(1S,12S,14R)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0^{1,12}.0^{6,17}]heptadeca-6,8,10(17),15-tetraen-14-ol hydrobromide

• ChemBase编号: 72627
• 分子式: C17H22BrNO3
• 平均质量: 368.26548
• 单一同位素质量: 367.07830557
• SMILES: c12c3c(ccc1CN(CC[C@]12[C@@H](O3)C[C@H](C=C1)O)C)OC.Br
• Canonical SMILES: COc1ccc2c3c1O[C@@H]1[C@@]3(CCN(C2)C)C=C[C@@H](C1)O.Br
• InChI: InChI=1S/C17H21NO3.BrH/c1-18-8-7-17-6-5-12(19)9-14(17)21-16-13(20-2)4-3-11(10-18)15(16)17;/h3-6,12,14,19H,7-10H2,1-2H3;1H/t12-,14-,17-;/m0./s1
• InChIKey: QORVDGQLPPAFRS-XPSHAMGMSA-N

名称和登记号

名称

• IUPAC标准名: (1S,12S,14R)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0^{1,12}.0^{6,17}]heptadeca-6,8,10(17),15-tetraen-14-ol hydrobromide; (1S,12S,14R)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0^1,^1^2.0^6,^1^7]heptadeca-6,8,10(17),15-tetraen-14-ol hydrobromide
• IUPAC传统名: galantamine hydrobromide
• 别名: GALANTHIAMIN HBR; Reminyl; Galanthamine hydrobromide; Galantamine hydrobromide; Galanthamine hydrobromide from Lycoris sp.

登记号

• CAS号: 1953-04-4; 69353-21-5
• EC号: 217-780-5
• MDL号: MFCD00067672
• PubChem SID: 162037552; 24895074
• PubChem CID: 121587

理论计算性质

• Acid pKa: 14.810377
• 质子受体: 4
• 质子供体: 1
• LogD (pH = 5.5): -1.9891269
• LogD (pH = 7.4): -0.35530484
• Log P: 1.1630428
• 摩尔折射率: 82.3049 cm^3
• 极化性: 31.647512 Å^3
• 极化表面积: 41.93 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

分子性质

安全信息

• 保存条件: -20°C
• RTECS编号: DF8075000
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 联合国危险货物编号: 2811
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 3
• 危险公开号: 25
• 安全公开号: 45
• GHS危险品标识: GHS06
• GHS警示词: Danger
• GHS危险声明: H301
• GHS警示性声明: P301 + P310
• 个人保护装置: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3
• 保存温度: -20°C

药理学性质

• 作用靶点: mAChRs mAChRs

产品相关信息

• 纯度: ≥94% (TLC)
• 成盐信息: Hydrobromide

详细说明

MP Biomedicals - 05209140

MP Biomedicals Rare Chemical collection

Selleck Chemicals - S1339

Research Area

• Description: Neurological Disease

Biological Activity

• Description: Galanthamine (Razadyne, Reminyl) is an AChE inhibitor with IC50 of 14 nM.
• Targets: AChE
• IC50: 14 nM ^[1]
• In Vitro: Galanthamine has been demonstrated to have an IC50 of 14 nM and 15 nM on AChE in post-mortem human brain frontal cortex and the hippocampus region. Red-cell cholinesterase activity in blood samples from the neurosurgery patients is 10 times more strongly inhibited by Galanthamine in brain tissue samples. ^[1] Galanthamine (1 μM) activates single channels with conductance’s of 18 and 30 pS in outside-out patches excised from dexamethasone mouse fibroblasts (M10 cells). ^[2] Galanthamine acts as ‘noncompetitive nicotinic receptor agonists’ on clonal rat pheochromocytoma (PC12) cells. Galanthamine (50 μM) activates single-channel currents in outside-out patches excised from clonal PC12 cells. ^[3]
• In Vivo: Galantamine significantly increases the number of living pyramidal neurons after ischemia-reperfusion injury. Galantamine significantly reduces TUNEL, active caspase-3, and SOD-2 immunoreactivity. The nicotinic antagonist mecamylamine blockes the protective effects of galantamine. The neuroprotective effects of galantamine are preserved even when first administered at 3 hours postischemia. ^[4]
• Clinical Trials: Galanthamine is now under the phase IV clinical trials for the efficacy and safety for improving dysfunction in people with bipolar disorder.

Protocol

• Protocol: Kinase Assay ^[1]
• Acetylcholinesterase Assay: The catalytic activity of acetylcholinesterase in erythrocytes and brain is measured using [^14C]acetylcholine iodide radiolabelled in the acetyl moiety at a final substrate concentration of 3.6 mmM, a pH of 7.4 and a temperature of 25 °C. Concentration response trials are then performed. After incubation of the sample with Galanthamine for 60 minutes at 25 °C in vitro, the catalytic reaction is started by the addition of substrate.
• Protocol: Animal Study ^[4]
• Animal Models: Gerbils
• Formulation: Galanthamine is dissolved in 0.9% NaCl saline solution.
• Doses: 10 mg/kg
• Administration: S.c. twice a day or 3 or 6 hours after ischemia and at subsequent 12-hours intervals until sacrifice

References

• References: [1] Thomsen T, et al. Eur J Clin Chem Clin Biochem, 1991, 29(8), 487-492.
• References: [2] Pereira EF, et al. J Pharmacol Exp Ther, 1994, 270(2), 768-778.
• References: [3] Storch A, et al. Eur J Pharmacol, 1995, 290(3), 207-219.
• References: [4] Lorrio S, et al. J Pharmacol Exp Ther, 2007, 322(2), 591-599.

Sigma Aldrich - G1660

Biochem/physiol Actions
Cholinesterase inhibitor; reverses scopolamine-induced amnesia; antimyasthenic.

参考文献

• Thomsen T, et al. Eur J Clin Chem Clin Biochem, 1991, 29(8), 487-492.
• Pereira EF, et al. J Pharmacol Exp Ther, 1994, 270(2), 768-778.
• Storch A, et al. Eur J Pharmacol, 1995, 290(3), 207-219.
• Lorrio S, et al. J Pharmacol Exp Ther, 2007, 322(2), 591-599.