Cicaprost (BioDeep_00000388654)

   


代谢物信息卡片


2-[2-[(2E,3aS,4S,5R,6aS)-hexahydro-5-hydroxy-4-[(3S,4S)-3-hydroxy-4-methyl-1,6-nonadiyn-1-yl]-2(1H)-pentalenylidene]ethoxy]-acetic acid

化学式: C22H30O5 (374.2093)
中文名称: 西卡前列素
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CCC#CCC(C)C(C#CC1C(CC2C1CC(=CCOCC(=O)O)C2)O)O
InChI: InChI=1S/C22H30O5/c1-3-4-5-6-15(2)20(23)8-7-18-19-12-16(9-10-27-14-22(25)26)11-17(19)13-21(18)24/h9,15,17-21,23-24H,3,6,10-14H2,1-2H3,(H,25,26)/b16-9+/t15-,17-,18+,19-,20+,21+/m0/s1

描述信息

D000970 - Antineoplastic Agents
C78568 - Prostaglandin Analogue

同义名列表

3 个代谢物同义名

Cicaprost; 2-[2-[(2E,3aS,4S,5R,6aS)-hexahydro-5-hydroxy-4-[(3S,4S)-3-hydroxy-4-methyl-1,6-nonadiyn-1-yl]-2(1H)-pentalenylidene]ethoxy]-acetic acid; ZK 96480



数据库引用编号

7 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。

亚细胞结构定位 关联基因列表


文献列表

  • Weisong Zhou, Jian Zhang, Shinji Toki, Kasia Goleniewska, Marc O Johnson, Melissa H Bloodworth, Dawn C Newcomb, R Stokes Peebles. The PGI2 Analog Cicaprost Inhibits IL-33-Induced Th2 Responses, IL-2 Production, and CD25 Expression in Mouse CD4+ T Cells. Journal of immunology (Baltimore, Md. : 1950). 2018 10; 201(7):1936-1945. doi: 10.4049/jimmunol.1700605. [PMID: 30127087]
  • Aparna Duggirala, Tomomi E Kimura, Graciela B Sala-Newby, Jason L Johnson, Yih-Jer Wu, Andrew C Newby, Mark Bond. cAMP-induced actin cytoskeleton remodelling inhibits MKL1-dependent expression of the chemotactic and pro-proliferative factor, CCN1. Journal of molecular and cellular cardiology. 2015 Feb; 79(?):157-68. doi: 10.1016/j.yjmcc.2014.11.012. [PMID: 25446180]
  • Tomomi E Kimura, Aparna Duggirala, Charles C T Hindmarch, Richard C Hewer, Mei-Zhen Cui, Andrew C Newby, Mark Bond. Inhibition of Egr1 expression underlies the anti-mitogenic effects of cAMP in vascular smooth muscle cells. Journal of molecular and cellular cardiology. 2014 Jul; 72(?):9-19. doi: 10.1016/j.yjmcc.2014.02.001. [PMID: 24534707]
  • Weisong Zhou, Dustin R Dowell, Matthew M Huckabee, Dawn C Newcomb, Madison G Boswell, Kasia Goleniewska, Matthew T Lotz, Shinji Toki, Huiyong Yin, Songyi Yao, Chandramohan Natarajan, Pingsheng Wu, Subramaniam Sriram, Richard M Breyer, Garret A Fitzgerald, R Stokes Peebles. Prostaglandin I2 signaling drives Th17 differentiation and exacerbates experimental autoimmune encephalomyelitis. PloS one. 2012; 7(5):e33518. doi: 10.1371/journal.pone.0033518. [PMID: 22590492]
  • Madison G Boswell, Weisong Zhou, Dawn C Newcomb, R Stokes Peebles. PGI2 as a regulator of CD4+ subset differentiation and function. Prostaglandins & other lipid mediators. 2011 Nov; 96(1-4):21-6. doi: 10.1016/j.prostaglandins.2011.08.003. [PMID: 21864703]
  • Paola Castagnino, Devashish Kothapalli, Elizabeth A Hawthorne, Tina Xu, Richard K Assoian. Cell-type- and cell-cycle-specific anti-mitogenesis by cicaprost. Prostaglandins & other lipid mediators. 2010 Sep; 93(1-2):20-4. doi: 10.1016/j.prostaglandins.2010.04.004. [PMID: 20457271]
  • Ying Yu, Jane Stubbe, Salam Ibrahim, Wen-liang Song, Emer M Smyth, Emer M Symth, Colin D Funk, Garret A FitzGerald. Cyclooxygenase-2-dependent prostacyclin formation and blood pressure homeostasis: targeted exchange of cyclooxygenase isoforms in mice. Circulation research. 2010 Feb; 106(2):337-45. doi: 10.1161/circresaha.109.204529. [PMID: 19940265]
  • Katarina Wikström, Helen M Reid, Maria Hill, Karol A English, Martina B O'Keeffe, Cisca C Kimbembe, B Therese Kinsella. Recycling of the human prostacyclin receptor is regulated through a direct interaction with Rab11a GTPase. Cellular signalling. 2008 Dec; 20(12):2332-46. doi: 10.1016/j.cellsig.2008.09.003. [PMID: 18832025]
  • Rico K H Lo, Andrew M F Liu, Helen Wise, Yung H Wong. Prostacyclin receptor-induced STAT3 phosphorylation in human erythroleukemia cells is mediated via Galpha(s) and Galpha(16) hybrid signaling. Cellular signalling. 2008 Nov; 20(11):2095-106. doi: 10.1016/j.cellsig.2008.08.003. [PMID: 18755267]
  • Martina B O'Keeffe, Helen M Reid, B Therese Kinsella. Agonist-dependent internalization and trafficking of the human prostacyclin receptor: a direct role for Rab5a GTPase. Biochimica et biophysica acta. 2008 Oct; 1783(10):1914-28. doi: 10.1016/j.bbamcr.2008.04.010. [PMID: 18498773]
  • R Scott Obach, Franco Lombardo, Nigel J Waters. Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds. Drug metabolism and disposition: the biological fate of chemicals. 2008 Jul; 36(7):1385-405. doi: 10.1124/dmd.108.020479. [PMID: 18426954]
  • Sarah J O'Meara, B Therese Kinsella. The effect of the farnesyl protein transferase inhibitor SCH66336 on isoprenylation and signalling by the prostacyclin receptor. The Biochemical journal. 2005 Feb; 386(Pt 1):177-89. doi: 10.1042/bj20041290. [PMID: 15469414]
  • Kerstin Rabausch, Ellen Bretschneider, Mario Sarbia, Jutta Meyer-Kirchrath, Petra Censarek, Robert Pape, Jens W Fischer, Karsten Schrör, Artur-Aron Weber. Regulation of thrombomodulin expression in human vascular smooth muscle cells by COX-2-derived prostaglandins. Circulation research. 2005 Jan; 96(1):e1-6. doi: 10.1161/01.res.0000153150.27690.f2. [PMID: 15591227]
  • Rania Nasrallah, Richard L Hébert. Reduced IP receptors in STZ-induced diabetic rat kidneys and high-glucose-treated mesangial cells. American journal of physiology. Renal physiology. 2004 Oct; 287(4):F673-81. doi: 10.1152/ajprenal.00025.2004. [PMID: 15161601]
  • Rania Nasrallah, Anne Landry, James W Scholey, Richard L Hébert. Characterization of the PGI2/IP system in cultured rat mesangial cells. Prostaglandins, leukotrienes, and essential fatty acids. 2004 May; 70(5):455-64. doi: 10.1016/j.plefa.2003.09.004. [PMID: 15062848]
  • Kevin B S Chow, Robert L Jones, Helen Wise. Protein kinase A-dependent coupling of mouse prostacyclin receptors to Gi is cell-type dependent. European journal of pharmacology. 2003 Aug; 474(1):7-13. doi: 10.1016/s0014-2999(03)02006-5. [PMID: 12909190]
  • Lucie H Clapp, Paul Finney, Sally Turcato, Sandy Tran, Lewis J Rubin, Andrew Tinker. Differential effects of stable prostacyclin analogs on smooth muscle proliferation and cyclic AMP generation in human pulmonary artery. American journal of respiratory cell and molecular biology. 2002 Feb; 26(2):194-201. doi: 10.1165/ajrcmb.26.2.4695. [PMID: 11804870]
  • O A Lawler, S M Miggin, B T Kinsella. Protein kinase A-mediated phosphorylation of serine 357 of the mouse prostacyclin receptor regulates its coupling to G(s)-, to G(i)-, and to G(q)-coupled effector signaling. The Journal of biological chemistry. 2001 Sep; 276(36):33596-607. doi: 10.1074/jbc.m104434200. [PMID: 11443126]
  • K Guyton, R Bond, C Reilly, G Gilkeson, P Halushka, J Cook. Differential effects of 15-deoxy-delta(12,14)-prostaglandin J2 and a peroxisome proliferator-activated receptor gamma agonist on macrophage activation. Journal of leukocyte biology. 2001 Apr; 69(4):631-8. doi: NULL. [PMID: 11310850]
  • J Wharton, N Davie, P D Upton, M H Yacoub, J M Polak, N W Morrell. Prostacyclin analogues differentially inhibit growth of distal and proximal human pulmonary artery smooth muscle cells. Circulation. 2000 Dec; 102(25):3130-6. doi: 10.1161/01.cir.102.25.3130. [PMID: 11120706]
  • S J Wort, J A Mitchell, M Woods, T W Evans, T D Warner. The prostacyclin-mimetic cicaprost inhibits endogenous endothelin-1 release from human pulmonary artery smooth muscle cells. Journal of cardiovascular pharmacology. 2000 Nov; 36(5 Suppl 1):S410-3. doi: 10.1097/00005344-200036051-00120. [PMID: 11078436]
  • M T Walsh, J F Foley, B T Kinsella. The alpha, but not the beta, isoform of the human thromboxane A2 receptor is a target for prostacyclin-mediated desensitization. The Journal of biological chemistry. 2000 Jul; 275(27):20412-23. doi: 10.1074/jbc.m907881199. [PMID: 10827090]
  • M Abramovitz, M Adam, Y Boie, M Carrière, D Denis, C Godbout, S Lamontagne, C Rochette, N Sawyer, N M Tremblay, M Belley, M Gallant, C Dufresne, Y Gareau, R Ruel, H Juteau, M Labelle, N Ouimet, K M Metters. The utilization of recombinant prostanoid receptors to determine the affinities and selectivities of prostaglandins and related analogs. Biochimica et biophysica acta. 2000 Jan; 1483(2):285-93. doi: 10.1016/s1388-1981(99)00164-x. [PMID: 10634944]
  • C Hillier, P J Cowburn, J J Morton, H J Dargie, J G Cleland, J J McMurray, J C McGrath. Structural and functional assessment of small arteries in patients with chronic heart failure. Clinical science (London, England : 1979). 1999 Dec; 97(6):671-9. doi: NULL. [PMID: 10585894]
  • M Schirner, C Kraus, R B Lichtner, M R Schneider, M Hildebrand. Tumor metastasis inhibition with the prostacyclin analogue cicaprost depends on discontinuous plasma peak levels. Prostaglandins, leukotrienes, and essential fatty acids. 1998 Apr; 58(4):311-7. doi: 10.1016/s0952-3278(98)90041-2. [PMID: 9654405]
  • E Villa, A Rábano, L M Ruilope, R García-Robles. Effects of cicaprost and fosinopril on the progression of rat diabetic nephropathy. American journal of hypertension. 1997 Feb; 10(2):202-8. doi: 10.1016/s0895-7061(96)00319-6. [PMID: 9037329]
  • J van Baal, M D de Jong, F J Zijlstra, P H Willems, R J Bindels. Endogenously produced prostanoids stimulate calcium reabsorption in the rabbit cortical collecting system. The Journal of physiology. 1996 Nov; 497 ( Pt 1)(?):229-39. doi: 10.1113/jphysiol.1996.sp021763. [PMID: 8951725]
  • M Hildebrand. Inter-species extrapolation of pharmacokinetic data of three prostacyclin-mimetics. Prostaglandins. 1994 Nov; 48(5):297-312. doi: 10.1016/0090-6980(94)90030-2. [PMID: 7531864]
  • D J Crutchley, L B Conanan, B G Que. Effects of prostacyclin analogs on the synthesis of tissue factor, tumor necrosis factor-alpha and interleukin-1 beta in human monocytic THP-1 cells. The Journal of pharmacology and experimental therapeutics. 1994 Oct; 271(1):446-51. doi: . [PMID: 7525928]
  • M Berg, S Offermanns, R Seifert, G Schultz. Synthetic lipopeptide Pam3CysSer(Lys)4 is an effective activator of human platelets. The American journal of physiology. 1994 Jun; 266(6 Pt 1):C1684-91. doi: 10.1152/ajpcell.1994.266.6.c1684. [PMID: 8023898]
  • M Hildebrand, B Nieuweboer, A Schütt. Development and validation of a sensitive and specific radioimmunoassay for the determination of cicaprost in biological samples. Journal of immunoassay. 1994 May; 15(2):171-90. doi: 10.1080/15321819408013946. [PMID: 8040351]
  • C S Holladay, R M Wright, B L Spangelo. Arachidonic acid stimulates interleukin-6 release from rat peritoneal macrophages in vitro: evidence for a prostacyclin-dependent mechanism. Prostaglandins, leukotrienes, and essential fatty acids. 1993 Dec; 49(6):915-22. doi: 10.1016/0952-3278(93)90176-w. [PMID: 7511246]
  • R G Robles, E Villa, A Rábano, E Alvarez, J Martínez, L M Ruilope, J M Sancho. Effect of cicaprost on the progression of diabetic nephropathy in uninephrectomized streptozotocin-induced diabetic rats. Journal of hypertension. Supplement : official journal of the International Society of Hypertension. 1993 Dec; 11(5):S208-9. doi: 10.1097/00004872-199312050-00083. [PMID: 8158348]
  • M Braun, T Hohlfeld, P Kienbaum, A A Weber, M Sarbia, K Schrör. Antiatherosclerotic effects of oral cicaprost in experimental hypercholesterolemia in rabbits. Atherosclerosis. 1993 Oct; 103(1):93-105. doi: 10.1016/0021-9150(93)90043-t. [PMID: 8280189]
  • M Hildebrand. Bioactivation of eptaloprost in animals and man. Prostaglandins. 1993 Aug; 46(2):177-89. doi: 10.1016/0090-6980(93)90043-7. [PMID: 7692471]
  • J J Belch, M McLaren, C S Lau, I R Mackay, A Bancroft, J McEwen, J M Thompson. Cicaprost, an orally active prostacyclin analogue: its effects on platelet aggregation and skin blood flow in normal volunteers. British journal of clinical pharmacology. 1993 Jun; 35(6):643-7. doi: 10.1111/j.1365-2125.1993.tb04195.x. [PMID: 8329292]
  • E Villa, J Martinez, L M Ruilope, F Mampaso, J M Sancho, R G Robles. Cicaprost, a prostacyclin analog, protects renal function in uninephrectomized dogs in the absence of changes in blood pressure. American journal of hypertension. 1993 Apr; 6(4):253-7. doi: 10.1093/ajh/6.4.253. [PMID: 8507442]
  • M Hildebrand. Pharmacokinetics of iloprost and cicaprost in mice. Prostaglandins. 1992 Nov; 44(5):431-42. doi: 10.1016/0090-6980(92)90138-j. [PMID: 1281921]
  • C S Lau, M McLaren, A Saniabadi, N Scott, J J Belch. The pharmacological effects of cicaprost, an oral prostacyclin analogue, in patients with Raynaud's syndrome secondary to systemic sclerosis--a preliminary study. Clinical and experimental rheumatology. 1991 May; 9(3):271-3. doi: NULL. [PMID: 1879086]
  • M Hildebrand, T Staks, B Nieuweboer. Pharmacokinetics and pharmacodynamics of cicaprost in healthy volunteers after oral administration of 5 to 20 micrograms. European journal of clinical pharmacology. 1990; 39(2):149-53. doi: 10.1007/bf00280049. [PMID: 2253664]
  • M Hildebrand, T Staks, A Schütt, H Matthes. Pharmacokinetics of 3H-cicaprost in healthy volunteers. Prostaglandins. 1989 Feb; 37(2):259-73. doi: 10.1016/0090-6980(89)90062-2. [PMID: 2657866]
  • T Duka, D N Stephens, W Krause, R Dorow. Human studies on the benzodiazepine receptor antagonist beta-carboline ZK 93,426: preliminary observations on psychotropic activity. Psychopharmacology. 1987; 93(4):421-7. doi: 10.1007/bf00207229. [PMID: 2829267]
  • M Hildebrand. Studies on the pharmacokinetics of ZK 96 480, a novel PGI2-mimetic, in rat and cynomolgus monkey. Prostaglandins. 1986 Sep; 32(3):425-38. doi: 10.1016/0090-6980(86)90010-9. [PMID: 3538205]