A rapid method for obtaining finasteride, a 5α-reductase inhibitor, from commercial tablets

Trapani, Giuseppe; Dazzi, Laura; Pisu, Maria Giuseppina; Reho, A.; Seu, Emanuele; Biggio, Giovanni

doi:10.1016/s1385-299x(02)00146-0

Cited by 14 publications

(12 citation statements)

References 7 publications

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“…The tablets were crushed and extracted with chloroform, and the solvent was eliminated in vacuum; the crude product was purified by silica gel column chromatography. The melting point of the isolated Finasteride (252-254 C) was identical to that reported in the literature 16 .…”

Section: Chemical and Radioactive Materialssupporting

confidence: 85%

“…Standards of 4-dione, T, were applied on two lanes, one on each side of the plate. These plates were eluted twice in a mixture of chloroform:acetone (9:1) 16 and air dried; the radioactivity on them was scanned using an AR2000 Bioscanner (Bioscan, Washington DC). Standards were developed by fluorescence (UV lamp; l ¼ 254 nm from UVP, Upland, CA) and the data obtained were plotted using SigmaPlot 12 software (Systat Software, Inc., San Jose, CA).…”

Section: Determination Of 17-hsd5 Activitymentioning

confidence: 99%

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Biological activity of pyrazole and imidazole-dehydroepiandrosterone derivatives on the activity of 17β-hydroxysteroid dehydrogenase

Cabeza

Posada

Sánchez-Márquez

et al. 2015

Journal of Enzyme Inhibition and Medicinal Chemistry

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The enzyme type 5 17b-hydroxysteroid dehydrogenase 5 (17b-HSD5) catalyzes the transformation of androstenedione (4-dione) to testosterone (T) in the prostate. This metabolic pathway remains active in cancer patients receiving androgen deprivation therapy. Since physicians seek to develop advantageous and better new treatments to increase the average survival of these patients, we synthesized several different dehydroepiandrosterone derivatives. These compounds have a pyrazole or imidazole function at C-17 and an ester moiety at C-3 and were studied as inhibitors of 17b-HSD5. The kinetic parameters of this enzyme were determined for use in inhibition assays. Their pharmacological effect was also determined on gonadectomized hamsters treated with D 4 -androstenedione (4-dione) or testosterone (T) and/or the novel compounds. The results indicated that the incorporation of a heterocycle at C-17 induced strong 17b-HSD5 inhibition. These derivatives decreased flank organ diameter and prostate weight in castrated hamsters treated with T or 4-dione. Inhibition of 17b-HSD5 by these compounds could have therapeutic potential for the treatment of prostate cancer and benign prostatic hyperplasia.

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Section: Chemical and Radioactive Materialssupporting

confidence: 85%

Section: Determination Of 17-hsd5 Activitymentioning

confidence: 99%

Biological activity of pyrazole and imidazole-dehydroepiandrosterone derivatives on the activity of 17β-hydroxysteroid dehydrogenase

Cabeza

Posada

Sánchez-Márquez

et al. 2015

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…In one series of experiments, pregnant rats were treated with finasteride (25 mg per kilogram of body mass) once a day from P12 to P18 . Finasteride was extracted and purified from commercial tablets as described previously (Trapani et al, 2002), suspended in a mixture of ethanol (20%) and corn oil (80%), and injected subcutaneously at the nape of the neck in a volume of 3 ml/kg. In another series of experiments, clomiphene citrate (Bruno Farmaceutici) was dissolved in physiological saline and administered intragastrically at a dose of 5 mg/kg once a day from P12 to P18.…”

Section: Methodsmentioning

confidence: 99%

Changes in Expression and Function of Extrasynaptic GABA_AReceptors in the Rat Hippocampus during Pregnancy and after Delivery

Sanna¹,

Mostallino²,

Murru³

et al. 2009

J. Neurosci.

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Pregnancy is associated with changes in mood and anxiety level as well as with marked hormonal fluctuations. Increases in the brain concentrations of neuroactive steroids during pregnancy in rats are accompanied by changes in expression of subunits of the GABA type A receptor (GABA A -R) in the brain. Granule cells of the dentate gyrus (DGGCs) exhibit two components of inhibitory GABAergic transmission: a phasic component mediated by synaptic GABA A -Rs, and a tonic component mediated by extrasynaptic GABA A -Rs. Recordings of GABAergic currents were obtained from hippocampal slices prepared from rats in estrus, at pregnancy day 15 (P15) or P19, or at 2 d after delivery. Exogenous GABA or 3␣,5␣-THP induced an increase in tonic current in DGGCs that was significantly greater at P19 than in estrus. Neither tonic nor phasic currents were affected by pregnancy in CA1 pyramidal cells. Immunohistochemical analysis revealed a marked increase in the abundance of the ␦ subunit of the GABA A -R and a concomitant decrease in that of the ␥ 2 subunit in the hippocampus at P19. Expression of the ␣ 4 subunit did not change during pregnancy but was increased 2 d after delivery. Treatment of rats from P12 to P18 with the 5␣-reductase inhibitor finasteride prevented the changes in tonic current and in ␦ and ␥ 2 subunit expression normally apparent at P19. These data suggest that the number of extrasynaptic GABA A -Rs is increased in DGGCs during late pregnancy as a consequence of the associated marked fluctuations in the brain levels of neuroactive steroids.

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“…F was obtained by extraction from Proscar Õ (Merck, Sharp & Dohm, Mexico City, Mexico) as follows: 180 Proscar tablets were crushed and extracted with 200 mL chloroform; after the solvent was removed under vacuum, the crude product was purified by silica gel 60 (63-200 mm) column chromatography (SigmaAldrich, Mexico City, Mexico) with ethyl acetate as eluant 6 .…”

Section: Reagentsmentioning

confidence: 99%

Novel dehydroepiandrosterone benzimidazolyl derivatives as 5α-reductase isozymes inhibitors

Arellano

Bratoeff

Segura

et al. 2015

Journal of Enzyme Inhibition and Medicinal Chemistry

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5a-R isozymes (types 1 and 2) play an important role in prostate gland development because they are responsible for intraprostatic dihydrotestosterone (DHT) levels when the physiological serum testosterone (T) concentration is low. In this study, we synthesized seven novel dehydroepiandrosterone derivatives with benzimidazol moiety at C-17, and determined their effect on the activity of 5a-reductase types 1 and 2. The derivatives with an aliphatic ester at C-3 of the dehydroepiandrosterone scaffold induced specific inhibition of 5a-R1 activity, whereas those with a cycloaliphatic ester (cyclopropyl, cyclobutyl, or cyclopentyl ring) or an alcohol group at C-3 inhibited the activity of both isozymes. Derivatives with a cyclohexyl or cycloheptyl ester at C-3 showed no inhibitory activity. In pharmacological experiments, derivatives with esters having an alcohol or the aliphatic group or one of the three smaller cycloaliphatic rings at C-3 decreased the diameter of male hamster flank organs, with the cyclobutyl and cyclopentyl esters exhibiting higher effect. With exception of the cyclobutyl and cyclopentyl esters, these compounds reduced the weight of the prostate and seminal vesicles.Keywords 5a-R isoenzyme, benign prostatic hyperplasia, dehydroepiandrosterone benzimidazolyl derivative, hamster flank organ, prostate gland History

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A rapid method for obtaining finasteride, a 5α-reductase inhibitor, from commercial tablets

Cited by 14 publications

References 7 publications

Biological activity of pyrazole and imidazole-dehydroepiandrosterone derivatives on the activity of 17β-hydroxysteroid dehydrogenase

Biological activity of pyrazole and imidazole-dehydroepiandrosterone derivatives on the activity of 17β-hydroxysteroid dehydrogenase

Changes in Expression and Function of Extrasynaptic GABA_AReceptors in the Rat Hippocampus during Pregnancy and after Delivery

Novel dehydroepiandrosterone benzimidazolyl derivatives as 5α-reductase isozymes inhibitors

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A rapid method for obtaining finasteride, a 5α-reductase inhibitor, from commercial tablets

Cited by 14 publications

References 7 publications

Biological activity of pyrazole and imidazole-dehydroepiandrosterone derivatives on the activity of 17β-hydroxysteroid dehydrogenase

Biological activity of pyrazole and imidazole-dehydroepiandrosterone derivatives on the activity of 17β-hydroxysteroid dehydrogenase

Changes in Expression and Function of Extrasynaptic GABAAReceptors in the Rat Hippocampus during Pregnancy and after Delivery

Novel dehydroepiandrosterone benzimidazolyl derivatives as 5α-reductase isozymes inhibitors

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Changes in Expression and Function of Extrasynaptic GABA_AReceptors in the Rat Hippocampus during Pregnancy and after Delivery