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4th unit drugs acting on endocrine system

This document provides information on drugs acting on the endocrine system. It discusses the introduction and nomenclature of steroids, including sex hormones and their biosynthesis. The structures, syntheses and properties of key sex hormones are described, such as testosterone, oestriol, oestradiol, diethylstilbestrol and progesterone. References on medicinal chemistry textbooks are also listed.

Education◦
4th UNIT DRUGS ACTING ON ENDOCRINE SYSTEM Prepared by G. Nikitha, M.Pharmacy Assistant Professor Department of Pharmaceutical Chemistry Sree Dattha Institute Of Pharmacy Hyderabad 1 Subject: Medicinal Chemistry-II Year: B.Pharmacy 3rd Year Semister: 1st Semister
Contents  Introduction of Steroids  Nomenclature  Sex Hormones  Biosynthesis of sex hormones  Structure, synthesis of Testosterone, Oestriol, Oestradiol, Diethyl stilbestrol, Progesterone  Reference 2
Introduction  Steroids are a unique class of chemical compounds found widely in the animal and plant kingdom.  These are characterized by the presence of 1,2- cyclopentanoperhydrophenanthrene nucleus in their structure.  The steroids include a wide variety of naturally occurring synthetic substances such as sterols, bile acids, sex hormones, adrenal cortical, various contraceptive drugs, cardiac-active lactones sapogenins and certain alkaloids and antibiotics. 3 Steroid backbone
 The term cholesterol was derived from the Greek words bile (which means chole) and solid (which means sterols). The modern era of steroid research began with steroids chemistry in 1900’s. Dr.AO Windaus worked for 20 years and received the noble prize in 1928 for his research on the constitution of sterols.  Dr. Heinrich and Wieland engaged in natural products chemistry including bile acids and were awarded the noble prize in 1928.  A total of 6 noble prizes were awarded to scientists working in the area of steroids, among the 6,4 prizes were in steroid chemistry category. The pioneer, work of the Adolf Winduas and Heinrich Wieland in the structure elucidation of a number important steroid led to the many discoveries in the world of steroids. 4
 The two important discoveries mentioned in 1940 and 1950 had a dramatic effect not only on the steroids. This led to an extensive research on medicinal chemistry, pharmacology and clinical studies of steroids against and antagonists.  The steroids are found as solids and M.P ranges from 100oC to 250oC, insoluble in water, soluble in ethanol, acetone, chloroform, (Organic Solvents). 5
Nomenclature 1. Steroids consist of 4 fused rings (A, B, C and D). Chemically these hydrocarbons. Are cyclopentanoperhydrophenanthrenes. They contain 5 membered cyclopentane (ring-D) and the 3 rings of phenanthrene (A, B, C). 2. Earlier the various steroids are generally designated by their common names such as cholesterol, progesterone, and testosterone. However these names were discarded due to development in chemistry and systemic names as per IUPAC nomenclature were favoured. 6
3. Steroids contain 17 carbon atoms and the numbering the remaining carbons of phenanthrene followed by numbering the remaining carbons of the cyclopentane ring. Additional carbon atoms on the steroids including methyl groups attached to C-10 and C-13 and alkyl substituent’s on C-17 are numbered. 4. If any unsaturation is present in the steroids the ane ending of the stem is replacing by ene if it contains one double bound, diene if it contains two double bounds, triene if it contains three double bounds. 5. If double bound is not between carbons both the carbons are indicated as same. 7
6. If the steroid contain 3-membered ring it is indicated by the prefix cyclo preceded by the numbers of positions concerned. 7. Any enlargement of steroid ring is indicated by the prefix homo preceded by small capital indicating the ring affected. 8. Circles were sometimes used to indicate α-hydrogens and dark dots are used to indicate β-hydrogens. 9.On the basis of following priorities suffix for stem name is selected carboxylic acid> carbonyl> alcohol> amine> ether. 8
Sex Hormones  Hormones are the organic substances which are secreted by the endocrine glands.  They are brought to the different organs of the body by means of blood stream to produce the various physiological functions.  The deficiency of hormone leads to particular disease can be cured by administration of hormone. 9
Classification  Steroid hormones are divided into two types Sex hormones (male and female) and adrenal cortical hormones  Sex hormones are produced in gonads (testes in male and ovaries in female). Their production is stimulated by pituitary gland. 10
Biosynthesis of sex hormones 11
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1. Testosterone: IUPAC: 17-Hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17- dodecahydrocyclopenta[a] phenanthren-3-one In 1935 Testosterone was isolated by E. Laqueru et al. from testes. 13 Molecular Formula: C19H28O2
Synthesis: 14
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Properties and Uses:  Creamy white crystalline powder, insoluble in water and soluble in alcohol.  It may be used for treatment of breast carcinoma in postmenopausal women. 16
2. Oestriol: IUPAC: 13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a] phenanthrene-3,16,17-triol It is isolated by Marrian from urine of pregnant women. It is useful in some cases of oestrogen defiency especially for the relief of menopausal symptoms. It occurs mainly in placenta and pregnant women. 17 Molecular Formula: C18H24O3
Synthesis:  Route-1 18
 Route-2: 19
3.Oestradiol: IUPAC: 13-methyltetracyclo heptadeca-1,3,5-triene-3,17-diol It exists as two stereoisomeric oestradiols (α and β) between them β- isomers is more active, α-isomer is less active. 20 Molecular Formula: C18H24O2
Synthesis: 21
4. Diethyl stilbestrol: IUPAC: 4,4'-[1,2-Diethyl-1,2-ethenediyl]bisphenol 22 Molecular Formula: C18H20O2
Synthesis:  Method-1: From anisaldehyde (Dodds Method) 23
 Method-2: From Anethole 24
5. Progesterone:  Progesterone means favoring pregnancy. These are substances in the Corpus Luteum. Which convert the oestrogen-primed endometrium to secretory endometrium and maintain pregnancy  Progesterone was isolated from the Corpus Luteum, the adrenal cortex, the placenta and testes. IUPAC:17-acetyl-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17- dodecahydrocyclopenta[a]phenanthren-3-one 25 Molecular Formula:C21H30O2
Synthesis: 26
Reference books  Text book of Medicinal chemistry volume-1-3rd edition by V.Alagarasamy.  Text book of Medicinal chemistry volume-2-3rd edition by V.Alagarasamy.  Medicinal Chemistry- 4th edition by Ashutosh Kar  Medicinal and Pharmaceutical Chemistry by Harkishan Singh, V.K Kapoor.  Wilson and Gisvolid’s Textbook of Organic Medicinal and Pharmaceutical chemistry-12th edition by John M. Beale, John. H. Block. 27
Thank YOU 28