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Progesterones

Progesterone is not only an important progestin, but is also an important precursor for androgen. It is synthesized according to the following scheme  [Pg.564]

Acetate — cholesterol — pregnenolone — progesterone — testosterone — estradiol [Pg.564]

FIGURE 61.7 The actions of progesterone. FSH = follicle-stimulating hormone. [Pg.564]

Hydroxyprogesterone caproate (Delalutin) Medroxyprogesterone acetate (Provera) Megestrol acetate (Megace) [Pg.565]

Must be given intramuscularly, brief duration of action Effective orally Potent progestin [Pg.565]


Has the properties of progesterone and is given orally for treating functional uterine haemorrhage. Norethisterone, 19-norelhisterone, m.p. 20I-206°C is one of the progestational steroids used in the contraceptive pill. [Pg.166]

C21H36O2. M,p. 238°C. There are four isomeric pregnane-3,20-diols differing only in the orientation of the hydroxyl groups at positions 3 and 20 and with the 5/ configuration. Only the 3a,20a occurs naturally. It is formed by reduction of progesterone in the liver and is the chief urinary metabolite of it, being... [Pg.326]

Progesterone can be manufactured from cholesterol, from certain steroid sapogenins and from stigmasierol. [Pg.327]

The early Escherunoser-Stork results indicated, that stereoselective cyclizations may be achieved, if monocyclic olefins with 1,5-polyene side chains are used as substrates in acid treatment. This assumption has now been justified by many syntheses of polycyclic systems. A typical example synthesis is given with the last reaction. The cyclization of a trideca-3,7-dien-11-ynyl cyclopentenol leads in 70% yield to a 17-acetyl A-norsteroid with correct stereochemistry at all ring junctions. Ozonolysis of ring A and aldol condensation gave dl-progesterone (M.B. Gravestock, 1978 see p. 279f.). [Pg.91]

Stigmasterol from soy bean extracts can be selectively ozonolyzed on the side-chain double bond. The 20-formyl group formed is converted to the enamine with piperidine. This can be oxidized to progesterone. [Pg.285]

The manufacture of prednisolone (30) follows a similar route. 11-Oxo-progesterone (34) is treated with two molar equivalents of diethyl oxalate and sodium methoxide in /-butanol. The product (39) is acidified and treated with... [Pg.99]

C25H32O4, an additive that is a synthetic progesterone, suppresses estms in heifers and results in increased weight gain and feed efficiency (5). [Pg.157]

Fig. 2. The four stmctural classes of progesterone. Carbon atoms are numbered as shown ia (7) and (8) and the rings are referred to as detailed ia (9). Fig. 2. The four stmctural classes of progesterone. Carbon atoms are numbered as shown ia (7) and (8) and the rings are referred to as detailed ia (9).
Extracts of corpora lutea were known ia the early tweatieth ceatury to inhibit ovulatioa ia animals. Pure progesterone (3), the active component of the extracts, was isolated ia 1934 and its stmcture reported (15). Several problems limited its use and drove efforts to develop progesterone analogues, ie, it was available only ia small quantities from animal sources, was not orally active, and was discovered to cause androgenic side effects. [Pg.208]

Eig. 3. Eirst degradation process used to produce progesterone. [Pg.208]

A direct, one-step aromatization of 19-substituted steroids has appeared in the Hterature, ie, cholesterol (3), dehydroisoandrosterone, androsterone, progesterone (1), and testosterone react with an electrophilic mthenium complex, C Ru , where Cp represents Tj -cyclopentadienyl, obtained through protonation of [Cp Ru(OCH2)]2 using triflic acid, to provide estrone (20) directly (46). [Pg.210]

EthynodlolDia.ceta.te, Ethynodiol diacetate has been used alone, and in combination with an strogen, as an oral contraceptive and to treat disorders associated with progesterone deficiency (76). It may be crystallised from aqueous methanol (77) and is soluble in chloroform, ether, and ethanol sparingly soluble in fixed oils and insoluble in water (76). Extensive spectral and chromatographic data have been compiled (78). [Pg.214]

Megestrol acetate (79) is stmcturaHy related to progesterone (1). It has been prepared from medroxyprogesterone acetate (74) by chloranil-mediated dehydrogenation. It also has been prepared from hydroxyprogesterone acetate (42) via 6-methylenation and double-bond migration (109,110). [Pg.217]

Progesterone. Progesterone (1) is not orally active. Although seldom used clinically, it can be adrninistered as an intramuscular injection, pessaries, or suppositories in the treatment of menstmal disorders and habitual abortion (121). Progesterone can be recrystaUized from dilute alcohol and exists in two crystalline forms (122). It is soluble in chloroform and ethanol sparingly soluble in acetone, dioxane, ether, and fixed oils and practically insoluble in water (121). Two syntheses of progesterone (1) are described in Figure 3. [Pg.218]


See other pages where Progesterones is mentioned: [Pg.327]    [Pg.327]    [Pg.280]    [Pg.62]    [Pg.685]    [Pg.1100]    [Pg.543]    [Pg.813]    [Pg.95]    [Pg.98]    [Pg.99]    [Pg.109]    [Pg.408]    [Pg.169]    [Pg.183]    [Pg.207]    [Pg.207]    [Pg.207]    [Pg.207]    [Pg.207]    [Pg.208]    [Pg.208]    [Pg.208]    [Pg.209]    [Pg.209]    [Pg.211]    [Pg.212]    [Pg.218]    [Pg.219]    [Pg.219]    [Pg.219]    [Pg.220]    [Pg.220]    [Pg.220]    [Pg.220]   
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See also in sourсe #XX -- [ Pg.593 , Pg.867 ]




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11 -Deoxycorticosterone, from progesterone

11 -Deoxycorticosterone, from progesterone 6/3-hydroxylation

17-hydroxy-progesterone

17a-Acetoxy-progesterone

17a-Hydroxy progesterone

17«-Hydroxy progesterone, hydroxylation

Action progesterone

Adverse Effects of Estrogen and Progesterone

Ai-Acid glycoprotein - progesterone

Ai-Acid glycoprotein - progesterone complex

Aldosterone formation from progesterone

Atherosclerosis progesterone

Binding of progesterone to a-acid glycoprotein

Biological effects of progesterone

Blood progesterone

Breast cancer progesterone receptor status

Breast, androgens progesterone

Capsules progesterone

Chicken progesterone

Cholesterol progesterone

Corticosterone, formation from progesteron

Creams progesterone

Cytochrome progesterone

Diosgenin progesterone from

Ent-Progesterone

Estradiol progesterone and

Estrogen and Progesterone Receptors

Estrogen and Progesterone Receptors in Fine-Needle Aspirates of Breast

Estrogen progesterone and

First Progesterone

Hormone estrogen and progesterone

Hormones progesterone

Johnson s synthesis of progesterone

Luteinizing hormone progesterone synthesis

Maternal behavior progesterone

Menstrual cycle progesterone

Metabolism of progesterone

Micronization progesterone

Monooxygenases progesterone monooxygenase

More Progesterone Analogues

Natural products progesterone

Natural progesterone

Oocyte interaction with progesterone

PR, Progesterone receptor

Particle size progesterone

Pharmaceutical industry progesterone

Pharmaceuticals progesterone

Prednisolone Progesterone

Pregnenolone, conversion into progesteron

Progesteron

Progesteron

Progesterone 11-keto derivatives

Progesterone 5«-reductase

Progesterone Cancer

Progesterone INDEX

Progesterone Johnson

Progesterone Ovaries

Progesterone Receptor Research

Progesterone T

Progesterone adrenal, production

Progesterone adverse effects

Progesterone agonists/antagonists

Progesterone aldosterone from

Progesterone allylic oxidation

Progesterone analogues

Progesterone and TBI

Progesterone and progestogens

Progesterone antagonists

Progesterone antibody specificity

Progesterone binding

Progesterone biosynthesis

Progesterone biotransformation

Progesterone brain receptors

Progesterone challenge

Progesterone chemistry

Progesterone cholesterol mixture

Progesterone clinical trials

Progesterone components

Progesterone contraceptive vaginal delivery

Progesterone cortisol from

Progesterone cortisone and

Progesterone crystals

Progesterone derivatives

Progesterone development

Progesterone dispersion

Progesterone effects

Progesterone enone

Progesterone exogenous

Progesterone fetal

Progesterone formation

Progesterone formula

Progesterone from pregnenolone

Progesterone from stigmasterol

Progesterone functional aspects

Progesterone functions

Progesterone gel

Progesterone gene expression

Progesterone hormone synthesis

Progesterone hydrogenation

Progesterone implant

Progesterone in Blood

Progesterone in Human Subjects

Progesterone in Saliva

Progesterone in plasma

Progesterone in women

Progesterone injection

Progesterone interactions with steroid receptors

Progesterone lactation

Progesterone membrane effects

Progesterone metabolism

Progesterone metabolites

Progesterone microbial transformation

Progesterone micronized

Progesterone molecular modifications

Progesterone nasal absorption

Progesterone natural modification

Progesterone natural sources

Progesterone occurrence

Progesterone oral delivery

Progesterone oxidation

Progesterone pathway

Progesterone pharmacokinetics

Progesterone physicochemical properties

Progesterone physiologic effects

Progesterone placental

Progesterone plants

Progesterone plasma concentration

Progesterone precursor

Progesterone pregn-4-ene-3, 20-dione

Progesterone preparation

Progesterone product standards

Progesterone production

Progesterone progestins

Progesterone radioactive

Progesterone reaction

Progesterone receptor

Progesterone receptor affinity

Progesterone receptor antagonist

Progesterone receptor binding agents

Progesterone receptor localization

Progesterone receptor phosphorylation

Progesterone receptor proteins

Progesterone receptor structure

Progesterone receptor, in breast cancer

Progesterone receptors concentration

Progesterone receptors measurement

Progesterone receptors prediction

Progesterone receptors prognostic usefulness

Progesterone receptors tamoxifen therapy

Progesterone reduction

Progesterone reduction-alkylation

Progesterone release

Progesterone response element

Progesterone responsive elements

Progesterone saliva

Progesterone structure

Progesterone synthesis

Progesterone synthetic, side effects

Progesterone tablets

Progesterone testosterone mixture

Progesterone transdermal

Progesterone transformation products

Progesterone transport

Progesterone vaginal

Progesterone vaginal delivery

Progesterone vaginal ring

Progesterone, 1 la-hydroxyenantiospecific synthesis

Progesterone, 21-methylsynthesis via acylation of organocadmiums

Progesterone, Oppenauer oxidation

Progesterone, Raman

Progesterone, acetate

Progesterone, biomimetic synthesis

Progesterone, biotransformations

Progesterone, formation from cholesterol

Progesterone, hydroxy-, caproate

Progesterone, hydroxylation

Progesterone, microbial hydroxylation

Progesterone, reaction with

Progesterone, total synthesis

Progesterone-dependent enzyme

Progesterone-receptor modulator

Progesterone-releasing intravaginal device

Progesterones, inactivation

Rhizopus arrhizus progesterone hydroxylation

Selective progesterone receptor modulator

Selective progesterone receptor modulators

Selective progesterone receptor modulators SPRMs)

Serum progesterone

Serum progesterone level

Solubilization progesterone

Sources of Progesterone

Steroid hormones progesterone

Steroid progesterone

Steroid progesterone receptor

Steroids Related to Progesterone

Study 6.34 Organic synthesis photobromination of progesterone

Treated with Estrogen and Progesterone

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