Summary: A group of compounds forming the nucleus of the estrogenic steroid family.

Top Publications

  1. Pathirathna S, Brimelow B, Jagodic M, Krishnan K, Jiang X, Zorumski C, et al. New evidence that both T-type calcium channels and GABAA channels are responsible for the potent peripheral analgesic effects of 5alpha-reduced neuroactive steroids. Pain. 2005;114:429-43 pubmed
    ..Our results also reveal a role of GABA-gated ion channels in peripheral nociceptive signaling. ..
  2. Pathirathna S, Todorovic S, Covey D, Jevtovic Todorovic V. 5alpha-reduced neuroactive steroids alleviate thermal and mechanical hyperalgesia in rats with neuropathic pain. Pain. 2005;117:326-39 pubmed
  3. Strahm E, Baume N, Mangin P, Saugy M, Ayotte C, Saudan C. Profiling of 19-norandrosterone sulfate and glucuronide in human urine: implications in athlete's drug testing. Steroids. 2009;74:359-64 pubmed publisher
    ..These findings indicate that more interest shall be given to this type of conjugation to deter a potential doping with norsteroids. ..
  4. Li J, Li Y, Zhang W, Chen Z, Fan G. Glucose-?-CD interaction assisted ACN field-amplified sample stacking in CZE for determination of trace amlodipine in beagle dog plasma. J Sep Sci. 2013;36:1817-25 pubmed publisher
    ..The calibration curve was linear for amlodipine from 1 to 200 ng/mL. The method developed was successfully applied to the pharmacokinetic studies of amlodipine besylate in beagle dogs. ..
  5. Kurfurst P, Marek J, Vančo J, Csollei J. (R)-4-(4-fluorophenyl)-1-[2-hydroxy-2-(3-methyl-1-benzofuran-2-yl)ethyl]piperazinium chloride propan-1-ol solvate. Acta Crystallogr C. 2004;60:o494-5 pubmed
    ..12 (13) degrees. In the crystal structure, ions and propanol solvent molecules are linked via N-H...Cl and O-H...Cl bonds into linear (010) chains. ..
  6. Watanabe M, Mataka S, Thiemann T. Benzothieno and benzofurano annelated estranes. Steroids. 2005;70:856-66 pubmed
    ..Keystep is an intramolecular thienyl(/furyl)-ene-yne cyclization of 16-ethynyl-17-heterarylestra-1,3,5(10),16-tetraenes. The cyclization was carried out under Pt as well as under Ru catalysis. ..
  7. Li Q, Huie C. Coupling of acetonitrile deproteinization and salting-out extraction with acetonitrile stacking for biological sample clean-up and the enrichment of hydrophobic compounds (porphyrins) in capillary electrophoresis. Electrophoresis. 2006;27:4219-29 pubmed
    ..2-0.5 and 0.8-2.9%, respectively. ..
  8. Dehennin L, Bonnaire Y, Plou P. Detection of nandrolone administration to the entire male horse by a provisional concentration threshold for urinary oestranediol determined by gas chromatography-mass spectrometry. Equine Vet J. 2007;39:186-8 pubmed
  9. Latham J, Pathirathna S, Jagodic M, Choe W, Levin M, Nelson M, et al. Selective T-type calcium channel blockade alleviates hyperalgesia in ob/ob mice. Diabetes. 2009;58:2656-65 pubmed publisher
    ..Our results indicate that pharmacological antagonism of T-channels is potentially an important novel therapeutic approach for the management of painful diabetic neuropathy. ..

More Information


  1. Guay C, Goudreault D, Schänzer W, Flenker U, Ayotte C. Excretion of norsteroids' phase II metabolites of different origin in human. Steroids. 2009;74:350-8 pubmed publisher
    ..The GC/C/IRMS is the only method permitting to distinguish between the exogenous and endogenous origin of the metabolites. ..
  2. Qi S, Li Y, Wu S, Chen X, Hu Z. Novel nonaqueous capillary electrophoresis separation and determination of bioactive flavone derivatives in Chinese herbs. J Sep Sci. 2005;28:2180-6 pubmed
    ..Method performances, including migration time and peak area reproducibility, linearity, sensitivity, and accuracy, were evaluated. The method was applied to determine bioactive flavone derivatives in seven Chinese herbs. ..
  3. Hemmersbach P, Hågensen Jetne A, Lund H. Determination of urinary norandrosterone excretion in females during one menstrual cycle by gas chromatography/mass spectrometry. Biomed Chromatogr. 2006;20:710-7 pubmed
    ..However, a threshold value of 2 ng/mL for reporting adversed findings in doping control of females was never reached in any of the samples. ..
  4. Buiarelli F, Giannetti L, Jasionowska R, Cruciani C, Neri B. Determination of nandrolone metabolites in human urine: comparison between liquid chromatography/tandem mass spectrometry and gas chromatography/mass spectrometry. Rapid Commun Mass Spectrom. 2010;24:1881-94 pubmed publisher
    ..4), and both were able to confirm unambiguously all the analytes, thus confirming the validity of both techniques. ..
  5. Akk G, Bracamontes J, Covey D, Evers A, Dao T, Steinbach J. Neuroactive steroids have multiple actions to potentiate GABAA receptors. J Physiol. 2004;558:59-74 pubmed
    ..These observations are also consistent with the idea that there is more than one distinguishable steroid recognition site on the GABAA receptor. ..
  6. van der Merwe P, Grobbelaar E. Unintentional doping through the use of contaminated nutritional supplements. S Afr Med J. 2005;95:510-1 pubmed
    ..6 ng/ml at 8 hours post administration. The results of this study showed that the intake of microgram amounts of a prohibited substance in a nutritional supplement could cause an athlete to fail a dope test. ..
  7. Handforth A, Homanics G, Covey D, Krishnan K, Lee J, Sakimura K, et al. T-type calcium channel antagonists suppress tremor in two mouse models of essential tremor. Neuropharmacology. 2010;59:380-7 pubmed publisher
    ..It is uncertain whether medications developed to block only the Cav3.1 subtype would exhibit efficacy. ..
  8. Tseng Y, Kuo F, Sun K. Quantification and profiling of 19-norandrosterone and 19-noretiocholanolone in human urine after consumption of a nutritional supplement and norsteroids. J Anal Toxicol. 2005;29:124-34 pubmed
    ..On the basis of this study, we postulate that some doping violations of nandrolone could be attributed by indiscriminate administration of the OTC nutritional supplements that contained 19-norsteroids. ..
  9. Nakashima Y, Pereverzev A, Schneider T, Covey D, Lingle C. Blockade of Ba2+ current through human alpha1E channels by two steroid analogs, (+)-ACN and (+)-ECN. Neuropharmacology. 1999;38:843-55 pubmed
  10. Matsumoto T, Watanabe M, Mataka S, Thiemann T. Estrano[17,16-e]pyrimidine-peptide conjugates. Steroids. 2003;68:751-7 pubmed
    ..Thereafter, protected amino acids were coupled iteratively by the DCC method, commencing at the amino group of the aminopyrimidine unit. ..
  11. De Wasch K, le Bizec B, De Brabander H, Andre F, Impens S. Consequence of boar edible tissue consumption on urinary profiles of nandrolone metabolites. II. Identification and quantification of 19-norsteroids responsible for 19-norandrosterone and 19-noretiocholanolone excretion in human urine. Rapid Commun Mass Spectrom. 2001;15:1442-7 pubmed
    ..A correlation between the bNT and NAED content of a typical meal prepared with boar parts and the excreted concentrations of 19-NA and 19-NE in human urine was demonstrated. ..
  12. Dumasia M, Houghton E, Jackiw M. Steroids in equine testes: the identification of endogenous 19-hydroxy and 19-nor neutral steroids by gas chromatography--mass spectrometry. J Endocrinol. 1989;120:223-9 pubmed
  13. Friedman J, Cremer M, Jelani Q, Huang X, Jian J, Shah S, et al. Oral contraceptive use, iron stores and vascular endothelial function in healthy women. Contraception. 2011;84:285-90 pubmed publisher
    ..FMD in the brachial artery was significantly associated with progestin type used (estranes/gonanes vs. drospirenone) and duration of OCP use (both p<.05) but not iron stores...
  14. Goel A, Mittal A, Evstatiev R, Nemeth M, Kruis W, Stolte M, et al. In vivo effects of mesalazine or E. coli Nissle 1917 on microsatellite instability in ulcerative colitis. Aliment Pharmacol Ther. 2009;30:634-42 pubmed publisher
    ..In the set of biopsies taken from patients treated with 1.5 g 5-ASA for 1 year, there was no improvement in the prevalence of MSI in the distal colon. ..
  15. Mathurin J, Herrou V, Bourgogne E, Pascaud L, de Ceaurriz J. Gas chromatography-combustion-isotope ratio mass spectrometry analysis of 19-norsteroids: application to the detection of a nandrolone metabolite in urine. J Chromatogr B Biomed Sci Appl. 2001;759:267-75 pubmed
    ..Evidence of exogenous administration of 19-NA may be established from isotope ratio determination from the 13C/12C ratios of several synthetic 19-norsteroids compared to those obtained for endogenous steroids. ..
  16. Kavran Belin G, Rudaz S, Veuthey J. Enantioseparation of baclofen with highly sulfated beta-cyclodextrin by capillary electrophoresis with laser-induced fluorescence detection. J Sep Sci. 2005;28:2187-92 pubmed
    ..998) for R-(-) and S-(+)-baclofen was in the 0.1-2.0 microM concentration range. After a simple ACN-protein precipitation, the LOD of baclofen in plasma sample was found as low as 50 nM. ..
  17. de Geus B, Delbeke F, Meeusen R, Van Eenoo P, De Meirleir K, Busschaert B. Norandrosterone and noretiocholanolone concentration before and after submaximal standardized exercise. Int J Sports Med. 2004;25:528-32 pubmed
    ..Our findings confirm that the current International Olympic Committee threshold level for nandrolone metabolites is sufficiently high to avoid false positive cases. ..
  18. Dervilly Pinel G, Rambaud L, Sitthisack P, Monteau F, Hewitt S, Kennedy D, et al. 5?-Estrane-3?,17?-diol and 5?-estrane-3?,17?-diol: definitive screening biomarkers to sign nandrolone abuse in cattle?. J Steroid Biochem Mol Biol. 2011;126:65-71 pubmed publisher
    ..This result may open a new way for the screening of anabolic steroid administration considering these 2 estranediols as biomarkers to indicate nandrolone abuse in cattle. ..
  19. Van Eenoo P, Van Gansbeke W, De Brabanter N, Deventer K, Delbeke F. A fast, comprehensive screening method for doping agents in urine by gas chromatography-triple quadrupole mass spectrometry. J Chromatogr A. 2011;1218:3306-16 pubmed publisher
    ..Moreover, using a short capillary column and hydrogen as a carrier gas the run time of the method is less than 8min. ..
  20. Le Bizec B, Bryand F, Gaudin I, Monteau F, Poulain F, Andre F. Endogenous nandrolone metabolites in human urine: preliminary results to discriminate between endogenous and exogenous origin. Steroids. 2002;67:105-10 pubmed
    ..This significant qualitative difference appears to be a promising complementary criterion to more definitively conclude about an athlete's culpability, especially when nandrolone metabolites are found in the low ng/ml range. ..
  21. Tai S, Xu B, Sniegoski L, Welch M. Development and evaluation of a candidate reference measurement procedure for the determination of 19-norandrosterone in human urine using isotope-dilution liquid chromatography/tandem mass spectrometry. Anal Chem. 2006;78:3393-8 pubmed
  22. Muller A, Düsterloh K, Ringseis R, Eder K, Steinhart H. Development of an alternative eluent system for Ag+-HPLC analysis of conjugated linoleic acid isomers. J Sep Sci. 2006;29:358-65 pubmed
    ..Therefore, results should be confirmed by GC-FID and GC-MS. ..
  23. Delbeke F, Van Eenoo P, Van Thuyne W, Desmet N. Prohormones and sport. J Steroid Biochem Mol Biol. 2002;83:245-51 pubmed
    ..The results of the excretion studies indicate that after the intake of amounts substantially lower than the recommended dose athletes can fail a doping test for periods up to 120 h. ..
  24. Matsumoto T, Matsumoto T, Watanabe M, Mataka S, Thiemann T. 2'-Amino-3-methoxypyrimidino[5',4':16,17]estra-1,3,5(10),16-tetraene. Acta Crystallogr C. 2004;60:o501-2 pubmed
    ..The compound shows intermolecular hydrogen bonding of the amine group to an N atom of the pyrimidine moiety, as well as weak intermolecular interactions involving H atoms in the hydrophobic residue of the molecule. ..
  25. Penov Gasi K, Miljković D, Medić Mijacević L, Djurendić E, Stojanović S, Sakac M, et al. Synthesis, X-ray crystal structures and biological activity of 16-amino-17-substituted-D-homo steroid derivatives. Steroids. 2003;68:667-76 pubmed
    ..Also, assessment of potential antiestrogenic activity of derivatives from estrane series showed absence of such an activity. ..
  26. Przybylski C, Segard C. Method for routine screening of pesticides and metabolites in meat based baby-food using extraction and gas chromatography-mass spectrometry. J Sep Sci. 2009;32:1858-67 pubmed publisher
    ..9814 for all target analytes. Best LODs and LOQs were established as 0.03 and 0.1 microg/kg, respectively. Total instrumental analysis of all molecules was carried out in less than 1 h. ..
  27. Baume N, Avois L, Schweizer C, Cardis C, Dvorak J, Cauderay M, et al. [13C]Nandrolone excretion in trained athletes: interindividual variability in metabolism. Clin Chem. 2004;50:355-64 pubmed
    ..More investigations are currently underway to estimate the influence of exhaustive exercises on excretion of labeled nandrolone metabolites in urine. ..
  28. Gaertner P, Bica K, Felzmann W, Forsdahl G, Gmeiner G. Synthesis and analytics of 2,2,3,4,4-d5-19-nor-5alpha-androsterone--an internal standard in doping analysis. Steroids. 2007;72:429-36 pubmed
    ..The use of compound 7 as internal standard for the detection of anabolic steroids via mass spectrometric techniques such as gas chromatography-mass spectrometry (GC-MS) is discussed. ..
  29. Strahm E, Saudan C, Sottas P, Mangin P, Saugy M. Direct detection and quantification of 19-norandrosterone sulfate in human urine by liquid chromatography-linear ion trap mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2007;852:491-6 pubmed
    ..2-20 ng/mL) and the standard-addition method. The results show the feasibility of applying this LC-MS/MS assay as a complementary tool to detect misuse of nandrolone or nandrolone precursors. ..
  30. Iida T, Ogawa S, Hosoi K, Makino M, Fujimoto Y, Goto T, et al. Regioselective oxyfunctionalization of unactivated carbons in steroids by a model of cytochrome P-450: osmiumporphyrin complex/tert-butyl hydroperoxide system. J Org Chem. 2007;72:823-30 pubmed
  31. Hebestreit M, Flenker U, Fusshöller G, Geyer H, Güntner U, Mareck U, et al. Determination of the origin of urinary norandrosterone traces by gas chromatography combustion isotope ratio mass spectrometry. Analyst. 2006;131:1021-6 pubmed
    ..By comparing delta(13)C(VPDB)-values of androsterone as endogenous reference compound with NA, the origin of NA in doping control samples was determined as either endogenous or exogenous. ..
  32. 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. ..
  33. Grosse J, Anielski P, Hemmersbach P, Lund H, Mueller R, Rautenberg C, et al. Formation of 19-norsteroids by in situ demethylation of endogenous steroids in stored urine samples. Steroids. 2005;70:499-506 pubmed
    ..g. EDTA). The application of the incubation experiments described may contribute to the clarification of adverse analytical findings regarding low levels of 19-norsteroid metabolites. ..
  34. Akk G, Bracamontes J, Steinbach J. Pregnenolone sulfate block of GABA(A) receptors: mechanism and involvement of a residue in the M2 region of the alpha subunit. J Physiol. 2001;532:673-84 pubmed
    ..It seems likely that this residue is involved in a conformational change underlying block by PS, instead of forming part of the binding site for PS. ..
  35. Watson P, Judkins C, Houghton E, Russell C, Maughan R. Urinary nandrolone metabolite detection after ingestion of a nandrolone precursor. Med Sci Sports Exerc. 2009;41:766-72 pubmed publisher
    ..The addition of as little as 2.5 microg of 19-norandrostenedione to a supplement (0.00005% contamination) appears sufficient to result in a doping violation in some individuals. ..
  36. Walker C, Cowan D, James V, Lau J, Kicman A. Doping in sport: 3. Metabolic conversion of oral norethisterone to urinary 19-norandrosterone. Steroids. 2009;74:341-9 pubmed publisher
    ..36. We provide data that should remove the need for time-consuming follow-up investigations to consider whether doping with 19-norandrogens has occurred. ..
  37. de la Torre X, Colamonici C, Curcio D, Molaioni F, Pizzardi M, Botre F. A simplified procedure for GC/C/IRMS analysis of underivatized 19-norandrosterone in urine following HPLC purification. Steroids. 2011;76:471-7 pubmed publisher
    ..The efficacy of the method was tested on real samples from routine antidoping analyses. ..
  38. Catlin D, Leder B, Ahrens B, Starcevic B, Hatton C, Green G, et al. Trace contamination of over-the-counter androstenedione and positive urine test results for a nandrolone metabolite. JAMA. 2000;284:2618-21 pubmed
    ..Some brands of androstenedione are grossly mislabeled. Careful analysis of androstenedione preparations is recommended in all studies of its biological effects. JAMA. 2000;284:2618-2621. ..
  39. Rodríguez Gonzalo E, Domínguez Álvarez J, Ruano Miguel L, Carabias Martínez R. In-capillary preconcentration of pirimicarb and carbendazim with a monolithic polymeric sorbent prior to separation by CZE. Electrophoresis. 2008;29:4066-77 pubmed publisher
    ..For a 15-min preconcentration time, the in-line SPE-CZE approach proposed here permitted the determination of these pesticides in drinking water at a concentration level of 0.1 microg/L, as demanded by current EU legislation. ..
  40. Horvath A, Szájli A, Kiss R, Kóti J, Maho S, Skoda Földes R. Ionic liquid-promoted Wagner-Meerwein rearrangement of 16?,17?-epoxyandrostanes and 16?,17?-epoxyestranes. J Org Chem. 2011;76:6048-56 pubmed publisher
    ..The ionic liquids were recirculated efficiently. ..
  41. Borissova M, Gorbatsova J, Ebber A, Kaljurand M, Koel M, Vaher M. Nonaqueous CE using contactless conductivity detection and ionic liquids as BGEs in ACN. Electrophoresis. 2007;28:3600-5 pubmed
    ..Some organic dyes were also successfully separated and detected by contactless conductivity detector in a 20 mM A6 separation electrolyte in ACN. ..
  42. Tseng Y, Sun C, Kuo F. Detection and quantification of glucuro- and sulfoconjugated metabolites in human urine following oral administration of xenobiotic 19-norsteroids. Steroids. 2006;71:817-27 pubmed
    ..Results from the excretion studies demonstrate significance of sulfate-conjugated metabolites on interpretation of misuse of the 19-norsteroids. ..
  43. Deutsch J, Jang H, Mansur N, Ilovich O, Shpolansky U, Galili D, et al. 4-(3'alpha15'beta-dihydroxy-5'beta-estran-17'beta-yl)furan-2-methyl alcohol: an anti-digoxin agent with a novel mechanism of action. J Med Chem. 2006;49:600-6 pubmed
    ..The steroid also inhibited digoxin-induced alteration in endocytosed membrane traffic, indicating a novel mechanism of action. ..
  44. Mák M, Francsics Czinege E, Tuba Z. Steroid epimers studied by different mass spectrometric methods. Steroids. 2004;69:831-40 pubmed
    ..Mass spectrometry has proved to be an effective tool when stereoisomer steroids are compared. ..
  45. Matsuda T, Yamashita K, Maeda H, Hashimoto M, Tsukagoshi K. Michrochip chromatography using an open-tubular microchannel and a ternary water-ACN-ethyl acetate mixture carrier solution. J Sep Sci. 2013;36:965-70 pubmed publisher
    ..The outer phase acts as a pseudo-stationary phase under laminar flow conditions in the system. The ILITC and the labeled BSA were eluted and detected with chemiluminescence reaction. ..
  46. Yamamoto C, Matsumoto T, Watanabe M, Hitzer E, Mataka S, Thiemann T. 6-[3-Hydroxy-17-oxoestra-1,3,5(10)-trien-7beta-yl]hexanenitrile. Acta Crystallogr C. 2004;60:o130-2 pubmed
    ..This conformation best accommodates adverse intramolecular H.H interactions between the H atoms of the 7beta-substituent and the two nearest ring H atoms. The tilt angle between rings A and D is 28.6 (1) degrees. ..
  47. Reznik Y, Dehennin L, Coffin C, Mahoudeau J, Leymarie P. Urinary nandrolone metabolites of endogenous origin in man: a confirmation by output regulation under human chorionic gonadotropin stimulation. J Clin Endocrinol Metab. 2001;86:146-50 pubmed
    ..The comparative kinetics of NA UER, plasma E(2), and E(2)/T ratio suggest a contribution of the aromatase process to nandrolone biosynthesis in man. ..
  48. Pokrywka A, Kwiatkowska D, Gorczyca D. [Possible reasons for the presence of nandrolone metabolites in urine]. Arch Med Sadowej Kryminol. 2009;59:155-8 pubmed
    ..The paper presents possible reasons for the presence of 19-norandrosterone in urine, as well as the difficulties associated with interpretation of 19-norandrosterone detection during the doping control. ..
  49. Maughan R. Contamination of dietary supplements and positive drug tests in sport. J Sports Sci. 2005;23:883-9 pubmed
  50. Pinel G, Rambaud L, Cacciatore G, Bergwerff A, Elliott C, Nielen M, et al. Elimination kinetic of 17beta-estradiol 3-benzoate and 17beta-nandrolone laureate ester metabolites in calves' urine. J Steroid Biochem Mol Biol. 2008;110:30-8 pubmed publisher
    ..The effect of several consecutive injections on elimination profiles was studied and revealed a tendency toward a decrease in the biotransformation of administered steroid 17beta form. ..
  51. Porras S, Jussila M. Electromigration of a heteroconjugated imidazole-acetate complex in ACN. Electrophoresis. 2007;28:3590-9 pubmed
    ..The possibility of multiple complexation of imidazole was discussed as well. ..
  52. Borges C, Miller N, Shelby M, Hansen M, White C, Slawson M, et al. Analysis of a challenging subset of World Anti-Doping Agency-banned steroids and antiestrogens by LC-MS-MS. J Anal Toxicol. 2007;31:125-31 pubmed
  53. Ayotte C. Significance of 19-norandrosterone in athletes' urine samples. Br J Sports Med. 2006;40 Suppl 1:i25-9 pubmed
    ..Whereas exercise does not seem to be a significant factor in 19-norandrosterone excretion, some rare urine samples were found to be a suitable medium for in situ 19-demethylation of urinary metabolites. ..