[(2S,4R,7R)-2-methoxy-6,11-dimethyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),9,12,14-tetraen-4-yl]methyl 5-bromopyridine-3-carboxylate

• ChemBase编号: 581
• 分子式: C24H26BrN3O3
• 平均质量: 484.38554
• 单一同位素质量: 483.11575371
• SMILES: Brc1cc(C(=O)OC[C@@H]2C[C@@]3(OC)[C@H](N(C2)C)Cc2c4c3cccc4n(c2)C)cnc1
• Canonical SMILES: CO[C@]12C[C@@H](COC(=O)c3cncc(c3)Br)CN([C@@H]1Cc1c3c2cccc3n(c1)C)C
• InChI: InChI=1S/C24H26BrN3O3/c1-27-13-17-8-21-24(30-3,19-5-4-6-20(27)22(17)19)9-15(12-28(21)2)14-31-23(29)16-7-18(25)11-26-10-16/h4-7,10-11,13,15,21H,8-9,12,14H2,1-3H3/t15-,21-,24+/m1/s1
• InChIKey: YSEXMKHXIOCEJA-FVFQAYNVSA-N

名称和登记号

名称

• IUPAC标准名: [(2S,4R,7R)-2-methoxy-6,11-dimethyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),9,12,14-tetraen-4-yl]methyl 5-bromopyridine-3-carboxylate; [(2S,4R,7R)-2-methoxy-6,11-dimethyl-6,11-diazatetracyclo[7.6.1.0^2,^7.0^1^2,^1^6]hexadeca-1(15),9,12(16),13-tetraen-4-yl]methyl 5-bromopyridine-3-carboxylate; [(2S,4R,7R)-2-methoxy-6,11-dimethyl-6,11-diazatetracyclo[7.6.1.0^2,^7.0^1^2,^1^6]hexadeca-1(16),9,12,14-tetraen-4-yl]methyl 5-bromopyridine-3-carboxylate
• IUPAC传统名: nicergoline; [(2S,4R,7R)-2-methoxy-6,11-dimethyl-6,11-diazatetracyclo[7.6.1.0^2,^7.0^1^2,^1^6]hexadeca-1(15),9,12(16),13-tetraen-4-yl]methyl 5-bromopyridine-3-carboxylate; [(2S,4R,7R)-2-methoxy-6,11-dimethyl-6,11-diazatetracyclo[7.6.1.0^2,^7.0^1^2,^1^6]hexadeca-1(16),9,12,14-tetraen-4-yl]methyl 5-bromopyridine-3-carboxylate
• 商标名: MNE; Nargoline; Nicergolin [German]; Nicergolina [Dcit]; Nicergoline [Usan:Ban:Inn:Jan]; Nicergolinum [INN-Latin]; Nicotergoline; Nimergoline; Nimergoline Base; Sermion; Vasospan
• 别名: 5-溴烟酸 10-甲氧基-1,6-二甲基麦角灵-8-甲酯; 尼麦角林; Nicergoline; Nicergoline; Nargoline; Nicotergoline; Nimergoline; Sermion

登记号

• CAS号: 27848-84-6
• EC号: 248-694-6
• MDL号: MFCD00869626
• PubChem SID: 46508741; 160964044; 24897843
• PubChem CID: 34040

理论计算性质

JChem

• 质子受体: 4
• 质子供体: 0
• LogD (pH = 5.5): 1.1122493
• LogD (pH = 7.4): 2.885367
• Log P: 3.695325
• 摩尔折射率: 123.2974 cm^3
• 极化性: 48.515564 Å^3
• 极化表面积: 56.59 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 3.99
• LOG S: -4.58
• 溶解度: 1.27e-02 g/l

分子性质

理化性质

• 疏水性(logP): 3.3

安全信息

• RTECS编号: KE6341000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 22
• 安全公开号: 36
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: 2-8°C

药理学性质

• 相关基因信息: human ... ADRA1A(148)
• 生物活性机理: a1-Adrenoceptor antagonist; Calcium channel antagonist; Cholinergic; Peripheral vasodilator

产品相关信息

• 纯度: ~97% (TLC)
• 级别: analytical standard, for drug analysis
• 应用领域: Cerebroprotective props; Has been used in treatment of senile dementia

详细说明

DrugBank - DB00699

• Drug Groups: approved
• Description: An ergot derivative that has been used as a cerebral vasodilator and in peripheral vascular disease. It has been suggested to ameliorate cognitive deficits in cerebrovascular disease. [PubChem]
• Indication: For the treatment of senile dementia, migraines of vascular origin, transient ischemia, platelet hyper-aggregability, and macular degeneration.
• Pharmacology: Nicergoline is a potent vasodilator (improves brain blood flow). On the cerebral level it prompts a lowering of vascular resistance, an increase in arterial flow and stimulates the use of oxygen and glucose. Nicergoline also improves blood circulation in the lungs and limbs and has been shown to inhibit blood platelet aggregation.
• Affected Organisms: Humans and other mammals
• References: Winblad B, Fioravanti M, Dolezal T, Logina I, Milanov IG, Popescu DC, Solomon A: Therapeutic use of nicergoline. Clin Drug Investig. 2008;28(9):533-52. [Pubmed]
• External Links: Wikipedia

Sigma Aldrich - N7889

Biochem/physiol Actions
大脑和周边血管舒张剂
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. N7889.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

参考文献

• Winblad B, Fioravanti M, Dolezal T, Logina I, Milanov IG, Popescu DC, Solomon A: Therapeutic use of nicergoline. Clin Drug Investig. 2008;28(9):533-52. Pubmed
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