Testolactone (BioDeep_00000004865)

 

Secondary id: BioDeep_00000410542, BioDeep_00000637509

human metabolite blood metabolite Chemicals and Drugs


代谢物信息卡片


(4aS,4bR,10aR,10bS,12aS)-10a,12a-dimethyl-3,4,4a,5,6,10a,10b,11,12,12a-decahydro-2H-naphtho[2,1-f]chromene-2,8(4bH)-dione

化学式: C19H24O3 (300.1725354)
中文名称: 睾内酯
谱图信息: 最多检出来源 Homo sapiens(urine) 13.64%

分子结构信息

SMILES: CC12CCC3C(C1CCC(=O)O2)CCC4=CC(=O)C=CC34C
InChI: InChI=1S/C19H24O3/c1-18-9-7-13(20)11-12(18)3-4-14-15(18)8-10-19(2)16(14)5-6-17(21)22-19/h7,9,11,14-16H,3-6,8,10H2,1-2H3/t14-,15+,16+,18+,19+/m1/s1

描述信息

Testolactone is only found in individuals that have used or taken this drug. It is an antineoplastic agent that is a derivative of progesterone and used to treat advanced breast cancer. [PubChem]Although the precise mechanism by which testolactone produces its clinical antineoplastic effects has not been established, its principal action is reported to be inhibition of steroid aromatase activity and consequent reduction in estrone synthesis from adrenal androstenedione, the major source of estrogen in postmenopausal women. Based on in vitro studies, the aromatase inhibition may be noncompetitive and irreversible. This phenomenon may account for the persistence of testolactones effect on estrogen synthesis after drug withdrawal.
C274 - Antineoplastic Agent > C2189 - Signal Transduction Inhibitor > C129824 - Antineoplastic Protein Inhibitor
C274 - Antineoplastic Agent > C129818 - Antineoplastic Hormonal/Endocrine Agent > C481 - Antiestrogen
C274 - Antineoplastic Agent > C163758 - Targeted Therapy Agent > C1740 - Aromatase Inhibitor
C471 - Enzyme Inhibitor > C129825 - Antineoplastic Enzyme Inhibitor
C147908 - Hormone Therapy Agent > C547 - Hormone Antagonist
D000970 - Antineoplastic Agents

同义名列表

25 个代谢物同义名

(4aS,4bR,10aR,10bS,12aS)-10a,12a-dimethyl-3,4,4a,5,6,10a,10b,11,12,12a-decahydro-2H-naphtho[2,1-f]chromene-2,8(4bH)-dione; (1R,2S,7S,10S,11R)-7,11-dimethyl-6-oxatetracyclo[8.8.0.0^{2,7}.0^{11,16}]octadeca-12,15-diene-5,14-dione; 13-hydroxy-3-oxo-13,17-secoandrosta-1,4-dien-17-oic acid delta-lactone; 13-Hydroxy-3-oxo-13,17-secoandrosta-1,4-dien-17-oic acid Δ-lactone; 13-Hydroxy-3-oxo-13,17-secoandrosta-1,4-dien-17-oate delta-lactone; 13-Hydroxy-3-oxo-13,17-secoandrosta-1,4-dien-17-oate Δ-lactone; 3-oxo-13,17-secoandrosta-1,4-dieno-17,13alpha-lactone; D-homo-17a-oxaandrosta-1,4-diene-3,17-dione; delta1-Dehydrotestololactone; 1,2-didehydrotestololactone; 1,2-Dehydrotestololactone; Δ1-Dehydrotestololactone; Delta(1)-testololactone; 1-dehydrotestololactone; 1-Dehydrotestolactone; delta(1)-Testolactone; 1 Dehydrotestolactone; delta1-Testololactone; delta1-Testolactone; Δ(1)-testololactone; Δ1-Testololactone; Δ1-Testolactone; Testolactone; D-homo; Teslac



数据库引用编号

17 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

  • Bashir Lawal, Saidu Sani, Amos S Onikanni, Yunusa O Ibrahim, Abdulhakeem R Agboola, Halimat Yusuf Lukman, Femi Olawale, Ali A Jigam, Gaber El-Saber Batiha, Shukurat B Babalola, Gomaa Mostafa-Hedeab, Clara Mariana Gonçalves Lima, Alexander T H Wu, Hsu-Shan Huang, Carlos Adam Conte-Junior. Preclinical anti-inflammatory and antioxidant effects of Azanza garckeana in STZ-induced glycemic-impaired rats, and pharmacoinformatics of it major phytoconstituents. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2022 Aug; 152(?):113196. doi: 10.1016/j.biopha.2022.113196. [PMID: 35667233]
  • Vinícius Figueiredo Sardela, Patricia D O Sardela, Raïssa R Lisboa, Bernardo F Matias, Carina S Anselmo, Aline R de Carvalho, Isabele K C Nunes, Monica C Padilha, Francisco R de Aquino Neto, Henrique M G Pereira. Comprehensive Zebrafish Water Tank Experiment for Metabolic Studies of Testolactone. Zebrafish. 2020 04; 17(2):104-111. doi: 10.1089/zeb.2019.1791. [PMID: 32096703]
  • Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
  • Ellen Werber Leschek, Armando C Flor, Joy C Bryant, Janet V Jones, Kevin M Barnes, Gordon B Cutler. Effect of Antiandrogen, Aromatase Inhibitor, and Gonadotropin-releasing Hormone Analog on Adult Height in Familial Male Precocious Puberty. The Journal of pediatrics. 2017 11; 190(?):229-235. doi: 10.1016/j.jpeds.2017.07.047. [PMID: 29144249]
  • 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]
  • Pairunyar Sawathiparnich, Prapanrat Osuwanaratana, Jeerunda Santiprabhob, Supawadee Likitmaskul. Tamoxifen improved final height prediction in a girl with McCune-Albright syndrome: patient report and literature review. Journal of pediatric endocrinology & metabolism : JPEM. 2006 Jan; 19(1):81-6. doi: 10.1515/jpem.2006.19.1.81. [PMID: 16509532]
  • Jonathan D Schiff, Gianpiero D Palermo, Lucinda L Veeck, Marc Goldstein, Zev Rosenwaks, Peter N Schlegel. Success of testicular sperm extraction [corrected] and intracytoplasmic sperm injection in men with Klinefelter syndrome. The Journal of clinical endocrinology and metabolism. 2005 Nov; 90(11):6263-7. doi: 10.1210/jc.2004-2322. [PMID: 16131585]
  • G Binder, D I Iliev, A Dufke, M Wabitsch, R Schweizer, M B Ranke, M Schmidt. Dominant transmission of prepubertal gynecomastia due to serum estrone excess: hormonal, biochemical, and genetic analysis in a large kindred. The Journal of clinical endocrinology and metabolism. 2005 Jan; 90(1):484-92. doi: 10.1210/jc.2004-1566. [PMID: 15483104]
  • Leandro Soriano-Guillén, Najiba Lahlou, Geneviève Chauvet, Marc Roger, Jean Louis Chaussain, Jean Claude Carel. Adult height after ketoconazole treatment in patients with familial male-limited precocious puberty. The Journal of clinical endocrinology and metabolism. 2005 Jan; 90(1):147-51. doi: 10.1210/jc.2004-1438. [PMID: 15522928]
  • Barnett Zumoff, Lorraine K Miller, Gladys W Strain. Reversal of the hypogonadotropic hypogonadism of obese men by administration of the aromatase inhibitor testolactone. Metabolism: clinical and experimental. 2003 Sep; 52(9):1126-8. doi: 10.1016/s0026-0495(03)00186-0. [PMID: 14506617]
  • Evangelia Charmandari, Karim A Calis, Margaret F Keil, Maryam R Mohassel, Alan Remaley, Deborah P Merke. Flutamide decreases cortisol clearance in patients with congenital adrenal hyperplasia. The Journal of clinical endocrinology and metabolism. 2002 Jul; 87(7):3197-200. doi: 10.1210/jcem.87.7.8652. [PMID: 12107224]
  • A Richter-Unruh, H T Wessels, U Menken, M Bergmann, K Schmittmann-Ohters, J Schaper, S Tappeser, B P Hauffa. Male LH-independent sexual precocity in a 3.5-year-old boy caused by a somatic activating mutation of the LH receptor in a Leydig cell tumor. The Journal of clinical endocrinology and metabolism. 2002 Mar; 87(3):1052-6. doi: 10.1210/jcem.87.3.8294. [PMID: 11889161]
  • Jay D Raman, Peter N Schlegel. Aromatase inhibitors for male infertility. The Journal of urology. 2002 Feb; 167(2 Pt 1):624-9. doi: 10.1097/00005392-200202000-00038. [PMID: 11792932]
  • C P Pavlovich, P King, M Goldstein, P N Schlegel. Evidence of a treatable endocrinopathy in infertile men. The Journal of urology. 2001 Mar; 165(3):837-41. doi: . [PMID: 11176482]
  • D P Merke, M F Keil, J V Jones, J Fields, S Hill, G B Cutler. Flutamide, testolactone, and reduced hydrocortisone dose maintain normal growth velocity and bone maturation despite elevated androgen levels in children with congenital adrenal hyperplasia. The Journal of clinical endocrinology and metabolism. 2000 Mar; 85(3):1114-20. doi: 10.1210/jcem.85.3.6462. [PMID: 10720048]
  • E A Cummings, S R Salisbury, M L Givner, R S Rittmaster. Testolactone-associated high androgen levels, a pharmacologic effect or a laboratory artifact?. The Journal of clinical endocrinology and metabolism. 1998 Mar; 83(3):784-7. doi: 10.1210/jcem.83.3.4623. [PMID: 9506727]
  • A G Herzog, P Klein, A R Jacobs. Testosterone versus testosterone and testolactone in treating reproductive and sexual dysfunction in men with epilepsy and hypogonadism. Neurology. 1998 Mar; 50(3):782-4. doi: 10.1212/wnl.50.3.782. [PMID: 9521275]
  • J M Zmuda, L L Bausserman, D Maceroni, P D Thompson. The effect of supraphysiologic doses of testosterone on fasting total homocysteine levels in normal men. Atherosclerosis. 1997 Apr; 130(1-2):199-202. doi: 10.1016/s0021-9150(96)06057-1. [PMID: 9126665]
  • L Laue, D P Merke, J V Jones, K M Barnes, S Hill, G B Cutler. A preliminary study of flutamide, testolactone, and reduced hydrocortisone dose in the treatment of congenital adrenal hyperplasia. The Journal of clinical endocrinology and metabolism. 1996 Oct; 81(10):3535-9. doi: 10.1210/jcem.81.10.8855797. [PMID: 8855797]
  • C J Bagatell, R H Knopp, J E Rivier, W J Bremner. Physiological levels of estradiol stimulate plasma high density lipoprotein2 cholesterol levels in normal men. The Journal of clinical endocrinology and metabolism. 1994 Apr; 78(4):855-61. doi: 10.1210/jcem.78.4.8157711. [PMID: 8157711]
  • P P Feuillan, J Jones, G B Cutler. Long-term testolactone therapy for precocious puberty in girls with the McCune-Albright syndrome. The Journal of clinical endocrinology and metabolism. 1993 Sep; 77(3):647-51. doi: 10.1210/jcem.77.3.8370686. [PMID: 8370686]
  • J M Zmuda, M C Fahrenbach, B T Younkin, L L Bausserman, R B Terry, D H Catlin, P D Thompson. The effect of testosterone aromatization on high-density lipoprotein cholesterol level and postheparin lipolytic activity. Metabolism: clinical and experimental. 1993 Apr; 42(4):446-50. doi: 10.1016/0026-0495(93)90101-s. [PMID: 8487666]
  • L Laue, J Jones, K M Barnes, G B Cutler. Treatment of familial male precocious puberty with spironolactone, testolactone, and deslorelin. The Journal of clinical endocrinology and metabolism. 1993 Jan; 76(1):151-5. doi: 10.1210/jcem.76.1.8421081. [PMID: 8421081]
  • P P Feuillan, J Jones, K E Oerter, P K Manasco, G B Cutler. Luteinizing hormone-releasing hormone (LHRH)-independent precocious puberty unresponsive to LHRH agonist therapy in two girls lacking features of the McCune-Albright syndrome. The Journal of clinical endocrinology and metabolism. 1991 Dec; 73(6):1370-3. doi: 10.1210/jcem-73-6-1370. [PMID: 1955519]
  • N Itoh, Y Kumamoto, H Maruta, T Tsukamoto, Y Takagi, N Mikuma, A Nanbu, H Tachiki. [Therapeutic efficacy of testolactone (aromatase inhibitor) to oligozoospermia with high estradiol/testosterone ratio]. Nihon Hinyokika Gakkai zasshi. The japanese journal of urology. 1991 Feb; 82(2):204-9. doi: 10.5980/jpnjurol1989.82.204. [PMID: 2041267]
  • A G Herzog. Reproductive endocrine considerations and hormonal therapy for men with epilepsy. Epilepsia. 1991; 32 Suppl 6(?):S34-7. doi: 10.1111/j.1528-1157.1991.tb05890.x. [PMID: 1959510]
  • K E Friedl, C J Hannan, R E Jones, S R Plymate. High-density lipoprotein cholesterol is not decreased if an aromatizable androgen is administered. Metabolism: clinical and experimental. 1990 Jan; 39(1):69-74. doi: 10.1016/0026-0495(90)90150-b. [PMID: 2294373]
  • R V Clark, R J Sherins. Treatment of men with idiopathic oligozoospermic infertility using the aromatase inhibitor, testolactone. Results of a double-blinded, randomized, placebo-controlled trial with crossover. Journal of andrology. 1989 May; 10(3):240-7. doi: 10.1002/j.1939-4640.1989.tb00094.x. [PMID: 2663800]
  • U Maier, G Hienert. Tamoxifen and testolactone in therapy of oligozoospermia: results of a randomized study. European urology. 1988; 14(6):447-9. doi: 10.1159/000473006. [PMID: 3141194]
  • B Zumoff. Hormonal abnormalities in obesity. Acta medica Scandinavica. Supplementum. 1988; 723(?):153-60. doi: 10.1111/j.0954-6820.1987.tb05939.x. [PMID: 3293358]
  • H Sekihara, K Yonemitsu, F Takaku. Enhancement of the hypertensinogenic action of 19-hydroxyandrostenedione by aromatase inhibitor, delta 1-testololactone. Endocrinology. 1987 Dec; 121(6):1931-6. doi: 10.1210/endo-121-6-1931. [PMID: 3678133]
  • W B Schill, F Reiter, H C Korting, H U Schweikert. [Long-term therapy of oligozoospermia with the aromatase inhibitor testolactone]. Der Hautarzt; Zeitschrift fur Dermatologie, Venerologie, und verwandte Gebiete. 1987 Jul; 38(7):395-9. doi: . [PMID: 3115914]
  • P P Feuillan, C M Foster, O H Pescovitz, K D Hench, T Shawker, A Dwyer, J D Malley, K Barnes, D L Loriaux, G B Cutler. Treatment of precocious puberty in the McCune-Albright syndrome with the aromatase inhibitor testolactone. The New England journal of medicine. 1986 Oct; 315(18):1115-9. doi: 10.1056/nejm198610303151802. [PMID: 3093862]
  • J M Dony, A G Smals, R Rolland, B C Fauser, C M Thomas. Effect of chronic aromatase inhibition by delta 1-testolactone on pituitary-gonadal function in oligozoospermic men. Andrologia. 1986 Jan; 18(1):69-78. doi: 10.1111/j.1439-0272.1986.tb01741.x. [PMID: 3082244]
  • M Zachmann, U Eiholzer, M Muritano, E A Werder, B Manella. Treatment of pubertal gynaecomastia with testolactone. Acta endocrinologica. Supplementum. 1986; 279(?):218-26. doi: 10.1530/acta.0.112s218. [PMID: 3535334]
  • R J Santen, D Leszczynski, N Tilson-Mallet, P D Feil, C Wright, A Manni, S J Santner. Enzymatic control of estrogen production in human breast cancer: relative significance of aromatase versus sulfatase pathways. Annals of the New York Academy of Sciences. 1986; 464(?):126-37. doi: 10.1111/j.1749-6632.1986.tb16000.x. [PMID: 3524346]
  • C M Foster, O H Pescovitz, F Comite, P Feuillan, T Shawker, D L Loriaux, G B Cutler. Testolactone treatment of precocious puberty in McCune-Albright syndrome. Acta endocrinologica. 1985 Jun; 109(2):254-7. doi: 10.1530/acta.0.1090254. [PMID: 3925675]
  • A G Smals, J M Dony, A E Smals, G F Pieters, A R Hermus, G H Boers, T J Benraad, P W Kloppenborg. Aromatase inhibition by delta 1-testolactone does not relieve the gonadotropin-induced late steroidogenic block in normal men. The Journal of clinical endocrinology and metabolism. 1985 Jun; 60(6):1127-31. doi: 10.1210/jcem-60-6-1127. [PMID: 3923019]
  • J M Dony, A G Smals, R Rolland, B C Fauser, C M Thomas. Effect of aromatase inhibition by delta 1-testolactone on basal and luteinizing hormone-releasing hormone-stimulated pituitary and gonadal hormonal function in oligospermic men. Fertility and sterility. 1985 May; 43(5):787-92. doi: 10.1016/s0015-0282(16)48567-5. [PMID: 3922803]
  • H Martikainen, A Ruokonen, L Rönnberg, R Vihko. Short-term effects of testolactone on human testicular steroid production and on the response to human chorionic gonadotropin. Fertility and sterility. 1985 May; 43(5):793-8. doi: 10.1016/s0015-0282(16)48568-7. [PMID: 3922804]
  • H M Nagler, R deVere White, I Dyrenfurth, W C Hembree. The effect of delta 1-testolactone on serum testosterone and estradiol in the adult male rat. Fertility and sterility. 1983 Dec; 40(6):818-22. doi: 10.1016/s0015-0282(16)47487-x. [PMID: 6653801]
  • N Tilson-Mallett, S J Santner, P D Feil, R J Santen. Biological significance of aromatase activity in human breast tumors. The Journal of clinical endocrinology and metabolism. 1983 Dec; 57(6):1125-8. doi: 10.1210/jcem-57-6-1125. [PMID: 6630410]
  • V L Pascucci, R L Yeager, R J Sherins, R V Clark, J F Gallelli, D C Chatterji. Quantitation of testolactone and 4,5-dihydrotestolactone in plasma and urine using high-performance liquid chromatography. Journal of chromatography. 1983 Oct; 277(?):79-85. doi: 10.1016/s0378-4347(00)84825-2. [PMID: 6643639]
  • R D'Agata, A Aliffi, G Maugeri, A Mongioi, E Vicari, S Gulizia, P Polosa. Hydrotestolactone lowers serum oestradiol and PRL levels in normal men: evidence of a role of oestradiol in prl secretion. Clinical endocrinology. 1982 Nov; 17(5):495-9. doi: 10.1111/j.1365-2265.1982.tb01617.x. [PMID: 7172459]
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  • R A Vigersky, D Mozingo, C Eil, V Purohit, J Bruton. The antiandrogenic effects of delta 1-testolactone (Teslac) in vivo in rats and in vitro in human cultured fibroblasts, rat mammary carcinoma cells, and rat prostate cytosol. Endocrinology. 1982 Jan; 110(1):214-9. doi: 10.1210/endo-110-1-214. [PMID: 7053985]
  • P Leinonen, N J Bolton, M Kontturi, R Vihko. Rapid endocrine effects of tamoxifen and testolactone in prostatic carcinoma patients. The Prostate. 1982; 3(6):589-97. doi: 10.1002/pros.2990030608. [PMID: 7155991]
  • R D'Agata, E Vicari, A Aliffi, S Gulizia, G Palumbo. Direct evidence in men for a role of endogenous oestrogens on gonadotrophin release. Acta endocrinologica. 1981 Jun; 97(2):145-9. doi: 10.1530/acta.0.0970145. [PMID: 6785950]
  • R A Vigersky, A R Glass. Effects of delta 1-testolactone on the pituitary-testicular axis in oligospermic men. The Journal of clinical endocrinology and metabolism. 1981 May; 52(5):897-902. doi: 10.1210/jcem-52-5-897. [PMID: 6785292]
  • R M Barone, I M Shamonki, P K Siiteri, H L Judd. Inhibition of peripheral aromatization of androstenedione to estrone in postmenopausal women with breast cancer using delta 1-testololactone. The Journal of clinical endocrinology and metabolism. 1979 Nov; 49(5):672-6. doi: 10.1210/jcem-49-5-672. [PMID: 489709]
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