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Lecture №11 Hormones of the sexual glands: androgens and their semi-synthetic derivatives, estrogens and their synthetic analogues. Prostaglandins as pharmaceuticals, their properties, application. ass. Medvid I.I. Androgenic hormones Male sex hormones called androgens (from the Greek word 'Andros' - a man and "Genetic" - birth). Androgenic hormones are produced by male gonads (testicular) during the puberty (sexual maturity period). Androgens are necessary for the formation of sexual sphere and development of secondary sexual characteristics in men. They also affect on various biochemical processes, not related to the characteristics of sex - cause anabolic effects, affect on the exchange of carbohydrates, lipids, cholesterol, electrolytes and other staff. Natural androgen is testosterone, which was at first dedicated in 1931 y. and synthesized in 1934 y. Testosterone creates male and his lack in the old age in man destroys the body, creating the conditions for heart attacks and strokes. Testosterone - unstable substance and is not used as a medicine. In medicine, testosterone derivatives (esters) are used, which are absorbed slowly and are more stanle; and also synthetic substitutes, such as methyltestosterone. They all have medicinal properties of the natural hormone. Subsequent research established that the testosterone effect is prolonged after the esterification by fatty acid. Ester creates original depot at the injection site from which they were gradually absorbed, while testosterone is quickly removed from the body by the kidneys. One of the most active and stable at the storage of testosterone esters is testosterone propionate. Methyltestosterone (17α-methyltestosterone), although by the force of action is weaker then testosterone propionate, but not destroyed by enzymes of the gastrointestinal tract and remains activity at the oral admission. Androgens are used for men with sexual underdevelopment, functional disorders of sexual sphere (eunuchoidism) and in old age with vascular and nerve disorders. Applied by older women (over 60) at the tumors of reproductive organs, mammary glands of uterine bleeding, as well as radiotherapy of ovarian cancer and breast cancer. Chemical signs of androgens 1. 2. 3. 4. Derivatives of androstane; Availability of oxogroup(=О) in position 3; In position 4 – double bond; Hydroxy-group (ОН) (can be esterificated) in position17. 1 19 CH3 18 CH3 12 17 11 13 16 9 2 8 10 3 15 7 5 4 14 6 Androstane CH3 CH3 O Testosterone OH General identification reactions on androgenic hormones On steroid system : Boscot’s reaction and reaction with concentrated sulfate acid. On keto-group in the position 3: reactions of the oximes, hydrazones, isonicotinoyl hydrazones, phenyl hydrazones formation. Esters of androgenic hormones (testosterone propionate): alkaline hydrolysis; hydroxamic reaction. Alcoholic hydroxyl in 17β-position: formation of esters with character melting temperature. Testosterone propionate (Testosteroni propionas) (SPhU 1.2) CH3 OCOC2H5 CH3 3-Oxandrost-4-ene-17β-yl propanoate or 17β-propioneoxyandrostene-4-one-3 Produce synthetically, based on cholesterol, which is produced with the processing of lanolin and pork fat of animals. Characters. White or almost white crystalline powder or colorless crystals. Practically insoluble in water, freely soluble in alcohol and acetone, soluble in fatty oils. O Identification of testosterone propionate 1. 2. 3. 4. 4. 5. 6. Absorption spectrophotometry in IR-spectrum. On steroid system – Boscot’s reaction. Intense yellow fluorescence. The drug is dissolved in СН3СООН conc., add by drops bromine water - its bleaching occurs (reaction on double bond). Establish a melting point of testosterone derived as a result of alkaline hydrolysis. On ester group – hydroxamic reaction (red-brown color). On oxo-group in position 3 – oxime formation, which can be identified by the temperature of melting. UV-spectrophotometry. Assay of testosterone UV-spectrophotometry (index method). Photocolorimetry (based on the reaction between the drug with isoniazid and establishment isonicotinoylhydrazone, colored in yellow). Storage and application In tightly corked container, protected from moisture and light action. Androgenic drug for the treatment of climacteric, vascular and nerve disorders and cancers of breast and ovaries in women. Enter by i/m way in oil solutions. Issue – amp. 1,0 and 5,0 % solution in oil. Omnadren – oil solution for injection amp. 1 ml №5 (contains a mixture of testosterone esters: propionate, phenylpropionate, capronate, isocapronate). Andriol (testosterone undecanoate) – caps. 40 mg № 30; Androgel (testosteron) – gel for the external usage 2,5 or 5 g №10. Proviron (mesterolone, derivative of 5-androstanone (3)) – tabl. by 25 mg №20. Testosterone enanthate (Testosteroni enanthas) CH3 OCO(CH2)5CH3 CH3 O 17-enanthoxyandrostene-4-one-3 Applied in same cases as testosterone propionate. Act slower but longer as testosterone propionate. Enter by i/m way as 20% solution in oil one time every 2-4 weeks. Included to the Testoenatum mixture pro injectionibus amp. by 1 ml of 10% solution in peach oil (contains 24 mg of testosterone propionate and 111 mg of testosterone enanthate). Methyltestosterone (Methyltestosteronum) CH3 OH CH3 CH3 O 17α-methyl-17β-oxyandrostene-4-one-3 Synthetic testosterone replacement. Characters. White crystalline powder, odorless. Practically not soluble in water, slightly soluble in ether and oils, soluble in acetone, easily soluble in ethanol. Identification of methyltestosterone On steroid system – Boscot’s reaction. Intense yellow fluorescence. 2. At the dissolving of the drug in conc. H2SO4 orangeyellow color appears, and after adding of water orange-yellow color with green fluorescence (steroid cycle). 3. On alcoholic group ОН – acetilation reaction, acting of (СН3СО)2О in pyridine; at the dilution with water select methyltestosterone acetate with melting temperature 173-176º С (with decomposition). 4. On oxo-group in position 3 –the substance is boiled in methanol with H2NOH*HCl – sediment of oxime falls (melting temperature – 210-216ºС). 1. Assay of methyltestosterone UV-spectrophotometry at λ=240 nm. Storage and application In tightly corked container, protected from moisture and light action. Androgenic medication. In 2-3 times less active than testosterone propionate, but remains activity at the inside usage (sublingual). Issue: tabl. by 5-10 mg. Anabolic steroid structure means Anabolic drugs called substance that in the body stimulate the synthesis of proteins. Under their influence increasing body weight, improves the general condition of patients. By their structure anabolic drug are similar to male sex hormones, which have anabolic activity as side effect. Apply of androgens with anabolic action is not possible to treat women and children. Therefore it became necessary to synthesize the substance, which would be rather weak androgenic effect but a stronger or equal with androgens anabolic activity. It turned out that this can be achieved at some changes of molecular structure of male sex hormones. • There are three major ways of androgenic activity lowering : 1) Transfering of double bond from position 4 to position 5 : CH3 5 2) Introduction of the additional double bond in position 1: 1 CH3 O 3) Elimination of methyl group at position 19. Derivatives of 19-nortestosterone are the best anabolic drug. O Methylandrostendiol (Methylandrostendiolum) Methandriol* CH3 OH CH3 CH3 HO 17α-methylandrostene-5-diol-3β,17β or 3β,17β-dioxy-17α-methylandrostene-5 Characters. White crystalline powder, odorless. Practically not soluble in water, soluble in ethanol, sparingly soluble in chloroform. Identification of methylandrostendiol 1. 2. 4. 5. 6. At the dissolving of the drug in conc. H2SO4 orangeyellow color appears, with green fluorescence (steroid cycle). On alcoholic group ОН – acetylation reaction, after the action of (СН3СО)2О in pyridine –17-monoacetate of methylandrostendiol appears with melting temperature –174-180º С. To the solution of drug in 80% СН3СООН carefully add conc. H2SO4 – on the border of phases appears orange color, the upper phase is characterized by yellow-green fluorescence. UV- spectroscopy. Specific optical rotation. Assay of methylandrostendiol Gravimetry. Storage and application In tightly corked container, protected from moisture and light action. By chemical structure resembles methyltestosterone, but has weaker androgenic anabolic effect and stronger anabolic activity. Apply at the disorders of protein metabolism after severe injuries, operations, at the exhaustion, after infectious diseases, at the lag growth in adolescents. Treatment of women should be under the supervision of the gynecologist to prevent the effects virilization. Adopt in the form of tablets for sublingual absorption by 25-50 mg per day. Not used in prostate cancer, liver diseases. Release in the form of tablets by 10 and 25 mg. Methandrostenolone (Methandrostenolonum) Анабол, Methandienone* CH3 OH CH3 CH3 O 17α -methyl-17β-oxy-1,4-androstanediene -3-one or 1,2-dihydromethyltestosterone Characters. White crystalline powder, are allowed a weak yellowish shade. Very little soluble in water, slightly soluble in ether, easily soluble in ethanol, chloroform. Identification of methandrostenolone 1. 2. 4. UV-spectroscopy. At the dissolving of the drug in conc. H2SO4 dark-red color formed. On oxo-group in position 3: after the interaction of the drug with 2,4-dinitrophenylhydrazine 2,4dinitrophenylhydrazone of methandrostenolonw formed, which has orange-red color. Test on purity The presence of side steroids as contaminant (methyltestosterone) is established by TLC. Selenium admixture (not more than 0,01%) - the method of combustion in oxygen followed by spectrophotometry. Assay of methandrostenolone UV-spectrophotometry. In tablets methandrostenolone is detected by photocolorimetric method by the interaction with conc. H2SO4 . Storage and application In tightly corked container, protected from moisture and light action. Androgenic action is in100 times weaker then in testosterone propionate, anabolic activity – the same . Apply at the protein metabolism disorder, chronic adrenal insufficiency, toxic goitre, diabetic angiopathy, steroid diabetes, chronic coronary insufficiency and myocardial infarction, rheumatic heart lesions, atherosclerotic cardiosclerosis, stomach ulcers and duodenal ulcers, osteoporosis, bone fractures, eczema, psoriasis and others. Produce in the form of tablets by 1 and 5 mg. Phenobolin (Phenobolinum), Nerobolil, Durabolin, Nandronolone phenylpropionate* CH3 OCOCH2CH2C6H5 O 17β-phenylpropioneoxy-19-norandrostene-4-one-3 or 19-nortestosterone phenylpropionate Characters. White, sometimes with a creamy tinct crystalline powder. Practically insoluble in water, slightly soluble in ethanol, freely soluble in chloroform and acetone. Identification of phenobolin 1. 2. 3. Melting temperature (95-99 °С). IR-spectroscopy. TLC. Assay UV-spectrophotometry. Storage and application In tightly corked container, protected from light action. Phenobolin –active anabolic mean with long action (7-15 days after single injection). Detects very weak androgenic effect, in women virilyzation phenomena almost not observed. Applied in those cases, as methandrostenolone, not used for the treatment of prostate cancer. Enter by the i/m way in oil solution by 25-50 mg 1 time every 7-10 days. Issue: by 1 ml of 1% and 2,5% solutions in oil. Retabolil (Retabolilum), Nandrolone CH3 O OCO(CH2)8CH3 17β-decanoyloxy-19-noradrenostene-4-one-3 or 19-noradrenostene decanoate Strong and long (3 weeks) anabolic effect. Low toxicity, androgenic effect is lover than in phenobolin. Enter by the i/m way by 25-50 mg 1 time every 2-3 weeks. Produce in the form of 5 % oil solution in amp. by 1 ml. Female sex hormones and synthetic substitutes Female sex hormones called estrogens (from the Greek word "estrus" - estrus and "Gennao" - birth). These hormones are produced in maturing ovarian follicles and participate in the implementation of menstruation. They are necessary for the formation of female sex and female secondary sexual characteristics and functions for having children. The natural estrogen is estradiol and estron. Among them estron is a medical drug and estradiol used in the form of esters and other derivatives, becouse estradiol itself very rapidly inactivates in the body. As medical drugs estrogens are used in low ovarian function (primary and secondary amenorrhea), underdevelopment of the uterus, sterility, post-castartion disorders, surgical removal of ovaries. Estrogens are used to treat parahormone cancer in men and increased of labor activity (causing contraction of the uterus). Do not apply to women aged up to 60 years for malignant and benign tumors of the genital organs and mammary glands. Earlier estrone (folliculine) and estradiol are obtained from the urine of pregnant women, then - from the urine of pregnant animals. Now them are obtained synthetically from cholesterol. Estrone CH3 O Estradiol CH3 HO HO OH Chemical signs of estrogens 1. CH3 12 11 13 16 1 10 2 9 14 8 3 7 5 4 2. 17 6 Estrane 15 3. 4. Derivatives of estrane. Presence of the tree double bounds in the positions 1, 3, 5(10). Group –ОН (oxy-group) in position 3. Group –ОН (can be esterificated) or oxo-group (=О) in position17. General identification reaction on estrogenic hormones On steroid system: Boscot’s reaction and reaction with concentrated sulfate acid. Esters of estrogenic hormones (estradiol dipropionate): hydrolysis with the following identification of the products of hydrolysis; hydroxamic reaction. Phenolic hydroxyl - reactions: а) electrophilic substitution (bromination, nitration, formation azo-dye, aurin stain); b) salt and complex formation with heavy metals salts (for example, FeCl3); c) Esters formation (for example, with benzoyl chloride), which have character melting temperature. Estrone (Oestronum) Folliculine CH3 O HO 3-oxyestratriene-1,3,5(10)-one-17 Characters. White crystalline powder. Practically insoluble in water, soluble in ethanol and ether, easily soluble in chloroform. Identification of estrone 1. Boscot’s reaction – green fluorescence appears. 2. Estrone solution in conc. H2SO4 ). has golden-yellow color with intense green fluorescence (steroid cycle). 3. At the interaction with NH2OH*HCl oxime precipitate falls (with melting point 228-233ºС). 4. At the interaction with з diazoreagent formation of azodye is observed (reaction on phenolic hydroxyl). 5. At the action of C6H5COCl phenolic hydroxyl esterificates and formed ester has melting temperature of 220ºС. Activity of estrone determined biologically (evocation of oestrus) in neutered female mice and rats. In 1 mg are 10000 UA. Assay of estrone Polarimetry (solution of the drug in dioxane). Photocolorimetry (by the reaction of azo-dye formation). Storage and application In tightly corked container, protected from light action. Enter by the i/m way in the form of oil solutions at the low ovarian function (primary and secondary amenorrhea), infertility, cancer and underdevelopment of secondary sexual characteristics, overterm pregnancy, the surgical removal of ovaries. Issue: amp. by 1 ml of 0,05% or 0,1 % oil solution. Estradiol dipropionate * (Oestradioli dipropionas) CH3 OCOC2H5 C2H5OCO 3,17-dipropioneoxyestratriene-1,3,5(10) Characters. White crystalline powder. Practically insoluble in water, very little soluble in ethanol and oils. Identification of estradiol dipropionate 1. IR- and UV-Spactroscopy. 2. At the Boscot’s reaction green fluorescence appears. 3. At the heating with conc. H2SO4 there is a brown coloration, which by dilution with water and heated changes to pink. 4. On esteric groups conducted hydroxamic reaction (look testosterone propionate). 5. At the hydrolysis by КОН in ethanol estradiol forms, which falls in the form of precipitate at the dilution with water and acidification by НСl. Melting temperature of estradoil is 177 ºС. 6. Propanoic acid, which formed after the acidic hydrolysis, can be identified by the reaction with ethanol - ester formed, which has a characteristic odor. CH3 OCOC2H5 CH3 OH 2H2O H2SO4 C2H5OCO HO C2H5COOH + C2H5OH C2H5COOC2H5 + H2O + 2 C2H5COOH Assay of estradoil dipropionate Alkalimetry, the reverse titration. Substance is hydrolyzed alcohol by the alcoholic solution of potassium hydroxide, an excess of which is titrated by hydrochloric acid solution by phenolphthalein, Ем = ½ М.m. CH3 OCOC2H5 CH3 OH + 2 KOH + 2 C2H5COOK HO C2H5OCO KOH + HCl KCl + H2O Storage and application • In tightly corked container, protected from light action. • In two times more active than estrone, has a strong and prolonged effect, apply in those cases, as estrone. Enter by i/m way by 1 ml of 0,1% solution in oil every 1-2 days. • Estradiol is a part of the following preparations“Estramone” (transderm. plaster, 4 mg 20 cm2 №6); “Estrogel” (gel for the local usage 0,6 mg/g 80 g); “Estrimax” (tabl. 2 mg №28). • Complex preparations – “Pausogest” (estradiol hemihydrate and norethisterone acetate); “Climodiene” (estardiol valerate and dienogest). • Estriol is a part of “Ovestine” (tabl., vag. cream, vag. suppos.). Ethinylestradiol (Aethinyloestradiolum) Ethynilestradiol* CH3 OH C CH HO 17α-ethinylestratriene-1,3,5(10)-diol-3,17β Characters. White or creamy white fine crystaline powder, odorless. Practically insoluble in water, slightly soluble in alkali, soluble in alcohol, chloroform, soluble in acetone, ether and dioxane. Identification of ethinylestradiol IR- and UV-spectroscopy, TLC To detect ethynil group substance is dissolved in H2SO4, add FeNH4(SO4)2 solution – reddish-brown precipitate falls after the dilution with water pinkred sediment falls. 3. At the Boscot’s reaction orange fluorescence appears, in 50-100 times stronger than estrone fluorescence. 4. At the action of conc. H2SO4 orange-red color forms with yellow-green fluorescence . 5. At the interaction with benzoyl chloride ethinylestradiol-3-benzoate forms with melting temperature of 199-202ºС (phenolic hydroxyl). 1. 2. CH3 OH C CH O + C Cl CH3 HO OH C O C CH + HCl O Assay of ethinylestradiol 1. Alkalimetry by the substituent(look pregnine). 2. Spectrophotometry or photocolorimetry by the formation of bis-diazocompound in alkaline medium at the interaction with diazoreagent : Ethinylestradiol is stored in tightly corked container in a dark place. Application of ethinylestradiol Ethinylestradiol - one of the most active estrogenic agents. Introduction of ethinyl residue to the estradiol molecule increases stability and activity, that is why ethinylestradiol is taking internally. Apply at the hypogenitalizm (primary amenorrhea, underdevelopment of the uterus), ovarian hypofunction and secondary amenorrhea by 0,05-0,1 mg; for elimination of neuro-vascular disorders of estrogenic insufficiency receiving by 0,01-0,02 mg per day; to treat cancer prostate and breast cancer in women over 60 years - to 3 mg per day over a long time. In the treatment of prostate cancer in men may be feminization. Issue: tabl. by 0,01 and 0,05 mg under the “Microfolin” and “Esterlan”. Is a part of oral contraceptive preparations. Synthetic steroidal structure estrogens Substances that have estrogenic activity, were found not only among the steroid, but in some aromatic compounds. Admitting that the effect of estrogen depends on the presence of aromatic nuclei in the molecule. Important role belongs to hydroxyl and keto-groupsgroups that can form hydrogen bonds and interact with proteins in the body. For the detection of estrogenic action is important the distance between the functional groups. It is determined that the distance between the hydroxyl groups (in position 3 and 17) in estradiol is 1,1 nm, in meso-form of synestrol 1,2 nm, in the trans-isomer of diethylstilbestrol – 1,22 nm. At the same cisisomer of diethylstilbestrol, in which the distance between the hydroxyls is 0,75 nm, is physiologically inactive. The formation of ethers and esters do not reduce estrogen activity, but increases the period of action. Synestrol (Synoestrolum) Hexestrol C2H5 HO H C C H OH C2H5 Meso-3,4-di-(p-oxyphenyl)-hexane Characters. White crystalline powder, can have a yellowish tint, odorless. Practically insoluble in water, soluble in ethanol, chloroform, vegetable oils, alkali solutions. Estrogenic activity of synestrol is equal to estrone activity. Is used for the treatment of those diseases as estrone. Issue: tabl. by 1 mg; amp by 1 ml of 0,1% and 2% oil solutions. Diethylstilbestrol (Diaethylstilboestrolum) C2H5 HO C C OH C2H5 Trans-3,4-di-(p-oxyphenyl)-hexene-3 Characters. White crystalline powder, odorless. Practically insoluble in water, soluble in ethanol, ether, vegetable oils, alkali solutions. Two times more active than estrone, but due to the side effect it is used only for the treatment of breast cancer in women older than 60 years. Issue: amp. 3% oil solutions by 1 ml. Identification of synestrol and diethylstilbestrol 1. At the interaction of synestrol chloroform solution with conc. H2SO4 (In the presence of formalin) chloroform layer is painted in a cherry-red color (phenyl radicals). Diethylstilbestrol solution in conc. H2SO4 has the orange color, which gradually disappears after the dilution with water. 2. When you add bromine water solution to synestrol in conc. СН3СООН yellow precipitate forms. Diethylstilbestrol with bromine water in the presence of liquid phenol at the heating forms the emerald-green color, after adding of few pieces of sugar and heating coloration turns into dark blue, and cherry-brownish. 3. At the adding of to the synestrol chloroform layer FeCl3 solution and pyridine – there is a blue coloration, which by the adding of pyridine in excess turns green. Alcohol solutions of diethylstilbestrol colored in green, which gradually turns into yellow (phenolic hydroxyl). 4. At the interaction of drugs with (СН3СО)2О or С6Н5СОСl diacetates (dibenzoates) form, which have characteristic temperature of melting. Assay of synestrol and diethylstilbestrol 1. Method of acylation. Based on the obtaining of esters (diacetyl derivatives) by heating with acetic anhydride in the presence of pyridine. Excess of (СН3СО)2О is transformed to СН3СООН and titrate acid by NaOH solution, indicator - phenolphthalein, Еm = ½ М.m. In parallel control experiment is conducted: 2. Assay of synestrol in oil solution is conducted solution after the extraction by aqueous solution of sodium hydroxide by the reverse bromatometry method with control experiment, Еm = 1/8 М.m.: KBrO3 + 5KBr + 6HCl 3Br2 + 6KCl + 3H2O C2H5 HO CH Br CH 4Br2 OH C2H5 Br C 2H 5 HO CH CH OH C2H5 Br Br2 + 2KCl I2 + 2Na2S2O3 I2 + 2KBr 2NaI + Na2S4O6 Br 4HBr 3. Synestrol and diethylstilbestrol can be determined by photometric method by the reaction of azoconnection with diazotated sulfanilic acid: N C2H5 HO CH CH OH N 2 HSO4 C2H5 SO3H C2H5 HO HO3S N CH N CH OH C2H5 N N SO3H 2H2SO4 Storage of synestrol and siethylstilbestrol In tightly corked container, protected from light action. Prostaglandins Prostaglandins - biologically active substances that are contained in various organs and tissues (blood, lung, kidney, intestine, uterus, etc.). They are a sort of intracellular hormones that have influence on many body functions . Produced in the body in very small quantities (about 100 micrograms per day). Most accumulate in the seminal fluid. The first data was in 1913, when from the male prostate extract was isolated, which puts down AP in dogs . Discoverer of prostaglandins is the Euler (Sweden), who investigated these matters since 1934 year. He proposed the term "prostaglandins" that is from the Latin name of the prostate gland (Glandula prostata). Like vitamins, prostaglandins are divided into groups with similar chemical structure. Each one has a Latin index E, F, A, B (abbreviated writing PGE, PGF, PGA, PGB). Prostaglandins - a compounds without azot, in the base of its structure is prostanoic acid: Individual prostaglandins distinguish by the number and placing of radicals (Hydroxyl, carboxyl) and double bonds in the molecule. Extraction of prostaglandins 1. Extraction from animal sources (semen body fluids, animal tissue, etc.). The method is laborious, long and expensive. 2. Biosynthesis of precursors - polyunsaturated fatty acids in the presence of appropriate enzymes. Almost biosynthesis is conducted by incubation of unsaturated fatty acids from homogenate tissues of cattle (mostly seminal glands). 3. Synthetic methods for prostaglandins extraction include up to 29 stages. It is difficult to provide the necessary isomers that have biological activity. Characters Selected as individual compounds prostaglandins - a white crystalline substances which are easily dissolved in organic solvents. To study the chemical structure of prostaglandins UV, IR, NMR spectroscopy, mass-spectrometry, X-ray analysis are used. Identification For the analysis of prostaglandins are widely used various types of chromatography: column, paper, thin layer, gas-liquid (GLC) and others. Especially effective for the quantitative analysis is combination of GLH and mass-spectrometry that allows to detect 9-10 g of prostaglandins. For quantitative determination UV-spectrophotometry are used. To evaluate the physiological activity and the content of prostaglandins in the tissues biological methods are used, which are based on their ability to affect on the smooth muscles (stomach, intestine, uterus), blood pressure and other functions. Use also enzymatic and radioimmunological methods of analysis. Usage of prostaglandins Prostaglandins affect on the contractile activity of smooth muscle, functions of the nervous and cardiovascular systems, blood circulation, support the tone of urinary tract and bladder, and exhibit bronholitic bronhodilatation action, involved in the inflammation processes. The most active groups of prostaglandins are E, F and A. Prostaglandins E1 and E2 affect on the function of the bronchi; PGE inhibits the secretion of gastric juice; PGE and PHF cause reduction of uterine muscle; PGA1 and PGA2 during the action on blood vessels, make lower a blood pressure . Various pharmacological activity of prostaglandins hampering their practical application in medicine, so it is nessesary to search their synthetic analogs, which are available obtained and are selectively derived on the specific systems and functions. Obtained in the present analogs contain in the molecule structure cyclopentane nucleus and are 7-oxyanalogs, 15-ketoanalogs, contain esteric group at the positions 1 and 15. Some analogues contain instead of cyclopentane other cycles, and shortened or elongated alkyl chains. Thank you for attention!