Dantrolene (BioDeep_00000002712)
human metabolite blood metabolite Chemicals and Drugs
代谢物信息卡片
1-({[5-(4-nitrophenyl)furan-2-yl]methylidene}amino)imidazolidine-2,4-dione
化学式: C14H10N4O5 (314.065117)
中文名称: 丹曲林, 旦著能
谱图信息:
最多检出来源 Homo sapiens(blood) 8.49%
分子结构信息
SMILES: C1C(=O)NC(=O)N1N=CC2=CC=C(O2)C3=CC=C(C=C3)[N+](=O)[O-]
InChI: InChI=1S/C14H10N4O5/c19-13-8-17(14(20)16-13)15-7-11-5-6-12(23-11)9-1-3-10(4-2-9)18(21)22/h1-7H,8H2,(H,16,19,20)
描述信息
Dantrolene is only found in individuals that have used or taken this drug.Chemically, dantrolene is a hydantoin derivative, but does not exhibit antiepileptic activity like other hydantoin derivates such as phenytoin.Dantrolene depresses excitation-contraction coupling in skeletal muscle by binding to the ryanodine receptor 1, and decreasing intracellular calcium concentration. Ryanodine receptors mediate the release of calcium from the sarcoplasmic reticulum, an essential step in muscle contraction.
M - Musculo-skeletal system > M03 - Muscle relaxants > M03C - Muscle relaxants, directly acting agents > M03CA - Dantrolene and derivatives
D018373 - Peripheral Nervous System Agents > D009465 - Neuromuscular Agents
C78281 - Agent Affecting Musculoskeletal System > C29696 - Muscle Relaxant
D002491 - Central Nervous System Agents
同义名列表
数据库引用编号
22 个数据库交叉引用编号
- ChEBI: CHEBI:4317
- KEGG: C06939
- KEGGdrug: D02347
- PubChem: 6914273
- PubChem: 2952
- HMDB: HMDB0015350
- Metlin: METLIN1926
- DrugBank: DB01219
- ChEMBL: CHEMBL1201288
- ChEMBL: CHEMBL1741132
- Wikipedia: Dantrolene
- MeSH: Dantrolene
- chemspider: 5290202
- CAS: 1185234-99-4
- CAS: 833480-90-3
- CAS: 85008-71-5
- CAS: 7261-97-4
- PMhub: MS000004583
- PubChem: 9154
- NIKKAJI: J8.920F
- RefMet: Dantrolene
- KNApSAcK: 4317
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)
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
- Kafa Walweel, Nicole Beard, Dirk F van Helden, Derek R Laver. Dantrolene inhibition of ryanodine channels (RyR2) in artificial lipid bilayers depends on FKBP12.6.
The Journal of general physiology.
2023 08; 155(8):. doi:
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The American journal of case reports.
2022 May; 23(?):e936217. doi:
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JCI insight.
2021 08; 6(15):. doi:
10.1172/jci.insight.145188. [PMID: 34185708] - Mohammed Salem Rizk, Maha Sultan, Dalia Mohamed, Rehab MoussaTony. Simultaneous determination of dantrolene and paracetamol in human plasma by liquid chromatography tandem mass spectrometry.
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2021 Aug; 1179(?):122816. doi:
10.1016/j.jchromb.2021.122816. [PMID: 34329892] - Beatriz Prieto-Moure, Dolores Cejalvo-Lapeña, Mariola Belda-Antolí, Carolina Padrón-Sanz, José Miguel Lloris-Cejalvo, José Miguel Lloris-Carsí. Combination Therapy of Allopurinol and Dantrolene and Its Role In The Prevention of Experimental Ischemia Reperfusion Injury Of The Small Intestine.
Journal of investigative surgery : the official journal of the Academy of Surgical Research.
2021 Jul; 34(7):800-807. doi:
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2021 06; 96(?):102369. doi:
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Journal of medical case reports.
2021 Apr; 15(1):201. doi:
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European review for medical and pharmacological sciences.
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Canadian journal of anaesthesia = Journal canadien d'anesthesie.
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10.1007/s12630-010-9314-4. [PMID: 20431982] - Hiroshi Kodaira, Hiroyuki Kusuhara, Junko Ushiki, Eiichi Fuse, Yuichi Sugiyama. Kinetic analysis of the cooperation of P-glycoprotein (P-gp/Abcb1) and breast cancer resistance protein (Bcrp/Abcg2) in limiting the brain and testis penetration of erlotinib, flavopiridol, and mitoxantrone.
The Journal of pharmacology and experimental therapeutics.
2010 Jun; 333(3):788-96. doi:
10.1124/jpet.109.162321. [PMID: 20304939] - Adem Aslan, Mustafa Cemek, Mehmet Emin Buyukokuroglu, Korhan Altunbas, Orhan Bas, Yusuf Yurumez, Murat Cosar. Dantrolene can reduce secondary damage after spinal cord injury.
European spine journal : official publication of the European Spine Society, the European Spinal Deformity Society, and the European Section of the Cervical Spine Research Society.
2009 Oct; 18(10):1442-51. doi:
10.1007/s00586-009-1033-6. [PMID: 19468761] - Jing Liu, Tie-Shan Tang, Huiping Tu, Omar Nelson, Emily Herndon, Duong P Huynh, Stefan M Pulst, Ilya Bezprozvanny. Deranged calcium signaling and neurodegeneration in spinocerebellar ataxia type 2.
The Journal of neuroscience : the official journal of the Society for Neuroscience.
2009 Jul; 29(29):9148-62. doi:
10.1523/jneurosci.0660-09.2009. [PMID: 19625506] - Roger A Bannister, Isaac N Pessah, Kurt G Beam. The skeletal L-type Ca(2+) current is a major contributor to excitation-coupled Ca(2+) entry.
The Journal of general physiology.
2009 Jan; 133(1):79-91. doi:
10.1085/jgp.200810105. [PMID: 19114636] - M Said, R Becerra, J Palomeque, G Rinaldi, M A Kaetzel, P L Diaz-Sylvester, J A Copello, J R Dedman, C Mundiña-Weilenmann, L Vittone, A Mattiazzi. Increased intracellular Ca2+ and SR Ca2+ load contribute to arrhythmias after acidosis in rat heart. Role of Ca2+/calmodulin-dependent protein kinase II.
American journal of physiology. Heart and circulatory physiology.
2008 Oct; 295(4):H1669-83. doi:
10.1152/ajpheart.00010.2008. [PMID: 18723772] - C-J Huang, C-L Chen, C-S Wang, K-W Cheng, K-H Chen, C-C Wang, A M Concejero, Y-F Cheng, T-L Huang, K-W Chiu, S-H Wang, C-C Lin, Y-W Liu, B Jawan. Rhabdomyolysis after liver transplantation: a case report.
Transplantation proceedings.
2008 Oct; 40(8):2821-2. doi:
10.1016/j.transproceed.2008.07.032. [PMID: 18929870] - Ian Daniels, Julie Turzanski, Andrew P Haynes. A requirement for calcium in the caspase-independent killing of Burkitt lymphoma cell lines by Rituximab.
British journal of haematology.
2008 Jul; 142(3):394-403. doi:
10.1111/j.1365-2141.2008.07193.x. [PMID: 18544085] - 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] - Junichi Enokizono, Hiroyuki Kusuhara, Atsushi Ose, Alfred H Schinkel, Yuichi Sugiyama. Quantitative investigation of the role of breast cancer resistance protein (Bcrp/Abcg2) in limiting brain and testis penetration of xenobiotic compounds.
Drug metabolism and disposition: the biological fate of chemicals.
2008 Jun; 36(6):995-1002. doi:
10.1124/dmd.107.019257. [PMID: 18322075] - Paula L Diaz-Sylvester, Maura Porta, Julio A Copello. Halothane modulation of skeletal muscle ryanodine receptors: dependence on Ca2+, Mg2+, and ATP.
American journal of physiology. Cell physiology.
2008 Apr; 294(4):C1103-12. doi:
10.1152/ajpcell.90642.2007. [PMID: 18305228] - Di Wu, Xiangmei Chen, Rui Ding, Xi Qiao, Suozhu Shi, Yuansheng Xie, Quan Hong, Zhe Feng. Ischemia/reperfusion induce renal tubule apoptosis by inositol 1,4,5-trisphosphate receptor and L-type Ca2+ channel opening.
American journal of nephrology.
2008; 28(3):487-99. doi:
10.1159/000113107. [PMID: 18185015] - Mijeung Gwak, Pyonghwan Park, Kisoo Kim, Keunho Lim, Sungmoon Jeong, Chongwha Baek, Jonghwan Lee. The effects of dantrolene on hypoxic-ischemic injury in the neonatal rat brain.
Anesthesia and analgesia.
2008 Jan; 106(1):227-33, table of contents. doi:
10.1213/01.ane.0000287663.81050.38. [PMID: 18165582] - H Hattori, E Nagata, Y Oya, T Takahashi, M Aoki, D Ito, N Suzuki. A novel compound heterozygous dysferlin mutation in Miyoshi myopathy siblings responding to dantrolene.
European journal of neurology.
2007 Nov; 14(11):1288-91. doi:
10.1111/j.1468-1331.2007.01958.x. [PMID: 17868276] - John Picard, Stephen Ward, Tim Meek. Antidotes to anesthetic catastrophe: lipid emulsion and dantrolene.
Anesthesia and analgesia.
2007 Jul; 105(1):283-4; author reply 284. doi:
10.1213/01.ane.0000261263.79735.2f. [PMID: 17578994] - Tomoko Morota, Katsuya Endo, Setsuo Furuta, Shinju Obara, Hiroshi Ohmuzo, Toshikazu Kaneko, Toshiyasu Onuma, Kazuhiro Watanabe. [Case of malignant hyperthermia in which treatment was carried out smoothly].
Masui. The Japanese journal of anesthesiology.
2007 Jul; 56(7):826-30. doi:
NULL. [PMID: 17633846] - Fernando López-Neblina, Luis H Toledo-Pereyra, Alexander H Toledo, Jon Walsh. Ryanodine receptor antagonism protects the ischemic liver and modulates TNF-alpha and IL-10.
The Journal of surgical research.
2007 Jun; 140(1):121-8. doi:
10.1016/j.jss.2006.12.003. [PMID: 17359999] - Ana-Maria Florea, Frank Splettstoesser, Dietrich Büsselberg. Arsenic trioxide (As2O3) induced calcium signals and cytotoxicity in two human cell lines: SY-5Y neuroblastoma and 293 embryonic kidney (HEK).
Toxicology and applied pharmacology.
2007 May; 220(3):292-301. doi:
10.1016/j.taap.2007.01.022. [PMID: 17376498] - Henry M Staines, Abdulnaser Alkhalil, Richard J Allen, Hugo R De Jonge, Elvira Derbyshire, Stéphane Egée, Hagai Ginsburg, David A Hill, Stephan M Huber, Kiaran Kirk, Florian Lang, Godfrey Lisk, Eugene Oteng, Ajay D Pillai, Kempaiah Rayavara, Sherin Rouhani, Kevin J Saliba, Crystal Shen, Tsione Solomon, Serge L Y Thomas, Patrick Verloo, Sanjay A Desai. Electrophysiological studies of malaria parasite-infected erythrocytes: current status.
International journal for parasitology.
2007 Apr; 37(5):475-82. doi:
10.1016/j.ijpara.2006.12.013. [PMID: 17292372] - Thorsten Lenhard, Sonja Külkens, Stefan Schwab. Cerebral salt-wasting syndrome in a patient with neuroleptic malignant syndrome.
Archives of neurology.
2007 Jan; 64(1):122-5. doi:
10.1001/archneur.64.1.122. [PMID: 17210819] - Nicolas André, Marie Boyer, Carole Coze, Jean Delorme, Angelique Rome, Jean Claude Gentet, Jean Louis Bernard. Can dantrolene contribute to methotrexate toxicity?.
The Annals of pharmacotherapy.
2006 Sep; 40(9):1695-6. doi:
10.1345/aph.1h082. [PMID: 16912244] - C K M Wong, T Lai, J M P Holly, M H Wheeler, C E H Stewart, J R Farndon. Insulin-like growth factors (IGF) I and II utilize different calcium signaling pathways in a primary human parathyroid cell culture model.
World journal of surgery.
2006 Mar; 30(3):333-45. doi:
10.1007/s00268-005-0339-8. [PMID: 16485066] - Yanyan Li, Peili Wang, Jianchao Xu, Gary V Desir. Voltage-gated potassium channel Kv1.3 regulates GLUT4 trafficking to the plasma membrane via a Ca2+-dependent mechanism.
American journal of physiology. Cell physiology.
2006 Feb; 290(2):C345-51. doi:
10.1152/ajpcell.00091.2005. [PMID: 16403947] - Toru Sanai, Rei Matsui, Tadashi Hirano, Shinichi Torichigai, Hideki Yotsueda, Harumichi Higashi, Hideki Hirakata, Mitsuo Iida. Successful treatment of six patients with neuroleptic malignant syndrome associated with myoglobulinemic acute renal failure.
Renal failure.
2006; 28(1):51-5. doi:
10.1080/08860220500461252. [PMID: 16526319] - S R R Hall, L Wang, B Milne, M Hong. Mannitol but not dantrolene prevents myocardial dysfunction following intra-cranial hypertension in rats.
American journal of transplantation : official journal of the American Society of Transplantation and the American Society of Transplant Surgeons.
2005 Dec; 5(12):2862-9. doi:
10.1111/j.1600-6143.2005.01127.x. [PMID: 16302998] - Tobias Podranski, Thomas Bouillon, Peter M Schumacher, Akikio Taguchi, Daniel I Sessler, Andrea Kurz. Compartmental pharmacokinetics of dantrolene in adults: do malignant hyperthermia association dosing guidelines work?.
Anesthesia and analgesia.
2005 Dec; 101(6):1695-1699. doi:
10.1213/01.ane.0000184184.40504.f3. [PMID: 16301243] - H Ucuncu, S Taysi, B Aktan, M E Buyukokuroglu, M Elmastas. Effect of dantrolene on lipid peroxidation, lutathione and glutathione-dependent enzyme activities in experimental otitis media with effusion in guinea pigs.
Human & experimental toxicology.
2005 Nov; 24(11):567-71. doi:
10.1191/0960327105ht569oa. [PMID: 16323573] - Prosper M'Bemba-Meka, Nicole Lemieux, Saroj K Chakrabarti. Nickel compound-induced DNA single-strand breaks in chromosomal and nuclear chromatin in human blood lymphocytes in vitro: role of oxidative stress and intracellular calcium.
Mutation research.
2005 Oct; 586(2):124-37. doi:
10.1016/j.mrgentox.2005.06.001. [PMID: 16099703] - Tokuaki Murakawa, Ichiro Sakai, Akitomo Matsuki. [Central hyperthermia suspected of malignant hyperthermia in a patient undergoing radical neck clipping for cerebral aneurysm].
Masui. The Japanese journal of anesthesiology.
2005 Jan; 54(1):49-53. doi:
. [PMID: 15717469] - Alan Sabirsh, Jesper Bristulf, Christer Owman. Exploring the pharmacology of the leukotriene B4 receptor BLT1, without the confounding effects of BLT2.
European journal of pharmacology.
2004 Sep; 499(1-2):53-65. doi:
10.1016/j.ejphar.2004.07.060. [PMID: 15363951] - Mehmet Emin Büyükokuroğlu, Seyithan Taysi, Mustafa Buyukavci, Ebubekir Bakan. Prevention of acute adriamycin cardiotoxicity by dantrolene in rats.
Human & experimental toxicology.
2004 May; 23(5):251-6. doi:
10.1191/0960327104ht443oa. [PMID: 15222403] - Forrest L Smith, Scott J LeBlanc, Richard Carter. Influence of intracellular Ca2+ release modulating drugs on bupivacaine infiltration anesthesia in mice.
European journal of pain (London, England).
2004 Apr; 8(2):153-61. doi:
10.1016/s1090-3801(03)00089-2. [PMID: 14987625] - Neil Kaplowitz. Drug-induced liver injury.
Clinical infectious diseases : an official publication of the Infectious Diseases Society of America.
2004 Mar; 38 Suppl 2(?):S44-8. doi:
10.1086/381446. [PMID: 14986274] - Erica C McKenzie, Stephanie J Valberg, Sandra M Godden, Carrie J Finno, Michael J Murphy. Effect of oral administration of dantrolene sodium on serum creatine kinase activity after exercise in horses with recurrent exertional rhabdomyolysis.
American journal of veterinary research.
2004 Jan; 65(1):74-9. doi:
10.2460/ajvr.2004.65.74. [PMID: 14719706] - M Martínez-Sánchez, F Striggow, U H Schröder, S Kahlert, K G Reymann, G Reiser. Na(+) and Ca(2+) homeostasis pathways, cell death and protection after oxygen-glucose-deprivation in organotypic hippocampal slice cultures.
Neuroscience.
2004; 128(4):729-40. doi:
10.1016/j.neuroscience.2004.06.074. [PMID: 15464281] - J G T Edwards, J R Newtont, P H L Ramzan, R C Pilsworth, M C Shepherd. The efficacy of dantrolene sodium in controlling exertional rhabdomyolysis in the Thoroughbred racehorse.
Equine veterinary journal.
2003 Nov; 35(7):707-11. doi:
10.2746/042516403775696221. [PMID: 14649364] - Shigetoshi Mieno, Kunio Asada, Hitoshi Horimoto, Shinjiro Sasaki. Neuroleptic malignant syndrome following cardiac surgery: successful treatment with dantrolene.
European journal of cardio-thoracic surgery : official journal of the European Association for Cardio-thoracic Surgery.
2003 Sep; 24(3):458-60. doi:
10.1016/s1010-7940(03)00332-4. [PMID: 12965323] - Masahiko Atsumi, Yuko Chimoto, Shogo Nishikawa, Haruyuki Mineta, Yoshikuni Nakasaka, Kazuhiro Nishimoto, Hisashi Tanaka, Masataka Kitaguchi. [Head retraction reflex-like movements with severe bulbar symptoms in a patient with stiff-person syndrome].
Rinsho shinkeigaku = Clinical neurology.
2003 Jun; 43(6):322-6. doi:
NULL. [PMID: 14503349]
