(+)-Norgestrel (BioDeep_00000171510)

   

human metabolite blood metabolite


代谢物信息卡片


15-ethyl-14-ethynyl-14-hydroxytetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

化学式: C21H28O2 (312.2089188)
中文名称: 炔诺孕酮
谱图信息: 最多检出来源 Homo sapiens(blood) 5.26%

分子结构信息

SMILES: CCC12CCC3C(C1CCC2(C#C)O)CCC4=CC(=O)CCC34
InChI: InChI=1S/C21H28O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,13,16-19,23H,3,5-12H2,1H3

描述信息

D012102 - Reproductive Control Agents > D003270 - Contraceptive Agents

同义名列表

12 个代谢物同义名

15-ethyl-14-ethynyl-14-hydroxytetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one; Methylnorethindrone; (-)-Norgestrel 98; Levonorgestrel; (+)-Norgestrel; DL Norgestrel; DL-Norgestrel; LD Norgestrel; Norgestrelum; Postinor; Ovrette; Neogest



数据库引用编号

8 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

  • Leo Han, Mitchell D Creinin, Agnes Hemon, Anna Glasier, Melissa J Chen, Alison Edelman. Mechanism of action of a 0.075 mg norgestrel progestogen-only pill 2. Effect on cervical mucus and theoretical risk of conception. Contraception. 2022 Aug; 112(?):43-47. doi: 10.1016/j.contraception.2022.03.016. [PMID: 35367204]
  • Madhu Sanga, Subusola Vaughan, Julius Nangosyah, Veronika Scholz, Sergio Fonseca. Randomized, double-blind, two-way crossover bioequivalence and adhesion study, in healthy women, of a transdermal contraceptive patch with a newly sourced adhesive component at the end of shelf life vs. the EVRA patch at the beginning of shelf life. International journal of clinical pharmacology and therapeutics. 2022 Jan; 60(1):67-78. doi: 10.5414/cp204034. [PMID: 34779392]
  • Giovanni Grandi, Maria Chiara Del Savio, Fabio Facchinetti. The paradigm of norgestimate: a third-generation testosterone-derivative progestin with a peripheral anti-androgenic activity and the lowest risk of venous thromboembolism. Expert review of clinical pharmacology. 2021 Feb; 14(2):211-224. doi: 10.1080/17512433.2021.1878876. [PMID: 33464138]
  • Concepción Guadarrama-García, Martiniano Bello, Marvin Soriano-Ursúa. Molecular insights into how SHBG dimerization exerts changes on ligand molecular recognition. The Journal of steroid biochemistry and molecular biology. 2020 03; 197(?):105502. doi: 10.1016/j.jsbmb.2019.105502. [PMID: 31689504]
  • Yang Xu, Kristin Gabriel, Yi Wang, Yanchen Zhou, Osaro Eisele, Apinya Vutikullird, Daniel D Mikol, Edward Lee. A Multi-Center, Open-Label, Pharmacokinetic Drug Interaction Study of Erenumab and a Combined Oral Contraceptive in Healthy Females. CNS drugs. 2019 05; 33(5):513-522. doi: 10.1007/s40263-019-00626-2. [PMID: 30963506]
  • Liping Hou, Shanduo Chen, Juan Liu, Jingwen Guo, Zhong Chen, Qiaoling Zhu, Wei Zhang, GuoLiang Xu, Ye Liang, Rongrong Wu, Xuwen Fang, Cuiping Zhang, Ke Xing. Transcriptomic and physiological changes in western mosquitofish (Gambusia affinis) after exposure to norgestrel. Ecotoxicology and environmental safety. 2019 Apr; 171(?):579-586. doi: 10.1016/j.ecoenv.2018.12.053. [PMID: 30654292]
  • Bing Zhu, Ivan Nestorov, Guolin Zhao, Venkata Meka, Mark Leahy, Jeanelle Kam, Sarah I Sheikh. Evaluation of Potential Drug-Drug Interaction Between Delayed-Release Dimethyl Fumarate and a Commonly Used Oral Contraceptive (Norgestimate/Ethinyl Estradiol) in Healthy Women. Clinical pharmacology in drug development. 2017 Nov; 6(6):604-613. doi: 10.1002/cpdd.377. [PMID: 28783872]
  • Jatuporn Kajaysri, Chaiwat Chumchoung, Supphathat Wutthiwitthayaphong, Wanvipa Suthikrai, Praphai Sangkamanee. Comparison of estrus synchronization by controlled internal drug release device (CIDR) and adhesive transdermal progestin patch in postpartum beef cows. Theriogenology. 2017 Sep; 100(?):66-71. doi: 10.1016/j.theriogenology.2017.06.006. [PMID: 28708535]
  • Deepak Ahire, Sarmistha Sinha, Barry Brock, Ramaswamy Iyer, Sandhya Mandlekar, Murali Subramanian. Metabolite Identification, Reaction Phenotyping, and Retrospective Drug-Drug Interaction Predictions of 17-Deacetylnorgestimate, the Active Component of the Oral Contraceptive Norgestimate. Drug metabolism and disposition: the biological fate of chemicals. 2017 06; 45(6):676-685. doi: 10.1124/dmd.116.073940. [PMID: 28283499]
  • Adeola A Adeniji, Paulina A Essah, John E Nestler, Kai I Cheang. Metabolic Effects of a Commonly Used Combined Hormonal Oral Contraceptive in Women With and Without Polycystic Ovary Syndrome. Journal of women's health (2002). 2016 06; 25(6):638-45. doi: 10.1089/jwh.2015.5418. [PMID: 26871978]
  • Xiangling Ma, Qing Wang, Lili Wang, Yanmei Huang, Xiaoxiang Liao, Hui Li. Investigation on the Interaction of Norgestrel with Human Serum Albumin Using Spectroscopy and Molecular-Docking Method. Journal of biochemical and molecular toxicology. 2016 Jun; 30(6):287-94. doi: 10.1002/jbt.21790. [PMID: 26778492]
  • LaQuana N Hordge, Kiara L McDaniel, Derick D Jones, Sayo O Fakayode. Simultaneous determination of estrogens (ethinylestradiol and norgestimate) concentrations in human and bovine serum albumin by use of fluorescence spectroscopy and multivariate regression analysis. Talanta. 2016 May; 152(?):401-9. doi: 10.1016/j.talanta.2016.02.034. [PMID: 26992536]
  • Mike-Qingtao Huang, Lijuan Kang, Weimin Wang, Donna Skee, Mu Chen, Zhongping John Lin, Tom Verhaeghe, Naidong Weng. UPLC-MS/MS assay for the simultaneous determination of ethinyl estradiol, norgestimate and 17-Desacetyl norgestimate at low pg/mL in human plasma. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2016 Apr; 1017-1018(?):1-9. doi: 10.1016/j.jchromb.2016.01.054. [PMID: 26930373]
  • Kazuhiro Tamura, Hiroaki Naraba, Takahiko Hara, Kota Nakamura, Mikihiro Yoshie, Hiroshi Kogo, Eiichi Tachikawa. A positive feedback loop between progesterone and microsomal prostaglandin E synthase-1-mediated PGE2 promotes production of both in mouse granulosa cells. Prostaglandins & other lipid mediators. 2016 03; 123(?):56-62. doi: 10.1016/j.prostaglandins.2016.05.002. [PMID: 27174800]
  • Ashleigh M Byrne, Sarah L Roche, Ana M Ruiz-Lopez, Alice C Wyse Jackson, Thomas G Cotter. The synthetic progestin norgestrel acts to increase LIF levels in the rd10 mouse model of retinitis pigmentosa. Molecular vision. 2016; 22(?):264-74. doi: NULL. [PMID: 27081297]
  • Adedoyin Igunnu, Young-Mi Seok, Lawrence A Olatunji, Seol-Hee Kang, Inkyeom Kim. Combined oral contraceptive synergistically activates mineralocorticoid receptor through histone code modifications. European journal of pharmacology. 2015 Dec; 769(?):48-54. doi: 10.1016/j.ejphar.2015.10.035. [PMID: 26506558]
  • Ivy H Song, Julie Borland, Shuguang Chen, Toshihiro Wajima, Amanda F Peppercorn, Stephen C Piscitelli. Dolutegravir Has No Effect on the Pharmacokinetics of Oral Contraceptives With Norgestimate and Ethinyl Estradiol. The Annals of pharmacotherapy. 2015 Jul; 49(7):784-9. doi: 10.1177/1060028015580637. [PMID: 25862012]
  • Françoise Paris, Patrick Balaguer, Frédéric Rimbault, Laura Gaspari, Charles Sultan. Molecular action of norgestimate: new developments. Gynecological endocrinology : the official journal of the International Society of Gynecological Endocrinology. 2015 Jun; 31(6):487-90. doi: 10.3109/09513590.2015.1016904. [PMID: 25970022]
  • Intira Sriprasert, Frank Z Stanczyk, David F Archer. Ethinyl estradiol and levonorgestrel in a transdermal contraceptive delivery system. Expert opinion on pharmacotherapy. 2015; 16(12):1901-9. doi: 10.1517/14656566.2015.1056733. [PMID: 26194214]
  • N Batta, R K Pigili, L M K Pallapothu, R P Yejella. A simple, rapid and sensitive UFLC-MS/MS method for the quantification of oral contraceptive norgestrel in human plasma and its pharmacokinetic applications. Drug research. 2014 Sep; 64(9):462-9. doi: 10.1055/s-0033-1361164. [PMID: 24310360]
  • Yi Rong, Wen-Ying Yu, Xia Guo, Shan-Shan Zeng, Zheng-Rong Shen, Su Zeng, Jin-Cui Ye. [The potential effects of linalool on enantioselective skin permeation of norgestrel]. Yao xue xue bao = Acta pharmaceutica Sinica. 2014 Aug; 49(8):1175-80. doi: ". [PMID: 25322561]
  • Jesus Hernandez-Juarez, Ethel A Garcia-Latorre, Manuel Moreno-Hernandez, Jose Fernando Moran-Perez, Miguel Angel Rodriguez-Escobedo, Gerardo Cogque-Hernandez, Rubén Julián-Nacer, Xochitl Hernandez-Giron, Rosalia Palafox-Gomez, Irma Isordia-Salas, Abraham Majluf-Cruz. Metabolic effects of the contraceptive skin patch and subdermal contraceptive implant in Mexican women: a prospective study. Reproductive health. 2014 Apr; 11(?):33. doi: 10.1186/1742-4755-11-33. [PMID: 24767248]
  • Marc Bifano, Heather Sevinsky, Carey Hwang, Hamza Kandoussi, Hao Jiang, Dennis Grasela, Richard Bertz. Effect of the coadministration of daclatasvir on the pharmacokinetics of a combined oral contraceptive containing ethinyl estradiol and norgestimate. Antiviral therapy. 2014; 19(5):511-9. doi: 10.3851/imp2718. [PMID: 24343001]
  • Sanna Kallio, Johanna Puurunen, Aimo Ruokonen, Tommi Vaskivuo, Terhi Piltonen, Juha S Tapanainen. Antimüllerian hormone levels decrease in women using combined contraception independently of administration route. Fertility and sterility. 2013 Apr; 99(5):1305-10. doi: 10.1016/j.fertnstert.2012.11.034. [PMID: 23260855]
  • Lawrence Aderemi Olatunji, Ibukun Peter Oyeyipo, Taofeek Oluwamayowa Usman. Effect of a high-fructose diet on glucose tolerance, plasma lipid and hemorheological parameters during oral contraceptive administration in female rats. Clinical hemorheology and microcirculation. 2013 Jan; 54(1):23-31. doi: 10.3233/ch-2012-1561. [PMID: 22648005]
  • V V Upreti, C B Hsiang, L Li, X Xu, F P LaCreta, D W Boulton. Effect of saxagliptin on the pharmacokinetics of the active components of Ortho-Cyclen(®), a combined oral contraceptive containing ethinyl estradiol and norgestimate, in healthy women. Diabetes, obesity & metabolism. 2012 Dec; 14(12):1155-7. doi: 10.1111/j.1463-1326.2012.01635.x. [PMID: 22776778]
  • Paulina A Essah, James A Arrowood, Kai I Cheang, Swati S Adawadkar, Dale W Stovall, John E Nestler. Effect of combined metformin and oral contraceptive therapy on metabolic factors and endothelial function in overweight and obese women with polycystic ovary syndrome. Fertility and sterility. 2011 Aug; 96(2):501-504.e2. doi: 10.1016/j.fertnstert.2011.05.091. [PMID: 21733508]
  • Kai I Cheang, Paulina A Essah, Susmeeta Sharma, Edmond P Wickham, John E Nestler. Divergent effects of a combined hormonal oral contraceptive on insulin sensitivity in lean versus obese women. Fertility and sterility. 2011 Aug; 96(2):353-359.e1. doi: 10.1016/j.fertnstert.2011.05.039. [PMID: 21676394]
  • A H Schmitt-Hoffmann, B Roos, J Sauer, M Schleimer, A Schoetzau, P T Leese, E Weidekamm, J Maares. Influence of alitretinoin on the pharmacokinetics of the oral contraceptive ethinyl estradiol/norgestimate. Clinical and experimental dermatology. 2011 Apr; 36 Suppl 2(?):4-11. doi: 10.1111/j.1365-2230.2011.04031.x. [PMID: 21443598]
  • Matt S Anderson, William D Hanley, Allison R Moreau, Bo Jin, Frederick A Bieberdorf, James T Kost, Larissa A Wenning, Julie A Stone, John A Wagner, Marian Iwamoto. Effect of raltegravir on estradiol and norgestimate plasma pharmacokinetics following oral contraceptive administration in healthy women. British journal of clinical pharmacology. 2011 Apr; 71(4):616-20. doi: 10.1111/j.1365-2125.2010.03885.x. [PMID: 21395656]
  • Jenny Zhang, Ellen Chung, Cynthia Yones, Anna Persson, Lisa Mahnke, Timothy Eley, Xiaohui Xu, Richard Bertz. The effect of atazanavir/ritonavir on the pharmacokinetics of an oral contraceptive containing ethinyl estradiol and norgestimate in healthy women. Antiviral therapy. 2011; 16(2):157-64. doi: 10.3851/imp1724. [PMID: 21447864]
  • Heather Sevinsky, Timothy Eley, Anna Persson, Dennis Garner, Cynthia Yones, Richard Nettles, Kathryn Krantz, Richard Bertz, Jenny Zhang. The effect of efavirenz on the pharmacokinetics of an oral contraceptive containing ethinyl estradiol and norgestimate in healthy HIV-negative women. Antiviral therapy. 2011; 16(2):149-56. doi: 10.3851/imp1725. [PMID: 21447863]
  • P Trebble, L Matthews, J Blaikley, A W O Wayte, G C M Black, A Wilton, D W Ray. Familial glucocorticoid resistance caused by a novel frameshift glucocorticoid receptor mutation. The Journal of clinical endocrinology and metabolism. 2010 Dec; 95(12):E490-9. doi: 10.1210/jc.2010-0705. [PMID: 20861124]
  • Mariangela Massaro, Costantino Di Carlo, Virginia Gargano, Carmen Formisano, Giuseppe Bifulco, Carmine Nappi. Effects of the contraceptive patch and the vaginal ring on bone metabolism and bone mineral density: a prospective, controlled, randomized study. Contraception. 2010 Mar; 81(3):209-14. doi: 10.1016/j.contraception.2009.09.011. [PMID: 20159176]
  • Zeev Harel, Suzanne Riggs, Rosalind Vaz, Patricia Flanagan, Dalia Harel, Jason T Machan. Bone accretion in adolescents using the combined estrogen and progestin transdermal contraceptive method Ortho Evra: a pilot study. Journal of pediatric and adolescent gynecology. 2010 Feb; 23(1):23-31. doi: 10.1016/j.jpag.2009.04.008. [PMID: 19647454]
  • Jules I Schwartz, Fang Liu, Ying-Hong Wang, Barnali Pramanik, Amy O Johnson-Levonas, Maria J Gutierrez, Eseng Lai, John A Wagner. Effect of laropiprant, a PGD2 receptor 1 antagonist, on estradiol and norgestimate pharmacokinetics after oral contraceptive administration in women. American journal of therapeutics. 2009 Nov; 16(6):487-95. doi: 10.1097/mjt.0b013e3181985130. [PMID: 19940609]
  • Quanlin Wang, Aizhi Zhang, Liren Chen. [Study on simultaneous determination method for banded synthesis hormones residues in egg products]. Wei sheng yan jiu = Journal of hygiene research. 2009 Nov; 38(6):740-6. doi: . [PMID: 20047238]
  • Brian P Kearney, Anita Mathias. Lack of effect of tenofovir disoproxil fumarate on pharmacokinetics of hormonal contraceptives. Pharmacotherapy. 2009 Aug; 29(8):924-9. doi: 10.1592/phco.29.8.924. [PMID: 19637945]
  • Xiaofen Liu, Cungang Ding, Qinghua Ge, Xiaojin Zhi, Zhen Zhou. Determination of norelgestromin in rabbit plasma by LC-MS/MS and its application to the pharmacokinetic study of ORTHO EVRA. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2009 Jan; 877(3):311-5. doi: 10.1016/j.jchromb.2008.11.034. [PMID: 19097950]
  • Jules I Schwartz, Stephanie Dunbar, Jinyu Yuan, Susie Li, Deborah L Miller, Kim Rosko, Amy O Johnson-Levonas, Kenneth C Lasseter, John A Wagner. Influence of taranabant, an orally active, highly selective, potent cannabinoid-1 receptor (CB1R) inverse agonist, on ethinyl estradiol and norelgestromin plasma pharmacokinetics. Journal of clinical pharmacology. 2009 Jan; 49(1):72-9. doi: 10.1177/0091270008325930. [PMID: 18936284]
  • Leigh A Jones, Jean-Paul Anthony, Fiona L Henriquez, Russell E Lyons, Mohammad B Nickdel, Katharine C Carter, James Alexander, Craig W Roberts. Toll-like receptor-4-mediated macrophage activation is differentially regulated by progesterone via the glucocorticoid and progesterone receptors. Immunology. 2008 Sep; 125(1):59-69. doi: 10.1111/j.1365-2567.2008.02820.x. [PMID: 18373668]
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