2-hydroxyflutamide (BioDeep_00000002431)

   

human metabolite Endogenous blood metabolite Chemicals and Drugs


代谢物信息卡片


2-hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanimidic acid

化学式: C11H11F3N2O4 (292.0670882)
中文名称: 羟基氟他胺
谱图信息: 最多检出来源 Danio rerio(blood) 9.52%

分子结构信息

SMILES: CC(C)(C(=O)NC1=CC(=C(C=C1)[N+](=O)[O-])C(F)(F)F)O
InChI: InChI=1S/C11H11F3N2O4/c1-10(2,18)9(17)15-6-3-4-8(16(19)20)7(5-6)11(12,13)14/h3-5,18H,1-2H3,(H,15,17)

描述信息

2-hydroxyflutamide is a metabolite of flutamide. Flutamide is an oral nonsteroidal antiandrogen drug primarily used to treat prostate cancer. It competes with testosterone and its powerful metabolite, dihydrotestosterone (DHT) for binding to androgen receptors in the prostate gland. By doing so, it prevents them from stimulating the prostate cancer cells to grow. Flutamide has been largely replaced by a newer member of this class, bicalutamide, due to a better side-effect profile. (Wikipedia)
CONFIDENCE standard compound; INTERNAL_ID 401; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4455; ORIGINAL_PRECURSOR_SCAN_NO 4452
CONFIDENCE standard compound; INTERNAL_ID 401; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4545; ORIGINAL_PRECURSOR_SCAN_NO 4543
CONFIDENCE standard compound; INTERNAL_ID 401; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4476; ORIGINAL_PRECURSOR_SCAN_NO 4471
CONFIDENCE standard compound; INTERNAL_ID 401; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4446; ORIGINAL_PRECURSOR_SCAN_NO 4442
CONFIDENCE standard compound; INTERNAL_ID 401; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4449; ORIGINAL_PRECURSOR_SCAN_NO 4447
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006727 - Hormone Antagonists > D000726 - Androgen Antagonists
C274 - Antineoplastic Agent > C163758 - Targeted Therapy Agent > C146993 - Androgen Receptor Inhibitor
C147908 - Hormone Therapy Agent > C547 - Hormone Antagonist > C242 - Anti-Androgen

同义名列表

4 个代谢物同义名

2-hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanimidic acid; 2-Hydroxyflutamide; Hydroxyflutamide; OH-Flutamide



数据库引用编号

19 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

  • R Z Huang, Y W Wang, H Y Huang, R H Jiang, N N Xue, S P Yin, H Y Zhao. [Application effect of a dual release system of androgen and its antagonist in the repair of full-thickness burn wounds in mice]. Zhonghua shao shang yu chuang mian xiu fu za zhi. 2024 Feb; 40(2):180-189. doi: 10.3760/cma.j.cn501225-20230802-00033. [PMID: 38418180]
  • Teuvo L Tammela, Michael Häggman, Sam Ladjevardi, Kimmo Taari, Taina Isotalo, Hans Lennernäs, Jan Weis, Catrin von Below, Cecilia Wassberg, Bo Lennernäs, Anna Tolf, Niklas Axén, Carl-Gustaf Gölander, Håkan Ahlström. An Intraprostatic Modified Release Formulation of Antiandrogen 2-Hydroxyflutamide for Localized Prostate Cancer. The Journal of urology. 2017 12; 198(6):1333-1339. doi: 10.1016/j.juro.2017.07.072. [PMID: 28736321]
  • Francisco Javier Mendoza, Juan Manuel Serrano-Rodriguez, Antonio Buzon-Cuevas, Alejandro Perez-Ecija. Pharmacokinetics of the anti-androgenic drug flutamide in healthy stallions. Veterinary journal (London, England : 1997). 2017 Jun; 224(?):50-54. doi: 10.1016/j.tvjl.2017.06.001. [PMID: 28697876]
  • Hiroyuki Kojima, Shinji Takeuchi, Nele Van den Eede, Adrian Covaci. Effects of primary metabolites of organophosphate flame retardants on transcriptional activity via human nuclear receptors. Toxicology letters. 2016 Mar; 245(?):31-9. doi: 10.1016/j.toxlet.2016.01.004. [PMID: 26778350]
  • Nada Lallous, Stanislav V Volik, Shannon Awrey, Eric Leblanc, Ronnie Tse, Josef Murillo, Kriti Singh, Arun A Azad, Alexander W Wyatt, Stephane LeBihan, Kim N Chi, Martin E Gleave, Paul S Rennie, Colin C Collins, Artem Cherkasov. Functional analysis of androgen receptor mutations that confer anti-androgen resistance identified in circulating cell-free DNA from prostate cancer patients. Genome biology. 2016 Jan; 17(?):10. doi: 10.1186/s13059-015-0864-1. [PMID: 26813233]
  • Marta Zarzycka, Malgorzata Kotwicka, Magdalena Jendraszak, Izabela Skibinska, Malgorzata Kotula-Balak, Barbara Bilinska. Hydroxyflutamide alters the characteristics of live boar spermatozoa. Theriogenology. 2014 Oct; 82(7):988-96. doi: 10.1016/j.theriogenology.2014.07.013. [PMID: 25129871]
  • Erik Sjögren, Teuvo L Tammela, Bo Lennernäs, Kimmo Taari, Taina Isotalo, Lars-Åke Malmsten, Niklas Axén, Hans Lennernäs. Pharmacokinetics of an injectable modified-release 2-hydroxyflutamide formulation in the human prostate gland using a semiphysiologically based biopharmaceutical model. Molecular pharmaceutics. 2014 Sep; 11(9):3097-111. doi: 10.1021/mp5002813. [PMID: 25055161]
  • M Lydka, M Piasecka, D Gaczarzewicz, M Koziorowski, B Bilinska. Administration of flutamide alters sperm ultrastructure, sperm plasma membrane integrity and its stability, and sperm mitochondrial oxidative capability in the boar: in vivo and in vitro approach. Reproduction in domestic animals = Zuchthygiene. 2012 Aug; 47(4):635-43. doi: 10.1111/j.1439-0531.2011.01935.x. [PMID: 22050361]
  • Michel Aubé, Christian Larochelle, Pierre Ayotte. Differential effects of a complex organochlorine mixture on the proliferation of breast cancer cell lines. Environmental research. 2011 Apr; 111(3):337-47. doi: 10.1016/j.envres.2011.01.010. [PMID: 21295777]
  • Jessica Amadio, Cormac D Murphy. Production of human metabolites of the anti-cancer drug flutamide via biotransformation in Cunninghamella species. Biotechnology letters. 2011 Feb; 33(2):321-6. doi: 10.1007/s10529-010-0425-3. [PMID: 20931353]
  • Heng Zheng, Dan Wu, Zhen-yu Qian, Yi Xiang. Determination of 2-hydroxyflutamide in human plasma by liquid chromatography-tandem mass spectrometry (LC-MS/MS): application to a bioequivalence study on Chinese volunteers. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2010 Jun; 878(19):1611-5. doi: 10.1016/j.jchromb.2010.03.042. [PMID: 20427247]
  • Michel Aubé, Christian Larochelle, Pierre Ayotte. 1,1-dichloro-2,2-bis(p-chlorophenyl)ethylene (p,p'-DDE) disrupts the estrogen-androgen balance regulating the growth of hormone-dependent breast cancer cells. Breast cancer research : BCR. 2008; 10(1):R16. doi: 10.1186/bcr1862. [PMID: 18275596]
  • Annica Tevell, Hans Lennernäs, Mats Jönsson, Maria Norlin, Bo Lennernäs, Ulf Bondesson, Mikael Hedeland. Flutamide metabolism in four different species in vitro and identification of flutamide metabolites in human patient urine by high performance liquid chromatography/tandem mass spectrometry. Drug metabolism and disposition: the biological fate of chemicals. 2006 Jun; 34(6):984-92. doi: 10.1124/dmd.105.008516. [PMID: 16540588]
  • A A L Ajayi, P V Halushka. Castration reduces platelet thromboxane A2 receptor density and aggregability. QJM : monthly journal of the Association of Physicians. 2005 May; 98(5):349-56. doi: 10.1093/qjmed/hci054. [PMID: 15820970]
  • Wenqing Gao, Jeffrey D Kearbey, Vipin A Nair, Kiwon Chung, A F Parlow, Duane D Miller, James T Dalton. Comparison of the pharmacological effects of a novel selective androgen receptor modulator, the 5alpha-reductase inhibitor finasteride, and the antiandrogen hydroxyflutamide in intact rats: new approach for benign prostate hyperplasia. Endocrinology. 2004 Dec; 145(12):5420-8. doi: 10.1210/en.2004-0627. [PMID: 15308613]
  • Masahiko Harano, Masako Kano, Tsukasa Hida, Yasuhito Fujisawa, Motonori Kano. [Examination of the change in plasma concentration of OH-flutamide in low-dose flutamide (250 mg/day) monotherapy for prostate cancer patients]. Gan to kagaku ryoho. Cancer & chemotherapy. 2004 Mar; 31(3):377-80. doi: NULL. [PMID: 15045944]
  • Shengjun Qiao, Pasi Pennanen, Nadja Nazarova, Yan-Ru Lou, Pentti Tuohimaa. Inhibition of fatty acid synthase expression by 1alpha,25-dihydroxyvitamin D3 in prostate cancer cells. The Journal of steroid biochemistry and molecular biology. 2003 May; 85(1):1-8. doi: 10.1016/s0960-0760(03)00142-0. [PMID: 12798352]
  • Sonia Godoy-Tundidor, Alfred Hobisch, Karina Pfeil, Georg Bartsch, Zoran Culig. Acquisition of agonistic properties of nonsteroidal antiandrogens after treatment with oncostatin M in prostate cancer cells. Clinical cancer research : an official journal of the American Association for Cancer Research. 2002 Jul; 8(7):2356-61. doi: . [PMID: 12114440]
  • I Niopas, A C Daftsios. Determination of 2-hydroxyflutamide in human plasma by high-performance liquid chromatography and its application to pharmacokinetic studies. Journal of chromatography. B, Biomedical sciences and applications. 2001 Aug; 759(1):179-83. doi: 10.1016/s0378-4347(01)00204-3. [PMID: 11499624]
  • F M Lyng, G R Jones, F F Rommerts. Rapid androgen actions on calcium signaling in rat sertoli cells and two human prostatic cell lines: similar biphasic responses between 1 picomolar and 100 nanomolar concentrations. Biology of reproduction. 2000 Sep; 63(3):736-47. doi: 10.1095/biolreprod63.3.736. [PMID: 10952915]
  • J A McCrohon, A K Death, S Nakhla, W Jessup, D J Handelsman, K K Stanley, D S Celermajer. Androgen receptor expression is greater in macrophages from male than from female donors. A sex difference with implications for atherogenesis. Circulation. 2000 Jan; 101(3):224-6. doi: 10.1161/01.cir.101.3.224. [PMID: 10645914]
  • N Kumar, A Crozat, F Li, J F Catterall, C W Bardin, K Sundaram. 7alpha-methyl-19-nortestosterone, a synthetic androgen with high potency: structure-activity comparisons with other androgens. The Journal of steroid biochemistry and molecular biology. 1999 Dec; 71(5-6):213-22. doi: 10.1016/s0960-0760(99)00143-0. [PMID: 10704910]
  • C J Xu, D Li. Pharmacokinetics of 2-hydroxyflutamide, a major metabolite of flutamide, in normal and CCl4-poisoned rats. Zhongguo yao li xue bao = Acta pharmacologica Sinica. 1999 Jul; 20(7):655-8. doi: NULL. [PMID: 10678134]
  • S Anjum, S K Swan, L J Lambrecht, E Radwanski, D L Cutler, M B Affrime, C E Halstenson. Pharmacokinetics of flutamide in patients with renal insufficiency. British journal of clinical pharmacology. 1999 Jan; 47(1):43-7. doi: 10.1046/j.1365-2125.1999.00831.x. [PMID: 10073738]
  • M S Lucia, M B Sporn, A B Roberts, L V Stewart, D Danielpour. The role of transforming growth factor-beta1, -beta2, and -beta3 in androgen-responsive growth of NRP-152 rat prostatic epithelial cells. Journal of cellular physiology. 1998 May; 175(2):184-92. doi: 10.1002/(sici)1097-4652(199805)175:2<184::aid-jcp8>3.0.co;2-k. [PMID: 9525477]
  • L G Hamann, R I Higuchi, L Zhi, J P Edwards, X N Wang, K B Marschke, J W Kong, L J Farmer, T K Jones. Synthesis and biological activity of a novel series of nonsteroidal, peripherally selective androgen receptor antagonists derived from 1,2-dihydropyridono[5,6-g]quinolines. Journal of medicinal chemistry. 1998 Feb; 41(4):623-39. doi: 10.1021/jm970699s. [PMID: 9484511]
  • J Szelei, J Jimenez, A M Soto, M F Luizzi, C Sonnenschein. Androgen-induced inhibition of proliferation in human breast cancer MCF7 cells transfected with androgen receptor. Endocrinology. 1997 Apr; 138(4):1406-12. doi: 10.1210/endo.138.4.5047. [PMID: 9075695]
  • J H Toney, Y Chen, S J Rutledge, A Schmidt, A Elbrecht. Non-steroidal L-245,976 acts as a classical antiandrogen in vitro. The Journal of steroid biochemistry and molecular biology. 1997 Jan; 60(1-2):131-6. doi: 10.1016/s0960-0760(96)00164-1. [PMID: 9182867]
  • J Leibinger, M Kapás. New and validated high-performance liquid chromatographic method for determination of hydroxyflutamide in human plasma. Journal of pharmaceutical and biomedical analysis. 1996 Jun; 14(8-10):1377-81. doi: 10.1016/0731-7085(95)01698-8. [PMID: 8818060]
  • D W Silversides, C A Price, G M Cooke. Effects of short-term exposure to hydroxyflutamide in utero on the development of the reproductive tract in male mice. Canadian journal of physiology and pharmacology. 1995 Nov; 73(11):1582-8. doi: 10.1139/y95-718. [PMID: 8789411]
  • G Dran, I A Luthy, A A Molinolo, F Montecchia, E H Charreau, C D Pasqualini, C Lanari. Effect of medroxyprogesterone acetate (MPA) and serum factors on cell proliferation in primary cultures of an MPA-induced mammary adenocarcinoma. Breast cancer research and treatment. 1995 Aug; 35(2):173-86. doi: 10.1007/bf00668207. [PMID: 7647339]
  • V Morvillo, I A Luthy, A I Bravo, M I Capurro, M Donaldson, C Quintans, R S Calandra, J Mordoh. Atypical androgen receptor in the human melanoma cell line IIB-MEL-J. Pigment cell research. 1995 Jun; 8(3):135-41. doi: 10.1111/j.1600-0749.1995.tb00654.x. [PMID: 7567789]
  • E Gorczynska, D J Handelsman. Androgens rapidly increase the cytosolic calcium concentration in Sertoli cells. Endocrinology. 1995 May; 136(5):2052-9. doi: 10.1210/endo.136.5.7720654. [PMID: 7720654]
  • D Farthing, D Sica, I Fakhry, D L Walters, E A Cefali, G Allan. Determination of flutamide and hydroxyflutamide in dog plasma by a sensitive high performance liquid chromatography method utilizing mid-bore chromatography. Biomedical chromatography : BMC. 1994 Sep; 8(5):251-4. doi: 10.1002/bmc.1130080511. [PMID: 7841771]
  • J T Hsieh, S H Lin. Androgen regulation of cell adhesion molecule gene expression in rat prostate during organ degeneration. C-CAM belongs to a class of androgen-repressed genes associated with enriched stem/amplifying cell population after prolonged castration. The Journal of biological chemistry. 1994 Feb; 269(5):3711-6. doi: 10.1016/s0021-9258(17)41918-1. [PMID: 8106416]
  • N Warriar, N Pagé, M Koutsilieris, M V Govindan. Interaction of antiandrogen-androgen receptor complexes with DNA and transcription activation. The Journal of steroid biochemistry and molecular biology. 1993 Dec; 46(6):699-711. doi: 10.1016/0960-0760(93)90311-j. [PMID: 8274404]
  • A C Levine, M Ren, G K Huber, A Kirschenbaum. The effect of androgen, estrogen, and growth factors on the proliferation of cultured fibroblasts derived from human fetal and adult prostates. Endocrinology. 1992 Apr; 130(4):2413-9. doi: 10.1210/endo.130.4.1372243. [PMID: 1372243]
  • J Geller, L R Sionit, K Connors, R M Hoffman. Measurement of androgen sensitivity in the human prostate in in vitro three-dimensional histoculture. The Prostate. 1992; 21(4):269-78. doi: 10.1002/pros.2990210403. [PMID: 1281320]
  • R Hallowes, S Cox, S Hayward, N Deshpande, J Towler. Effects of flutamide and hydroxy-flutamide on the growth of human benign prostatic hyperplasia cells in primary culture: a preliminary report. Anticancer research. 1991 Sep; 11(5):1799-805. doi: . [PMID: 1722658]
  • Y Chandrasekhar, D T Armstrong. Effects of the antiandrogen hydroxyflutamide on progesterone secretion by preovulatory rat follicles in vivo and in vitro. Canadian journal of physiology and pharmacology. 1991 Sep; 69(9):1288-93. doi: 10.1139/y91-189. [PMID: 1756426]
  • F H Yu, Y W Yun, B H Yuen, Y S Moon. Effects of hydroxyflutamide on rats treated with a superovulatory dose of pregnant mare serum gonadotropin. Canadian journal of physiology and pharmacology. 1991 Feb; 69(2):185-90. doi: 10.1139/y91-027. [PMID: 2054733]
  • R H Asade, L Prizont, J P Muiño, J Tessler. Steady-state hydroxyflutamide plasma levels after the administration of two dosage forms of flutamide. Cancer chemotherapy and pharmacology. 1991; 27(5):401-5. doi: 10.1007/bf00688866. [PMID: 1999002]
  • A Reznikov. Feedback control of gonadotropin secretion in mammalian and human males: effects of gonadotropin receptor blockers. Endocrinologia experimentalis. 1990 Mar; 24(1-2):267-73. doi: NULL. [PMID: 2113858]
  • N Olea, K Sakabe, A M Soto, C Sonnenschein. The proliferative effect of "anti-androgens" on the androgen-sensitive human prostate tumor cell line LNCaP. Endocrinology. 1990 Mar; 126(3):1457-63. doi: 10.1210/endo-126-3-1457. [PMID: 2307113]
  • Y Chandrasekhar, D T Armstrong, T G Kennedy. Implantation delay and anti-deciduogenic activity in the rat by the anti-androgen, hydroxyflutamide. Biology of reproduction. 1990 Jan; 42(1):120-5. doi: 10.1095/biolreprod42.1.120. [PMID: 2310812]
  • E Radwanski, G Perentesis, S Symchowicz, N Zampaglione. Single and multiple dose pharmacokinetic evaluation of flutamide in normal geriatric volunteers. Journal of clinical pharmacology. 1989 Jun; 29(6):554-8. doi: 10.1002/j.1552-4604.1989.tb03381.x. [PMID: 2754024]
  • C H Kasperk, J E Wergedal, J R Farley, T A Linkhart, R T Turner, D J Baylink. Androgens directly stimulate proliferation of bone cells in vitro. Endocrinology. 1989 Mar; 124(3):1576-8. doi: 10.1210/endo-124-3-1576. [PMID: 2521824]
  • Y Chandrasekhar, D T Armstrong. Ability of progesterone to reverse anti-androgen (hydroxyflutamide)-induced interference with the preovulatory LH surge and ovulation in PMSG-primed immature rats. Journal of reproduction and fertility. 1989 Jan; 85(1):309-16. doi: 10.1530/jrf.0.0850309. [PMID: 2915358]
  • T A Swift, J A Dias. Testosterone suppression of ornithine decarboxylase activity in rat Sertoli cells. Endocrinology. 1988 Aug; 123(2):687-93. doi: 10.1210/endo-123-2-687. [PMID: 2840265]
  • Y Chandrasekhar, D T Armstrong. Human chorionic gonadotropin and luteinizing hormone-releasing hormone reverse the blockade of ovulation in pregnant mare's serum gonadotropin-primed immature rats by the anti-androgenic drug, hydroxyflutamide. Canadian journal of physiology and pharmacology. 1988 Jun; 66(6):783-7. doi: 10.1139/y88-124. [PMID: 3048618]
  • M Schulz, A Schmoldt, F Donn, H Becker. The pharmacokinetics of flutamide and its major metabolites after a single oral dose and during chronic treatment. European journal of clinical pharmacology. 1988; 34(6):633-6. doi: 10.1007/bf00615229. [PMID: 3169114]
  • A Bélanger, M Giasson, J Couture, A Dupont, L Cusan, F Labrie. Plasma levels of hydroxy-flutamide in patients with prostatic cancer receiving the combined hormonal therapy: an LHRH agonist and flutamide. The Prostate. 1988; 12(1):79-84. doi: 10.1002/pros.2990120110. [PMID: 3279409]
  • N V Sologub, S V Varga. [Antiandrogenic effects of hydroxyniftolide in male rats]. Problemy endokrinologii. 1987 Jul; 33(4):74-6. doi: NULL. [PMID: 3658955]
  • M A Opavsky, Y Chandrasekhar, M Roe, D T Armstrong. Interference with the preovulatory luteinizing hormone surge and blockade of ovulation in immature pregnant mare's serum gonadotropin-primed rats with the anti-androgenic drug, hydroxyflutamide. Biology of reproduction. 1987 Apr; 36(3):636-42. doi: 10.1095/biolreprod36.3.636. [PMID: 3593836]
  • D J Handelsman, J A Spaliviero, J R Turtle. Hypothalamic-pituitary function in experimental uremic hypogonadism. Endocrinology. 1985 Nov; 117(5):1984-95. doi: 10.1210/endo-117-5-1984. [PMID: 3930221]
  • H Takahashi, A J Duleba, B H Yuen, Y S Moon. Steroidogenic capabilities of various compartments of rat ovarian follicles in culture. Steroids. 1984 Oct; 44(4):337-48. doi: 10.1016/s0039-128x(84)80026-4. [PMID: 6545071]
  • C R Clark, B J Merry, N W Nowell. Effect of alpha, alpha, alpha-trifluoro-2-methyl-4'-nitro-m-lactotoluidide (Sch 16423) on serum testosterone and LH in rats. Journal of reproduction and fertility. 1981 Jan; 61(1):189-91. doi: 10.1530/jrf.0.0610189. [PMID: 7452616]