androstanes

Summary

Summary: The family of steroids from which the androgens are derived.

Top Publications

  1. Lieb K, Fiebich B, Herpfer I, Mantovani M, Löffler M, Feuerstein T. No modulatory effect of neurokinin-1 receptor antagonists on serotonin uptake in human and rat brain synaptosomes. Eur Neuropsychopharmacol. 2005;15:641-6 pubmed
    ..These results show that in humans, as in rodents, inhibition of the 5-HT transporter is probably not the underlying mechanism of the assumed antidepressant activity of NK-1-RA. ..
  2. Aoki S, Watanabe Y, Sanagawa M, Setiawan A, Kotoku N, Kobayashi M. Cortistatins A, B, C, and D, anti-angiogenic steroidal alkaloids, from the marine sponge Corticium simplex. J Am Chem Soc. 2006;128:3148-9 pubmed
    ..0018 muM) against HUVECs, in which the selective index was more than 3000-fold in comparison with that of normal fibroblast or several tumor cell lines. ..
  3. Perez C, Falero A, Duc H, Balcinde Y, Hung B. A very efficient bioconversion of soybean phytosterols mixtures to androstanes by mycobacteria. J Ind Microbiol Biotechnol. 2006;33:719-23 pubmed
    ..These results may be better when scaling-up such a procedure of phytosterols conversion. ..
  4. Ramirez J, Bruttomesso A, Michelini F, Acebedo S, Alché L, Galagovsky L. Syntheses of immunomodulating androstanes and stigmastanes: comparison of their TNF-alpha inhibitory activity. Bioorg Med Chem. 2007;15:7538-44 pubmed
    ..A preliminary qualitative structure-activity relationship was established. ..
  5. Cepa M, Tavares da Silva E, Correia da Silva G, Roleira F, Teixeira N. Structure-activity relationships of new A,D-ring modified steroids as aromatase inhibitors: design, synthesis, and biological activity evaluation. J Med Chem. 2005;48:6379-85 pubmed
    ..From the results obtained, it may be concluded that the binding pocket of the active site of aromatase requires planarity in the region of the steroid A,B-rings and the D-ring structure is critical for the binding. ..
  6. Fattorusso E, Taglialatela Scafati O, Petrucci F, Bavestrello G, Calcinai B, Cerrano C, et al. Polychlorinated androstanes from the burrowing sponge Cliona nigricans. Org Lett. 2004;6:1633-5 pubmed
    ..and they represent the first polyhalogenated steroids found in a natural organism, either marine or terrestrial, and the first examples of halogenated androstanes in nature. Both clionastatins proved to be potently cytotoxic.
  7. Perez C, Falero A, Llanes N, Hung B, Hervé M, Palmero A, et al. Resistance to androstanes as an approach for androstandienedione yield enhancement in industrial mycobacteria. J Ind Microbiol Biotechnol. 2003;30:623-6 pubmed
    ..An apparent reduction from ADD to androstandione and testosterone was also noticed. Furthermore, the ADD resistance phenotype may be related to the increase in steroid 1,2 dehydrogenase activity. ..
  8. Moreira V, Salvador J, Vasaitis T, Njar V. CYP17 inhibitors for prostate cancer treatment--an update. Curr Med Chem. 2008;15:868-99 pubmed
    ..It covers almost 4 decades of literature with highlights on the most significant achievements in this area, providing insight into PC pathophysiology, management and treatment options. ..
  9. Malafronte N, Sanogo R, Vassallo A, De Tommasi N, Bifulco G, Dal Piaz F. Androstanes and pregnanes from Trichilia emetica ssp. suberosa J.J. de Wilde. Phytochemistry. 2013;96:437-42 pubmed publisher
    ..acid-16-oxo-dimethyl ester (4), 2?,3?,16?-trihydroxy-5?-pregnan-17(R)-20-yl acetate (7), three androstanes: 1-methoxy-androstan-1,4-dien-3,16-dione (3), 2,3-seco-androstan-2,3-dioic acid-16-oxo-dimethyl ester (5), 3-..

More Information

Publications62

  1. Guieu R, Fenouillet E, Devaux C, Fajloun Z, Carrega L, Sabatier J, et al. CD26 modulates nociception in mice via its dipeptidyl-peptidase IV activity. Behav Brain Res. 2006;166:230-5 pubmed
    ..Our observations represent the first fundamental evidence showing that DPP-IV influences pain perception via modulation of the peripheral SP concentration. Our work also highlights the role of peripheral NK1 receptors in nociception. ..
  2. Matthiesson K, Stanton P, O Donnell L, Meachem S, Amory J, Berger R, et al. Effects of testosterone and levonorgestrel combined with a 5alpha-reductase inhibitor or gonadotropin-releasing hormone antagonist on spermatogenesis and intratesticular steroid levels in normal men. J Clin Endocrinol Metab. 2005;90:5647-55 pubmed
    ..The heterogeneity of the germ cell response, regardless of treatment, gonadotropins or iT steroids, points to the individual sensitivity of sites in germ cell development, which is worthy of additional exploration. ..
  3. Fenske M. Excretion of 11-17 dioxoandrostanes in the urine of cynomolgus monkeys--why is the possible influence of urine volume ignored?. J Med Primatol. 2008;37:166-7; author reply 168 pubmed publisher
  4. Makeham J, Goodchild A, Pilowsky P. NK1 receptor activation in rat rostral ventrolateral medulla selectively attenuates somato-sympathetic reflex while antagonism attenuates sympathetic chemoreflex. Am J Physiol Regul Integr Comp Physiol. 2005;288:R1707-15 pubmed
    ..Our findings suggest that substance P and the NK1 receptor play a significant role in the cardiorespiratory reflexes integrated within the RVLM. ..
  5. Crisóstomo Ayala V, Maynar Moliner M, Sun F, Usón Gargallo J, Sanchez Margallo F. [Ultrasonographic histological study on the evolution of a canine model of hormone-induced benign prostatic hyperplasia]. Actas Urol Esp. 2009;33:895-901 pubmed
    ..In order to be useful for experimental studies, hormones should be administered for at least three months before commencing any treatment, and they should be continued throughout the length of the study.. ..
  6. Yao R, Yasuoka A, Kamei A, Kitagawa Y, Tateishi N, Tsuruoka N, et al. Dietary flavonoids activate the constitutive androstane receptor (CAR). J Agric Food Chem. 2010;58:2168-73 pubmed publisher
    ..A significant increase in cyp2b10 mRNA content was observed only in wild-type mice fed chrysin. These results suggest that dietary flavonoids regulate CAR activity and thereby accelerate both detoxification and energy metabolism. ..
  7. Taylor M, Wang M, Bhattacharyya A, Chiang N, Tai H, Collins D. Expression of rat steroid 5 alpha-reductase (isozyme-1) in Spodoptera frugiperda, SF21, insect cells: expression of rat steroid 5 alpha-reductase. Steroids. 1997;62:373-8 pubmed
    ..Photoaffinity labeling by [2'-32P]-2-azido-NAD P+ ([2'-32P]2N3-NAD P+) and [1,2(3)H] N-(benzylbenzoyl)-3-oxo-4-aza-4-methyl-5 alpha androstane-17 beta-carboxamide ([3H]-4MABP) also showed a labeled protein band at 26 kDa. ..
  8. Kadar Z, Baji Á, Zupko I, Bartók T, Wolfling J, Frank E. Efficient approach to novel 1?-triazolyl-5?-androstane derivatives as potent antiproliferative agents. Org Biomol Chem. 2011;9:8051-7 pubmed publisher
    ..All triazolyl compounds were tested in vitro on three malignant gynecological cell lines (HeLa, MCF7 and A2780). ..
  9. Chen H, Zhou Y, Qiao L, Cao J, Yao Y, Hua H, et al. Androstane and monoterpene glucoside sinapoyl ester from Cynanchum amplexicaule SIEB. et ZUCC. Chem Pharm Bull (Tokyo). 2007;55:1416-8 pubmed
    ..et ZUCC. (Asclepiadaceae), along with two known monoterpenes, (3R)-8-hydroxylinalool (3) and (6R)-menthiafolic acid (4). Their structures were elucidated on the basis of analyses of physical, chemical, and spectral data. ..
  10. Cherrington N, Hartley D, Li N, Johnson D, Klaassen C. Organ distribution of multidrug resistance proteins 1, 2, and 3 (Mrp1, 2, and 3) mRNA and hepatic induction of Mrp3 by constitutive androstane receptor activators in rats. J Pharmacol Exp Ther. 2002;300:97-104 pubmed
    ..We conclude that rat hepatic Mrp3 is induced by CAR activators, thus enhancing the vectoral excretion of some phase II metabolites from the liver to the blood. ..
  11. Muller P, Herrmann A. Rapid transbilayer movement of spin-labeled steroids in human erythrocytes and in liposomes. Biophys J. 2002;82:1418-28 pubmed
    ..5 min). The results are discussed with regard to the transbilayer dynamics of cholesterol. ..
  12. Oh S, Lee J, Chang S, Shin D, Ahn K, Min B, et al. Androstane alkaloids from musk of Moschus moschiferus. Chem Pharm Bull (Tokyo). 2002;50:663-4 pubmed
    ..The structures were elucidated to be 3alpha-ureido-androst-4-en-17-one (1) and 3alpha-ureido-androst-4-en-17beta-ol (2) by two-dimensional NMR analysis (HMQC, 1H-1H COSY, HMBC, and NOESY). ..
  13. Hunter A, Watts K, Dedi C, Dodd H. An unusual ring--a opening and other reactions in steroid transformation by the thermophilic fungus Myceliophthora thermophila. J Steroid Biochem Mol Biol. 2009;116:171-7 pubmed publisher
    ..The range of steroidal modification achieved with this fungus indicates that these organisms may be a rich source of novel steroid biocatalysis which deserve greater investigation in the future. ..
  14. Sinclair P, Squires E, Raeside J, Renaud R. Synthesis of free and sulphoconjugated 16-androstene steroids by the Leydig cells of the mature domestic boar. J Steroid Biochem Mol Biol. 2005;96:217-28 pubmed
    ..These findings emphasise the need to consider the impact of sulphoconjugation of the 16-androstene steroids and their role in contributing to boar taint. ..
  15. Jursic B, Upadhyay S, Creech C, Neumann D. Novel and efficient synthesis and antifungal evaluation of 2,3-functionalized cholestane and androstane derivatives. Bioorg Med Chem Lett. 2010;20:7372-5 pubmed publisher
    ..In this Letter, we outline a novel and efficient approach to the synthesis of 2,3-functionalized cholestane and androstane derivatives and present their promising preliminary antifungal activities against a number of fungal species. ..
  16. Hnilickova J, Kohout L, Capdevila E, Esteve A, Vilaplana M, Molist M, et al. The synthesis of androstane brassinosteroid analogues with alpha-azido acid ester groups in position 17beta. Steroids. 2010;75:1005-10 pubmed publisher
    ..The biological activities were evaluated in two bioassays: a rice lamina inclination test and bean second internode bioassays. The activities of the new analogues differ in these two bioassays. ..
  17. Puia G, Mienville J, Matsumoto K, Takahata H, Watanabe H, Costa E, et al. On the putative physiological role of allopregnanolone on GABA(A) receptor function. Neuropharmacology. 2003;44:49-55 pubmed
  18. Linares Fernández B, Alfieri A. [Changes in nitric oxide, prostaglandins and myeloperoxidase activity in acrolein-induced cystitis in rats]. Invest Clin. 2009;50:23-33 pubmed
    ..ACR could stimulate iNOS and COX-1/COX-2, producing lymphocyte migration and increases of NO and PGs. ..
  19. Manosroi A, Wongtrakul P, Manosroi J, Midorikawa U, Hanyu Y, Yuasa M, et al. The entrapment of kojic oleate in bilayer vesicles. Int J Pharm. 2005;298:13-25 pubmed
    ..From the release study of kojic acid through the dialysis membrane, it indicated that the intercalation of kojic oleate in the vesicular membranes did not significantly affect the release of kojic acid from the vesicles. ..
  20. Hill M, Zarubova J, Marusic P, Vrbikova J, Velíková M, Kancheva R, et al. Effects of valproate and carbamazepine monotherapy on neuroactive steroids, their precursors and metabolites in adult men with epilepsy. J Steroid Biochem Mol Biol. 2010;122:239-52 pubmed publisher
    ..Reduced steroid 20?-hydroxy-metabolites and cortisol were connected with epilepsy without an effect of AEDs. Carbamazepine induced only slight decrease in isopregnanolone, 5?,20?-tetrahydroprogesterone, and androstanediol levels. ..
  21. Kiss M, Pálinkás N, Takacs A, Maho S, Kollár L. A systematic approach to the synthesis of androstane-based 3,17-dicarboxamides (homo- and mixed dicarboxamides) via palladium-catalyzed aminocarbonylation. Steroids. 2013;78:693-9 pubmed publisher
  22. Möstl E, Messmann S, Bagu E, Robia C, Palme R. Measurement of glucocorticoid metabolite concentrations in faeces of domestic livestock. Zentralbl Veterinarmed A. 1999;46:621-31 pubmed
    ..In frozen samples this effect was diminished after thawing samples at 40 degrees C; thawing the samples at 95 degrees C prevented an increase in immunoreactive substances. ..
  23. Lanzafame A, Sexton P, Christopoulos A. Interaction studies of multiple binding sites on m4 muscarinic acetylcholine receptors. Mol Pharmacol. 2006;70:736-46 pubmed
    ..Together, these results provide insight into the nature of the interaction between two distinct allosteric sites on the M(4) mAChR and how this interaction is perturbed upon occupancy of the orthosteric site. ..
  24. Filippelli A, Esposito C, Falciani M, Costa C, Cozzolino A, Rossi F, et al. Transglutaminase-synthesized spermine derivative of substance P recognizes rat portal vein neurokinin-3 receptors. Life Sci. 1997;60:403-11 pubmed
    ..Therefore, the reported results suggest that the introduction of a Spm moiety into the SP alters the parent peptide molecule by increasing its affinity for NK-3 receptors and/or by preventing its degradation by some proteolytic enzymes. ..
  25. Cepa M, Correia da Silva G, da Silva E, Roleira F, Borges M, Teixeira N. New steroidal aromatase inhibitors: suppression of estrogen-dependent breast cancer cell proliferation and induction of cell death. BMC Cell Biol. 2008;9:41 pubmed publisher
    ..Our results are important for the elucidation of the cellular effects of steroidal AIs on breast cancer. ..
  26. Sakac M, Gaković A, Stojanović S, Djurendić E, Kojic V, Bogdanovic G, et al. Synthesis and biological evaluation of a series of A,B-ring modified 16,17-secoandrostane derivatives. Bioorg Chem. 2008;36:128-32 pubmed publisher
    ..Compound 2 exhibited a relatively strong inhibition of aromatase and extremely potent cytotoxicity against PC3 cells. Compound 8 showed satisfactory cytotoxicity against MCF-7 cells. ..
  27. Claus R, Hoffman B, Karg H. Determination of 5 -androst-16-en-3-one, a boar taint steroid in pigs, with reference to relationships to testosterone. J Anim Sci. 1971;33:1293-7 pubmed
  28. Halling K, Slotte J. Membrane properties of plant sterols in phospholipid bilayers as determined by differential scanning calorimetry, resonance energy transfer and detergent-induced solubilization. Biochim Biophys Acta. 2004;1664:161-71 pubmed
  29. Patel R, Hollingshead B, Omiecinski C, Perdew G. Aryl-hydrocarbon receptor activation regulates constitutive androstane receptor levels in murine and human liver. Hepatology. 2007;46:209-18 pubmed
    ..This study identifies a mode of up-regulating CAR and potentially expands the role of AhR in drug metabolism. This study also demonstrates in vivo up-regulation of CAR through chemical exposure. ..
  30. Baranovsky A, Bolibrukh D, Khripach V, Schneider B. Diels-Alder reaction of androsta-14,16-dien-17-yl acetates with nitroethylene: product distribution and selected adduct transformations. Steroids. 2013;78:282-7 pubmed publisher
    ..14?-Cyanomethyl steroids were obtained via the reductive cleavage reaction of bridged nitro compounds. The structures of the new compounds have been fully characterized by 2D NMR and tandem mass-spectrometry methods. ..
  31. Davidson C, Lee T, Ellinwood E. The NK(1) receptor antagonist WIN51708 reduces sensitization after chronic cocaine. Eur J Pharmacol. 2004;499:355-6 pubmed
    ..p.) given 3.5 h after each cocaine injection was given. WIN51708 reversed sensitization but had no effect on controls. NK(1) receptor antagonists may have use in stimulant abuse and schizophrenia treatment. ..
  32. Brodlie M, Spencer D. Growth recovery after withdrawal of inappropriate inhaled fluticasone proprionate. Pediatr Pulmonol. 2008;43:307-8 pubmed publisher
  33. Nheu L, Nazareth L, Xu G, Xiao F, Luo R, Komesaroff P, et al. Physiological effects of androgens on human vascular endothelial and smooth muscle cells in culture. Steroids. 2011;76:1590-6 pubmed publisher
    ..The relationship of these in vitro effects by androgens to in vivo vascular function and atherogenesis needs to be further clarified. ..
  34. Yadav M, Sabale P, Giridhar R, Zimmer C, Haupenthal J, Hartmann R. Synthesis of some novel androstanes as potential aromatase inhibitors. Steroids. 2011;76:464-70 pubmed publisher
    ..Isomeric forms of isoxazole (7 and 8) showed very poor activity compared to fadrozole and aminoglutethimide. Preliminary kinetic studies have shown that both of the active compounds (6 and 9) are reversible inhibitors of the enzyme. ..
  35. Hanson J. Steroids: reactions and partial synthesis. Nat Prod Rep. 2002;19:381-9 pubmed
    ..The reactions and partial syntheses of estrogens, androgens, pregnanes, cholic acid derivatives, cholestanes and vitamin D analogues are covered. There are 169 references. ..
  36. Bóta A, Varga Z, Goerigk G. Biological systems as nanoreactors: anomalous small-angle scattering study of the CdS nanoparticle formation in multilamellar vesicles. J Phys Chem B. 2007;111:1911-5 pubmed
    ..The ASAXS method provides the separation of the scattering of nanoparticles present in a small amount, whereby the monitoring of their formation and growth in the whole time range of manufacturing has become possible. ..
  37. Hoby S, Schwarzenberger F, Doherr M, Robert N, Walzer C. Steroid hormone related male biased parasitism in chamois, Rupicapra rupicapra rupicapra. Vet Parasitol. 2006;138:337-48 pubmed
    ..Our study shows that sex differences in steroid levels play an important role to explain MBP, although they alone cannot fully explain the phenomenon...
  38. Baji Á, Kiss T, Wolfling J, Kovacs D, Igaz N, Gopisetty M, et al. Multicomponent access to androstano-arylpyrimidines under microwave conditions and evaluation of their anti-cancer activity in vitro. J Steroid Biochem Mol Biol. 2017;172:79-88 pubmed publisher
    ..Furthermore, in case of three 2'-arylpyrimidine derivatives a strong prostate cancer cell specific activity has been identified. ..
  39. Belanger B, Caron S, Boudou P, Fiet J, Belanger A. Adrenal steroidogenesis in the guinea pig: effects of androgens. Steroids. 1992;57:76-81 pubmed
    ..abstract truncated at 250 words)..
  40. Bourgogne E, Herrou V, Mathurin J, Becchi M, de Ceaurriz J. Detection of exogenous intake of natural corticosteroids by gas chromatography/combustion/isotope ratio mass spectrometry: application to misuse in sport. Rapid Commun Mass Spectrom. 2000;14:2343-7 pubmed
    ..Therefore, a positive criterion, to detect exogenous administration of synthetic corticosteroids in anti-doping control, is proposed. ..
  41. Gallardo F, Lloreta J, Garcia F, Moll X, Baro T, González L, et al. Immunolocalization of androgen receptors, estrogen alpha receptors, and estrogen beta receptors in experimentally induced canine prostatic hyperplasia. J Androl. 2009;30:240-7 pubmed publisher
    ..Results indicate that AR, ER alpha, and ER beta are differently expressed in canine prostate tissue and that they show specific expression patterns in response to the hormonal induction of BPH. ..
  42. Błazewicz A, Fijałek Z, Warowna Grześkiewicz M, Banasiuk J. Application of high-performance liquid chromatography with amperometric and coulometric detection to the analysis of SZ1677, a new neuromuscular blocking agent, and its two derivatives. J Chromatogr A. 2008;1204:114-8 pubmed publisher
    ..The elaborate method for the simultaneous analysis of SZ1677 and its two derivatives proved to be fast, precise, accurate and sensitive. ..
  43. Berquand A, Mingeot Leclercq M, Dufrene Y. Real-time imaging of drug-membrane interactions by atomic force microscopy. Biochim Biophys Acta. 2004;1664:198-205 pubmed
    ..This work provides direct evidence that the perturbation of lipid domains by azithromycin strongly depends on the lipid nature and opens the door for developing new applications in membrane biophysics and pharmacology. ..
  44. Kim Y, Han J, Lee S, Shimizu K, Tsutsumi Y, Kondo R. Steroid 9alpha-hydroxylation during testosterone degradation by resting rhodococcus equi cells. Arch Pharm (Weinheim). 2007;340:209-14 pubmed
  45. Kyrikou I, Daliani I, Mavromoustakos T, Maswadeh H, Demetzos C, Hatziantoniou S, et al. The modulation of thermal properties of vinblastine by cholesterol in membrane bilayers. Biochim Biophys Acta. 2004;1661:1-8 pubmed
    ..Preliminary studies show that such properties directly affect the encapsulation efficiency and the pharmacokinetics of liposomes. ..
  46. Takagi S, Adachi Y, Saubermann A, Vizi E. Presynaptic inhibitory effects of rocuronium and SZ1677 on [3H]acetylcholine release from the mouse hemidiaphragm preparation. Neurochem Int. 2002;40:655-9 pubmed
    ..The finding that alpha-bungarotoxin does not inhibit the release and does not produce tetanic fade indicates that it possesses affinity only for the postsynaptic muscle nAChRs. ..
  47. Cimpoiu C, Hosu A, Hodisan S. Analysis of some steroids by thin-layer chromatography using optimum mobile phases. J Pharm Biomed Anal. 2006;41:633-7 pubmed
    ..The optimum TLC system can be applied for the separation of androstane isomers from real samples such as drug formulation, biological and natural sources. ..
  48. Perez C, Falero A, Hung B, Tirado S, Balcinde Y. Bioconversion of phytosterols to androstanes by mycobacteria growing on sugar cane mud. J Ind Microbiol Biotechnol. 2005;32:83-6 pubmed
    ..For the various concentrations assayed, concomitant higher yields for both androstanes were achieved at 20% (w/w) sugar cane mud in media...
  49. Kárpáti E, Bíró K, Kukorelli T. [Investigation of neuromuscular blocking agents at Richter Ltd]. Acta Pharm Hung. 2002;72:37-48 pubmed
    ..It showed slight atropin-like cardio-vagolytic effect in animal experiments. In the clinical studies, however, the cardiovascular side effects were found to be too strong. Therefore, it was not introduced in clinical practice. ..
  50. Feldkoren B, Andersson S. Anabolic-androgenic steroid interaction with rat androgen receptor in vivo and in vitro: a comparative study. J Steroid Biochem Mol Biol. 2005;94:481-7 pubmed
    ..Based on these results, we conclude that anabolic steroids with low affinity to AR in vitro, can in fact in vivo act on the AR to cause biological responses. ..
  51. Parr M, Zapp J, Becker M, Opfermann G, Bartz U, Schanzer W. Steroidal isomers with uniform mass spectra of their per-TMS derivatives: synthesis of 17-hydroxyandrostan-3-ones, androst-1-, and -4-ene-3,17-diols. Steroids. 2007;72:545-51 pubmed
  52. Ajduković J, Djurendić E, Petri E, Klisurić O, Celic A, Sakac M, et al. 17(E)-picolinylidene androstane derivatives as potential inhibitors of prostate cancer cell growth: antiproliferative activity and molecular docking studies. Bioorg Med Chem. 2013;21:7257-66 pubmed publisher
    ..anticancer drugs (ER?, AR, Aromatase and CYP17A1) suggests that 17(E)-picolinylidene, but not 17?-picolyl androstanes could specifically interact with CYP17A1 (17?-hydroxylase) with similar geometry and affinity as Abiraterone, a ..
  53. Bortolato M, Frau R, Orru M, Bourov Y, Marrosu F, Mereu G, et al. Antipsychotic-like properties of 5-alpha-reductase inhibitors. Neuropsychopharmacology. 2008;33:3146-56 pubmed publisher
    ..induced no catalepsy in either the bar test or the paw test. Our results suggest that 5AR inhibitors elicit antipsychotic-like effects in animals and may be proposed as a putative novel target in the management of psychotic disorders. ..