化工社化工社 化学情報印刷レポート · 研究参考用
プロガビド
4-[[(4-クロロフェニル)(5-フルオロ-2-ヒドロキシフェニル)メチレン]アミノ]ブタンアミド · ハロガビド · 4-[α-(p-クロロフェニル)-5-フルオロ-2-ヒドロキシベンジリデンアミノ]ブチルアミド · プロガビド · 4-{[(4-クロロフェニル)(5-フルオロ-2-ヒドロキシフェニル)メチリデン]アミノ}ブタンアミド · Gabren · Gabrene · SL-76．002
識別子と物理属性
| CAS No. | 104880-78-6 |
|---|---|
| 分子式 | C17H16ClFN2O2 |
| 平均分子量 | 334.8 g/mol |
| SMILES | NC(=O)CCCN=C(c1ccc(Cl)cc1)c1cc(F)ccc1O |
| InChIKey | IBALRBWGSVJPAP-UHFFFAOYSA-N |
| PubChem CID | 44115 |
| ChEMBL | CHEMBL287631 |
| ChEBI | CHEBI:135422 |
| EC No. | 263-679-4 |
| DTXSID | DTXSID00878140 |
| 現地名 | プロガビド |
化学・物理的性質
| XLogP | 3 |
|---|---|
| 極性表面積 | 75.7 |
| 水素結合供与体数 | 2 |
| 水素結合受容体数 | 4 |
| 回転可能結合数 | 6 |
| 重原子数 | 23 |
| 形式電荷 | 0 |
| 複雑度 | 425 |
| 医薬品 | Pharmaceuticals -> Nervous system -> AntiepilepticsPharmaceuticals -> Listed in ZINC15 |
| LogP（分配係数） | 2.97 |
| 融点 | 133-135 °C133-135°mp 142.5° (Kaplan, J. Med. Chem.) |
| 沸点 | 525.4±50.0 °C(Predicted) |
| 密度 | 1.2822 (estimate) |
| 貯蔵条件 | 2-8°C |
| 溶解度 | クロロホルム（軽く超音波処理）、DMSO、メタノール（軽く超音波処理）37.16mg/L(37℃) |
| 外観・状態 | 個体 |
| pKa（酸解離定数） | pKa 3.41 ± 0.04(0.4% MeOH,t=37,Iundefined)(Approximate) |
| 色 | 薄黄色～黄色 |
| CAS データベース | 62666-20-0 |
化学的特性
Bright Yellow Solid
安全性と法規制
| 健康影響 | May cause a potentially dangerous rash that may develop into Stevens Johnson syndrome, an extremely rare but potentially fatal skin disease. |
|---|---|
| 暴露経路 | Well absorbed with a bioavailability of 60% |
| 毒性の概要 | Progabide binds to both GABA<sub>A</sub> and GABA<sub>B</sub> receptors located on the terminals of primary afferent fibers. Binding to GABA<sub>A</sub> results in an increased affinity of the GABA receptor for the amino acid, an augmented flux of chloride ions across the terminal membrane, and an increase in the amount of presynaptic inhibition. Activation of the GABA<sub>B</sub> receptors retards the influx of calcium ions into the terminals, thereby reducing the evoked release of excitatory amino acids and possibly other transmitters. |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| 毒性 | LD50 i.p. in mice: 900 mg/kg (Kaplan) |
用途
説明
Progabide is a broad-spectrum anticonvulsant agent indicated for the treatment of a wide variety of seizure disorders. Synthesized as a GABA-prodrug, anticonvulsant activity appears due to the parent drug and its acid metabolite, as well as to GABAmide and GABA liberated therefrom.
使用
Progabide is a gamma-aminobutyric acid (GABA) antagonist with antiepileptic activity.