Etretinate (BioDeep_00000592689)

   


代谢物信息卡片


(2E,4E,6E,8E)-9-(4-Methoxy-2,3,6-trimethyl-phenyl)-3,7-dimethyl-nona-2,4,6,8-tetraenoic acid ethyl ester

化学式: C23H30O3 (354.2195)
中文名称: 依曲替酯
谱图信息: 最多检出来源 Homo sapiens(lipidomics) 75%

分子结构信息

SMILES: C1(C)=C(C)C(/C=C/C(=C/C=C/C(=C/C(=O)OCC)/C)/C)=C(C)C=C1OC
InChI: InChI=1S/C23H30O3/c1-8-26-23(24)14-17(3)11-9-10-16(2)12-13-21-18(4)15-22(25-7)20(6)19(21)5/h9-15H,8H2,1-7H3/b11-9+,13-12+,16-10+,17-14+

描述信息

D - Dermatologicals > D05 - Antipsoriatics > D05B - Antipsoriatics for systemic use > D05BB - Retinoids for treatment of psoriasis
C274 - Antineoplastic Agent > C2122 - Cell Differentiating Agent > C1934 - Differentiation Inducer
C274 - Antineoplastic Agent > C163758 - Targeted Therapy Agent > C804 - Retinoic Acid Agent
C308 - Immunotherapeutic Agent > C129820 - Antineoplastic Immunomodulating Agent
D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids
D003879 - Dermatologic Agents > D007641 - Keratolytic Agents

同义名列表

2 个代谢物同义名

Etretinate; (2E,4E,6E,8E)-9-(4-Methoxy-2,3,6-trimethyl-phenyl)-3,7-dimethyl-nona-2,4,6,8-tetraenoic acid ethyl ester



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。

亚细胞结构定位 关联基因列表


文献列表

  • Yuya Murase, Takuya Takeichi, Akane Kawamoto, Kana Tanahashi, Yusuke Okuno, Hiroyuki Takama, Eri Shimizu, Junko Ishikawa, Tomoo Ogi, Masashi Akiyama. Reduced stratum corneum acylceramides in autosomal recessive congenital ichthyosis with a NIPAL4 mutation. Journal of dermatological science. 2020 Jan; 97(1):50-56. doi: 10.1016/j.jdermsci.2019.12.001. [PMID: 31836270]
  • Takaya Komori, Maria Cho, Akiha Inoue, Megumi Aoki, Shigeto Matsushita. Effectiveness of etretinate/yokuinin combination therapy for lip squamous cell carcinoma. The Journal of dermatology. 2019 Feb; 46(2):e71-e72. doi: 10.1111/1346-8138.14546. [PMID: 30035310]
  • Tsuyoshi Inoue, Masaomi Nangaku, Koei Yamada. Vitamin A treatment for psoriasis vulgaris in a dialysis patient. American journal of kidney diseases : the official journal of the National Kidney Foundation. 2013 Nov; 62(5):1020-1. doi: 10.1053/j.ajkd.2013.07.018. [PMID: 24011973]
  • S Y Shin, Y H Shin, S W Lee, J Y Shin, C H Kim. Blood donors on teratogenic drugs and donor deferral periods in a clinical situation. Vox sanguinis. 2012 May; 102(4):362-4. doi: 10.1111/j.1423-0410.2011.01566.x. [PMID: 22211799]
  • H-D Park, H-K Kim, M-R Chun, J-W Kim, D-W Kim, J-H Lee, W S Huh, J-I Youn, H-G Kim, Y G Kim, M-H Kim, S-Y Lee. A fully validated HPLC method for the simultaneous determination of acitretin and etretinate in plasma and its application to a pharmacokinetic study in healthy Korean subjects. International journal of clinical pharmacology and therapeutics. 2009 Jul; 47(7):476-82. doi: 10.5414/cpp47476. [PMID: 19640355]
  • Hyung-Doo Park, Hye-Kyung Kim, Jong-Won Kim, Dae-Won Kim, Joo-Heung Lee, Wooseong Huh, Jai-Il Youn, Hyung-Gun Kim, Yoon-Gyoon Kim, Myung-Hwa Kim, Soo-Youn Lee. Evaluation of the transfusion safety of blood products and determination of plasma concentrations of acitretin and etretinate in patients receiving transfusions. Transfusion. 2008 Nov; 48(11):2395-400. doi: 10.1111/j.1537-2995.2008.01850.x. [PMID: 18657077]
  • Min Zhang, Peirong Hu, Charles R Krois, Maureen A Kane, Joseph L Napoli. Altered vitamin A homeostasis and increased size and adiposity in the rdh1-null mouse. FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 2007 Sep; 21(11):2886-96. doi: 10.1096/fj.06-7964com. [PMID: 17435174]
  • N Komatsu, K Saijoh, C Kuk, F Shirasaki, K Takehara, E P Diamandis. Aberrant human tissue kallikrein levels in the stratum corneum and serum of patients with psoriasis: dependence on phenotype, severity and therapy. The British journal of dermatology. 2007 May; 156(5):875-83. doi: 10.1111/j.1365-2133.2006.07743.x. [PMID: 17459012]
  • Peirong Hu, Min Zhang, Joseph L Napoli. Ontogeny of rdh9 (Crad3) expression: ablation causes changes in retinoid and steroid metabolizing enzymes, but RXR and androgen signaling seem normal. Biochimica et biophysica acta. 2007 Apr; 1770(4):694-705. doi: 10.1016/j.bbagen.2006.12.008. [PMID: 17270348]
  • Masashi Akiyama, Kaori Sakai, Yoriko Sugiyama-Nakagiri, Yasuko Yamanaka, James R McMillan, Daisuke Sawamura, Hironori Niizeki, Sachiko Miyagawa, Hiroshi Shimizu. Compound heterozygous mutations including a de novo missense mutation in ABCA12 led to a case of harlequin ichthyosis with moderate clinical severity. The Journal of investigative dermatology. 2006 Jul; 126(7):1518-23. doi: 10.1038/sj.jid.5700295. [PMID: 16675967]
  • R P Katugampola, A Y Finlay. Oral retinoid therapy for disorders of keratinization: single-centre retrospective 25 years' experience on 23 patients. The British journal of dermatology. 2006 Feb; 154(2):267-76. doi: 10.1111/j.1365-2133.2005.06906.x. [PMID: 16433796]
  • A Górnicki, A Gutsze. In vivo and in vitro influence of etretinate on erythrocyte membrane fluidity. European journal of pharmacology. 2001 Jul; 423(2-3):127-34. doi: 10.1016/s0014-2999(01)01126-8. [PMID: 11448476]
  • F Grønhøj Larsen, B Steinkjer, P Jakobsen, A Hjorter, P B Brockhoff, F Nielsen-Kudsk. Acitretin is converted to etretinate only during concomitant alcohol intake. The British journal of dermatology. 2000 Dec; 143(6):1164-9. doi: 10.1046/j.1365-2133.2000.03883.x. [PMID: 11122016]
  • H I Katz, J Waalen, E E Leach. Acitretin in psoriasis: an overview of adverse effects. Journal of the American Academy of Dermatology. 1999 Sep; 41(3 Pt 2):S7-S12. doi: 10.1016/s0190-9622(99)70359-2. [PMID: 10459140]
  • M L Khatri, M Bemghazil, M Shafi, A Machina. Xeroderma pigmentosum in Libya. International journal of dermatology. 1999 Jul; 38(7):520-4. doi: 10.1046/j.1365-4362.1999.00751.x. [PMID: 10440281]
  • A Utani, Y Hattori. A reactive acrosyringeal proliferation in a patient with ectodermal dysplasia: eccrine syringofibroadenoma-like lesion. The Journal of dermatology. 1999 Jan; 26(1):36-43. doi: 10.1111/j.1346-8138.1999.tb03507.x. [PMID: 10063211]
  • R E Schopf, T Hultsch, J Lotz, M Bräutigam. Eosinophils, pruritus and psoriasis: effects of treatment with etretinate or cyclosporin-A. Journal of the European Academy of Dermatology and Venereology : JEADV. 1998 Nov; 11(3):234-9. doi: 10.1111/j.1468-3083.1998.tb00975.x. [PMID: 9883435]
  • J B Robinson, D D Im, E Simmons-O'Brien, N B Rosenshein. Etretinate: therapy for plasma cell vulvitis. Obstetrics and gynecology. 1998 Oct; 92(4 Pt 2):706. doi: 10.1016/s0029-7844(98)00238-5. [PMID: 9764673]
  • N H Brockmeyer, S Frühauf, L Mertins, B Barthel, M Goos. Effects of antipsoriatic therapies on hepatic microsomal enzyme activity in patients with psoriasis. European journal of medical research. 1998 Aug; 3(8):361-6. doi: NULL. [PMID: 9707517]
  • G E Gibson, A O'Grady, E W Kay, M Leader, G M Murphy. Langerhans cells in benign, premalignant and malignant skin lesions of renal transplant recipients and the effect of retinoid therapy. Journal of the European Academy of Dermatology and Venereology : JEADV. 1998 Mar; 10(2):130-6. doi: NULL. [PMID: 9553909]
  • G E Gibson, A O'Grady, E W Kay, G M Murphy. Low-dose retinoid therapy for chemoprophylaxis of skin cancer in renal transplant recipients. Journal of the European Academy of Dermatology and Venereology : JEADV. 1998 Jan; 10(1):42-7. doi: NULL. [PMID: 9552756]
  • A Mussi, C Bonifati, M Carducci, G D'Agosto, F Pimpinelli, D D'Urso, L D'Auria, M Fazio, F Ameglio. Serum TNF-alpha levels correlate with disease severity and are reduced by effective therapy in plaque-type psoriasis. Journal of biological regulators and homeostatic agents. 1997 Jul; 11(3):115-8. doi: NULL. [PMID: 9498161]
  • G E Gibson, A O'Grady, E W Kay, M Leader, G M Murphy. p53 tumor suppressor gene protein expression in premalignant and malignant skin lesions of kidney transplant recipients. Journal of the American Academy of Dermatology. 1997 Jun; 36(6 Pt 1):924-31. doi: 10.1016/s0190-9622(97)80274-5. [PMID: 9204056]
  • H Maier, H Hönigsmann. Concentration of etretinate in plasma and subcutaneous fat after long-term acitretin. Lancet (London, England). 1996 Oct; 348(9034):1107. doi: 10.1016/s0140-6736(05)64457-1. [PMID: 8874484]
  • F Pomponi, R Cariati, P Zancai, P De Paoli, S Rizzo, R M Tedeschi, B Pivetta, S De Vita, M Boiocchi, R Dolcetti. Retinoids irreversibly inhibit in vitro growth of Epstein-Barr virus-immortalized B lymphocytes. Blood. 1996 Oct; 88(8):3147-59. doi: 10.1182/blood.v88.8.3147.bloodjournal8883147. [PMID: 8874215]
  • M Haftek, F Cambazard, D Dhouailly, A Réano, M Simon, A Lachaux, G Serre, A Claudy, D Schmitt. A longitudinal study of a harlequin infant presenting clinically as non-bullous congenital ichthyosiform erythroderma. The British journal of dermatology. 1996 Sep; 135(3):448-53. doi: ". [PMID: 8949442]
  • B Almond-Roesler, C E Orfanos. [Trans-acitretin is metabolized back to etretinate. Importance for oral retinoid therapy]. Der Hautarzt; Zeitschrift fur Dermatologie, Venerologie, und verwandte Gebiete. 1996 Mar; 47(3):173-7. doi: 10.1007/s001050050398. [PMID: 8647698]
  • O Bäck, T K Nilsson. Retinoids and fibrinolysis. Acta dermato-venereologica. 1995 Jul; 75(4):290-2. doi: 10.2340/0001555575290292. [PMID: 8578951]
  • M A Decker, C L Zimmerman. Simultaneous determination of etretinate, acitretin and their metabolites in perfusate, perfusate plasma, bile or hepatic tissue with reversed-phase high-performance liquid chromatography. Journal of chromatography. B, Biomedical applications. 1995 May; 667(1):105-13. doi: 10.1016/0378-4347(94)00600-a. [PMID: 7663673]
  • A H Rook, C Jaworsky, T Nguyen, R A Grossman, J T Wolfe, W K Witmer, A M Kligman. Beneficial effect of low-dose systemic retinoid in combination with topical tretinoin for the treatment and prophylaxis of premalignant and malignant skin lesions in renal transplant recipients. Transplantation. 1995 Mar; 59(5):714-9. doi: 10.1097/00007890-199503150-00013. [PMID: 7886798]
  • K Osada, M Seishima, S Mori, M Seishima, M Takemura, A Noma. Etretinate administration reduces serum propeptide of type I procollagen level in patients with psoriasis. The British journal of dermatology. 1994 Nov; 131(5):655-9. doi: 10.1111/j.1365-2133.1994.tb04977.x. [PMID: 7999596]
  • M C Sturkenboom, L T de Jong-Van Den Berg, P C van Voorst-Vader, M C Cornel, B H Stricker, H Wesseling. Inability to detect plasma etretinate and acitretin is a poor predictor of the absence of these teratogens in tissue after stopping acitretin treatment. British journal of clinical pharmacology. 1994 Sep; 38(3):229-35. doi: 10.1111/j.1365-2125.1994.tb04346.x. [PMID: 7826824]
  • S Takizawa, N Fukatsu, I Horii, T Fujii. Effect of etretinate (aromatic retinoid) treatment during gestation and lactation periods on viability and somatic growth in F1 rats. The Journal of toxicological sciences. 1994 May; 19(2):107-18. doi: 10.2131/jts.19.2_107. [PMID: 8072039]
  • M T Glover, N Niranjan, J T Kwan, I M Leigh. Non-melanoma skin cancer in renal transplant recipients: the extent of the problem and a strategy for management. British journal of plastic surgery. 1994 Mar; 47(2):86-9. doi: 10.1016/0007-1226(94)90164-3. [PMID: 8149064]
  • E U Eisenhardt, M H Bickel. Kinetics of tissue distribution and elimination of retinoid drugs in the rat. II. Etretinate. Drug metabolism and disposition: the biological fate of chemicals. 1994 Jan; 22(1):31-5. doi: NULL. [PMID: 8149886]
  • C Frati, L Bevilacqua, V Apostolico. Association of etretinate and fish oil in psoriasis therapy. Inhibition of hypertriglyceridemia resulting from retinoid therapy after fish oil supplementation. Acta dermato-venereologica. Supplementum. 1994; 186(?):151-3. doi: NULL. [PMID: 8073820]
  • M S Matsui, I Illarda, N Wang, V A DeLeo. Protein kinase C agonist and antagonist effects in normal human epidermal keratinocytes. Experimental dermatology. 1993 Dec; 2(6):247-56. doi: 10.1111/j.1600-0625.1993.tb00041.x. [PMID: 8162345]
  • F G Larsen, P Jakobsen, J Knudsen, K Weismann, K Kragballe, F Nielsen-Kudsk. Conversion of acitretin to etretinate in psoriatic patients is influenced by ethanol. The Journal of investigative dermatology. 1993 May; 100(5):623-7. doi: 10.1111/1523-1747.ep12472293. [PMID: 8491984]
  • E Meyer, J de Bersaques, W E Lambert, A P de Leenheer, A H Kint. Skin, adipose tissue and plasma levels of acitretin with rare occurrence of esterified acitretin during long-term treatment. Acta dermato-venereologica. 1993 Apr; 73(2):113-5. doi: 10.2340/0001555573113115. [PMID: 8103254]
  • A B Watson. Etretinate therapy of solar-related kerato acanthoma. The Australasian journal of dermatology. 1993; 34(1):9-11. doi: 10.1111/j.1440-0960.1993.tb00836.x. [PMID: 8240190]
  • I R Webber, D J Back. Effect of etretinate on cyclosporin metabolism in vitro. The British journal of dermatology. 1993 Jan; 128(1):42-4. doi: 10.1111/j.1365-2133.1993.tb00145.x. [PMID: 8427820]
  • W E Lambert, E Meyer, A P De Leenheer, J De Bersaques, A H Kint. Pharmacokinetics and drug interactions of etretinate and acitretin. Journal of the American Academy of Dermatology. 1992 Dec; 27(6 Pt 2):S19-22. doi: 10.1016/s0190-9622(08)80255-1. [PMID: 1460119]
  • S Urien, P Claudepierre, J Meyer, R Brandt, J P Tillement. Comparative binding of etretinate and acitretin to plasma proteins and erythrocytes. Biochemical pharmacology. 1992 Nov; 44(9):1891-3. doi: 10.1016/0006-2952(92)90087-y. [PMID: 1449542]
  • C C Zouboulis, S Biczó, H Gollnick, H J Reupke, G Rinck, M Szabó, J Fekete, C E Orfanos. Elephantiasis nostras verrucosa: beneficial effect of oral etretinate therapy. The British journal of dermatology. 1992 Oct; 127(4):411-6. doi: 10.1111/j.1365-2133.1992.tb00465.x. [PMID: 1419764]
  • T Shiohara, K Imanishi, Y Sagawa, M Nagashima. Differential effects of cyclosporine and etretinate on serum cytokine levels in patients with psoriasis. Journal of the American Academy of Dermatology. 1992 Oct; 27(4):568-74. doi: 10.1016/0190-9622(92)70224-4. [PMID: 1401309]
  • R C Chou, R Wyss, C A Huselton, U W Wiegand. A potentially new metabolic pathway: ethyl esterification of acitretin. Xenobiotica; the fate of foreign compounds in biological systems. 1992 Aug; 22(8):993-1002. doi: 10.3109/00498259209049905. [PMID: 1413887]
  • S L Marks, M D Song, A A Stannard, H T Power. Clinical evaluation of etretinate for the treatment of canine solar-induced squamous cell carcinoma and preneoplastic lesions. Journal of the American Academy of Dermatology. 1992 Jul; 27(1):11-6. doi: 10.1016/0190-9622(92)70147-8. [PMID: 1619058]
  • J Klein, D Fernandes, A Pastuszak, G Koren. Therapeutic drug monitoring of retinoids. Therapeutic drug monitoring. 1992 Jun; 14(3):197-202. doi: 10.1097/00007691-199206000-00005. [PMID: 1412605]
  • A M Arnold, G P Browman, M N Levine, T D'Souza, B Johnstone, P Skingley, L Turner-Smith, R Cayco, L Booker, M Newhouse. The effect of the synthetic retinoid etretinate on sputum cytology: results from a randomised trial. British journal of cancer. 1992 May; 65(5):737-43. doi: 10.1038/bjc.1992.156. [PMID: 1586601]
  • M L Bouvy, M C Sturkenboom, M C Cornel, L T De Jong-Van den Berg, B H Stricker, H Wesseling. Acitretin (Neotigason). A review of pharmacokinetics and teratogenicity and hypothesis on metabolic pathways. Pharmaceutisch weekblad. Scientific edition. 1992 Apr; 14(2):33-7. doi: 10.1007/bf01980479. [PMID: 1388261]
  • B Cribier, M Welsch, E Heid. Renal impairment probably induced by etretinate. Dermatology (Basel, Switzerland). 1992; 185(4):266-8. doi: 10.1159/000247465. [PMID: 1477420]
  • P Palungwachira, K Iwahara, H Ogawa. Keratoderma hereditaria mutilans. Etretinate treatment and electron microscope studies. The Australasian journal of dermatology. 1992; 33(1):19-30. doi: 10.1111/j.1440-0960.1992.tb00048.x. [PMID: 1445089]
  • J W Kelly, J Sabto, F W Gurr, F Bruce. Retinoids to prevent skin cancer in organ transplant recipients. Lancet (London, England). 1991 Nov; 338(8779):1407. doi: 10.1016/0140-6736(91)92292-a. [PMID: 1682775]
  • R M Grossman, R J Delaney, E A Brinton, D M Carter, A B Gottlieb. Hypertriglyceridemia in patients with psoriasis treated with cyclosporine. Journal of the American Academy of Dermatology. 1991 Oct; 25(4):648-51. doi: 10.1016/0190-9622(91)70247-y. [PMID: 1791223]
  • D Taruoura, P Higueret, H Garcin, D Higueret. Effects of a synthetic retinoid, etretinate (RO 10-9359), on the peripheral metabolism of thyroid hormones in rats. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 1991 Sep; 29(9):595-9. doi: 10.1016/0278-6915(91)90140-3. [PMID: 1937290]
  • N Okada, M Higashiyama, S Morimoto, K Yoshikawa. [Skeletal alterations associated with long-term etretinate therapy]. Nihon Hifuka Gakkai zasshi. The Japanese journal of dermatology. 1991 Apr; 101(5):547-52. doi: NULL. [PMID: 1890751]
  • J C Beani, D Bonnot, F Berthod, M Boitard, J L Reymond, H Beriel, P Amblard. [Influence of retinoids on the bioavailability of methoxy-8-psoralen]. Annales de dermatologie et de venereologie. 1991; 118(4):273-5. doi: NULL. [PMID: 2069337]
  • V Carillet, P Morlière, J C Mazière, G Hüppe, R Santus, L Dubertret. Uptake of the aromatic retinoids Ro 10-9359 (etretinate) and Ro 10-1670 (acitretin), its main metabolite, delivered to cultured human fibroblasts by serum proteins. Lack of evidence for perturbation of LDL catabolism. Biochimica et biophysica acta. 1990 Nov; 1055(2):102-6. doi: 10.1016/0167-4889(90)90109-q. [PMID: 2146974]
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  • F G Larsen, F Nielsen-Kudsk, P Jakobsen, H Schrøder, K Kragballe. Interaction of etretinate with methotrexate pharmacokinetics in psoriatic patients. Journal of clinical pharmacology. 1990 Sep; 30(9):802-7. doi: 10.1002/j.1552-4604.1990.tb01877.x. [PMID: 2277127]
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  • P J McNamara, R A Blouin. Pharmacokinetic profile of two aromatic retinoids (etretinate and acitretin) in the obese Zucker rat. Journal of pharmaceutical sciences. 1990 Apr; 79(4):301-4. doi: 10.1002/jps.2600790406. [PMID: 2141075]
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  • H Katayama, N Okabe, T Kano, H Yaoita. Granulation tissue that developed after a minor trauma in a psoriatic patient on long-term etretinate therapy. The Journal of dermatology. 1990 Mar; 17(3):187-90. doi: 10.1111/j.1346-8138.1990.tb01623.x. [PMID: 2141341]
  • A P De Leenheer, W E Lambert, J P De Bersaques, A H Kint. High-performance liquid chromatographic determination of etretinate and all-trans- and 13-cis-acitretin in human plasma. Journal of chromatography. 1990 Feb; 500(?):637-42. doi: 10.1016/s0021-9673(00)96098-9. [PMID: 2139439]
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