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66085-59-4 分子结构
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3-(2-methoxyethyl) 5-propan-2-yl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

ChemBase编号:276
分子式:C21H26N2O7
平均质量:418.44034
单一同位素质量:418.17400118
SMILES和InChIs

SMILES:
O(C(=O)C1=C(NC(=C(C1c1cc([N+](=O)[O-])ccc1)C(=O)OCCOC)C)C)C(C)C
Canonical SMILES:
COCCOC(=O)C1=C(C)NC(=C(C1c1cccc(c1)[N+](=O)[O-])C(=O)OC(C)C)C
InChI:
InChI=1S/C21H26N2O7/c1-12(2)30-21(25)18-14(4)22-13(3)17(20(24)29-10-9-28-5)19(18)15-7-6-8-16(11-15)23(26)27/h6-8,11-12,19,22H,9-10H2,1-5H3
InChIKey:
UIAGMCDKSXEBJQ-UHFFFAOYSA-N

引用这个纪录

CBID:276 http://www.chembase.cn/molecule-276.html

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
3-(2-methoxyethyl) 5-propan-2-yl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
IUPAC传统名
nimodipine
3-(2-methoxyethyl) 5-propan-2-yl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
商标名
Nimotop
Periplum
别名
Nimodipino [INN-Spanish]
Nimodipinum [INN-Latin]
Isopropyl 2-methoxyethyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
Nimodipine
Bay-E 9736
1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid
3-isopropyl 5-(2-methoxyethyl) 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
2-Methoxyethyl-1-methylethyl ester
Isopropyl 2-methoxyethyl 1,4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)-3,5-pyridinedicarboxylate
Nimotop
1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid 2-methoxyethyl 1-methylethyl ester
1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid 3-(2-Methoxyethyl) 5-(1-Methylethyl) Ester
(+/-)-Nimodipine
Admon
Nimodipine AP
Nimotop
Periplum
Calnit
Kenesil
3-(2-methoxyethyl) 5-propan-2-yl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
Nimodipine
CAS号
66085-59-4
EC号
266-127-0
MDL号
MFCD00153848
PubChem SID
46508497
24277858
160963739
PubChem CID
4497

理论计算性质

理论计算性质

JChem ALOGPS 2.1
质子受体 质子供体
LogD (pH = 5.5) 2.2858284  LogD (pH = 7.4) 2.5375297 
Log P 2.5419018  摩尔折射率 112.3756 cm3
极化性 42.033375 Å3 极化表面积 119.68 Å2
可自由旋转的化学键 10  里宾斯基五规则 true 
Log P 3.41  LOG S -4.54 
溶解度 1.20e-02 g/l 

分子性质

分子性质

理化性质 安全信息 药理学性质 产品相关信息 生物活性(PubChem)
溶解度
45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: insoluble expand 查看数据来源
Chloroform expand 查看数据来源
H2O: insoluble expand 查看数据来源
Methanol expand 查看数据来源
methanol: soluble62.5 mg/mL expand 查看数据来源
外观
Pale Yellow Solid expand 查看数据来源
white solid expand 查看数据来源
熔点
116-121°C expand 查看数据来源
疏水性(logP)
2.7 expand 查看数据来源
4.144 expand 查看数据来源
保存条件
-20°C expand 查看数据来源
-20°C Freezer expand 查看数据来源
Room Temperature (15-30°C), Protect from light expand 查看数据来源
保存注意事项
IRRITANT expand 查看数据来源
RTECS编号
US7975500 expand 查看数据来源
欧盟危险性物质标志
有害性(Harmful) 有害性(Harmful) (Xn) expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
德国WGK号
1 expand 查看数据来源
危险公开号
48/22 expand 查看数据来源
TSCA收录
false expand 查看数据来源
GHS危险品标识
GHS08 expand 查看数据来源
GHS警示词
Warning expand 查看数据来源
GHS危险声明
H373 expand 查看数据来源
个人保护装置
dust mask type N95 (US), Eyeshields, Gloves expand 查看数据来源
相关基因信息
human ... ADORA3(140), CACNG1(786)rat ... Adora1(29290), Adora2a(25369) expand 查看数据来源
生物活性机理
Blocks intracellular influx of calcium that is thought to be a central to ischaemic neuronal damage. expand 查看数据来源
Calcium channel blockader expand 查看数据来源
Nimodipine binds specifically to L-type voltage-gated calcium channels expand 查看数据来源
纯度
95% expand 查看数据来源
成盐信息
Free Base expand 查看数据来源
质检报告
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
应用领域
Cerebral vasodilator expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich TRC TRC MP Biomedicals MP Biomedicals
DrugBank -  DB00393 external link
Item Information
Drug Groups approved
Description Nimodipine is a 1,4-dihydropyridine calcium channel blocker. It acts primarily on vascular smooth muscle cells by stabilizing voltage-gated L-type calcium channels in their inactive conformation. By inhibiting the influx of calcium in smooth muscle cells, nimodipine prevents calcium-dependent smooth muscle contraction and subsequent vasoconstriction. Compared to other calcium channel blocking agents, nimodipine exhibits greater effects on cerebral circulation than on peripheral circulation. Nimodipine is used to as an adjunct to improve the neurologic outcome following subarachnoid hemorrhage from ruptured intracranial aneurysm.
Indication For use as an adjunct to improve neurologic outcome following subarachnoid hemorrhage (SAH) from ruptured intracranial berry aneurysms by reducing the incidence and severity of ischemic deficits.
Pharmacology Nimodipine belongs to the class of pharmacological agents known as calcium channel blockers. Nimodipine is indicated for the improvement of neurological outcome by reducing the incidence and severity of ischemic deficits in patients with subarachnoid hemorrhage from ruptured congenital aneurysms who are in good neurological condition post-ictus (e.g., Hunt and Hess Grades I-III). The contractile processes of smooth muscle cells are dependent upon calcium ions, which enter these cells during depolarization as slow ionic transmembrane currents. Nimodipine inhibits calcium ion transfer into these cells and thus inhibits contractions of vascular smooth muscle. In animal experiments, nimodipine had a greater effect on cerebral arteries than on arteries elsewhere in the body perhaps because it is highly lipophilic, allowing it to cross the blood brain barrier.
Toxicity Symptoms of overdosage would be expected to be related to cardiovascular effects such as excessive peripheral vasodilation with marked systemic hypotension.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic metabolism via cytochrome P450 3A4.
Absorption Bioavailability is 100% following intravenous administration and 3-30% following oral administration due to extensive first-pass metabolism.
Half Life 1.7-9 hours
Protein Binding 95%
References
Janjua N, Mayer SA: Cerebral vasospasm after subarachnoid hemorrhage. Curr Opin Crit Care. 2003 Apr;9(2):113-9. [Pubmed]
Allen GS, Ahn HS, Preziosi TJ, Battye R, Boone SC, Boone SC, Chou SN, Kelly DL, Weir BK, Crabbe RA, Lavik PJ, Rosenbloom SB, Dorsey FC, Ingram CR, Mellits DE, Bertsch LA, Boisvert DP, Hundley MB, Johnson RK, Strom JA, Transou CR: Cerebral arterial spasm--a controlled trial of nimodipine in patients with subarachnoid hemorrhage. N Engl J Med. 1983 Mar 17;308(11):619-24. [Pubmed]
Belfort MA, Anthony J, Saade GR, Allen JC Jr: A comparison of magnesium sulfate and nimodipine for the prevention of eclampsia. N Engl J Med. 2003 Jan 23;348(4):304-11. # [Pubmed]
Kim JH, Park IS, Park KB, Kang DH, Hwang SH: Intraarterial nimodipine infusion to treat symptomatic cerebral vasospasm after aneurysmal subarachnoid hemorrhage. J Korean Neurosurg Soc. 2009 Sep;46(3):239-44. Epub 2009 Sep 30. [Pubmed]
Tomassoni D, Lanari A, Silvestrelli G, Traini E, Amenta F: Nimodipine and its use in cerebrovascular disease: evidence from recent preclinical and controlled clinical studies. Clin Exp Hypertens. 2008 Nov;30(8):744-66. [Pubmed]
Vergouwen MD, Vermeulen M, Roos YB: Effect of nimodipine on outcome in patients with traumatic subarachnoid haemorrhage: a systematic review. Lancet Neurol. 2006 Dec;5(12):1029-32. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com
Selleck Chemicals -  S1747 external link
Research Area: Cardiovascular Disease
Biological Activity:
Nimodipine(Nimotop) is a dihydropyridine derivative and an analogue of the calcium channel blocker nifedipine, with antihypertensive activity. Nimodipine inhibits the transmembrane influx of calcium ions in response to depolarization in smooth muscle cells, thereby inhibiting vascular smooth muscle contraction and inducing vasodilatation. Nimodipine has a greater effect on cerebral arteries than on peripheral smooth muscle cells and myocardial cells, probably because this agent can cross the blood brain barrier due to its lipophilic nature. Furthermore, this agent also inhibits the drug efflux pump P-glycoprotein, which is overexpressed in some multi-drug resistant tumors, and may improve the efficacy of some antineoplastic agents. [1, 2]
Sigma Aldrich -  N149 external link
Biochem/physiol Actions
Potent L-type Ca2+ channel antagonist.
Caution
Photosensitive
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. N149.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Toronto Research Chemicals -  N478200 external link
A dihydropyridine calcium channel blocker. It is used as a vasodilator (cerebral).
MP Biomedicals -  02159803 external link
Potent calcium channel antagonist.

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Janjua N, Mayer SA: Cerebral vasospasm after subarachnoid hemorrhage. Curr Opin Crit Care. 2003 Apr;9(2):113-9. Pubmed
  • Allen GS, Ahn HS, Preziosi TJ, Battye R, Boone SC, Boone SC, Chou SN, Kelly DL, Weir BK, Crabbe RA, Lavik PJ, Rosenbloom SB, Dorsey FC, Ingram CR, Mellits DE, Bertsch LA, Boisvert DP, Hundley MB, Johnson RK, Strom JA, Transou CR: Cerebral arterial spasm--a controlled trial of nimodipine in patients with subarachnoid hemorrhage. N Engl J Med. 1983 Mar 17;308(11):619-24. Pubmed
  • Belfort MA, Anthony J, Saade GR, Allen JC Jr: A comparison of magnesium sulfate and nimodipine for the prevention of eclampsia. N Engl J Med. 2003 Jan 23;348(4):304-11. Pubmed#
  • Kim JH, Park IS, Park KB, Kang DH, Hwang SH: Intraarterial nimodipine infusion to treat symptomatic cerebral vasospasm after aneurysmal subarachnoid hemorrhage. J Korean Neurosurg Soc. 2009 Sep;46(3):239-44. Epub 2009 Sep 30. Pubmed
  • Tomassoni D, Lanari A, Silvestrelli G, Traini E, Amenta F: Nimodipine and its use in cerebrovascular disease: evidence from recent preclinical and controlled clinical studies. Clin Exp Hypertens. 2008 Nov;30(8):744-66. Pubmed
  • Vergouwen MD, Vermeulen M, Roos YB: Effect of nimodipine on outcome in patients with traumatic subarachnoid haemorrhage: a systematic review. Lancet Neurol. 2006 Dec;5(12):1029-32. Pubmed
  • Kappelle, et al., Brit. J. Pharm. , 111 : 887 (1994).
  • Allen, G.S., et al.: N. Engl. J. Med., 308, 619 (1983)
  • Schluter, H.: Arzneim.-Forsch., 36, 1733 (1983)
  • Deyo, R.A., et al.: Science, 243, 809 (1983)
  • U.K. Pat., 1979, Bayer, 2 018 134; CA, 92, 220691r, (synth, pharmacol)
  • Meyer, H. et al., Arzneim.-Forsch., 1981, 31, 407; 1982, 32, 338; 1983, 33, 106, (synth, pharmacol, enantiomers)
  • Ger. Pat., 1981, Bayer, 2 935 451; CA, 95, 42922j, (synth, resoln)
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  • Scriabine, A. et al., Ann. N.Y. Acad. Sci., 1988, 522, 698, (rev, pharmacol)
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  • Langley, M.S. et al., Drugs, 1989, 37, 669, (rev)
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  • Nimodipine, (Eds. Scriabine, A. et al), Springer-Verlag, 1991, (book)
  • Wadworth, A.N. et al., Drugs Aging, 1992, 2, 262, (rev)
  • Whitfield, P.C. et al., Br. J. Hosp. Med., 1994, 52, 539, (rev)
  • Kakarieka, A. et al., J. Neural Trans. Suppl., 1994, 43, 13, (clin trial, rev)
  • Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 8483, (synonyms)
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