Mesterolone (BioDeep_00000014547)

   

human metabolite Endogenous


代谢物信息卡片


(1S,2S,3S,7S,10R,11S,14S,15S)-14-hydroxy-2,3,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one

化学式: C20H32O2 (304.24021719999996)
中文名称: 美睾酮
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC1CC(=O)CC2C1(C3CCC4(C(C3CC2)CCC4O)C)C
InChI: InChI=1S/C20H32O2/c1-12-10-14(21)11-13-4-5-15-16-6-7-18(22)19(16,2)9-8-17(15)20(12,13)3/h12-13,15-18,22H,4-11H2,1-3H3/t12-,13-,15-,16-,17-,18-,19-,20-/m0/s1

描述信息

Mesterolone is a synthetic anabolic androgenic steroid (AAS) with reported abuses in human sports. As for other AAS, mesterolone is also a potential doping agent in equine sports. In humans, mesterolone exhibits no inhibitory effects on hypophysial gonadotropin secretion or on spermatogenesis, unlike most androgens. Mesterolone has been used in the treatment of primary nocturnal enuresis in boys six to ten years of age. Mesterolone probably modulates the autonomic innervation of the vesical musculature with correction of the defective neural mechanism which is believed to be implicated in the pathogenesis of nocturnal enuresis. Mesterolone has been utilized in hypogonadism patients to increase total ejaculation volume and the concentration of fructose in the spermatic plasma to normal levels. Mesterolone treatment decreases cholesterol, beta-lipoproteins, fatty acid esters, free fatty acids, triglycerides and glycerol in human serum. (PMID: 4880965, 17616252, 10796496, 17636603, 2087834, 6111418, 6142498, 6386424, 7558381, 792898) [HMDB]
Mesterolone is a synthetic anabolic androgenic steroid (AAS) with reported abuses in human sports. As for other AAS, mesterolone is also a potential doping agent in equine sports. In humans, mesterolone exhibits no inhibitory effects on hypophysial gonadotropin secretion or on spermatogenesis, unlike most androgens. Mesterolone has been used in the treatment of primary nocturnal enuresis in boys six to ten years of age. Mesterolone probably modulates the autonomic innervation of the vesical musculature with correction of the defective neural mechanism which is believed to be implicated in the pathogenesis of nocturnal enuresis. Mesterolone has been utilized in hypogonadism patients to increase total ejaculation volume and the concentration of fructose in the spermatic plasma to normal levels. Mesterolone treatment decreases cholesterol, beta-lipoproteins, fatty acid esters, free fatty acids, triglycerides and glycerol in human serum. (PMID: 4880965, 17616252, 10796496, 17636603, 2087834, 6111418, 6142498, 6386424, 7558381, 792898).
G - Genito urinary system and sex hormones > G03 - Sex hormones and modulators of the genital system > G03B - Androgens > G03BB - 5-androstanon (3) derivatives
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D045930 - Anabolic Agents
C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone

同义名列表

21 个代谢物同义名

(1S,2S,3S,7S,10R,11S,14S,15S)-14-hydroxy-2,3,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one; (1a,5a,17b)-17-Hydroxy-1-methyl-androstan-3-one; 17b-Hydroxy-1a-methyl-5a-androstan-3-one; 1a-Methyl-17b-hydroxy-5a-androstan-3-one; 1a-Methyl-5a-androstan-17b-ol-3-one; 17-Hydroxy-1-methylandrostan-3-one; 1a-Methyl-5a-dihydrotestosterone; Jenapharm brand OF mesterolone; Schering brand OF mesterolone; Mesterolone jenapharm brand; Mesterolone schering brand; SH-723Mesterolone; Provirone 25; Mesterolone; Androviron; Mestoranum; Mesteranum; Vistimon; Proviron; Testiwop; SH 723



数据库引用编号

14 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

1 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Michael Polet, Wim Van Gansbeke, Aðalheiður Dóra Albertsdóttir, Gilles Coppieters, Koen Deventer, Peter Van Eenoo. Gas chromatography-mass spectrometry analysis of non-hydrolyzed sulfated steroids by degradation product formation. Drug testing and analysis. 2019 Nov; 11(11-12):1656-1665. doi: 10.1002/dta.2606. [PMID: 31009554]
  • Andrea Camargo Casquero, Jairo Augusto Berti, Laura Lauand Sampaio Teixeira, Helena Coutinho Franco de Oliveira. Chronic Exercise Reduces CETP and Mesterolone Treatment Counteracts Exercise Benefits on Plasma Lipoproteins Profile: Studies in Transgenic Mice. Lipids. 2017 Dec; 52(12):981-990. doi: 10.1007/s11745-017-4299-1. [PMID: 29058169]
  • Kejing Lao, Jie Sun, Chong Wang, Ying Wang, Qidong You, Hong Xiao, Hua Xiang. Design, synthesis and biological evaluation of novel 3-oxo-4-oxa-5α-androst-17β-amide derivatives as dual 5α-reductase inhibitors and androgen receptor antagonists. Bioorganic & medicinal chemistry letters. 2017 09; 27(17):4212-4217. doi: 10.1016/j.bmcl.2017.05.078. [PMID: 28757062]
  • Sonia Ricotti, Maria Inés Garcia, Carolina Veaute, Alejandra Bailat, Eduardo Lucca, R Frank Cook, Sheila J Cook, Adriana Soutullo. Serologically silent, occult equine infectious anemia virus (EIAV) infections in horses. Veterinary microbiology. 2016 May; 187(?):41-49. doi: 10.1016/j.vetmic.2016.03.007. [PMID: 27066707]
  • S Rzeppa, G Heinrich, P Hemmersbach. Analysis of anabolic androgenic steroids as sulfate conjugates using high performance liquid chromatography coupled to tandem mass spectrometry. Drug testing and analysis. 2015 Nov; 7(11-12):1030-9. doi: 10.1002/dta.1895. [PMID: 26472592]
  • Jianghai Lu, María Fernández-Álvarez, Sheng Yang, Genye He, Youxuan Xu, Rodigo Aguilera. New potential biomarkers for mesterolone misuse in human urine by liquid chromatography quadrupole time-of-flight mass spectrometry. Journal of mass spectrometry : JMS. 2015 Jan; 50(1):153-9. doi: 10.1002/jms.3508. [PMID: 25601687]
  • Karina Fontana, Gerson E R Campos, Robert S Staron, Maria Alice da Cruz-Höfling. Effects of anabolic steroids and high-intensity aerobic exercise on skeletal muscle of transgenic mice. PloS one. 2013; 8(11):e80909. doi: 10.1371/journal.pone.0080909. [PMID: 24260508]
  • Karina Fontana, Thalita Rocha, Maria Alice da Cruz-Höfling. Regulation of neuronal and endothelial nitric oxide synthase by anabolic-androgenic steroid in skeletal muscles. Histology and histopathology. 2012 11; 27(11):1449-58. doi: 10.14670/hh-27.1449. [PMID: 23018244]
  • Randor Radakovits, Robert E Jinkerson, Susan I Fuerstenberg, Hongseok Tae, Robert E Settlage, Jeffrey L Boore, Matthew C Posewitz. Draft genome sequence and genetic transformation of the oleaginous alga Nannochloropis gaditana. Nature communications. 2012 Feb; 3(?):686. doi: 10.1038/ncomms1688. [PMID: 22353717]
  • Juliana C Monteiro, Marcos L M Gomes, Tatiana C Tomiosso, Wilson R Nakagaki, Mariana M Sbervelheri, Danilo L Ferrucci, Edson R Pimentel, Heidi Dolder. More resistant tendons obtained from the association of Heteropterys aphrodisiaca and endurance training. BMC complementary and alternative medicine. 2011 Jun; 11(?):51. doi: 10.1186/1472-6882-11-51. [PMID: 21711561]
  • M Widschwendter, H Lichtenberg-Frate, G Hasenbrink, S Schwarzer, A Dawnay, A Lam, U Menon, S Apostolidou, E Raum, C Stegmaier, I J Jacobs, H Brenner. Serum oestrogen receptor alpha and beta bioactivity are independently associated with breast cancer: a proof of principle study. British journal of cancer. 2009 Jul; 101(1):160-5. doi: 10.1038/sj.bjc.6605106. [PMID: 19491898]
  • Karina Fontana, Helena Coutinho Franco Oliveira, Marta Beatriz Leonardo, Carlos Alberto Mandarim-de-Lacerda, Maria Alice da Cruz-Höfling. Adverse effect of the anabolic-androgenic steroid mesterolone on cardiac remodelling and lipoprotein profile is attenuated by aerobicz exercise training. International journal of experimental pathology. 2008 Oct; 89(5):358-66. doi: 10.1111/j.1365-2613.2008.00601.x. [PMID: 18808528]
  • Marcello Cocuzza, Ashok Agarwal. Nonsurgical treatment of male infertility: specific and empiric therapy. Biologics : targets & therapy. 2007 Sep; 1(3):259-69. doi: NULL. [PMID: 19707335]
  • Emmie N M Ho, David K K Leung, Gary N W Leung, Terence S M Wan, Henry N C Wong, Xiaohua Xu, John H K Yeung. Metabolic studies of mesterolone in horses. Analytica chimica acta. 2007 Jul; 596(1):149-55. doi: 10.1016/j.aca.2007.05.052. [PMID: 17616252]
  • Per-Erik Olsson, A Håkan Berg, Jonas von Hofsten, Birgitta Grahn, Anna Hellqvist, Anders Larsson, Johnny Karlsson, Carina Modig, Bertil Borg, Peter Thomas. Molecular cloning and characterization of a nuclear androgen receptor activated by 11-ketotestosterone. Reproductive biology and endocrinology : RB&E. 2005 Aug; 3(?):37. doi: 10.1186/1477-7827-3-37. [PMID: 16107211]
  • E Caroppo, C Niederberger, P A Iacovazzi, M Correale, A Palagiano, G D'Amato. Human chorionic gonadotropin free beta-subunit in the human seminal plasma: a new marker for spermatogenesis?. European journal of obstetrics, gynecology, and reproductive biology. 2003 Feb; 106(2):165-9. doi: 10.1016/s0301-2115(02)00231-2. [PMID: 12551786]
  • F Jockenhövel, C Bullmann, M Schubert, E Vogel, W Reinhardt, D Reinwein, D Müller-Wieland, W Krone. Influence of various modes of androgen substitution on serum lipids and lipoproteins in hypogonadal men. Metabolism: clinical and experimental. 1999 May; 48(5):590-6. doi: 10.1016/s0026-0495(99)90056-2. [PMID: 10337859]
  • F Jockenhövel, E Vogel, W Reinhardt, D Reinwein. Effects of various modes of androgen substitution therapy on erythropoiesis. European journal of medical research. 1997 Jul; 2(7):293-8. doi: . [PMID: 9233903]
  • M T Mbizvo. Functional motion changes during sperm transit to the site of fertilization and in-vitro applications: a review. International journal of andrology. 1995 Jun; 18 Suppl 1(?):1-6. doi: 10.1111/j.1365-2605.1995.tb00630.x. [PMID: 7558381]
  • R Masse, D Goudreault. Studies on anabolic steroids--11. 18-hydroxylated metabolites of mesterolone, methenolone and stenbolone: new steroids isolated from human urine. The Journal of steroid biochemistry and molecular biology. 1992 May; 42(3-4):399-410. doi: 10.1016/0960-0760(92)90145-9. [PMID: 1606051]
  • D de Boer, E G de Jong, R A Maes, J M van Rossum. The methyl-5 alpha-dihydrotestosterones mesterolone and drostanolone; gas chromatographic/mass spectrometric characterization of the urinary metabolites. The Journal of steroid biochemistry and molecular biology. 1992 May; 42(3-4):411-9. doi: 10.1016/0960-0760(92)90146-a. [PMID: 1606052]
  • T R Varma, R H Patel. The effect of mesterolone on sperm count, on serum follicle stimulating hormone, luteinizing hormone, plasma testosterone and outcome in idiopathic oligospermic men. International journal of gynaecology and obstetrics: the official organ of the International Federation of Gynaecology and Obstetrics. 1988 Feb; 26(1):121-8. doi: 10.1016/0020-7292(88)90206-8. [PMID: 2892728]
  • J B Schmidt, J Spona. [An effective topical antiandrogen--17 alpha-propylmesterolone--in acne]. Der Hautarzt; Zeitschrift fur Dermatologie, Venerologie, und verwandte Gebiete. 1987 Aug; 38(8):470-3. doi: ". [PMID: 2958430]
  • J B Schmidt, J Spona. Efficacy of topically applied 17 alpha-propylmesterolone in acne patients. Endocrinologia experimentalis. 1987 Mar; 21(1):71-8. doi: NULL. [PMID: 2952489]
  • C Luderschmidt, W Eiermann, J Jawny, F Bidlingmaier, J Ring. 17 alpha-Propylmesterolone (SH 434): an antiandrogenic sebosuppressive substance not influencing circulating testosterone concentrations. Experimental studies in Syrian hamsters. Naunyn-Schmiedeberg's archives of pharmacology. 1984 Dec; 328(2):214-8. doi: 10.1007/bf00512076. [PMID: 6527707]
  • T M Itil, S T Michael, D M Shapiro, K Z Itil. The effects of mesterolone, a male sex hormone in depressed patients (a double blind controlled study). Methods and findings in experimental and clinical pharmacology. 1984 Jun; 6(6):331-7. doi: NULL. [PMID: 6431212]
  • W Krause, U Jakobs. Determination of 17 beta-hydroxy-1 alpha-methyl-17 alpha-propyl-5-alpha-androstan-3-one in plasma by gas chromatography-mass spectrometry with single-ion detection. Journal of pharmaceutical sciences. 1984 Apr; 73(4):563-4. doi: 10.1002/jps.2600730433. [PMID: 6726647]
  • L Abrahamsson, H Hackl, S Orstam. [Non-virilizing hormonal therapy in women with secondary disorders of sexual responsiveness]. Wiener klinische Wochenschrift. 1983 Jun; 95(13):455-8. doi: NULL. [PMID: 6227141]
  • G Verhoeven, P Franchimont. Regulation of inhibin secretion by Sertoli cell-enriched cultures. Acta endocrinologica. 1983 Jan; 102(1):136-43. doi: 10.1530/acta.0.1020136. [PMID: 6218726]
  • P Schramm, P Benes, B Morsches. [Effects of long-term use of mesterolone on different urine metabolites in andrological patients (author's transl)]. Archives of dermatological research. 1981; 270(3):333-40. doi: 10.1007/bf00403937. [PMID: 6455971]
  • D Kraft. [Long-term treatment of renal anaemia with mesterolone (author's transl)]. Deutsche medizinische Wochenschrift (1946). 1980 Jun; 105(23):830-2. doi: 10.1055/s-2008-1070763. [PMID: 6447589]
  • S Roy, S Chatterjee. Studies with cyproterone acetate for male contraception. Journal of steroid biochemistry. 1979 Jul; 11(1B):675-80. doi: 10.1016/0022-4731(79)90099-2. [PMID: 491632]
  • V Nikkanen. Plasma cholesterol, triglycerides, FSH and testosterone levels of normolipemic male patients with decreased fertility treated with mesterolone. Andrologia. 1979 Jan; 11(1):33-6. doi: 10.1111/j.1439-0272.1979.tb02155.x. [PMID: 420413]
  • G D Lowe, J E Thomson, M M Reavey, C D Forbes, C R Prentice. Mesterolone: thrombosis during treatment, and a study of its prothrombotic effects. British journal of clinical pharmacology. 1979 Jan; 7(1):107-9. doi: 10.1111/j.1365-2125.1979.tb00905.x. [PMID: 760733]
  • V Nikkanen. The effects of mesterolone on the male accessory sex organs, on spermiogram, plasma testosterone and FSH. Andrologia. 1978 Jul; 10(4):299-306. doi: 10.1111/j.1439-0272.1978.tb03037.x. [PMID: 717809]
  • J Szöllösi, G Y Falkay, M Sas. Mesterolone treatment of patients with pathospermia. International urology and nephrology. 1978; 10(3):251-6. doi: 10.1007/bf02082034. [PMID: 689818]
  • P M Kövary, H Lenau, H Niermann, E Zierden, H Wagner. Testosterone levels and gonadotrophins in Klinefelter's patients treated with injections of mesterolone cipionate. Archives for dermatological research = Archiv fur dermatologische Forschung. 1977 May; 258(3):289-94. doi: 10.1007/bf00561132. [PMID: 883846]
  • K Bandhauer, H U Meili. [Varicocele: spermiogram, testicular biopsy, plasma testosterone. Results of therapy (author's transl)]. Der Urologe. Ausg. A. 1977 May; 16(3):154-7. doi: NULL. [PMID: 878109]
  • F R Jackaman, I D Ansell, R Ghanadian, P V McLoughlin, J G Lewis, G D Chisholm. The hormone response to a synthetic androgen (mesterolone) in oligospermia. Clinical endocrinology. 1977 May; 6(5):339-45. doi: 10.1111/j.1365-2265.1977.tb02020.x. [PMID: 872444]
  • K Bandhauer, H U Meili. Combined mesterolon-clomiphene citrate therapy for treatment of oligospermia. European urology. 1977; 3(5):292-4. doi: 10.1159/000472119. [PMID: 913461]
  • E L Bock, H H Fülle, H Heimpel, W Pribilla. [The effect of mesterolone in panmyelopathic anemia and anemia of renal failure]. Medizinische Klinik. 1976 Mar; 71(13):539-47. doi: NULL. [PMID: 772394]
  • C J Horst, J J Bol. Sterility of three brothers in connection with a disturbed carbohydrate metabolism in semen. Andrologia. 1975; 7(1):15-24. doi: 10.1111/j.1439-0272.1975.tb01221.x. [PMID: 1163820]