves symptoms of itching, redness, and swelling.
-Cortisone is also used to replace steroids in conditions of adrenal
insufficiency (low production of needed steroids produced by the
adrenal glands).
USES OF CORTISONE
•used as an anti-inflammatory medication.
-used to treat or prevent allergic reactions.
•used as treatment of certain kinds of autoimmune diseases, skin
conditions, asthma and other lung conditions.

17. •Vitamin D is a group of fat-soluble secosteroids responsible for increasing intestinal
absorption of calcium, magnesium, and phosphate, and many other biological effects.
•Upto now five vitamins of this group have been isolated, viz. D1 , D2 , D3 , D4 , and D5 .
•Vitamin D1 or D is the molecular compound of D1 and lumisterol.
•Biologically vitamin D is termed as Calciferol.
•It is also known as “Sunshine Vitamin” , because the sterols which are present in the
skin can be converted to vitamin D with the help of UV rays from the sun.

18. •Acts as hormone because it is synthesized in the body.
•All the vitamins of this group are formed by irradiation of the specific sterols. These
sterols are known as “Pro- Vitamins”.
VITAMINS PRO- VITAMINS
Vitamin D2 (Ergocalciferol) Ergosterol
Vitamin D3 ( Cholecalciferol ) 7-dehydro-cholesterol
Vitamin D4 22,23-dihydroergosterol
Vitamin D5 7-dehydro-sitosterol

19. →In the early 19th centuary, Edward Mellanby noticed dogs that were fed cod liver oil
did not develop rickets and concluded vitamin A, or a closely associated factor, could
prevent the disease.
→In 1914 Elmer McCollum and Marguerite Davis discovered a substance in cod liver
oil which later was called "vitamin A".
→Later in 1922 McCollum tested modified cod liver oil in which the vitamin A had
been destroyed. The modified oil cured the sick dogs, so he concluded the factor in cod
liver oil differs from vitamin A. He called it vitamin D because it was the fourth vitamin
to be named.
→In 1932 Askew et al. isolated vitamin D2 from irradiation mixture of ergosterol.
windaus and Linsert proved vitamin D1 as the adduct between vitamin D2 and
lumisterol.

20.  Vitmin D is a generic term and
consists of similar structure as
steroids.
 The A, B,C and D ring structure
is derived from
cyclopetanoperhydrophenanthrene
ring structure of steroids.
A
B
C
The only difference between steroids and vitamin D is that one of the rings in vitamin D
are broken. In vitamin D the 9,10 carbon- carbon bond of ring B is broke so it is indicated
as “9, 10- seco” in the nomanclature.
The numbering will be same as the parent compound cholesterol.
A B
C D

21. The IUPAC name of vitamin D2 is 9,10- secoergosta- 5,7,10 (19), 22- tetra-en-3-ol.
and the IUPAC name of vitamin D3 is 9,10- seco-cholesta- 5,7,10(19)- trien-3-ol.

22. All the pro- vitamins of vitamin D possess certain essential characteristics :
-OH group at C3 position
-Two conjugated double- bonds between C5- C6 and C7 - C8
-A Hydrocarbon chain at C17 .
Vitamin D1 contains molecular compound of lumisterol and vitamin D2 in 1:1 ratio.

23. Transformation of inactive pro-vitamins into active vitamins is accomplished by
ultraviolet rays .

24. Vitamin D2 and vitamin D3 are not stable forms so they are converted into
biologically active and stable form, Calcitriol in kidneys. It occurs in 2 steps
1. coverts to calcidiol in liver
2. converts to calcitriol in kidneys.
calcifediol

25. DIETARY SOURCES :
Sunlight is the major source.
Found mainly in the cod- liver oil and other fish
liver oils.
Egg yolk is another rich source of vtamin D.
Ergocalciferol occurs naturally in some
mushrooms. Cholecalciferol occurs naturally in some
fish like eel, tuna, salmon, catfish.
Milk and plant foods are poor sources of vitamin
D.

26. MECHANISM OF ACTION OF VITAMIN - D

27. FUNCTIONS OF VITAMIN- D
VITAMIN D
FUNCTIONS
CLASSICAL
ACTIONS
NON- CLASSICAL
ACTIONS
Calcium and phosphate homeostasis
Bone mineralisation
Regulation of cell proliferation and differentation
Regulation of immune function
Endocrine effects
Insulin resistance
Inflammation
Modulation of Renin angiotensin system
Renal function
Muscle function

28. VITAMIN D DEFICIENCY
•Rickets is the primary disease caused by vitamin D
deficiency in young and children.
•Osteomalacia - occurs in adults
•Milk fever is seen in cattle
•Osteoporosis
•In polutry leads to reduced egg production
•Infectious diseases
•Inflammatory bowel disease :Crohn's disease and
ulcerative colitis
•Other conditions include diabetes, depression,
schizoprenia, weight loss ,dementia.

29. 1.WILSON and GISVOLD’S text book of organic medicinal and pharmaceutical
chemistry, twelfth edition John M. Beale, Jr. John H. Block.
2. An introduction to Medicinal chemistry by GRAHAM L. PATRICK.
3. Thomas L. Lemke; David A. Williams (2008). Foye's Principles of Medicinal
Chemistry. Lippincott Williams & Wilkins. pp. 889–. ISBN 978-0-7817-6879-5.
4. ChemIDplus Chemical Information Classification.
5.Norman AW (August 2008). "From vitamin D to hormone D: fundamentals of the
vitamin D endocrine system essential for good health". The American Journal of
Clinical Nutrition.