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At least 37 records · Page 2Linked to original sources
PubMed1980

The addition of hypobromous acid to 3 beta, 17 beta-diacetoxy-4-estrene and an equilibration study involving neighboring group participation by the A-ring acetoxy group.

The reaction of 3 beta, 17 beta-diacetoxy-4-estrene with N-bromoacetamide in a two phase ether/water solvent mixture gave 5-bromo-4 beta, 17 beta-diacetoxy-5 alpha-estran-3 beta-ol as the major product (75%). Four minor products were also isolated and identified. These were: 4 alpha-bromo-3 beta, 17 beta-diacetoxy-5 alpha-estran-5-ol (5%), 5-bromo-3 beta, 17 beta-diacetoxy-5 alpha-estran-4 beta-ol (6%), 5-bromo-4 alpha, 17 beta-diacetoxy-5 alpha-estran-3 beta-ol (3%), and 4 beta-bromo-3 beta, 17 beta-diacetoxy-5 alpha-estran-5-ol (4%). The 5-bromo-4 beta, 17 beta-diacetoxy-5 alpha-estran-3 beta-ol was equilibrated by heating with oxalic acid in refluxing benzene for ca. 16 h to give a mixture of it and 5-bromo-3 beta, 17 beta-diacetoxy-5 alpha-estran-4 beta-ol in the ratio of 16:84 respectively. A similar equilibration mixture (14:86) was obtained under identical conditions when 5-bromo-3 beta, 17 beta-diacetoxy-5 alpha-estran-4 beta-ol was the starting material.

Bromates↗
PubMed2007

Urinary excretion of 5(10)-estrene-3beta,17alpha-diol and estrone by the female horse: complementary indicators of early pregnancy screened with regard to a putative anabolic doping practice.

Rules of horse racing stipulate that pregnant mares may compete under definite conditions of date, because early pregnant status may be misused for the sake of enhancing physical performance by putative anabolic steroid action. Screening for pregnancy is generally performed by plasma equine gonadotrophin (eCG) immunoassay, which covers the period between Days 40 and 120. In common screening for urinary anabolic steroids performed by gas chromatography-mass spectrometry, inclusion of two complementary criteria, i.e. the evaluation of total conjugates of 5(10)-estrene-3beta,17alpha-diol (EED) and estrone (E1), can easily be performed. Although EED and E1 have no anabolic property per se in the horse, assessing these two markers may be helpful in the period comprised between Days 70 and 250, thereby prolonging the detection period behind that of eCG. Peak values of EED and E1 are then attained, so that visual inspection of chromatographic tracings remains in general sufficient as a diagnostic tool. Comparison of EED and E1 during pregnancy and in an estrus cycle indicates a drastic difference in the attained excretion values, attributable to either the placenta or the ovarian follicle. The identity of EED has been proven by GC-MS(n) in urine and in placental tissue.

Anabolic Agents↗
PubMed1979

[Inhibition of ovulation with 17-alpha-ethinyl-18-methyl-11-methylene-4-estren-17-ol plus ethinylestradiol].

A combined oral application of 30 micrograms ethinylestradiol with 50 micrograms 17 alpha-ethinyl-18-methyl-11-methylene-4-estren-17-ol (a newly developed progestagen) -- for 21 days resulted in a distinct antigonadotrophic effect, shown by hormone analysis (LH, FSH, estradiol and progesterone) in serum samples of three healthy and fertile women. A final recommendation on the daily dosage, however, depends on the results of clinical experimental investigation still in progress.

Estradiol↗
PubMed1977

A novel chemical modification of delta 5-3-ketosteroid isomerase occurring during its 3-oxo-4-estren-17 beta-yl acetate-dependent photoinactivation.

The chemical change responsible for the 3-oxo-4-estren-17 beta-yl acetate-dependent photoinactivation of delta 5-3-ketosteroid isomerase has been identified by amino acid analysis and amino acid sequencing. Amino acid analysis of the enzyme and its photoinactivated derivative shows that photoinactivation is accompanied by loss of nearly 1 residue of aspartic acid/polypeptide chain and an increase in nearly 1 residue of alanine. Edman degradation of a peptide comprising residues 31 to 48 from native isomerase showed the presence of aspartic acid at residue 38. When the corresponding peptide from photoinactivated enzyme was sequenced, residue 38 was revealed to be alanine.

Alanine↗
PubMed1977

Strategy in drug research. Synthesis and study of the progestational and ovulation inhibitory activity of a series of 11beta-substituted-17alpha-ethynyl-4-estren-17beta-ols.

Using the strategy based on the Hansch method which analyses effects of substituents on biological activity in terms of their hydrophobic, electronic and steric effects we selectively synthesised a series of 11beta-substituted-17alpha-ethynyl-4-estren-17beta-ols that combine ease of synthesis with good discrimination between these factors aiming at finding the compounds with optimum biological activity in that series. The compounds were tested quantitatively in the Clauberg test (rabbit) and the ovulation inhibition test (rat). The differences in biological activity could reasonably be correlated with two steric effects introduced by the 11beta-substituent. These were a change in the overall shape of the 11beta-substituent and the angular methyl group, and direct steric hindrance of the steroid-receptor protein binding. Some exceptions were found possibly due to metabolic conversion of these compounds to the corresponding 11beta-substituted-17alpha-ethynyl-1,3,5(10)-estra-triene-3,17beta-diols.

Animals↗
PubMed1981

5alpha-reduction of an anti-androgen TSAA-291, 16beta-ethyl-17beta-hydroxy-4-estren-3-one, by nuclear 5alpha-reductase in rat prostates.

Inhibition of 5alpha-reduction of testosterone by an anti-androgen TSAA-291 (16beta-ethyl-17beta-hydroxy-4-estren-3-one) was studied in rat ventral prostates and the metabolic conversion of 3H-TSAA-291 was examined both in vitro and in vivo. In the in vitro experiment using nuclear 5alpha-reductase of the prostate, 5alpha-dihydrostestosterone formation from 3H-testosterone was inhibited in a competitive manner by the anti-androgen. In the in vitro experiment using 3H-TSAA-291, 5alpha-reduction of the anti-androgen occurred. One, 2 and 4 hr after an intravenous administration of 140 muCi/rat of 3H-TSAA-291 to castrated rats, the unchanged TSAA-291 accumulated in higher amounts in the ventral prostate than in the plasma, skeletal muscle and levator ani muscle, thereby indicating the selective uptake of the anti-androgen by the androgen target organ. No appreciable amounts of the 5alpha-reduced metabolite of TSAA-291 were detected in the prostate, thus suggesting that TSAA-291 itself may be responsible for the anti-androgenic properties. The inhibitory potency of the 5alpha-reductase activity of several other 16beta-substituted androstane and estrane analogues was also examined.

5-alpha Reductase Inhibitors↗
PubMed1990

Reaction of thiol nucleophiles with 1,2-epoxy- and 4,5-epoxy-estrene-3-one-17 beta-ols.

Four ring A steroidal epoxyenones as probable intermediate in the formation of catechol estrogens were synthesized. The isomeric 1 alpha,2 alpha-epoxy-17 beta-hydroxyestr-4-en-3-one (9) and 1 beta,2 beta-epoxy-17 beta-hydroxyestr-4-en-3-one (8) were synthesized from 17 beta-hydroxy-5 alpha-estra-3-one. The isomeric 4 alpha,5 alpha-epoxy-17 beta-hydroxyestr-1-en-3-one (11) and 4 beta,5 beta-epoxy-17 beta-hydroxyestr-1-en-3-one (10) were prepared from 19-nortestosterone. The reaction of 9 and 10 with sodium/ethanethiol resulted in the formation of three types of reactions leading to multiple products: 1,4-addition, opening of epoxide, and epoxide opening followed by dehydration. Reaction of 8 with ethanethiol gave only one compound identified as 2-ethanethio-1,4-estradien-17 beta-ol-3-one, while reaction of 9 with ethanethiol gave an unusual product identified as 4-estren-1 alpha,17 beta-diol-3-one. Unlike reaction of ethanethiol with 9 and 10, reaction with N-acetylecysteine or glutathione results in epoxide opening followed by dehydration leading to the formation of estradiol-4-thioethers.

Epoxy Compounds↗
PubMed1975

Studies on the effect of 17alpha-ethinyl-6-estrene-5alpha, 7beta-diol on menstrual cycle and plasma and urinary hormones in normal women.

Pharmacological tests on rats and dogs showed that a novel steroid substance, ORG OI-65 (code name for 17alpha-ethinyl-6-estrene-5alpha, 7beta-diol) has both progestational and estrogenic properties. The effect of this substance on menstrual cycle was studied on 13 healthy fertile women, who received 2 mg of ORG OI-65 daily for 20 consecutive days from the 5th day of cycle. The following parameters were studied during pretreatment and treatment cycles: bleeding pattern, plasma progesterone, urinary excretion of FSH, LH and estrone, vaginal cytology, cervical mucus, endometrium biopsy and basal body temperature. Treatment with ORG OI-65 did not change the bleeding pattern or inhibit ovulation: all 12 cases with ovulatory pretreatment cycles showed evidence of ovulation--timely or delayed--also during ORG OI-65 treatment. The vaginal cytology and cervical mucus remained almost unaffected by the treatment. No serious side-effects were found. The authors conclude that ORG OI-65 2 mg daily is not effective enough for oral contraception.

17-Ketosteroids↗
PubMedDate not supplied

Radioimmunoassay of norethindrone (17 alpha-ethynyl-17 beta-hydroxy-4-estren-3-one) and ethynyl-estradiol (17 alpha-ethynyl-1,3,5, (10)-estratien-3, 17 beta-diol). Application to human plasma determination of norethindrone after oral administration of this steroid.

The experiment conditions for the evaluation of Norethindrone (17 alpha-Ethynyl-17 beta-hydroxy-4-estren-3-one, NET) and Ethynyl-estradiol (17 alpha-ethynyl-1, 3, 5 (10) estratrien-3, 17 beta-diol, EE) by radioimmunoassay are described. A minimal quantity of 25 pg of these two steroids could be evaluated using different reduced metabolites of NET, very little cross reaction is observed with 200 pg of these metabolites. No effect was observed with estradiol for the EE-antiserum. The NET-antiserum was used to evaluate this steroid and ethynodiol diacetate after oral administration to female volunteers. Maximal values in the plasma (2-3% of the administered dose) was found between 1-3 h after administration and at 24 h a concentration of 0.1-0.3% still remained in the plasma.

Administration, Oral↗
PubMed1987

(Z)-17 beta-hydroxy-17 alpha-(2-[125I]iodovinyl)-4-estren-3-one: a new specific gamma-emitting ligand for determination of progesterone receptor.

An iodine-125 labeled ligand for progesterone receptor determination was synthesized: (Z)-17 beta-hydroxy-17 alpha-(2-[125I]iodovinyl)-4-estren-3-one ([125I]SH-D 510). The ligand is stable chemically as well as under the conditions of a receptor assay. The relative binding affinity of the nonradioactive compound towards human uterine progesterone receptor was 7.0 for the Z-isomer (promegestone (R5020) 1.0) and 0.95 for the E-isomer. 4 S and 8 S receptor forms were obtained on sucrose density gradient analysis. Progesterone receptors were assayed in 103 human mammary tumour cytosols, using either [3H]promegestone or [125I]SH-D 510. The coefficient of correlation was r = 0.951.

Animals↗
PubMed1984

Progressive preleukemia with a chromosomally abnormal clone in a kindred with the Estren-Dameshek variant of Fanconi's anemia.

One of two sisters with hypoplastic anemia and increased chromosomal fragility, but no clinical stigmata of Fanconi's anemia (FA), progressed to preleukemia (with a clone of chromosomally abnormal cells in the bone marrow), and then to acute nonlymphocytic leukemia. The findings indicate that constitutional genetic instability can lead to karyotypically aberrant neoplastic clones in the Estren-Dameshek variant of FA as well as in the more typical chromosomal fragility syndromes.

Adolescent↗
PubMedDate not supplied

[Fanconi's anemia type Estren-Dameshek. A case report (author's transl)].

A clinical, hematological and cytogenetical study has been carried out in a patient with Fanconi's anemia. The absence of phenotypical alterations at clinical and instrumental surveyor suggested a frame in a variant type Estren-Dameshek. The genetical problem between the classical and variant form is not yet established. The cytogenetical analysis in this case, and recent data show the impossibility to distinguish between the two forms, as regard to the frequency and characters of chromosomical instability. On the whole, the chromosomes data derived from recent studies give no support to the idea of cytogenetic heterogeneity between subjects affected by these two forms of childhood aplastic anemia.

Anemia, Aplastic↗
PubMed1991

Structure of 6 beta,6'beta-bi(7 alpha-allyl-3-oxo-4-estren-17 beta-yl acetate).

C46H62O6, Mr = 711.0, orthorhombic, P2(1)2(1)2(1), a = 20.187 (3), b = 22.004 (3), c = 9.180 (1) A, V = 4078 (2) A3, Z = 4, Dx = 1.16 g cm-3, lambda (Mo K alpha) = 0.71069 A, mu = 0.7 cm-1, F(000) = 1544, T = 295 K, R = 0.096 for 3894 unique observed reflections with Fo greater than 2 sigma(Fo). The title compound is a dimer connected by a single bound between C6 and C6' [bond length 1.560 (7) A]. The two steroid moieties are oriented beta-face to beta-face, head to head and lie in almost parallel planes (7.6 degrees), rotated by 45 degrees to one another. The two conformations of the identical portions of the dimer differ chiefly in the orientation of the allyl and acetate groups. C23' (acetate) and O3' form the shortest intermolecular contact less than 3.5 A; C...O = 3.35 (1) A.

Allyl Compounds↗