Chapter 10. Analysis of the derivatives of cyclopentano-perhydrophenanthrene

Sterane (cyclopentanoperhyd rophenanthrene) compounds are a class of tetracyclic compounds. This class includes cardenolides, steroid hormones (glucocorticoids, anabolic hormones, gestagens, androgens, estrogens), group of D-vitamins, etc.

Classification:

Pregnane derivatives

1. Gestagens (hormones of Corpus Luteum) and their synthetic analogues: progesterone, norethisterone, medroxyprogesterone acetate.
2. Glucocorticoids: deoxycorticosterone acetate, cortisone acetate, hydrocortisone, prednisolone, fluor-substituted compounds, such as dexamethasone.

Androstane derivatives

Androgenic hormones and half-synthetic derivatives, showing anabolic effects: testosterone propionate, methyltestosterone, methandienone, methandriol, compound of the group of nandrolone (phenobolinum, retabolyl), cyproterone acetate.

Estrane derivatives

Estrogens: ethinylestradiol, ethers of estradiol.

Cardiac glycosides

Cardenolides: digitoxin, digoxin, strophanthin K, corglycone.

D-vitamins

Cholecalciferol ― D₃, ergocalciferol ― D₂

Name and chemical formula	Properties
Gestagens
Progesteronum Progesteron Pregnane-4-dion-3.20 М.м. 314.47 С21Н30О2	White crystalline powder. Melting point is 127-131 °С. Specific rotation is from +190° to +200° (0.5% alcohol solution)
Norethisteronum Norethisterone (Norcolute) 19-Norpregnane-4-in-10-ol-17β-on-3 М.м. 300.47 С20Н26О2	White or white with yellowish color crystal powder. Melting point is 270-276 °С. Specific rotation is from +28° to +32° (0,5% solution in alcohol and chloroform)
Medroxyprogesteroniacetas Medroxyprogesterone acetate 6α-methyl-pregnane-4-ol-17α-dion-3.20-17 acetate М.м. 344.49 С22Н32О3	White or almost white crystal odorless powder. Melting point is 205 °С. Specific rotation is from +45° to +51° (1% solution in dioxane)
Anabolic hormones
Testosteronipropionas Testosterone Androsten-4-ol-17β-one-3-propionate М.м. 288.43 С19Н28О2	White crystal powder. Melting point is 118-123 °С. Specific rotation is from +87° to +90° (1.0% alcohol solution)
Methyltestosteronum Methyltestosterone 17β-Methylandrostane-4-ol-17 М.м. 302.45 С20Н30О2	White odorless crystalline powder; Hydroscopic. Melting point is 162-168 °C. Specific rotation is from +87° to +90° (1% solution is alcohol)
Methylandrostendiolum Methandriol or Methasterone (methylenandrostendiol) 2α,17α-Dimethyl-5α-androstan-17β-ol-3-one М.м. 304,47 С20Н32О2	White odorless crystalline powder, whose it melting point is 199-206 °С. Specific rotation is from -70° to -77° (1.0% solution in alcohol)
Methandrostenolonum Metandienone 17α-methylandrostadien-1,4-ol-17β-оne-3 М.м. 300.44 С20Н28О2	White or yellowish-white crystalline powder. Melting point is 162-170 °С. Specific rotation is from 0° to +5° (1.0% solution in chloroform)
Phenobolinum Phenobolinum Nandronolonephenylpropionate 17β-hydroxy-19-nor-4-androstane 19-nortestosterone М.м. 406.56 С27Н34О3	White or creamy-white crystal powder. Slightly soluble in alcohol, practically insoluble in water. Melting point is 95-99 °С. Specific rotation is from +48° to +51° (2.0% dioxane solution)
Retabolil Nandrolone 19-nortestosterone-17-decanoate М.м. 429.37 С28Н45О3	Creamy white crystal powder. Melting point is 33-37 °С. Specific rotation is from +32° to +36° (1.0% dioxane solution)
Corsticosteroids
Desoxуcorticosteroniacetas Deoxycorticosterone acetate Pregnane-4-ol-21-dion-3,20-acetate-21 М.м. 372.5 С23Н32О4	Creamy white crystal powder. Melting point is 155-160 °С. Specific rotation is from +176° to +184° (1.0% solution in chloroform)
Cortisoniacetas Cortisone acetate Pregnane-4-diol-17α,21-trione-3,11,20-аcetate-21 М.м. 376.49 С21Н28О6	White or yellowish-white crystal powder. Melting point is 238-243 °С. Specific rotation is from +178° to +194° (0.5% acetone solution)
Prednisonum Prednisone Pregnanedien-1,4-diol-17α,21-trione-3,11,20 М.м. 358.44 С21Н26О5	White crystal powder. Melting point is 223-228 °С, with decomposition. Specific rotation is from +168° to +174° (0.5% acetone solution)
Prednisolonum Prednisolone 1, 4-Pregnadien-11β, 17, 21-triol-3, 20-dione М.м. 360.52 С21Н28О5	White or yellowish-white crystal powder. Melting point is 227-230 °С. Specific rotation is from +96° to +104° (1% dioxane solution)
Dexamethasonum Dexametasone (11β,16α)-9-Fluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione М.м. 392.47 С22Н29FO5	White or almost white odorless powder. Melting point is nearly 250 °C. Specific rotation is from +72° to +80° (1.0% solution in dioxane)
Flumethasonum Flumetasone 6,9-difluor-16-methylprednisolone-21-trimethylacetate М.м. 494.25 С27Н36F2O6	White or almost white odorless crystal powder. Specific rotation is from +71° to +82° (1% dioxane solution)
Triamcinolonum Triamcionolone 9-fluor-16-hydroxyprednisolone М.м. 394.41 С24Н31FO6	White or yellowish-white crystal powder. Melting point is +65-72 °С. (1% dimethylformamide solution)
Fluocinoloniacetonidum Fluocinolone acetonide 6α,9α-difluor-16α-hydroxyprednisolone-16,17-acetonide М.м. 452.50 С24Н30F2O6	White crystal powder. Stable in the atmospheric air. Melting point after 270 °С with decomposition
Estradiols
Aethinyloestradiolum Ethiniestradiol 17α-Ethinilestratrien-1,3,5(10)-diol-3,17β М.м. 296.41 С20Н24О2	White or creamy-white crystal powder. Melting point is 181-186 °С. Specific rotation is from 0° to +3° (1% dioxane solution)
Оestradiolidipropionas Estradiol dipropionate М.м. 272.37 С18Н24О2	White crystalline powder with no odor. Melting point is 104-108 °C. Specific rotation is from +37° to +41° (1% dioxane solution)