Oxybutynin (BioDeep_00000398964)

Main id: BioDeep_00000002466

 

natural product


代谢物信息卡片


Oxybutynin (Ditropan)

化学式: C22H31NO3 (357.2304)
中文名称: 奥昔布宁
谱图信息: 最多检出来源 Homo sapiens(blood) 10.14%

分子结构信息

SMILES: C1(=CC=CC=C1)C(C2CCCCC2)(C(=O)OCC#CCN(CC)CC)O
InChI: InChI=1S/C22H31NO3/c1-3-23(4-2)17-11-12-18-26-21(24)22(25,19-13-7-5-8-14-19)20-15-9-6-10-16-20/h5,7-8,13-14,20,25H,3-4,6,9-10,15-18H2,1-2H3

描述信息

G - Genito urinary system and sex hormones > G04 - Urologicals > G04B - Urologicals > G04BD - Drugs for urinary frequency and incontinence
C78272 - Agent Affecting Nervous System > C66880 - Anticholinergic Agent > C29704 - Antimuscarinic Agent
D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D010276 - Parasympatholytics
D000890 - Anti-Infective Agents > D000892 - Anti-Infective Agents, Urinary > D008333 - Mandelic Acids
D018377 - Neurotransmitter Agents > D018678 - Cholinergic Agents > D018680 - Cholinergic Antagonists
D000089162 - Genitourinary Agents > D064804 - Urological Agents
CONFIDENCE standard compound; INTERNAL_ID 2516
CONFIDENCE standard compound; INTERNAL_ID 8497
Oxybutynin is an anticholinergic agent, which inhibits vascular Kv channels in a concentration-dependent manner, with an IC50 of 11.51 μM[1]. Oxybutynin is a click chemistry reagent, it contains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups.

同义名列表

4 个代谢物同义名

Oxybutynin; Oxybutynin (Ditropan); Oxybutynin; Oxybutynin



数据库引用编号

27 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
Cytoplasm 10 ABCB1, ACE, AXIN2, CENPJ, CES1, CYP1A1, CYP2C19, CYP2C9, CYP2D6, CYP3A4
Peripheral membrane protein 2 CYP1A1, CYP1B1
Endoplasmic reticulum membrane 7 CYP1A1, CYP1B1, CYP2C19, CYP2C9, CYP2D6, CYP3A4, CYP3A5
Nucleus 3 AXIN2, CES1, FOS
cytosol 6 AVP, AXIN2, CENPJ, CES1, FOS, SLC22A16
dendrite 1 AVP
centrosome 2 AXIN2, CENPJ
nucleoplasm 1 FOS
RNA polymerase II transcription regulator complex 1 FOS
Cell membrane 4 ABCB1, ACE, ADRB3, SLC22A16
Multi-pass membrane protein 5 ABCB1, ADRB3, CACNA1I, KCNA3, SLC22A16
cell surface 1 ABCB1
glutamatergic synapse 1 KCNA3
mitochondrial inner membrane 1 CYP1A1
presynaptic membrane 1 KCNA3
Lysosome 1 ACE
endosome 1 ACE
plasma membrane 10 ABCB1, ACE, ADRB3, AXIN2, BCHE, CACNA1I, CYP2C19, CYP2C9, KCNA3, SLC22A16
Membrane 9 ABCB1, ACE, CACNA1I, CYP1B1, CYP2D6, CYP3A4, CYP3A5, KCNA3, SLC22A16
apical plasma membrane 1 ABCB1
axon 1 KCNA3
extracellular exosome 2 ABCB1, ACE
endoplasmic reticulum 3 CES1, CYP2D6, FOS
extracellular space 3 ACE, AVP, BCHE
perinuclear region of cytoplasm 1 KCNA3
mitochondrion 3 CYP1A1, CYP1B1, CYP2D6
intracellular membrane-bounded organelle 7 CYP1A1, CYP1B1, CYP2C19, CYP2C9, CYP2D6, CYP3A4, CYP3A5
Microsome membrane 6 CYP1A1, CYP1B1, CYP2C9, CYP2D6, CYP3A4, CYP3A5
Single-pass type I membrane protein 1 ACE
Secreted 3 ACE, AVP, BCHE
extracellular region 3 ACE, AVP, BCHE
Single-pass membrane protein 1 CYP2D6
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 CENPJ
external side of plasma membrane 1 ACE
beta-catenin destruction complex 1 AXIN2
postsynaptic membrane 1 KCNA3
Apical cell membrane 1 ABCB1
Mitochondrion inner membrane 1 CYP1A1
Membrane raft 1 KCNA3
microtubule 1 CENPJ
secretory granule 1 AVP
receptor complex 1 ADRB3
ciliary basal body 1 CENPJ
chromatin 1 FOS
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome, centriole 1 CENPJ
centriole 1 CENPJ
brush border membrane 1 ACE
blood microparticle 1 BCHE
sperm midpiece 1 ACE
[Isoform 2]: Cell membrane 1 KCNA3
Lipid droplet 1 CES1
basal plasma membrane 1 ACE
voltage-gated potassium channel complex 1 KCNA3
endoplasmic reticulum lumen 2 BCHE, CES1
nuclear matrix 1 FOS
voltage-gated calcium channel complex 1 CACNA1I
procentriole replication complex 1 CENPJ
neuronal dense core vesicle 1 AVP
nuclear envelope lumen 1 BCHE
calyx of Held 1 KCNA3
clathrin-coated endocytic vesicle membrane 1 AVP
protein-DNA complex 1 FOS
external side of apical plasma membrane 1 ABCB1
[Isoform 1]: Cell membrane 1 KCNA3
transcription factor AP-1 complex 1 FOS
[Angiotensin-converting enzyme, soluble form]: Secreted 1 ACE
[Isoform Testis-specific]: Cell membrane 1 ACE
[Isoform 3]: Cytoplasm, perinuclear region 1 KCNA3
gamma-tubulin small complex 1 CENPJ


文献列表

  • Lorena M D Cirino, Daviane M C Vergne, Gabrielle B Novais, Amanda Cano, Francine F Padilha, Patrícia Severino, Ricardo L C de Albuquerque Júnior, Juliana C Cardoso, Eliana B Souto. Liposomal formulations of oxybutynin and resiniferatoxin for the treatment of urinary diseases: improvement of drug tolerance upon intravesical. Drug delivery and translational research. 2022 07; 12(7):1738-1752. doi: 10.1007/s13346-021-01082-6. [PMID: 34671947]
  • Yuze Sheng, Shuang Zhang, Jiawei Ling, Chenlu Hu, Zhenhai Zhang, Huixia Lv. Oxybutynin nanosuspension gel for enhanced transdermal treatment for overactive bladder syndrome. Pharmaceutical development and technology. 2022 Apr; 27(4):459-468. doi: 10.1080/10837450.2022.2078983. [PMID: 35575444]
  • Toshiro Suzuki, Tomonori Minagawa, Tetsuichi Saito, Tatsuo Nakagawa, Tomio Suzuki, Masayuki Furuhata, Kyoko Hosaka, Teruyuki Ogawa, Osamu Ishizuka. Effect of oxybutynin patch versus mirabegron on nocturia-related quality of life in female overactive bladder patients: A multicenter randomized trial. International journal of urology : official journal of the Japanese Urological Association. 2021 Sep; 28(9):944-949. doi: 10.1111/iju.14608. [PMID: 34053119]
  • Ali Gözüküçük, Mehmet Kılıç, Basri Çakıroğlu. Desmopressin versus desmopressin + oxybutynin in the treatment of children with nocturnal enuresis. Journal of pediatric urology. 2021 08; 17(4):451.e1-451.e6. doi: 10.1016/j.jpurol.2021.04.001. [PMID: 33931318]
  • Matthew S Lee, Mark Assmus, Deepak Agarwal, Marcelino E Rivera, Tim Large, Amy E Krambeck. Opioid Free Ureteroscopy: What is the True Failure Rate?. Urology. 2021 08; 154(?):89-95. doi: 10.1016/j.urology.2021.03.011. [PMID: 33774043]
  • Melanie Kretschmar, Ahmed Abbas Suleiman, Petra Krause, Uwe Albrecht, Raimund Stein, Peter Rubenwolf, Uwe Fuhr, Max Taubert. A Population Pharmacokinetic Model of (R)- and (S-) Oxybutynin and Its Active Metabolites After Oral and Intravesical Administration to Healthy Volunteers. Journal of clinical pharmacology. 2021 07; 61(7):961-971. doi: 10.1002/jcph.1809. [PMID: 33368382]
  • Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. Cell reports. 2021 04; 35(4):109040. doi: 10.1016/j.celrep.2021.109040. [PMID: 33910017]
  • Koosha Kamali, Javad Nikbakht, Erfan Ayubi, Mostafa Nabizadeh, Saeedeh Sarhadi. Comparison of the Efficacy of Oxybutynin, Phenazopyridine, Celecoxib, and Placebo in the Treatment of Urinary Tract Symptoms after BCG Therapy in Patients with Bladder Tumors. Urology journal. 2020 Sep; 18(4):439-444. doi: 10.22037/uj.v16i7.5947. [PMID: 32981029]
  • Ahmed Abdelhalim, Ahmed S El-Hefnawy, Mohamed E Dawaba, Mahmoud A Bazeed, Ashraf T Hafez. Effect of Early Oxybutynin Treatment on Posterior Urethral Valve Outcomes in Infants: A Randomized Controlled Trial. The Journal of urology. 2020 04; 203(4):826-831. doi: 10.1097/ju.0000000000000691. [PMID: 31821098]
  • Katja Walpurgis, Anja B Scheiff, Meike Welz, Jutta Müller-Reul, Nick Webborn, Christian Görgens, Sven Guddat, Gregor Fußhöller, Josef Dib, Mario Thevis. Pilot study on the effects of intravesical oxybutynin hydrochloride instillations on the validity of doping control urine samples. Drug testing and analysis. 2019 Nov; 11(11-12):1755-1760. doi: 10.1002/dta.2705. [PMID: 31670462]
  • Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
  • Hongliang Li, Mi Seon Seo, Jin Ryeol An, Hee Seok Jung, Kwon-Soo Ha, Eun-Taek Han, Seok-Ho Hong, Young Min Bae, Dong Ryeol Ryu, Won Sun Park. The anticholinergic drug oxybutynin inhibits voltage-dependent K+ channels in coronary arterial smooth muscle cells. Clinical and experimental pharmacology & physiology. 2019 11; 46(11):1030-1036. doi: 10.1111/1440-1681.13138. [PMID: 31330060]
  • Yongzhi Tian, Yongqing Wen, Jinghan Sun, Longshan Zhao, Zhili Xiong, Feng Qin. Simultaneous quantification of oxybutynin and its active metabolite N-desethyl oxybutynin in rat plasma by ultra-high-performance liquid chromatography-tandem mass spectrometry and its application in a pharmacokinetic study of oxybutynin transdermal patch. Biomedical chromatography : BMC. 2019 Apr; 33(4):e4456. doi: 10.1002/bmc.4456. [PMID: 30536598]
  • Silvio Aprile, Rossana Canavesi, Rosanna Matucci, Cristina Bellucci, Erika Del Grosso, Giorgio Grosa. New insights in the metabolism of oxybutynin: evidence of N-oxidation of propargylamine moiety and rearrangement to enaminoketone. Xenobiotica; the fate of foreign compounds in biological systems. 2018 May; 48(5):478-487. doi: 10.1080/00498254.2017.1342288. [PMID: 28608746]
  • Luise Borch, Soeren Hagstroem, Konstantinos Kamperis, C V Siggaard, Soeren Rittig. Transcutaneous Electrical Nerve Stimulation Combined with Oxybutynin is Superior to Monotherapy in Children with Urge Incontinence: A Randomized, Placebo Controlled Study. The Journal of urology. 2017 08; 198(2):430-435. doi: 10.1016/j.juro.2017.03.117. [PMID: 28327453]
  • Joe Hong, Jooyeon Lee, Holly Totouom-Tangho, Norma Ramos Dunn, Ronnie Gorman Swift. Methadone-Induced Hyperhidrosis Treated With Oxybutynin. Journal of addiction medicine. 2017 May; 11(3):237-238. doi: 10.1097/adm.0000000000000300. [PMID: 28244893]
  • A Fukata, T Yamazaki. Comparative Influence of Imidafenacin and Oxybutynin on Voiding Function in Rats with Functional Urethral Obstruction. Drug research. 2016 Jun; 66(6):306-11. doi: 10.1055/s-0035-1569410. [PMID: 26979753]
  • Yoshihiko Ito, Michishi Kashiwabara, Akira Yoshida, Eriko Hikiyama, Satomi Onoue, Shizuo Yamada. Muscarinic Receptor Binding in Rat Bladder Urothelium and Detrusor Muscle by Intravesical Solifenacin. Biological & pharmaceutical bulletin. 2016; 39(7):1167-71. doi: 10.1248/bpb.b16-00194. [PMID: 27374291]
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  • Martien Humblet, Carla Verpoorten, Maria-Helena Christiaens, Herbert Hirche, Katrien Jansen, Gunnar Buyse, Jan D van Gool. Long-term outcome of intravesical oxybutynin in children with detrusor-sphincter dyssynergia: with special reference to age-dependent parameters. Neurourology and urodynamics. 2015 Apr; 34(4):336-42. doi: 10.1002/nau.22560. [PMID: 24436114]
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  • Imran Ali, Zeid A Al-Othman, Abdulrahman Al-Warthan, Syed Dilshad Alam, Javed A Farooqi. Enantiomeric separation and simulation studies of pheniramine, oxybutynin, cetirizine, and brinzolamide chiral drugs on amylose-based columns. Chirality. 2014 Mar; 26(3):136-43. doi: 10.1002/chir.22276. [PMID: 24464520]
  • Primal Sharma, Daxesh P Patel, Mallika Sanyal, Swati Guttikar, Pranav S Shrivastav. Parallel achiral-chiral determination of oxybutynin, N-desethyl oxybutynin and their enantiomers in human plasma by LC-MS/MS to support a bioequivalence trial. Journal of pharmaceutical and biomedical analysis. 2014 Jan; 88(?):81-91. doi: 10.1016/j.jpba.2013.08.032. [PMID: 24036364]
  • Petra Krause, Uwe Fuhr, Jörg Schnitker, Uwe Albrecht, Raimund Stein, Peter Rubenwolf. Pharmacokinetics of intravesical versus oral oxybutynin in healthy adults: results of an open label, randomized, prospective clinical study. The Journal of urology. 2013 Nov; 190(5):1791-7. doi: 10.1016/j.juro.2013.05.011. [PMID: 23669567]
  • Primal Sharma, Daxesh P Patel, Mallika Sanyal, Hiren Berawala, Swati Guttikar, Pranav S Shrivastav. Simultaneous analysis of oxybutynin and its active metabolite N-desethyl oxybutynin in human plasma by stable isotope dilution LC-MS/MS to support a bioequivalence study. Journal of pharmaceutical and biomedical analysis. 2013 Oct; 84(?):244-55. doi: 10.1016/j.jpba.2013.06.024. [PMID: 23867086]
  • Toshiki Hatanaka, Masashi Ukai, Mai Watanabe, Akiyoshi Someya, Akiyoshi Ohtake, Masanori Suzuki, Koji Ueshima, Shuichi Sato, Seiji Kaku. Effect of mirabegron, a novel β3-adrenoceptor agonist, on bladder function during storage phase in rats. Naunyn-Schmiedeberg's archives of pharmacology. 2013 Jan; 386(1):71-8. doi: 10.1007/s00210-012-0814-3. [PMID: 23224420]
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  • Yuichiro Sato, Aiji Miyashita, Takafumi Iwatsubo, Takashi Usui. Simultaneous absolute protein quantification of carboxylesterases 1 and 2 in human liver tissue fractions using liquid chromatography-tandem mass spectrometry. Drug metabolism and disposition: the biological fate of chemicals. 2012 Jul; 40(7):1389-96. doi: 10.1124/dmd.112.045054. [PMID: 22504157]
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  • Aniruddh V Deshpande, Patrina H Y Caldwell. Medical management of nocturnal enuresis. Paediatric drugs. 2012 Apr; 14(2):71-7. doi: 10.2165/11594870-000000000-00000. [PMID: 22168597]
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  • Yasuto Kido, Pär Matsson, Kathleen M Giacomini. Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. Journal of medicinal chemistry. 2011 Jul; 54(13):4548-58. doi: 10.1021/jm2001629. [PMID: 21599003]
  • Hiroshi Nagabukuro, Katherine L Villa, L Alexandra Wickham, Alison A Kulick, Loise Gichuru, Marcie J Donnelly, Gregory O Voronin, Tony Pereira, Xinchun Tong, Andrew Nichols, Stephen E Alves, Gary P O'Neill, Christopher V Johnson, Emily J Hickey. Comparative analysis of the effects of antimuscarinic agents on bladder functions in both nonhuman primates and rodents. The Journal of pharmacology and experimental therapeutics. 2011 Jul; 338(1):220-7. doi: 10.1124/jpet.111.179747. [PMID: 21459965]
  • Stine Mjåvatn Jakobsen, Hege Kersten, Espen Molden. Evaluation of brain anticholinergic activities of urinary spasmolytic drugs using a high-throughput radio receptor bioassay. Journal of the American Geriatrics Society. 2011 Mar; 59(3):501-5. doi: 10.1111/j.1532-5415.2010.03307.x. [PMID: 21391941]
  • Birger Wenge, Joachim Geyer, Heinz Bönisch. Oxybutynin and trospium are substrates of the human organic cation transporters. Naunyn-Schmiedeberg's archives of pharmacology. 2011 Feb; 383(2):203-8. doi: 10.1007/s00210-010-0590-x. [PMID: 21212936]
  • Shizuo Yamada, Masanao Seki, Masaki Ogoda, Ayako Fukata, Miho Nakamura, Yoshihiko Ito. Selective binding of bladder muscarinic receptors in relation to the pharmacokinetics of a novel antimuscarinic agent, imidafenacin, to treat overactive bladder. The Journal of pharmacology and experimental therapeutics. 2011 Feb; 336(2):365-71. doi: 10.1124/jpet.110.172288. [PMID: 21047953]
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  • David R Staskin, Dudley Robinson. Oxybutynin chloride topical gel: a new formulation of an established antimuscarinic therapy for overactive bladder. Expert opinion on pharmacotherapy. 2009 Dec; 10(18):3103-11. doi: 10.1517/14656560903451682. [PMID: 19954278]
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