Dorzolamide (BioDeep_00000006388)

 

Secondary id: BioDeep_00001868364

human metabolite blood metabolite Chemicals and Drugs


代谢物信息卡片


(4S,6S)-4-Ethylamino-6-methyl-7,7-dioxo-4,5,6,7-tetrahydro-7lambda*6*-thieno[2,3-b]thiopyran-2-sulphonic acid amide

化学式: C10H16N2O4S3 (324.0272176)
中文名称: 多佐胺
谱图信息: 最多检出来源 Homo sapiens(blood) 11.43%

分子结构信息

SMILES: CCNC1CC(C)S(=O)(=O)c2sc(S(N)(=O)=O)cc21
InChI: InChI=1S/C10H16N2O4S3/c1-3-12-8-4-6(2)18(13,14)10-7(8)5-9(17-10)19(11,15)16/h5-6,8,12H,3-4H2,1-2H3,(H2,11,15,16)/t6-,8-/m0/s1

描述信息

Dorzolamide is only found in individuals that have used or taken this drug. It is a carbonic anhydrase (CA) inhibitor. It is used in ophthalmic solutions (Trusopt) to lower intraocular pressure (IOP) in open-angle glaucoma and ocular hypertension.Dorzolamide is a sulfonamide and a highly specific carbonic anhydrase II (CA-II) inhibitor, which is the main CA isoenzyme involved in aqueous humor secretion. Inhibition of CA-II in the ciliary processes of the eye decreases aqueous humor secretion, presumably by slowing the formation of bicarbonate ions with subsequent reduction in sodium and fluid transport. Dorzolamide also accumulates in red blood cells as a result of CA-II binding, as CA-II is found predominantly in erythrocytes. However, sufficient CA-II activity remains so that adverse effects due to systemic CA inhibition are not observed.
S - Sensory organs > S01 - Ophthalmologicals > S01E - Antiglaucoma preparations and miotics > S01EC - Carbonic anhydrase inhibitors
D004791 - Enzyme Inhibitors > D002257 - Carbonic Anhydrase Inhibitors
D002317 - Cardiovascular Agents > D000959 - Antihypertensive Agents
C471 - Enzyme Inhibitor > C29577 - Carbonic Anhydrase Inhibitor

同义名列表

26 个代谢物同义名

(4S,6S)-4-Ethylamino-6-methyl-7,7-dioxo-4,5,6,7-tetrahydro-7lambda*6*-thieno[2,3-b]thiopyran-2-sulphonic acid amide; (4S,6S)-4-Ethylamino-6-methyl-7,7-dioxo-4,5,6,7-tetrahydro-7lambda*6*-thieno[2,3-b]thiopyran-2-sulfonic acid amide; (4S,6S)-4-Ethylamino-6-methyl-7,7-dioxo-4,5,6,7-tetrahydro-7lambda*6*-thieno[2,3-b]thiopyran-2-sulphonate amide; (4S,6S)-4-Ethylamino-6-methyl-7,7-dioxo-4,5,6,7-tetrahydro-7lambda*6*-thieno[2,3-b]thiopyran-2-sulfonate amide; 4-Ethylamino-6-methyl-7,7-dioxo-4,5,6,7-tetrahydro-7lambda*6*-thieno[2,3-b]thiopyran-2-sulphonic acid amide; 4-Ethylamino-6-methyl-7,7-dioxo-4,5,6,7-tetrahydro-7lambda*6*-thieno[2,3-b]thiopyran-2-sulfonic acid amide; 4-Ethylamino-6-methyl-7,7-dioxo-4,5,6,7-tetrahydro-7lambda6-thieno[2,3-b]thiopyran-2-sulphonic acid amide; 4-Ethylamino-6-methyl-7,7-dioxo-4,5,6,7-tetrahydro-7lambda6-thieno[2,3-b]thiopyran-2-sulfonic acid amide; 4-Ethylamino-6-methyl-7,7-dioxo-4,5,6,7-tetrahydro-7lambda*6*-thieno[2,3-b]thiopyran-2-sulphonate amide; 4-Ethylamino-6-methyl-7,7-dioxo-4,5,6,7-tetrahydro-7lambda*6*-thieno[2,3-b]thiopyran-2-sulfonate amide; 4-Ethylamino-6-methyl-7,7-dioxo-4,5,6,7-tetrahydro-7lambda6-thieno[2,3-b]thiopyran-2-sulphonate amide; 4-Ethylamino-6-methyl-7,7-dioxo-4,5,6,7-tetrahydro-7lambda6-thieno[2,3-b]thiopyran-2-sulfonate amide; (4S-trans)-4-(ETHYLAMINO)-5,6-dihydro-6-methyl-4H-thieno(2,3-b)thiopyran-2-sulphonamide-7,7-dioxide; (4S,trans)-4-(Ethylamino)-6-methyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran-2-sulphonamide 7,7-dioxide; (4S-trans)-4-(ETHYLAMINO)-5,6-dihydro-6-methyl-4H-thieno(2,3-b)thiopyran-2-sulfonamide-7,7-dioxide; (4S,trans)-4-(Ethylamino)-6-methyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran-2-sulfonamide 7,7-dioxide; (2S,4S)-4-(ethylamino)-2-methyl-1,1-dioxo-2H,3H,4H-1λ⁶-thieno[2,3-b]thiopyran-6-sulfonamide; 4-(ethylamino)-6-methyl-5,6-dihydro-4h-thieno[2,3-b]thiopyran-2-sulfonamide 7,7-dioxide; 4-Ethylamino-5,6-dihydro-6-methyl-7,7-dioxide-4H-thieno(2,3-b)thiopyran-2-sulfonamide; 5,6-Dihydro-4-ethylamino-6-methyl-4H-thieno(2,3-b)thiopyran-2-sulfonamide-7,7-dioxide; Dorzolamide, (trans)-isomer; dorzolamide hydrochloride; Dorzolamide chibret; 4S,6S-Dorzolamide; Dorzolamide; Trusopt



数据库引用编号

18 个数据库交叉引用编号

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代谢反应

0 个相关的代谢反应过程信息。

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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

  • Andrzej Pokrywka, Monika Skrzypiec-Spring, Jarosław Krzywański, Michał Rynkowski, Martial Saugy, Raphael Faiss. Cases reports: Unintended anti-doping rule violation after dorzolamide use several months prior to a doping control. Drug testing and analysis. 2021 Oct; 13(10):1803-1806. doi: 10.1002/dta.3156. [PMID: 34463045]
  • Christopher Päslack, Chandan K Das, Jürgen Schlitter, Lars V Schäfer. Spectrally Resolved Estimation of Water Entropy in the Active Site of Human Carbonic Anhydrase II. Journal of chemical theory and computation. 2021 Aug; 17(8):5409-5418. doi: 10.1021/acs.jctc.1c00554. [PMID: 34259506]
  • Tara M Czepiel, Neal T Wasserman. Hypokalemia associated with topical administration of dorzolamide 2\% ophthalmic solution in cats. Veterinary ophthalmology. 2021 Jan; 24(1):12-19. doi: 10.1111/vop.12773. [PMID: 33085174]
  • Xi Han, Shan Yang, Wendy R Kam, David A Sullivan, Yang Liu. The Carbonic Anhydrase Inhibitor Dorzolamide Stimulates the Differentiation of Human Meibomian Gland Epithelial Cells. Current eye research. 2020 12; 45(12):1604-1610. doi: 10.1080/02713683.2020.1772832. [PMID: 32434386]
  • Sang M Lee, Ji-Eun Lee, Sung I Kim, Jae H Jung, Jonghoon Shin. Effect of topical glaucoma medication on tear lipid layer thickness in patients with unilateral glaucoma. Indian journal of ophthalmology. 2019 08; 67(8):1297-1302. doi: 10.4103/ijo.ijo_2100_18. [PMID: 31332113]
  • Devesh Kumawat, Vinod Kumar. Double trouble: exudative hypertensive retinopathy in a patient with retinitis pigmentosa. BMJ case reports. 2018 Nov; 2018(?):. doi: 10.1136/bcr-2018-226950. [PMID: 30413460]
  • Iva Hoffmanová, Daniel Sánchez. Metabolic acidosis and anaemia associated with dorzolamide in a patient with impaired renal function. British journal of clinical pharmacology. 2018 04; 84(4):796-799. doi: 10.1111/bcp.13499. [PMID: 29333622]
  • Charlotte E Thiessen, Kyle L Tofflemire, Kelly M Makielski, Gil Ben-Shlomo, R David Whitley, Rachel A Allbaugh. Hypokalemia and suspected renal tubular acidosis associated with topical carbonic anhydrase inhibitor therapy in a cat. Journal of veterinary emergency and critical care (San Antonio, Tex. : 2001). 2016 Nov; 26(6):870-874. doi: 10.1111/vec.12417. [PMID: 26595765]
  • Billie Beckwith-Cohen, Ellison Bentley, David J Gasper, Gillian J McLellan, Richard R Dubielzig. Keratitis in six dogs after topical treatment with carbonic anhydrase inhibitors for glaucoma. Journal of the American Veterinary Medical Association. 2015 Dec; 247(12):1419-26. doi: 10.2460/javma.247.12.1419. [PMID: 26642138]
  • Mutay Aslan, Serdar Dogan, Ertan Kucuksayan. Oxidative stress and potential applications of free radical scavengers in glaucoma. Redox report : communications in free radical research. 2013; 18(2):76-87. doi: 10.1179/1351000212y.0000000033. [PMID: 23485101]
  • Rajendra S Kadam, Gajanan Jadhav, Miller Ogidigben, Uday B Kompella. Ocular pharmacokinetics of dorzolamide and brinzolamide after single and multiple topical dosing: implications for effects on ocular blood flow. Drug metabolism and disposition: the biological fate of chemicals. 2011 Sep; 39(9):1529-37. doi: 10.1124/dmd.111.040055. [PMID: 21673129]
  • Rana Sorkhabi, Amir Ghorbanihaghjo, Alireza Javadzadeh, Nadereh Rashtchizadeh, Melorina Moharrery. Oxidative DNA damage and total antioxidant status in glaucoma patients. Molecular vision. 2011 Jan; 17(?):41-6. doi: NULL. [PMID: 21245957]
  • Antonio Caccavale, Filippo Romanazzi, Manuela Imparato, Angelo Negri, Anna Morano, Fabio Ferentini. Central serous chorioretinopathy: a pathogenetic model. Clinical ophthalmology (Auckland, N.Z.). 2011; 5(?):239-43. doi: 10.2147/opth.s17182. [PMID: 21386917]
  • Rana Sorkhabi, Amir Ghorbanihaghjo, Alireza Javadzadeh, Behzad Fallahi Motlagh, Solmaz Shoa Ahari. Aqueous humor hepcidin prohormone levels in patients with primary open angle glaucoma. Molecular vision. 2010 Sep; 16(?):1832-6. doi: NULL. [PMID: 21031015]
  • Kelly C Albin, Christopher T Simons. Psychophysical evaluation of a sanshool derivative (alkylamide) and the elucidation of mechanisms subserving tingle. PloS one. 2010 Mar; 5(3):e9520. doi: 10.1371/journal.pone.0009520. [PMID: 20209090]
  • Mika Hilvo, Anna Maria Salzano, Alessio Innocenti, Markku S Kulomaa, Andrea Scozzafava, Andrea Scaloni, Seppo Parkkila, Claudiu T Supuran. Cloning, expression, post-translational modifications and inhibition studies on the latest mammalian carbonic anhydrase isoform, CA XV. Journal of medicinal chemistry. 2009 Feb; 52(3):646-54. doi: 10.1021/jm801267c. [PMID: 19193158]
  • Jerry Yee. Chronic kidney disease--a disease domain complex. Geriatrics. 2008 Mar; 63(3):30-7. doi: NULL. [PMID: 18312026]
  • Renate J Scheibe, Karsten Mundhenk, Tilman Becker, Janine Hallerdei, Abdul Waheed, Gul N Shah, William S Sly, Gerolf Gros, Petra Wetzel. Carbonic anhydrases IV and IX: subcellular localization and functional role in mouse skeletal muscle. American journal of physiology. Cell physiology. 2008 Feb; 294(2):C402-12. doi: 10.1152/ajpcell.00228.2007. [PMID: 18003750]
  • Eitan Z Rath, Shimon Rumelt. Acute visual loss due to serous retinal detachment from acquired optic pit may be a rare presentation of primary open-angle glaucoma. Canadian journal of ophthalmology. Journal canadien d'ophtalmologie. 2007 Apr; 42(2):339-40. doi: 10.3129/can j ophthalmol.i07-027. [PMID: 17392876]
  • Jonna M Lehtonen, Seppo Parkkila, Daniela Vullo, Angela Casini, Andrea Scozzafava, Claudiu T Supuran. Carbonic anhydrase inhibitors. Inhibition of cytosolic isozyme XIII with aromatic and heterocyclic sulfonamides: a novel target for the drug design. Bioorganic & medicinal chemistry letters. 2004 Jul; 14(14):3757-62. doi: 10.1016/j.bmcl.2004.04.106. [PMID: 15203157]
  • Shay-Whey M Koh, Timothy J Coll, Linda Rose, Yukihiro Matsumoto, Eve J Higginbotham. Antiglaucoma eye drop pulses--increased interleukin-6 secretion by Tenon's capsule fibroblast cultures. Journal of glaucoma. 2004 Jun; 13(3):200-9. doi: 10.1097/00061198-200406000-00005. [PMID: 15118463]
  • Kenji Inoue, Kazuko Okugawa, Satoshi Kato, Yuji Inoue, Goji Tomita, Tetsuro Oshika, Shiro Amano. Ocular factors relevant to anti-glaucomatous eyedrop-related keratoepitheliopathy. Journal of glaucoma. 2003 Dec; 12(6):480-5. doi: 10.1097/00061198-200312000-00007. [PMID: 14646683]
  • José Melena, Neville N Osborne. Metipranolol attenuates lipid peroxidation in rat brain: a comparative study with other antiglaucoma drugs. Graefe's archive for clinical and experimental ophthalmology = Albrecht von Graefes Archiv fur klinische und experimentelle Ophthalmologie. 2003 Oct; 241(10):827-33. doi: 10.1007/s00417-003-0726-5. [PMID: 12898280]
  • R C Tim, R A Kautz, B L Karger. Ultratrace analysis of drugs in biological fluids using affinity probe capillary electrophoresis: analysis of dorzolamide with fluorescently labeled carbonic anhydrase. Electrophoresis. 2000 Jan; 21(1):220-6. doi: 10.1002/(sici)1522-2683(20000101)21:1<220::aid-elps220>3.0.co;2-d. [PMID: 10634490]
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  • A Scozzafava, F Briganti, G Mincione, L Menabuoni, F Mincione, C T Supuran. Carbonic anhydrase inhibitors: synthesis of water-soluble, aminoacyl/dipeptidyl sulfonamides possessing long-lasting intraocular pressure-lowering properties via the topical route. Journal of medicinal chemistry. 1999 Sep; 42(18):3690-700. doi: 10.1021/jm9901879. [PMID: 10479300]
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  • A Scozzafava, L Menabuoni, F Mincione, F Briganti, G Mincione, C T Supuran. Carbonic anhydrase inhibitors. Synthesis of water-soluble, topically effective, intraocular pressure-lowering aromatic/heterocyclic sulfonamides containing cationic or anionic moieties: is the tail more important than the ring?. Journal of medicinal chemistry. 1999 Jul; 42(14):2641-50. doi: 10.1021/jm9900523. [PMID: 10411484]
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  • G S Ponticello, M F Sugrue, B Plazonnet, G Durand-Cavagna. Dorzolamide, a 40-year wait. From an oral to a topical carbonic anhydrase inhibitor for the treatment of glaucoma. Pharmaceutical biotechnology. 1998; 11(?):555-74. doi: . [PMID: 9760696]
  • L I Larsson, A Alm. Aqueous humor flow in human eyes treated with dorzolamide and different doses of acetazolamide. Archives of ophthalmology (Chicago, Ill. : 1960). 1998 Jan; 116(1):19-24. doi: 10.1001/archopht.116.1.19. [PMID: 9445204]
  • C Landolfi, M Marchetti, G Ciocci, C Milanese. Development and pharmacological characterization of a modified procedure for the measurement of carbonic anhydrase activity. Journal of pharmacological and toxicological methods. 1997 Nov; 38(3):169-72. doi: 10.1016/s1056-8719(97)00095-6. [PMID: 9523771]
  • M L Constanzer, C M Chavez, B K Matuszewski. Low level determination of dorzolamide and its de-ethylated metabolite in human plasma by liquid chromatography with atmospheric pressure chemical ionization tandem mass spectrometry. Journal of pharmaceutical and biomedical analysis. 1997 Apr; 15(7):1001-8. doi: 10.1016/s0731-7085(96)01935-8. [PMID: 9160268]
  • T H Maren, C W Conroy, G C Wynns, N S Levy. Ocular absorption, blood levels, and excretion of dorzolamide, a topically active carbonic anhydrase inhibitor. Journal of ocular pharmacology and therapeutics : the official journal of the Association for Ocular Pharmacology and Therapeutics. 1997 Feb; 13(1):23-30. doi: 10.1089/jop.1997.13.23. [PMID: 9029437]
  • B K Wong, P J Bruhin, A Barrish, J H Lin. Nonlinear dorzolamide pharmacokinetics in rats: concentration-dependent erythrocyte distribution and drug-metabolite displacement interaction. Drug metabolism and disposition: the biological fate of chemicals. 1996 Jun; 24(6):659-63. doi: . [PMID: 8781782]
  • T Nakagami, Y Yamazaki, S Miyamoto, M Sawa. [The time required topical carbonic anhydrase inhibitor (MK-507) to take effect on intraocular pressure of normal human eyes]. Nippon Ganka Gakkai zasshi. 1995 Sep; 99(9):1022-5. doi: NULL. [PMID: 7484502]
  • J Biollaz, A Munafo, T Buclin, J P Gervasoni, J L Magnin, F Jaquet, F Brunner-Ferber. Whole-blood pharmacokinetics and metabolic effects of the topical carbonic anhydrase inhibitor dorzolamide. European journal of clinical pharmacology. 1995; 47(5):455-60. doi: 10.1007/bf00196861. [PMID: 7720769]
  • T Hasegawa, K Hara, T Kenmochi, S Hata. In vitro metabolism of dorzolamide, a novel potent carbonic anhydrase inhibitor, in rat liver microsomes. Drug metabolism and disposition: the biological fate of chemicals. 1994 Nov; 22(6):916-21. doi: . [PMID: 7895610]
  • Y Yamazaki, S Miyamoto, M Sawa. [Effect of topical carbonic anhydrase inhibitor (MK-507) on intraocular pressure of normal human eyes]. Nippon Ganka Gakkai zasshi. 1994 Mar; 98(3):293-7. doi: NULL. [PMID: 8154389]
  • B K Matuszewski, M L Constanzer, E J Woolf, T Au, H Haddix. Determination of MK-507, a novel topically effective carbonic anhydrase inhibitor, and its de-ethylated metabolite in human whole blood, plasma, and urine by high-performance liquid chromatography. Journal of chromatography. B, Biomedical applications. 1994 Feb; 653(1):77-85. doi: 10.1016/0378-4347(93)e0412-j. [PMID: 8012563]
  • B K Matuszewski, M L Constanzer. Indirect chiral separation and analyses in human biological fluids of the stereoisomers of a thienothiopyran-2-sulfonamide (TRUSOPT), a novel carbonic anhydrase inhibitor with two chiral centers in the molecule. Chirality. 1992; 4(8):515-9. doi: 10.1002/chir.530040810. [PMID: 1476862]