Latanoprost (BioDeep_00000405636)
代谢物信息卡片
9α,11α,15R-trihydroxy-17-phenyl-18,19,20-trinor-prost-5Z-en-1-oic acid, isopropyl ester
化学式: C26H40O5 (432.28755900000004)
中文名称: 拉坦前列素
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CC(C)OC(=O)CCCC=CCC1C(CC(C1CCC(CCC2=CC=CC=C2)O)O)O
InChI: InChI=1S/C26H40O5/c1-19(2)31-26(30)13-9-4-3-8-12-22-23(25(29)18-24(22)28)17-16-21(27)15-14-20-10-6-5-7-11-20/h3,5-8,10-11,19,21-25,27-29H,4,9,12-18H2,1-2H3/b8-3-/t21-,22+,23+,24-,25+/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
D019999 - Pharmaceutical Solutions > D009883 - Ophthalmic Solutions
C78568 - Prostaglandin Analogue
同义名列表
数据库引用编号
11 个数据库交叉引用编号
- ChEBI: CHEBI:6384
- KEGGdrug: D00356
- PubChem: 5311221
- Metlin: METLIN45708
- DrugBank: DB00654
- ChEMBL: CHEMBL1051
- MeSH: Latanoprost
- CAS: 155551-81-8
- CAS: 130209-82-4
- MoNA: FiehnHILIC002045
- MoNA: FiehnHILIC000473
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
- Maria Chiara Saija, Katarina Vazdar, Wojciech Pajerski, Agnieszka Olżyńska, Philippe Daull, Jean-Sebastien Garrigue, Lukasz Cwiklik. Comparative Study of Latanoprost Drug Delivery Systems for Glaucoma Treatment and Their Interaction with the Tear Film Lipid Layer Models.
Molecular pharmaceutics.
2024 Jan; 21(1):126-136. doi:
10.1021/acs.molpharmaceut.3c00635. [PMID: 38110329] - Kamila Riedlová, Maria Chiara Saija, Agnieszka Olżyńska, Katarina Vazdar, Philippe Daull, Jean-Sebastien Garrigue, Lukasz Cwiklik. Latanoprost incorporates in the tear film lipid layer: An experimental and computational model study.
International journal of pharmaceutics.
2023 Oct; 645(?):123367. doi:
10.1016/j.ijpharm.2023.123367. [PMID: 37666309] - Jillian F Ziemanski, Landon Wilson, Stephen Barnes, Kelly K Nichols. Evaluation of the effects of latanoprost and benzalkonium chloride on the cell viability and nonpolar lipid profile produced by human meibomian gland epithelial cells in culture.
Molecular vision.
2023; 29(?):289-305. doi:
". [PMID: 38264609] - Xiu-Ying Jiang, Ping-Sun Yang, Ou Xiao, Kang Yu, Shu-Yi Wang, Shuang-Jian Yang, Shi-You Zhou. Effects of PPAR-γ and RXR-α on mouse meibomian gland epithelial cells during inflammation induced by latanoprost.
Experimental eye research.
2022 11; 224(?):109251. doi:
10.1016/j.exer.2022.109251. [PMID: 36150542] - Liping Chen, Ruixin Wu. Brinzolamide- and latanoprost-loaded nano lipid carrier prevents synergistic retinal damage in glaucoma.
Acta biochimica Polonica.
2022 May; 69(2):423-428. doi:
10.18388/abp.2020_5885. [PMID: 35617132] - Paula M Oliveira, Thuany Alencar-Silva, Felipe Q Pires, Marcilio Cunha-Filho, Tais Gratieri, Juliana Lott Carvalho, Guilherme M Gelfuso. Nanostructured lipid carriers loaded with an association of minoxidil and latanoprost for targeted topical therapy of alopecia.
European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V.
2022 Mar; 172(?):78-88. doi:
10.1016/j.ejpb.2022.02.003. [PMID: 35143972] - Hui Dang, Chunyun Dong, Li Zhang. Sustained latanoprost release from PEGylated solid lipid nanoparticle-laden soft contact lens to treat glaucoma.
Pharmaceutical development and technology.
2022 Feb; 27(2):127-133. doi:
10.1080/10837450.2021.1999471. [PMID: 34704874] - Xianbo Wu, Xinwei Yang, Qi Liang, Xiali Xue, Jianli Huang, Jie Wang, Yihua Xu, Rongsheng Tong, Maoyu Liu, Qiaodan Zhou, Jianyou Shi. Drugs for the treatment of glaucoma: Targets, structure-activity relationships and clinical research.
European journal of medicinal chemistry.
2021 Dec; 226(?):113842. doi:
10.1016/j.ejmech.2021.113842. [PMID: 34536672] - Arindam Halder, Ajay J Khopade. Pharmacokinetics and Pharmacology of Latanoprost 0.005\% without Benzalkonium Chloride Vs Latanoprost 0.005\% with Benzalkonium Chloride in New Zealand White Rabbits and Beagles.
Current eye research.
2021 07; 46(7):1031-1037. doi:
10.1080/02713683.2020.1855660. [PMID: 33719796] - Yasuko Yamamoto, Takazumi Taniguchi, Tomoaki Inazumi, Ryo Iwamura, Kenji Yoneda, Noriko Odani-Kawabata, Takeshi Matsugi, Yukihiko Sugimoto, Naveed K Shams. Effects of the Selective EP2 Receptor Agonist Omidenepag on Adipocyte Differentiation in 3T3-L1 Cells.
Journal of ocular pharmacology and therapeutics : the official journal of the Association for Ocular Pharmacology and Therapeutics.
2020 04; 36(3):162-169. doi:
10.1089/jop.2019.0079. [PMID: 31934812] - Alexandra Robciuc, Joanna Witos, Suvi-Katriina Ruokonen, Antti H Rantamäki, Pierre-Jean Pisella, Susanne K Wiedmer, Juha M Holopainen. Pure Glaucoma Drugs Are Toxic to Immortalized Human Corneal Epithelial Cells, but They Do Not Destabilize Lipid Membranes.
Cornea.
2017 Oct; 36(10):1249-1255. doi:
10.1097/ico.0000000000001322. [PMID: 28825921] - Jun-Wei Shen, Ming Shan, Yuan-Yuan Peng, Ting-Jun Fan. Cytotoxic Effect of Latanoprost on Human Corneal Stromal Cells in vitro and its Possible Mechanisms.
Current eye research.
2017 04; 42(4):534-541. doi:
10.1080/02713683.2016.1225770. [PMID: 27749098] - Richard A Lewis, Brian Levy, Nancy Ramirez, Casey C Kopczynski, Dale W Usner, Gary D Novack. Fixed-dose combination of AR-13324 and latanoprost: a double-masked, 28-day, randomised, controlled study in patients with open-angle glaucoma or ocular hypertension.
The British journal of ophthalmology.
2016 03; 100(3):339-44. doi:
10.1136/bjophthalmol-2015-306778. [PMID: 26209587] - Shinichiro Fuma, Masamitsu Shimazawa, Tomoyo Imamura, Yusuke Kanno, Norihito Takano, Kazuhiro Tsuruma, Hideaki Hara. Neuroprotective Effect of Ocular Hypotensive Drugs: Latanoprost/Timolol in Combination Are More Effective than Each as Monotherapy in RGC-5.
Biological & pharmaceutical bulletin.
2016; 39(2):192-8. doi:
10.1248/bpb.b15-00584. [PMID: 26830479] - Karsten Voss, Karen Falke, Arne Bernsdorf, Niels Grabow, Christian Kastner, Katrin Sternberg, Ingo Minrath, Thomas Eickner, Andreas Wree, Klaus-Peter Schmitz, Rudolf Guthoff, Martin Witt, Marina Hovakimyan. Development of a novel injectable drug delivery system for subconjunctival glaucoma treatment.
Journal of controlled release : official journal of the Controlled Release Society.
2015 Sep; 214(?):1-11. doi:
10.1016/j.jconrel.2015.06.035. [PMID: 26160303] - Jason Bacharach, Harvey B Dubiner, Brian Levy, Casey C Kopczynski, Gary D Novack. Double-masked, randomized, dose-response study of AR-13324 versus latanoprost in patients with elevated intraocular pressure.
Ophthalmology.
2015 Feb; 122(2):302-7. doi:
10.1016/j.ophtha.2014.08.022. [PMID: 25270273] - Gaihong Wang, Xing Xu, Xingang Yao, Zhiyuan Zhu, Liang Yu, Lili Chen, Jing Chen, Xu Shen. Latanoprost effectively ameliorates glucose and lipid disorders in db/db and ob/ob mice.
Diabetologia.
2013 Dec; 56(12):2702-12. doi:
10.1007/s00125-013-3032-8. [PMID: 23989723] - 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] - Reiko Arita, Kouzo Itoh, Shuji Maeda, Koshi Maeda, Ayumu Furuta, Atsuo Tomidokoro, Makoto Aihara, Shiro Amano. Effects of long-term topical anti-glaucoma medications on meibomian glands.
Graefe's archive for clinical and experimental ophthalmology = Albrecht von Graefes Archiv fur klinische und experimentelle Ophthalmologie.
2012 Aug; 250(8):1181-5. doi:
10.1007/s00417-012-1943-6. [PMID: 22349978] - 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] - Jayaganesh V Natarajan, Marcus Ang, Anastasia Darwitan, Sujay Chattopadhyay, Tina T Wong, Subbu S Venkatraman. Nanomedicine for glaucoma: liposomes provide sustained release of latanoprost in the eye.
International journal of nanomedicine.
2012; 7(?):123-31. doi:
10.2147/ijn.s25468. [PMID: 22275828] - Susan Raber, Rachel Courtney, Tomoko Maeda-Chubachi, Brad D Simons, Sharon F Freedman, Barbara Wirostko. Latanoprost systemic exposure in pediatric and adult patients with glaucoma: a phase 1, open-label study.
Ophthalmology.
2011 Oct; 118(10):2022-7. doi:
10.1016/j.ophtha.2011.03.039. [PMID: 21788077] - Jayaganesh V Natarajan, Sujay Chattopadhyay, Marcus Ang, Anastasia Darwitan, Selin Foo, Ma Zhen, Magdalene Koo, Tina T Wong, Subbu S Venkatraman. Sustained release of an anti-glaucoma drug: demonstration of efficacy of a liposomal formulation in the rabbit eye.
PloS one.
2011; 6(9):e24513. doi:
10.1371/journal.pone.0024513. [PMID: 21931735] - Michaela E Kraft, Hartmut Glaeser, Kathrin Mandery, Jörg König, Daniel Auge, Martin F Fromm, Ursula Schlötzer-Schrehardt, Ulrich Welge-Lüssen, Friedrich E Kruse, Oliver Zolk. The prostaglandin transporter OATP2A1 is expressed in human ocular tissues and transports the antiglaucoma prostanoid latanoprost.
Investigative ophthalmology & visual science.
2010 May; 51(5):2504-11. doi:
10.1167/iovs.09-4290. [PMID: 20019365] - 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] - Akiyasu Kanamori, Maiko Naka, Masahide Fukuda, Makoto Nakamura, Akira Negi. Latanoprost protects rat retinal ganglion cells from apoptosis in vitro and in vivo.
Experimental eye research.
2009 Mar; 88(3):535-41. doi:
10.1016/j.exer.2008.11.012. [PMID: 19084521] - D Călugăru, M Călugăru. [Bimatoprost therapy in glaucoma].
Oftalmologia (Bucharest, Romania : 1990).
2009; 53(3):34-45. doi:
". [PMID: 19899545] - H Ozdemir, M Karacorlu, S A Karacorlu. Serous detachment of macula in cystoid macular edema associated with latanoprost.
European journal of ophthalmology.
2008 Nov; 18(6):1014-6. doi:
10.1177/112067210801800627. [PMID: 18988179] - Berna Ozkan, V Levent Karabaş, Nurşen Yüksel, Yusuf Cağlar. Serous retinal detachment in the macula related to latanoprost use.
International ophthalmology.
2008 Oct; 28(5):363-5. doi:
10.1007/s10792-007-9137-7. [PMID: 17805489] - Diana Melinte Dumitrica, C Stefan. [Open-angle glaucoma associated with Groenblad-Strandberg syndrome].
Oftalmologia (Bucharest, Romania : 1990).
2008; 52(4):44-52. doi:
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Biochimica et biophysica acta.
2007 May; 1768(5):1083-92. doi:
10.1016/j.bbamem.2006.12.015. [PMID: 17307133] - 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] - Yoriko Nakanishi, Makoto Nakamura, Hirokazu Mukuno, Akiyasu Kanamori, Gail M Seigel, Akira Negi. Latanoprost rescues retinal neuro-glial cells from apoptosis by inhibiting caspase-3, which is mediated by p44/p42 mitogen-activated protein kinase.
Experimental eye research.
2006 Nov; 83(5):1108-17. doi:
10.1016/j.exer.2006.05.018. [PMID: 16839545] - 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] - Bernhard T Gehr, Christel Weiss, Franz Porzsolt. The fading of reported effectiveness. A meta-analysis of randomised controlled trials.
BMC medical research methodology.
2006 May; 6(?):25. doi:
10.1186/1471-2288-6-25. [PMID: 16689990] - Ciro Costagliola, Francesco Parmeggiani, Antonio Caccavale, Adolfo Sebastiani. Nimesulide oral administration increases the intraocular pressure-lowering effect of latanoprost in patients with primary open-angle glaucoma.
American journal of ophthalmology.
2006 Feb; 141(2):379-81. doi:
10.1016/j.ajo.2004.11.062. [PMID: 16458700] - 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] - Yusuke Sakai, Shin-Ichi Yasueda, Akira Ohtori. Stability of latanoprost in an ophthalmic lipid emulsion using polyvinyl alcohol.
International journal of pharmaceutics.
2005 Nov; 305(1-2):176-9. doi:
10.1016/j.ijpharm.2005.08.017. [PMID: 16207517] - Burkhard Hinz, Susanne Rösch, Robert Ramer, Ernst R Tamm, Kay Brune. Latanoprost induces matrix metalloproteinase-1 expression in human nonpigmented ciliary epithelial cells through a cyclooxygenase-2-dependent mechanism.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology.
2005 Nov; 19(13):1929-31. doi:
10.1096/fj.04-3626fje. [PMID: 16076963] - 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] - Richard L Hébert, Monica Carmosino, Osamu Saito, Guangrui Yang, Cynthia A Jackson, Zhonghua Qi, Richard M Breyer, Chandramohan Natarajan, Aaron N Hata, Yahua Zhang, Youfei Guan, Matthew D Breyer. Characterization of a rabbit kidney prostaglandin F(2{alpha}) receptor exhibiting G(i)-restricted signaling that inhibits water absorption in the collecting duct.
The Journal of biological chemistry.
2005 Oct; 280(41):35028-37. doi:
10.1074/jbc.m505852200. [PMID: 16096282] - Kwou-Yeung Wu, Hwei-Zu Wang, Show-Jen Hong. Effect of latanoprost on cultured porcine corneal stromal cells.
Current eye research.
2005 Oct; 30(10):871-9. doi:
10.1080/02713680591006237. [PMID: 16251124] - Robert N Weinreb, James D Lindsey, George Marchenko, Natalia Marchenko, Mila Angert, Alex Strongin. Prostaglandin FP agonists alter metalloproteinase gene expression in sclera.
Investigative ophthalmology & visual science.
2004 Dec; 45(12):4368-77. doi:
10.1167/iovs.04-0413. [PMID: 15557445] - 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:
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Journal of glaucoma.
2003 Dec; 12(6):480-5. doi:
10.1097/00061198-200312000-00007. [PMID: 14646683] - Catherine Blondin, Pascale Hamard, Béatrice Cholley, Nicole Haeffner-Cavaillon, Christophe Baudouin. In vitro effects of preserved or preservative-free antiglaucoma medications on human complement system.
Current eye research.
2003 Oct; 27(4):253-9. doi:
10.1076/ceyr.27.4.253.16603. [PMID: 14562177] - Yoko Goto, Nobuhiro Ibaraki, Kensaku Miyake. Human lens epithelial cell damage and stimulation of their secretion of chemical mediators by benzalkonium chloride rather than latanoprost and timolol.
Archives of ophthalmology (Chicago, Ill. : 1960).
2003 Jun; 121(6):835-9. doi:
10.1001/archopht.121.6.835. [PMID: 12796255] - 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] - Todd L Anthony, James D Lindsey, Robert N Weinreb. Latanoprost's effects on TIMP-1 and TIMP-2 expression in human ciliary muscle cells.
Investigative ophthalmology & visual science.
2002 Dec; 43(12):3705-11. doi:
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Survey of ophthalmology.
2002 Aug; 47 Suppl 1(?):S6-12. doi:
10.1016/s0039-6257(02)00302-8. [PMID: 12204697] - Martin Wand, Bruce M Shields. Cystoid macular edema in the era of ocular hypotensive lipids.
American journal of ophthalmology.
2002 Mar; 133(3):393-7. doi:
10.1016/s0002-9394(01)01412-x. [PMID: 11915838] - Kenji Kashiwagi, Naoaki Kanai, Takayuki Tsuchida, Michihiro Suzuki, Yoko Iizuka, Yuko Tanaka, Shigeo Tsukahara. Comparison between isopropyl unoprostone and latanoprost by prostaglandin E(2)induction, affinity to prostaglandin transporter, and intraocular metabolism.
Experimental eye research.
2002 Jan; 74(1):41-9. doi:
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Prostaglandins & other lipid mediators.
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Archives of ophthalmology (Chicago, Ill. : 1960).
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Arzneimittel-Forschung.
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Arzneimittel-Forschung.
1999 Mar; 49(3):240-9. doi:
10.1055/s-0031-1300408. [PMID: 10219468] - B Sjöquist, S Tajallaei, J Stjernschantz. Pharmacokinetics of latanoprost in the cynomolgus monkey. 1st communication: single intravenous, oral or topical administration on the eye.
Arzneimittel-Forschung.
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Drug metabolism and disposition: the biological fate of chemicals.
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Progress in retinal and eye research.
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Prostaglandins, leukotrienes, and essential fatty acids.
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Journal of lipid mediators.
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". [PMID: 8358014]