Bimatoprost (BioDeep_00000398890)

   

natural product


代谢物信息卡片


N-ethyl-9α,11α,15S-trihydroxy-17-phenyl-18,19,20-trinor-prosta-5Z,13E-dien-1-amide

化学式: C25H37NO4 (415.27224420000005)
中文名称: 比马前列素
谱图信息: 最多检出来源 Escherichia coli(natural_products) 50%

分子结构信息

SMILES: C1=CC=C(C=C1)CCC(O)/C=C/[C@@H]2[C@H]([C@H](C[C@H]2O)O)C/C=C\CCCC(=O)NCC
InChI: InChI=1S/C25H37NO4/c1-2-26-25(30)13-9-4-3-8-12-21-22(24(29)18-23(21)28)17-16-20(27)15-14-19-10-6-5-7-11-19/h3,5-8,10-11,16-17,20-24,27-29H,2,4,9,12-15,18H2,1H3,(H,26,30)/b8-3-,17-16+/t20-,21+,22+,23-,24+/m0/s1

描述信息

S - Sensory organs > S01 - Ophthalmologicals > S01E - Antiglaucoma preparations and miotics > S01EE - Prostaglandin analogues
C78283 - Agent Affecting Organs of Special Senses > C29705 - Anti-glaucoma Agent
D002317 - Cardiovascular Agents > D000959 - Antihypertensive Agents
C78568 - Prostaglandin Analogue

同义名列表

5 个代谢物同义名

Bimatoprost; N-ethyl-9α,11α,15S-trihydroxy-17-phenyl-18,19,20-trinor-prosta-5Z,13E-dien-1-amide; 17-phenyl trinor Prostaglandin F2α 17-phenyl trinor PGF2α ethyl amide



数据库引用编号

9 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)

0 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

  • Yosuke Ida, Megumi Watanabe, Araya Umetsu, Hiroshi Ohguro, Fumihito Hikage. Addition of EP2 agonists to an FP agonist additively and synergistically modulates adipogenesis and the physical properties of 3D 3T3-L1 sphenoids. Prostaglandins, leukotrienes, and essential fatty acids. 2021 08; 171(?):102315. doi: 10.1016/j.plefa.2021.102315. [PMID: 34246925]
  • Fumihito Hikage, Yosuke Ida, Yuika Ouchi, Megumi Watanabe, Hiroshi Ohguro. Omidenepag, a Selective, Prostanoid EP2 Agonist, Does Not Suppress Adipogenesis in 3D Organoids of Human Orbital Fibroblasts. Translational vision science & technology. 2021 04; 10(4):6. doi: 10.1167/tvst.10.4.6. [PMID: 34003984]
  • Chauncey C Barbulescu, Nathaniel B Goldstein, Dennis R Roop, David A Norris, Stanca A Birlea. Harnessing the Power of Regenerative Therapy for Vitiligo and Alopecia Areata. The Journal of investigative dermatology. 2020 01; 140(1):29-37. doi: 10.1016/j.jid.2019.03.1142. [PMID: 31196751]
  • Philip R Cohen. Laser-assisted drug delivery for the treatment of androgenetic alopecia: ablative laser fractional photothermolysis to enhance cutaneous topical delivery of platelet-rich plasma - with or without concurrent bimatoprost and/or minoxidil. Dermatology online journal. 2019 Feb; 25(2):. doi: NULL. [PMID: 30865404]
  • Catherine J Choi, Wensi Tao, Ravi Doddapaneni, Zenith Acosta-Torres, Nathan W Blessing, Bradford W Lee, Daniel Pelaez, Sara T Wester. The Effect of Prostaglandin Analogue Bimatoprost on Thyroid-Associated Orbitopathy. Investigative ophthalmology & visual science. 2018 12; 59(15):5912-5923. doi: 10.1167/iovs.18-25134. [PMID: 30551199]
  • Wendy R Kam, Yang Liu, Juan Ding, David A Sullivan. Do Cyclosporine A, an IL-1 Receptor Antagonist, Uridine Triphosphate, Rebamipide, and/or Bimatoprost Regulate Human Meibomian Gland Epithelial Cells?. Investigative ophthalmology & visual science. 2016 08; 57(10):4287-94. doi: 10.1167/iovs.16-19937. [PMID: 27552406]
  • Iwona Dams, Jaromir Wasyluk, Marek Prost, Andrzej Kutner. Therapeutic uses of prostaglandin F(2α) analogues in ocular disease and novel synthetic strategies. Prostaglandins & other lipid mediators. 2013 Jul; 104-105(?):109-21. doi: 10.1016/j.prostaglandins.2013.01.001. [PMID: 23353557]
  • Norihito Takano, Kazuhiro Tsuruma, Yuta Ohno, Masamitsu Shimazawa, Hideaki Hara. Bimatoprost protects retinal neuronal damage via Akt pathway. European journal of pharmacology. 2013 Feb; 702(1-3):56-61. doi: 10.1016/j.ejphar.2013.01.038. [PMID: 23395963]
  • Lauren L Nicotra, Megan Vu, Benjamin S Harvey, Scott D Smid. Prostaglandin ethanolamides attenuate damage in a human explant colitis model. Prostaglandins & other lipid mediators. 2013 Jan; 100-101(?):22-9. doi: 10.1016/j.prostaglandins.2013.01.003. [PMID: 23380599]
  • Hee Young Choi, Ji Eun Lee, Ji Woong Lee, Hyun Jun Park, Ji Eun Lee, Jae Ho Jung. In vitro study of antiadipogenic profile of latanoprost, travoprost, bimatoprost, and tafluprost in human orbital preadiopocytes. Journal of ocular pharmacology and therapeutics : the official journal of the Association for Ocular Pharmacology and Therapeutics. 2012 Apr; 28(2):146-52. doi: 10.1089/jop.2011.0160. [PMID: 22107041]
  • D Călugăru, M Călugăru. [Monotherapy with lipid structural derivatives in glaucoma]. Oftalmologia (Bucharest, Romania : 1990). 2010; 54(2):30-43. doi: ". [PMID: 20827909]
  • Sudharshan Hariharan, Mukul Minocha, Gyan P Mishra, Dhananjay Pal, Rohit Krishna, Ashim K Mitra. Interaction of ocular hypotensive agents (PGF2 alpha analogs-bimatoprost, latanoprost, and travoprost) with MDR efflux pumps on the rabbit cornea. Journal of ocular pharmacology and therapeutics : the official journal of the Association for Ocular Pharmacology and Therapeutics. 2009 Dec; 25(6):487-98. doi: 10.1089/jop.2009.0049. [PMID: 20028257]
  • Scott D Smid, Karin M Svensson. Inhibition of cyclooxygenase-2 and EP1 receptor antagonism reduces human colonic longitudinal muscle contractility in vitro. Prostaglandins & other lipid mediators. 2009 Apr; 88(3-4):117-21. doi: 10.1016/j.prostaglandins.2008.12.004. [PMID: 19126433]
  • D Călugăru, M Călugăru. [Bimatoprost therapy in glaucoma]. Oftalmologia (Bucharest, Romania : 1990). 2009; 53(3):34-45. doi: ". [PMID: 19899545]
  • Egidio Fortuna, Rene A Cervantes-Castañeda, Rene A Castañeda-Cervantes, Pooja Bhat, Priyanka Doctor, C Stephen Foster. Flare-up rates with bimatoprost therapy in uveitic glaucoma. American journal of ophthalmology. 2008 Dec; 146(6):876-82. doi: 10.1016/j.ajo.2008.08.022. [PMID: 19027422]
  • John G Walt, Jacob T Wilensky, Richard Fiscella, Tina H Chiang, Angela Guckian. Refill rates and budget impact of glaucoma lipid therapy: a retrospective database analysis. Clinical drug investigation. 2007; 27(12):819-25. doi: 10.2165/00044011-200727120-00003. [PMID: 18020539]
  • Steven Kymes. Cost-effectiveness of monotherapy treatment of glaucoma and ocular hypertension with the lipid class of medications. American journal of ophthalmology. 2006 Aug; 142(2):354; author reply 354-5. doi: 10.1016/j.ajo.2006.04.022. [PMID: 16876536]
  • Shannon L Steinhäuser. Decreased high-density lipoprotein serum levels associated with topical bimatoprost therapy. Optometry (St. Louis, Mo.). 2006 Apr; 77(4):177-9. doi: 10.1016/j.optm.2006.02.001. [PMID: 16567279]
  • Robert J Noecker, John G Walt. Cost-effectiveness of monotherapy treatment of glaucoma and ocular hypertension with the lipid class of medications. American journal of ophthalmology. 2006 Jan; 141(1 Suppl):S15-21. doi: 10.1016/j.ajo.2005.06.030. [PMID: 16389056]
  • Alain Regnier, Capucine Lemagne, Alice Ponchet, Guillaume Cazalot, Didier Concordet, Kirk N Gelatt. Ocular effects of topical 0.03\% bimatoprost solution in normotensive feline eyes. Veterinary ophthalmology. 2006 Jan; 9(1):39-43. doi: 10.1111/j.1463-5224.2005.00435.x. [PMID: 16409244]
  • Stefan Holmstrom, Patricia Buchholz, John Walt, Jannie Wickstrøm, Mark Aagren. Analytic review of bimatoprost, latanoprost and travoprost in primary open angle glaucoma. Current medical research and opinion. 2005 Nov; 21(11):1875-83. doi: 10.1185/030079905x65600. [PMID: 16307709]
  • Clayton S Spada, Achim H-P Krauss, David F Woodward, June Chen, Charles E Protzman, Amelia L Nieves, Larry A Wheeler, David F Scott, George Sachs. Bimatoprost and prostaglandin F(2 alpha) selectively stimulate intracellular calcium signaling in different cat iris sphincter cells. Experimental eye research. 2005 Jan; 80(1):135-45. doi: 10.1016/j.exer.2004.08.019. [PMID: 15652534]
  • Punita Kumari Sodhi, Lalit Verma, Simmi K Ratan. Increased periocular pigmentation with ocular hypotensive lipid use in African Americans. American journal of ophthalmology. 2004 Apr; 137(4):783. doi: 10.1016/j.ajo.2003.11.073. [PMID: 15059736]
  • N A Sharif, C R Kelly, J Y Crider, G W Williams, S X Xu. Ocular hypotensive FP prostaglandin (PG) analogs: PG receptor subtype binding affinities and selectivities, and agonist potencies at FP and other PG receptors in cultured cells. Journal of ocular pharmacology and therapeutics : the official journal of the Association for Ocular Pharmacology and Therapeutics. 2003 Dec; 19(6):501-15. doi: 10.1089/108076803322660422. [PMID: 14733708]
  • Leon W Herndon, Robert D Williams, Martin Wand, Sanjay Asrani. Increased periocular pigmentation with ocular hypotensive lipid use in African Americans. American journal of ophthalmology. 2003 May; 135(5):713-5. doi: 10.1016/s0002-9394(02)02146-3. [PMID: 12719085]
  • Mark R Hellberg, Tai-Lee Ke, Karen Haggard, Peter G Klimko, Tom R Dean, Gustav Graff. The hydrolysis of the prostaglandin analog prodrug bimatoprost to 17-phenyl-trinor PGF2alpha by human and rabbit ocular tissue. Journal of ocular pharmacology and therapeutics : the official journal of the Association for Ocular Pharmacology and Therapeutics. 2003 Apr; 19(2):97-103. doi: 10.1089/108076803321637627. [PMID: 12804054]
  • Sean S Davies, Won-Kyu Ju, Arthur H Neufeld, Daniel Abran, Sylvain Chemtob, L Jackson Roberts. Hydrolysis of bimatoprost (Lumigan) to its free acid by ocular tissue in vitro. Journal of ocular pharmacology and therapeutics : the official journal of the Association for Ocular Pharmacology and Therapeutics. 2003 Feb; 19(1):45-54. doi: 10.1089/108076803762718105. [PMID: 12648303]
  • Curtis R Kelly, Gary W Williams, Najam A Sharif. Real-time intracellular Ca2+ mobilization by travoprost acid, bimatoprost, unoprostone, and other analogs via endogenous mouse, rat, and cloned human FP prostaglandin receptors. The Journal of pharmacology and experimental therapeutics. 2003 Jan; 304(1):238-45. doi: 10.1124/jpet.102.042556. [PMID: 12490597]
  • N A Sharif, C R Kelly, G W Williams. Bimatoprost (Lumigan((R))) is an agonist at the cloned human ocular FP prostaglandin receptor: real-time FLIPR-based intracellular Ca(2+) mobilization studies. Prostaglandins, leukotrienes, and essential fatty acids. 2003 Jan; 68(1):27-33. doi: 10.1016/s0952-3278(02)00232-6. [PMID: 12538087]
  • Kirk M Maxey, Jennifer L Johnson, Jennifer LaBrecque. The hydrolysis of bimatoprost in corneal tissue generates a potent prostanoid FP receptor agonist. Survey of ophthalmology. 2002 Aug; 47 Suppl 1(?):S34-40. doi: 10.1016/s0039-6257(02)00323-5. [PMID: 12204699]
  • N A Sharif, G W Williams, C R Kelly. Bimatoprost and its free acid are prostaglandin FP receptor agonists. European journal of pharmacology. 2001 Dec; 432(2-3):211-3. doi: 10.1016/s0014-2999(01)01486-8. [PMID: 11740958]
  • R A Laibovitz, A M VanDenburgh, C Felix, R David, A Batoosingh, A Rosenthal, J Cheetham. Comparison of the ocular hypotensive lipid AGN 192024 with timolol: dosing, efficacy, and safety evaluation of a novel compound for glaucoma management. Archives of ophthalmology (Chicago, Ill. : 1960). 2001 Jul; 119(7):994-1000. doi: 10.1001/archopht.119.7.994. [PMID: 11448321]
  • R F Brubaker, E O Schoff, C B Nau, S P Carpenter, K Chen, A M Vandenburgh. Effects of AGN 192024, a new ocular hypotensive agent, on aqueous dynamics. American journal of ophthalmology. 2001 Jan; 131(1):19-24. doi: 10.1016/s0002-9394(00)00843-6. [PMID: 11162974]