Nalbuphine (BioDeep_00000002835)

human metabolite blood metabolite Chemicals and Drugs Volatile Flavor Compounds

代谢物信息卡片

(1S,5R,13R,14S,17S)-4-(cyclobutylmethyl)-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7,9,11(18)-triene-10,14,17-triol

化学式: C21H27NO4 (357.19399820000007)
中文名称: 纳布啡
谱图信息: 最多检出来源 Homo sapiens(blood) 22.33%

分子结构信息

SMILES: C1CC(C1)CN1CC[C@]23c4c5ccc(c4O[C@H]2[C@H](CC[C@]3([C@H]1C5)O)O)O
InChI: InChI=1S/C21H27NO4/c23-14-5-4-13-10-16-21(25)7-6-15(24)19-20(21,17(13)18(14)26-19)8-9-22(16)11-12-2-1-3-12/h4-5,12,15-16,19,23-25H,1-3,6-11H2/t15-,16+,19-,20-,21+/m0/s1

描述信息

Nalbuphine is only found in individuals that have used or taken this drug. It is a narcotic used as a pain medication. It appears to be an agonist at kappa opioid receptors and an antagonist or partial agonist at mu opioid receptors. [PubChem]The exact mechanism of action is unknown, but is believed to interact with an opiate receptor site in the CNS (probably in or associated with the limbic system). The opiate antagonistic effect may result from competitive inhibition at the opiate receptor, but may also be a result of other mechanisms. Nalbuphine is thought primarily to be a kappa agonist. It is also a partial mu antagonist analgesic, with some binding to the delta receptor and minimal agonist activity at the sigma receptor.
D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D009294 - Narcotics
D002492 - Central Nervous System Depressants > D009294 - Narcotics > D053610 - Opiate Alkaloids
N - Nervous system > N02 - Analgesics > N02A - Opioids > N02AF - Morphinan derivatives
D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents
C78272 - Agent Affecting Nervous System > C67413 - Opioid Receptor Agonist
D002491 - Central Nervous System Agents > D000700 - Analgesics

同义名列表

17 个代谢物同义名

(1S,5R,13R,14S,17S)-4-(cyclobutylmethyl)-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7,9,11(18)-triene-10,14,17-triol; N-Cyclobutylmethyl-4,5alpha-epoxy-3,6alpha,14-morphinantriol; N-Cyclobutylmethyl-4,5α-epoxy-3,6α,14-morphinantriol; N-Cyclobutylmethyl-4,5a-epoxy-3,6a,14-morphinantriol; N-Cyclobutylmethyl-14-hydroxydihydronormorphine; Hydrochloride, nalbuphine; SERB brand OF nalbuphine; Nalbuphine Hydrochloride; Nalbuphine serb brand; Serb, nalbuphine; Nalbuphine serb; Nalbuphinum; nalbuphine; Nalbufina; Intapan; Nubain; Nalbuphine

数据库引用编号

18 个数据库交叉引用编号

ChEBI: CHEBI:7454
KEGG: C07251
KEGGdrug: D08246
PubChem: 5311304
PubChem: 4419
HMDB: HMDB0014982
Metlin: METLIN1399
DrugBank: DB00844
ChEMBL: CHEMBL895
Wikipedia: Nalbuphine
MeSH: Nalbuphine
chemspider: 4470813
CAS: 20594-83-6
PMhub: MS000006395
PubChem: 9460
NIKKAJI: J14.212C
RefMet: Nalbuphine
KNApSAcK: 7454

分类词条

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)

1 个相关的物种来源信息

9606 - Homo sapiens: -

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

Shylo R Johnson, Christine K Ellis, Chad K Wickham, Molly R Selleck, Amy T Gilbert. Comparison of Ketamine-Xylazine, Butorphanol-Azaperone-Medetomidine, and Nalbuphine-Medetomidine-Azaperone for Raccoon (Procyon Lotor) Immobilization. Journal of wildlife diseases. 2023 Nov; ?(?):. doi: 10.7589/jwd-d-23-00060. [PMID: 37924235]
Wei Shi, Jing Dong, Jian-Feng Chen, Hai Yu. A meta-analysis showing the quantitative evidence base of perineural nalbuphine for wound pain from upper-limb orthopaedic trauma surgery. International wound journal. 2023 May; 20(5):1476-1490. doi: 10.1111/iwj.14002. [PMID: 36330591]
Meng-Si Luo. Nalbuphine reduces the incidence of emergence agitation in children undergoing adenotonsillectomy. Journal of clinical anesthesia. 2023 Apr; 87(?):111115. doi: 10.1016/j.jclinane.2023.111115. [PMID: 37018929]
Bingxu Ren, Jiannan Zhang, Xiaohu Yang, Dapeng Sun, Duanyang Sheng, Qiang Fang, Zhonghua Ji. Co-Administration of nalbuphine to improve morphine tolerance in mice with bone cancer pain. Molecular pain. 2023 Jan; 19(?):17448069231178741. doi: 10.1177/17448069231178741. [PMID: 37226458]
Chenran Wang, Shen Sun, Jing Jiao, Xinhua Yu, Shaoqiang Huang. Effects of nalbuphine on the cardiotoxicity of ropivacaine in rats. Fundamental & clinical pharmacology. 2022 Oct; 36(5):811-817. doi: 10.1111/fcp.12778. [PMID: 35373856]
Dijiao Ruan, Yuanyuan Wang, Sisi Li, Chao Zhang, Wenwen Zheng, Cong Yu. Nalbuphine alleviates inflammation by down-regulating NF-κB in an acute inflammatory visceral pain rat model. BMC pharmacology & toxicology. 2022 06; 23(1):34. doi: 10.1186/s40360-022-00573-7. [PMID: 35642022]
Jing Dong, Yi-Feng Ren, Meng-Ling Wei, Xin Ye, Xiao-Yun Peng, Long-Fei Zhang, Fang Li, Wei Shi. Re-evaluating the clinical efficacy of intrathecal nalbuphine: Based on minimal clinically important difference and statistical threshold correction. Pain practice : the official journal of World Institute of Pain. 2022 04; 22(4):497-499. doi: 10.1111/papr.13104. [PMID: 35178877]
Mahmoud Agami, Rasha A Shaalan, Saied F Belal, Marwa A A Ragab. LC-MS bioanalysis of targeted nasal galantamine bound chitosan nanoparticles in rats' brain homogenate and plasma. Analytical and bioanalytical chemistry. 2021 Aug; 413(20):5181-5191. doi: 10.1007/s00216-021-03487-1. [PMID: 34173038]
Kun He, Wei Ji, Hengli Zhao, Yilin Wei, Shaomei Yang, Qing Wen. Pharmacokinetic comparison of nalbuphine with single injection and patient-controlled analgesia mimic method in healthy Chinese volunteers. Journal of clinical pharmacy and therapeutics. 2021 Aug; 46(4):1166-1172. doi: 10.1111/jcpt.13421. [PMID: 33942343]
Xingfeng Sun, Qun Zhou, Min Zhou, Rong Cao, Zuolei Chen, Songjiang Tang, Shaoqiang Huang. The Effect of Epidural Nalbuphine Combined With Ropivacaine on Epidural Analgesia During Labor: A Multicenter, Randomized, Double-blind, Controlled Study. The Clinical journal of pain. 2021 06; 37(6):437-442. doi: 10.1097/ajp.0000000000000928. [PMID: 33758132]
Shang-Wen Lin, Yan-Jye Shyong, Ping-Chung Kuo, Jui-Chen Tsai. Topical application of sebacoyl dinalbuphine ester-loaded nanostructured lipid carriers alleviate pruritus in scratching mouse model. International journal of pharmaceutics. 2021 May; 600(?):120400. doi: 10.1016/j.ijpharm.2021.120400. [PMID: 33636328]
Kushagra Khanna, Nitin Sharma, Sonalika Rawat, Nazia Khan, Ritu Karwasra, Nazeer Hasan, Abhishek Kumar, Gaurav Kumar Jain, Dhruv Kumar Nishad, Sakshum Khanna, Harvinder Popli, Aseem Bhatnagar. Intranasal solid lipid nanoparticles for management of pain: A full factorial design approach, characterization & Gamma Scintigraphy. Chemistry and physics of lipids. 2021 05; 236(?):105060. doi: 10.1016/j.chemphyslip.2021.105060. [PMID: 33582127]
Michael Voronkov, Georgiy Nikonov, Roman Naumov, John Abernethy, Levon Isakulyan. NB-33, a bioreversible opioid derivative of Nalbuphine, shows enhanced pharmacodynamics. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2021 Apr; 159(?):105734. doi: 10.1016/j.ejps.2021.105734. [PMID: 33515698]
Jia-Wei Chen, Lin Tian, Le Zhang, Jian-Ying Hu, Shao-Qiang Huang, Jing Jiao. Nalbuphine on postoperative gastrointestinal tract dysfunction after laparoscopic surgery for gynaecological malignancies: A randomized controlled trial. Clinical and experimental pharmacology & physiology. 2021 02; 48(2):170-176. doi: 10.1111/1440-1681.13421. [PMID: 33063882]
Yifeng Ren, Hong Liu, Yuting Wang, Xi Fu, Fengming You. Efficacy of Nalbuphine as an Adjuvant to Ropivacaine in Ultrasound-guided Supraclavicular Brachial Block: A Prospective Randomized Controlled Study. The Clinical journal of pain. 2021 02; 37(2):158-159. doi: 10.1097/ajp.0000000000000899. [PMID: 33165020]
Lining Wu, Junma Yu, Qiuyue Wang, Yao Lu. Effects of nalbuphine on the cardioprotective effect of morphine in rats. International journal of cardiology. 2021 01; 322(?):207-210. doi: 10.1016/j.ijcard.2020.08.064. [PMID: 32828962]
Changcheng Jiang, Wenji Xie, Huijuan Xie, Wenqin Xie, Zhenming Kang, Naizhen Liu. Nalbuphine Exhibited a Better Adjuvant Than Dexmedetomidine in Supraclavicular Brachial Plexus Block in Youths. Clinical neuropharmacology. 2020 Sep; 43(5):134-138. doi: 10.1097/wnf.0000000000000410. [PMID: 32947423]
Yajing Dong, Zhi Liang, Zhe Xu, Wei Hao, Dandan Wang, Shuping Huo, Huayu Zhao. Effects of dezocine, morphine and nalbuphine on electropain threshold, temperature pain threshold and cardiac function in rats with myocardial ischemia. Annals of palliative medicine. 2020 Jul; 9(4):1556-1563. doi: 10.21037/apm-19-460. [PMID: 32762221]
Meng Ying Xi, Si Si Li, Chao Zhang, Lin Zhang, Tao Wang, Cong Yu. Nalbuphine for Analgesia After Orthognathic Surgery and Its Effect on Postoperative Inflammatory and Oxidative Stress: A Randomized Double-Blind Controlled Trial. Journal of oral and maxillofacial surgery : official journal of the American Association of Oral and Maxillofacial Surgeons. 2020 Apr; 78(4):528-537. doi: 10.1016/j.joms.2019.10.017. [PMID: 31785250]
Mona E El Sharkasy, M Walash, F Belal, M M Salim. Conventional and first derivative synchronous spectrofluorimetric methods for the simultaneous determination of cisatracurium and nalbuphine in biological fluids. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2020 Mar; 228(?):117841. doi: 10.1016/j.saa.2019.117841. [PMID: 31784219]
Ren-Jong Liang, Yin-Ning Shih, Yen-Lun Chen, Wei-Yang Liu, Wan-Ling Yang, Shih-Yu Lee, Hong-Jaan Wang. A dual system platform for drug metabolism: Nalbuphine as a model compound. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2020 Jan; 141(?):105093. doi: 10.1016/j.ejps.2019.105093. [PMID: 31648049]
Mansour Sobeh, Samar Rezq, Omar M Sabry, Mohamed A O Abdelfattah, Mohamed A El Raey, Walaa A El-Kashak, Assem M El-Shazly, Mona F Mahmoud, Michael Wink. Albizia anthelmintica: HPLC-MS/MS profiling and in vivo anti-inflammatory, pain killing and antipyretic activities of its leaf extract. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2019 Jul; 115(?):108882. doi: 10.1016/j.biopha.2019.108882. [PMID: 31029001]
Pamela D Reiter, Amy C Clevenger. Nalbuphine Reduces Opioid-Associated Urinary Retention in Pediatric Patients. Pediatric critical care medicine : a journal of the Society of Critical Care Medicine and the World Federation of Pediatric Intensive and Critical Care Societies. 2019 05; 20(5):e240-e244. doi: 10.1097/pcc.0000000000001920. [PMID: 31013261]
Abdisamad M Ibrahim, Zainab Obaidi, Gordon Ruan, Dorcas Adaramola, Sharon Onguti. Nalbuphine for Opioid-Induced Urine Retention. Annals of internal medicine. 2018 12; 169(12):894-895. doi: 10.7326/l18-0387. [PMID: 30178006]
Radomir Reszke, Jacek C Szepietowski. End-Stage Renal Disease Chronic Itch and Its Management. Dermatologic clinics. 2018 Jul; 36(3):277-292. doi: 10.1016/j.det.2018.02.007. [PMID: 29929599]
F Belal, F Ibrahim, Z A Sheribah, H Alaa. New spectrophotometric/chemometric assisted methods for the simultaneous determination of imatinib, gemifloxacin, nalbuphine and naproxen in pharmaceutical formulations and human urine. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2018 Jun; 198(?):51-60. doi: 10.1016/j.saa.2018.02.048. [PMID: 29518680]
Lisa L Wolfe, Pauline Nol, Matthew P McCollum, Travis Mays, Morgan E Wehtje, William R Lance, Mark C Fisher, Michael W Miller. Tissue Residue Levels after Immobilization of Rocky Mountain Elk ( Cervus elaphus nelsoni) using a Combination of Nalbuphine, Medetomidine, and Azaperone Antagonized with Naltrexone, Atipamezole, and Tolazoline. Journal of wildlife diseases. 2018 04; 54(2):362-365. doi: 10.7589/2017-06-132. [PMID: 29148888]
Brenda L Kick, Pan Shu, Bo Wen, Duxin Sun, Douglas K Taylor. Pharmacokinetic Profiles of Nalbuphine after Intraperitoneal and Subcutaneous Administration to C57BL/6 Mice. Journal of the American Association for Laboratory Animal Science : JAALAS. 2017 Sep; 56(5):534-538. doi: NULL. [PMID: 28903824]
Lisa L Wolfe, Mary E Wood, Pauline Nol, Matthew P McCollum, Mark C Fisher, William R Lance. THE EFFICACY OF NALBUPHINE, MEDETOMIDINE, AND AZAPERONE IN IMMOBILIZING AMERICAN BISON (BISON BISON). Journal of wildlife diseases. 2017 04; 53(2):304-310. doi: 10.7589/2016-05-107. [PMID: 28051569]
Lisa F Potts, Eun S Park, Jong-Min Woo, Bhagya L Dyavar Shetty, Arun Singh, Steven P Braithwaite, Michael Voronkov, Stella M Papa, M Maral Mouradian. Dual κ-agonist/μ-antagonist opioid receptor modulation reduces levodopa-induced dyskinesia and corrects dysregulated striatal changes in the nonhuman primate model of Parkinson disease. Annals of neurology. 2015 Jun; 77(6):930-41. doi: 10.1002/ana.24375. [PMID: 25820831]
Amale Hawi, Harry Alcorn, Jolene Berg, Carey Hines, Howard Hait, Thomas Sciascia. Pharmacokinetics of nalbuphine hydrochloride extended release tablets in hemodialysis patients with exploratory effect on pruritus. BMC nephrology. 2015 Apr; 16(?):47. doi: 10.1186/s12882-015-0043-3. [PMID: 25885112]
Hong-Jaan Wang, Cheng-Huei Hsiong, Shung-Tai Ho, Min-Jen Lin, Tung-Yuan Shih, Pei-Wei Huang, Oliver Yoa-Pu Hu. Commonly used excipients modulate UDP-glucuronosyltransferase 2b7 activity to improve nalbuphine oral bioavailability in humans. Pharmaceutical research. 2014 Jul; 31(7):1676-88. doi: 10.1007/s11095-013-1272-4. [PMID: 24526241]
J F Coetzee, K F Lechtenberg, M L Stock, B Kukanich. Pharmacokinetics and effect of intravenous nalbuphine in weaned Holstein calves after surgical castration. Journal of veterinary pharmacology and therapeutics. 2014 Apr; 37(2):169-77. doi: 10.1111/jvp.12077. [PMID: 23931676]
Pei-Wei Huang, Hung-Ta Liu, Cheng-Huei Hsiong, Li-Heng Pao, Chih-Cherng Lu, Shung-Tai Ho, Oliver Yoa-Pu Hu. Simultaneous determination of nalbuphine and its prodrug sebacoly dinalbuphine ester in human plasma by ultra-performance liquid chromatography-tandem mass spectrometry and its application to pharmacokinetic study in humans. Biomedical chromatography : BMC. 2013 Jul; 27(7):831-7. doi: 10.1002/bmc.2867. [PMID: 23460034]
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David Sanchez-Migallon Guzman, Butch KuKanich, Timothy D Heath, Lisa A Krugner-Higby, Steven A Barker, Carolyn S Brown, Joanne R Paul-Murphy. Pharmacokinetics of long-acting nalbuphine decanoate after intramuscular administration to Hispaniolan Amazon parrots (Amazona ventralis). American journal of veterinary research. 2013 Feb; 74(2):191-5. doi: 10.2460/ajvr.74.2.191. [PMID: 23363341]
Li-Jing Cai, Jun Zhang, Xiu-Mei Wang, R H Zhu, Jian Yang, Qi-Zhi Zhang, W X Peng. Validated LC-MS/MS assay for the quantitative determination of nalbuphine in human plasma and its application to a pharmacokinetic study. Biomedical chromatography : BMC. 2011 Dec; 25(12):1308-14. doi: 10.1002/bmc.1601. [PMID: 21337353]
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