6-(2,3-dichlorophenyl)-1,2,4-triazine-3,5-diamine

• ChemBase编号: 437
• 分子式: C9H7Cl2N5
• 平均质量: 256.09138
• 单一同位素质量: 255.00785061
• SMILES: Clc1c(c2nnc(nc2N)N)cccc1Cl
• Canonical SMILES: Nc1nnc(c(n1)N)c1cccc(c1Cl)Cl
• InChI: InChI=1S/C9H7Cl2N5/c10-5-3-1-2-4(6(5)11)7-8(12)14-9(13)16-15-7/h1-3H,(H4,12,13,14,16)
• InChIKey: PYZRQGJRPPTADH-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 6-(2,3-dichlorophenyl)-1,2,4-triazine-3,5-diamine
• IUPAC传统名: lamotrigine; 6-(2,3-dichlorophenyl)-1,2,4-triazine-3,5-diamine
• 商标名: Lamictal; Lamictal CD; Lamictin; Lamictal XR
• 别名: Lamotrigina [Spanish]; Lamotriginum [Latin]; GW 273293; lamotrigine; Lamotrigine; 3,5-Diamino-6-(2,3-dichlorophenyl)-1,2,4-triazine; BW 430C; LTG; Lamictal; Lamictal XR; Lamotrigin; 6-(2,3-dichlorophenyl)-1,2,4-triazine-3,5-diamine; 6-(2,3-Dichlorophenyl)-1,2,4-triazine-3,5-diamine; GI 267119X; Lamotrigine; Lamictin

登记号

• CAS号: 84057-84-1
• EC号: 281-901-8
• MDL号: MFCD00865333
• PubChem SID: 24278792; 160963900; 46505408
• PubChem CID: 3878

理论计算性质

JChem

• Acid pKa: 14.979241
• 质子受体: 5
• 质子供体: 2
• LogD (pH = 5.5): 1.4001383
• LogD (pH = 7.4): 1.9137787
• Log P: 1.9265221
• 摩尔折射率: 66.6197 cm^3
• 极化性: 24.699194 Å^3
• 极化表面积: 90.71 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 1.87
• LOG S: -2.72
• 溶解度: 4.88e-01 g/l

分子性质

理化性质

• 溶解度: DMSO; DMSO: soluble20 mg/mL at 60 °C; Ethanol; H2O: insoluble; Methanol
• 外观: white powder; White to Cream Coloured Solid
• 熔点: 216-218°C
• 疏水性(logP): 2.5; 2.534

安全信息

• 保存条件: -20°C Freezer
• RTECS编号: XY5850700
• 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: 2-8°C

药理学性质

• 作用靶点: Sodium Channel
• 相关基因信息: human ... SCN5A(6331)rat ... Scn2a1(24766), Scnn1a(25122)
• 生物活性机理: Inhibits release of excitatory amino acids via blockage of neuronal voltage-dependent sodium channels

产品相关信息

• 纯度: ≥98%; 95%; 95+%
• 成盐信息: Free Base
• 应用领域: Anticonvulsant; Used in the treatment of epilepsy and bipolar disorder
• Empirical Formula (Hill Notation): C9H7Cl2N5

详细说明

DrugBank - DB00555

• Drug Groups: approved; investigational
• Description: Lamotrigine is an anticonvulsant drug used in the treatment of epilepsy and bipolar disorder. For epilepsy it is used to treat partial seizures, primary and secondary tonic-clonic seizures, and seizures associated with Lennox-Gastaut syndrome. Lamotrigine also acts as a mood stabilizer. It is the first medication since lithium granted Food and Drug Administration (FDA) approval for the maintenance treatment of bipolar type I. Chemically unrelated to other anticonvulsants, lamotrigine has relatively few side-effects and does not require blood monitoring. The exact way lamotrigine works is unknown. [Wikipedia]
• Indication: For the adjunctive treatment of partial seizures in epilepsy and generalized seizures of Lennox-Gastaut syndrome. Also for the maintenance treatment of bipolar I disorder and depression.
• Pharmacology: Lamotrigine, an antiepileptic drug (AED) of the phenyltriazine class, is chemically unrelated to existing antiepileptic drugs. Lamotrigine is also used in the treatment of depression and bipolar disorder. Lamotrigine is thought to exert its anticonvulsant effect by stabilizing presynaptic neuronal membranes. Lamotrigine inhibits sodium currents by selectively binding to the inactivated state of the sodium channel and subsequently suppresses the release of the excilatory amino acid, glutamate.
• Toxicity: LD₅₀=250 (mg/kg) (in rat, mice); LD₅₀>640 orally (mg/kg) (in rat, mice) (Sawyer). Symptoms of overdose include decreased level of consciousness, coma, delayed heartbeat, increased seizures, lack of coordination, and rolling eyeballs.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: 98%
• Half Life: 25 +/- 10 hours (healthy individuals); 42.9 hours (chronic renal failure)
• Protein Binding: 55%
• Distribution: * 0.9 to 1.3 L/kg
• Clearance: * Apparent plasma cl=0.44 mL/min/kg [healthy volunteers taking single-dose LAMICTAL]; * Apparent plasma cl=0.58 mL/min/kg [healthy volunteers taking multiple-dose LAMICTAL]; * Apparent plasma cl=0.30 mL/min/kg [healthy volunteers taking valproate and single-dose LAMICTAL]; * Apparent plasma cl=0.18 mL/min/kg [healthy volunteers taking valproate and multiple-dose LAMICTAL]; * Apparent plasma cl=1.1 mL/min/kg [Patients with epilepsy taking carbamazepine, phenytoin, phenobarbital, or primidone plus valproate and single-dose LAMICTAL]; * Apparent plasma cl=1.12 mL/min/kg [Patients with epilepsy taking carbamazepine, phenytoin, phenobarbital, or primidone plus valproate and multiple-dose LAMICTAL]
• References: Backonja M: Neuromodulating drugs for the symptomatic treatment of neuropathic pain. Curr Pain Headache Rep. 2004 Jun;8(3):212-6. [Pubmed] ; Barbosa L, Berk M, Vorster M: A double-blind, randomized, placebo-controlled trial of augmentation with lamotrigine or placebo in patients concomitantly treated with fluoxetine for resistant major depressive episodes. J Clin Psychiatry. 2003 Apr;64(4):403-7. [Pubmed] ; Jensen TS: Anticonvulsants in neuropathic pain: rationale and clinical evidence. Eur J Pain. 2002;6 Suppl A:61-8. [Pubmed] ; Pappagallo M: Newer antiepileptic drugs: possible uses in the treatment of neuropathic pain and migraine. Clin Ther. 2003 Oct;25(10):2506-38. [Pubmed] ; Tehrani SP, Daryaafzoon M, Bakhtiarian A, Ejtemaeemehr S, Sahraei H: The effects of lamotrigine on the acquisition and expression of morphine-induced place preference in mice. Pak J Biol Sci. 2009 Jan 1;12(1):33-9. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - L3791

Biochem/physiol Actions
Anticonvulsant.
包装
10, 50 mg in glass bottle
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. L3791.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - L173250

An anticonvulsant. Inhibits glutamate release, possible through inhibition of Sodium, Potassium and Calcium currents. Used in treatment of bipolar depression.

参考文献

• Backonja M: Neuromodulating drugs for the symptomatic treatment of neuropathic pain. Curr Pain Headache Rep. 2004 Jun;8(3):212-6. Pubmed
• Barbosa L, Berk M, Vorster M: A double-blind, randomized, placebo-controlled trial of augmentation with lamotrigine or placebo in patients concomitantly treated with fluoxetine for resistant major depressive episodes. J Clin Psychiatry. 2003 Apr;64(4):403-7. Pubmed
• Jensen TS: Anticonvulsants in neuropathic pain: rationale and clinical evidence. Eur J Pain. 2002;6 Suppl A:61-8. Pubmed
• Pappagallo M: Newer antiepileptic drugs: possible uses in the treatment of neuropathic pain and migraine. Clin Ther. 2003 Oct;25(10):2506-38. Pubmed
• Tehrani SP, Daryaafzoon M, Bakhtiarian A, Ejtemaeemehr S, Sahraei H: The effects of lamotrigine on the acquisition and expression of morphine-induced place preference in mice. Pak J Biol Sci. 2009 Jan 1;12(1):33-9. Pubmed
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