Cyclofenil (BioDeep_00000177806)

 

Secondary id: BioDeep_00000015141

human metabolite blood metabolite


代谢物信息卡片


4-{[4-(acetyloxy)phenyl](cyclohexylidene)methyl}phenyl acetic acid

化学式: C23H24O4 (364.1674504)
中文名称: 环芬尼
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC(=O)OC1=CC=C(C=C1)C(=C1CCCCC1)C1=CC=C(OC(C)=O)C=C1
InChI: InChI=1S/C23H24O4/c1-16(24)26-21-12-8-19(9-13-21)23(18-6-4-3-5-7-18)20-10-14-22(15-11-20)27-17(2)25/h8-15H,3-7H2,1-2H3

描述信息

G - Genito urinary system and sex hormones > G03 - Sex hormones and modulators of the genital system > G03G - Gonadotropins and other ovulation stimulants > G03GB - Ovulation stimulants, synthetic
C274 - Antineoplastic Agent > C129818 - Antineoplastic Hormonal/Endocrine Agent > C481 - Antiestrogen
D012102 - Reproductive Control Agents > D005299 - Fertility Agents
C147908 - Hormone Therapy Agent > C547 - Hormone Antagonist

同义名列表

7 个代谢物同义名

4-{[4-(acetyloxy)phenyl](cyclohexylidene)methyl}phenyl acetic acid; 4-{[4-(acetyloxy)phenyl](cyclohexylidene)methyl}phenyl acetate; 4-((4-(Acetyloxy)phenyl)cyclohexylidenemethyl)phenol acetate; Cyclophenil; Cyclofenil; Ondogyne; Sexovid



数据库引用编号

10 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

  • Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. Cell reports. 2021 04; 35(4):109040. doi: 10.1016/j.celrep.2021.109040. [PMID: 33910017]
  • 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]
  • D Eads, Rl Hansen, Ao Oyegunwa, Ce Cecil, Ca Culver, F Scholle, Itd Petty, Sm Laster. Terameprocol, a methylated derivative of nordihydroguaiaretic acid, inhibits production of prostaglandins and several key inflammatory cytokines and chemokines. Journal of inflammation (London, England). 2009 Jan; 6(?):2. doi: 10.1186/1476-9255-6-2. [PMID: 19133137]
  • Peter Gärtner, Karin Hofbauer, Christian Reichel, Thomas Geisendorfer, Günter Gmeiner. Synthesis and identification of hydroxylated metabolites of the anti-estrogenic agent cyclofenil. Journal of mass spectrometry : JMS. 2008 Jul; 43(7):958-64. doi: 10.1002/jms.1462. [PMID: 18576435]
  • Seung-Woon Myung, Hye-Ki Min, Dong-Hyun Kim, Myungsoo Kim, SuJin Cha, Eun-Ah Yoo, Yong-Hyeon Yim. Mass spectrometric analysis of cyclofenil and its metabolites in human urine. Rapid communications in mass spectrometry : RCM. 2002; 16(8):761-7. doi: 10.1002/rcm.636. [PMID: 11921260]
  • S Batra, C S Iosif. Elevated concentrations of antiestrogen binding sites in membrane fractions of human ovarian tumors. Gynecologic oncology. 1996 Feb; 60(2):228-32. doi: 10.1006/gyno.1996.0030. [PMID: 8631543]
  • R M Mason, C A Lancaster. Effects of cyclofenil diphenol, an agent which disrupts Golgi structure, on proteoglycan synthesis in chondrocytes. The Biochemical journal. 1992 Jan; 281 ( Pt 2)(?):525-31. doi: 10.1042/bj2810525. [PMID: 1736900]
  • E L Yong, A Glasier, H Hillier, W Ledger, L Caird, G Beattie, V Sweeting, J Thong, D T Baird. Effect of cyclofenil on hormonal dynamics, follicular development and cervical mucus in normal and oligomenorrhoeic women. Human reproduction (Oxford, England). 1992 Jan; 7(1):39-43. doi: 10.1093/oxfordjournals.humrep.a137553. [PMID: 1551955]
  • A Akesson, B Blom-Bülow, A Scheja, P Wollmer, S Valind, F A Wollheim. Long-term evaluation of penicillamine or cyclofenil in systemic sclerosis. Results from a two-year randomized study. Scandinavian journal of rheumatology. 1992; 21(5):238-44. doi: 10.3109/03009749209099231. [PMID: 1439632]
  • A Scheja, A Akesson, K Hørslev-Petersen. Serum levels of aminoterminal type III procollagen peptide and hyaluronan predict mortality in systemic sclerosis. Scandinavian journal of rheumatology. 1992; 21(1):5-9. doi: 10.3109/03009749209095054. [PMID: 1570489]
  • C A Lancaster, P R Fryer, S Griffiths, R M Mason. Ultrastructural changes accompany inhibition of proteoglycan synthesis in chondrocytes by Cyclofenil diphenol. Journal of cell science. 1989 Feb; 92 ( Pt 2)(?):271-80. doi: 10.1242/jcs.92.2.271. [PMID: 2777926]
  • T R Varma, R H Patel, U Pillai. Ultrasonic assessment of ovulation in cyclofenil induced ovulatory cycles. International journal of gynaecology and obstetrics: the official organ of the International Federation of Gynaecology and Obstetrics. 1988 Oct; 27(2):231-8. doi: 10.1016/0020-7292(88)90013-6. [PMID: 2903090]
  • M S D'Amato, G Morozzi, A Renieri, A Fioravanti, A Taddeo, E Parrini, A A Calabria. [Influence of some sexual hormones on the binding of uric acid- plasma proteins: ex vivo and in vitro experience]. Bollettino della Societa italiana di biologia sperimentale. 1985 Aug; 61(8):1177-83. doi: NULL. [PMID: 4063107]
  • G Herbai, S Ljunghall. Lipid-lowering effects of two synthetic oestrogen derivatives with weak genital oestrogen properties. Upsala journal of medical sciences. 1985; 90(1):67-72. doi: 10.3109/03009738509178641. [PMID: 4002442]
  • R M Mason, J D Lineham, M A Phillipson, C M Black. Selective inhibition of proteoglycan and hyaluronate synthesis in chondrocyte cultures by cyclofenil diphenol, a non-steroidal weak oestrogen. The Biochemical journal. 1984 Oct; 223(2):401-12. doi: 10.1042/bj2230401. [PMID: 6437390]
  • G Herbai, S Ljunghall. Treatment of primary hyperparathyroidism with cyclofenil--a synthetic stilbestrol derivative with minimal feminizing effects. Hormone and metabolic research = Hormon- und Stoffwechselforschung = Hormones et metabolisme. 1984 Jul; 16(7):374-6. doi: 10.1055/s-2007-1014794. [PMID: 6489922]
  • G Moggi, O Giampietro, I De Luca Brunori. Bromocryptine-cyclofenil associated therapy: an effective and safe mode of treatment of female normoprolactinemic infertility. Acta Europaea fertilitatis. 1983 Sep; 14(5):319-25. doi: . [PMID: 6424373]
  • G Thorbert, M Akerlund. Inhibition of lactation by cyclofenil and bromocriptine. British journal of obstetrics and gynaecology. 1983 Aug; 90(8):739-42. doi: 10.1111/j.1471-0528.1983.tb09304.x. [PMID: 6411113]
  • T Nencioni, A Miragoli, M G Bertaglia, J Parini. Plasma FSH, LH and prolactin levels in postmenopausal women undergoing cyclofenil treatment. Acta obstetricia et gynecologica Scandinavica. 1982; 61(6):487-90. doi: 10.3109/00016348209156597. [PMID: 6299050]
  • L Schubert, M L Livello, M Belloni, F Polvani. Changes in calcium absorption during hormonal replacement therapy in postmenopausal osteoporosis. Acta Europaea fertilitatis. 1981 Sep; 12(3):223-37. doi: NULL. [PMID: 7340364]
  • L Borgström. Plasma levels and pharmacokinetics of cyclofenil after oral administration to man. European journal of clinical pharmacology. 1981 Feb; 19(3):213-6. doi: 10.1007/bf00561952. [PMID: 7215420]
  • D Bentue-Ferrer, J van den Driessche, J Duval. [Action of epimestrol on pituitary thymidine kinase and gonadotropins in the rat. Comparison with clomiphene and cyclofenil (author's transl)]. Annales d'endocrinologie. 1980 May; 41(3):203-14. doi: . [PMID: 6774656]
  • F Polati, P Pesando, C Nava, C Zara. Serum prolactin levels during inhibition of lactation by cyclofenil. Clinical and experimental obstetrics & gynecology. 1980; 7(2):131-4. doi: NULL. [PMID: 7249350]
  • T P Singh, A K Singh. Ovarian activity, and total gonadotrophin and gonadotrophin releasing hormone levels in response to some synthetic non-steroidal ovulating agents in the catfish, Heteropneustes fossilis (Bloch). The Journal of endocrinology. 1979 Sep; 82(3):341-5. doi: 10.1677/joe.0.0820341. [PMID: 117067]
  • C Ciocîrdia, A Cristoveanu, A Tache, M Bunea, M Popa. The level of urinary and plasma steroids after oral administration of cyclofenil to hirsute women with menstrual disorders and obesity. Endocrinologie. 1979 Jul; 17(3):197-200. doi: NULL. [PMID: 504960]
  • L Mettler, E Brandl, H Dahlen, K J Gräf. [Ovulation induction by cyclofenil (author's transl)]. MMW, Munchener medizinische Wochenschrift. 1977 Dec; 119(48):1553-6. doi: NULL. [PMID: 414097]
  • A K Singh, T P Singh. Thyroid activity and TSH levels in pituitary gland and blood serum in response to clomid, sexovid and prostaglandins treatment in Heteropneustes fossilis (Bloch). Endokrinologie. 1977 Sep; 70(1):69-76. doi: NULL. [PMID: 923531]
  • C Melega, V M Jasonni, A Di Leo, S Venturoli, G Fuschini, C Flamigni. Induction of ovulation with cyclophenyl. Acta Europaea fertilitatis. 1977 Jun; 8(2):119-32. doi: NULL. [PMID: 335763]
  • L Schubert, G Sansa, T Nencioni, F Polvani, C Pruneri, M Sostero, A D Peruzy, A M De Santis. The use of cyclofenil in menopausal women. Acta Europaea fertilitatis. 1977 Mar; 8(1):83-110. doi: NULL. [PMID: 868455]
  • D De Aloysio, A Fronticelli, S Venturoli, P Farello, M Nardi, C Flamigni. [Dynamic tests with GnRH, L-dopa, clomiphene, cyclophenyl, HCG and HMG in 98 cases of dysspermia due to a variety of causes]. Acta Europaea fertilitatis. 1977 Mar; 8(1):1-59. doi: . [PMID: 325983]
  • G Herbai, B Blom, H Boström. Treatment of progressive systemic sclerosis (scleroderma, PSS) with a new drug influencing connective tissue. Acta medica Scandinavica. 1977; 201(3):203-6. doi: 10.1111/j.0954-6820.1977.tb15682.x. [PMID: 848357]
  • B S Sengupta. Defective luteal phase--measurement and evaluation of the ovarian hormone before and during cyclofenil (bis-P-acetoxphenyl) cyclo-hexylidenemethane (Compound 6066) treatment. The West Indian medical journal. 1976 Jun; 25(2):107-20. doi: NULL. [PMID: 960689]
  • A K Singh, T P Singh. Effect of clomid, sexovid and prostaglandins on induction of ovulation and gonadotropin secretion in a freshwater catfish, Heteropneustes fossilis (Bloch). Endokrinologie. 1976; 68(2):129-36. doi: NULL. [PMID: 1009898]
  • B S Sengupta. Clinical aspects of defective luteal phase and its treatment with cyclofenil. The West Indian medical journal. 1975 Dec; 24(4):182-95. doi: NULL. [PMID: 1224629]
  • W Schmitt, W Nocke, M Hamacher, G Leyendecker, M Hansmann. [Steriod and proteohormones in the urine and blood in hydatidiform mole pregnancies following normal and induced ovulation]. Archiv fur Gynakologie. 1975 Nov; 219(1-4):599-602. doi: 10.1007/bf00669269. [PMID: 1243504]
  • F Cismigiu, A Ruffié. [Hormonal behavior during the menstrual cycle after administration of cyclofenil]. Journal de gynecologie, obstetrique et biologie de la reproduction. 1974 Oct; 3(7):997-1014. doi: NULL. [PMID: 4470780]
  • K Iida, S Hashimoto, T Motoe. [Changes of blood LH, FSH as well as urinary LH in sterile patients (author's transl)]. Nihon Funin Gakkai zasshi. 1974 Oct; 19(4):1-5. doi: NULL. [PMID: 4478826]
  • N Ishizuka, S Mizutani, O Narita, Y Tomoda. Effect of cyclophenyl and clomiphene on excretion of urinary LH. Endocrinologia japonica. 1973 Feb; 20(1):51-7. doi: 10.1507/endocrj1954.20.51. [PMID: 4740643]
  • H R Maeda, M Seki, K Seki, T Yoshihara. Effects of clomiphene, cyclofenil, epimestrol and Ro 4-8347 on pituitary and serum prolactin in mature female rats. Endocrinologia japonica. 1972 Dec; 19(6):525-32. doi: 10.1507/endocrj1954.19.525. [PMID: 4679231]
  • M Suzuki, T Takahashi, T Abe. The effect of chemical ovulation-inducing substances on gonadotropin secretion in incubation experiments of the anterior pituitary. The Tohoku journal of experimental medicine. 1972 Oct; 108(2):123-31. doi: 10.1620/tjem.108.123. [PMID: 4675686]
  • Y Tomoda, N Ishizuka. [Secretion dynamics of luteinizing hormone (LH) and follicle stimulating hormone (FSH) and their anomaly]. Nihon rinsho. Japanese journal of clinical medicine. 1971 Jul; 29(7):1681-9. doi: NULL. [PMID: 4948486]
  • S Mizutani. [Determination of human urinary luteinizing hormone in the fields of obstetrics and gynecology]. Nihon Sanka Fujinka Gakkai zasshi. 1971 Jun; 23(6):471-80. doi: NULL. [PMID: 5104695]
  • O Narita, E Mizutani, Y Tomoda, N Ishizuka. [Clinical study of hypophyseal luteinizing hormone secretion caused by F 6066 and Clomid]. Horumon to rinsho. Clinical endocrinology. 1970 Aug; 18(8):685-9. doi: NULL. [PMID: 5466330]
  • O Nunokawa. [Follicle stimulating hormone secretion in ovulation]. Nihon Naibunpi Gakkai zasshi. 1970 Apr; 46(1):32-52. doi: 10.1507/endocrine1927.46.1_32. [PMID: 5462804]
  • T Sato, Y Ibuki, M Hirono, M Igarashi, S Matsumoto. Induction of ovulation with sexovid (Compound F6066) and its mode of action. Fertility and sterility. 1969 Nov; 20(6):965-74. doi: 10.1016/s0015-0282(16)37214-4. [PMID: 5391264]
  • T Hojo. [Effects of ovulation-inducing substances on secretion of LH]. Nihon Sanka Fujinka Gakkai zasshi. 1969 Nov; 21(11):1301-8. doi: ". [PMID: 5390721]
  • T Nishimura, O Sugimoto, T Mori, I Yogo. [Clinical effect of F 6066 on ovulation]. Sanfujinka no jissai. Practice of gynecology and obstetrics. 1969 Apr; 18(4):301-6. doi: NULL. [PMID: 5819855]
  • H Adlercreutz, C J Johansson, T Luukkainen. Gas chromatographic and mass spectrometric studies in the influence of metabolites of bis(p-acetoxyphenyl)cyclohexylidenemethane on the estimation of estrogens in urine. Annales medicinae experimentalis et biologiae Fenniae. 1967; 45(3):269-76. doi: NULL. [PMID: 5583963]
  • A Hanngren, N Einer-Jensen, S Ullberg. Distribution pattern of a non-steroid compound with endocrine actions, 14C-bis(p-hydroxyphenyl)cyclohexylidenemethane (compound F6060) and its diacetate (compound F6066). Acta endocrinologica. 1965 Sep; 50(1):35-43. doi: 10.1530/acta.0.0500035. [PMID: 5897064]
  • H Larsson. The metabolic fate of bis (p-hydroxyphenyl) cyclohexylidenemethane--F6060--and its diacetate--F6066. Acta pharmacologica et toxicologica. 1965; 23(4):337-59. doi: 10.1111/j.1600-0773.1965.tb00359.x. [PMID: 5899692]
  • B H PERSSON. THE EFFECT OF BIS(P-ACETOXYPHENYL)CYCLOHEXYLIDENE-METHANE (COMPOUND F 6066) ON HORMONE EXCRETION IN POSTMENOPAUSAL WOMEN. Acta Societatis Medicorum Upsaliensis. 1965; 70(?):1-6. doi: NULL. [PMID: 14277887]