基本情報
- CAS
478296-72-9- 標準SMILES
CC(OC(=O)NCC1(CC(=O)O)CCCCC1)OC(=O)C(C)C- InChIKey
TZDUHAJSIBHXDL-UHFFFAOYSA-N- 分子式
- C16H27NO6
- 平均分子量
- 329.39 g/mol
- 単同位体質量
- 329.18383758
概要
Gabapentin enacarbil is a carbamate ester that is the N-[1-(isobutyryloxy)ethoxy]carbonyl derivative of [1-(aminomethyl)cyclohexyl]acetic acid. The prodrug for gabapentin, used for treatment of neuropathic pain and restless legs syndrome. It has a role as an anticonvulsant, a calcium channel blocker and a prodrug. It is a carbamate ester, a monocarboxylic acid, a carboxylic ester and an acetal. It is functionally related to a gamma-aminobutyric acid and a gabapentin.
名称と識別子
- 優先名称
- Gabapentin Enacarbil
- IUPAC
- 2-[1-[[1-(2-methylpropanoyloxy)ethoxycarbonylamino]methyl]cyclohexyl]acetic acid
- 現地名
- ガバペンチンエナカルビル
- 英語名
- Gabapentin enacarbil
- 分子式
- C16H27NO6
- 分子量
- 329.39
名称と別名
Gabapentin enacarbil478296-72-9HorizantRegniteXP-13512XP13512ASP8825gabapentine enacarbilXP 13512gabapentina enacarbilogabapentinum enacarbilumGSK1838262
名称をさらに表示
ガバペンチンエナカルビルガバペンチン エナカルビルGabapen DingnakabiGabapentin EnarcarbilGabapentin Impurity 11Gabapentin enacarbil (XP-13512)TIANFUCHEM-478296-72-9---Gabapentin enacarbil1-[[[[1-(2-Methyl-1-oxopropoxy)ethoxy]carbonyl]amino]methyl]...2-(1-((((1-(Isobutyryloxy)ethoxy)carbonyl)amino)methyl)cyclohexyl)acetic acid1-[[[[1-(2-Methyl-1-oxopropoxy)ethoxy]carbonyl]amino]methyl]cyclohexaneacetic acid
75OCL1SPBQASP-88252-[1-[[1-(2-methylpropanoyloxy)ethoxycarbonylamino]methyl]cyclohexyl]acetic acidGSK-1838262CHEBI:68840DTXSID30870359{1-[({[1-(isobutyryloxy)ethoxy]carbonyl}amino)methyl]cyclohexyl}acetic acidGabapentinenacarbil
データベース識別子
- CAS
物性
構造計算による物性
- XLogP
- 3.1
- 極性表面積
- 102 Ų
- 水素結合供与体数
- 2
- 水素結合受容体数
- 6
- 回転可能結合数
- 9
- 重原子数
- 23
- 形式電荷
- 0
- 複雑度
- 428
実験および物理化学的性質
SolubilitySolubility of 0.5 mg/mL in water
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Melting PointMelting onset of about 64°C.
Dissociation ConstantspKa 5.0
物理化学的性質
- 融点
- 65 °C · 65 °C
- 沸点
- 482 · 482.0±20.0 °C(Predicted)
- 比重(密度)
- 1.134 · 1.134
- 貯蔵温度
- -20 °C · Store at -20°C
- 溶解性
- 100 · DMSO:100.0(Max Conc. mg/mL);303.59(Max Conc. mM)Ethanol:100.0(Max Conc. mg/mL);303.59(Max Conc. mM)Water:0.67(Max Conc. mg/mL);2.03(Max Conc. mM)
- 外見
- Powder
- 酸解離定数(Pka)
- 4.72 · 4.72±0.10(Predicted)
- 色
- Light yellow to brown
- InChI
- InChI=1S/C16H27NO6/c1-11(2)14(20)22-12(3)23-15(21)17-10-16(9-13(18)19)7-5-4-6-8-16/h11-12H,4-10H2,1-3H3,(H,17,21)(H,18,19)
- InChIKey
- TZDUHAJSIBHXDL-UHFFFAOYSA-N
安全と法規制
GHS分類
GHS Classification
This chemical does not meet GHS hazard criteria for 100% (2 of 2) of all reports.
Not Classified
Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory.
危険有害性情報
Hazard Classes and CategoriesNot Classified
毒性情報
Hepatotoxicity
In prelicensure clinical trials, gabapentin enacarbil was not linked to an increased rate of serum enzyme elevations during treatment or to episodes of clinically apparent acute liver injury. Gabapentin has been implicated in isolated cases of acute liver injury, but in most instances the association was weakened by the coadministration with other potentially hepatotoxic agents. Too few cases have been reported in sufficient detail to characterize the clinical features of the associated injury. No published case has specifically implicated gabapentin enacarbil. Thus, gabapentin enacarbil may be associated with isolated instances of clinically apparent liver injury, but they must be rare, if they occur at all.
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Gabapentin enacarbil
vNo-DILI-concern
0
No match
DOI:10.1016/j.drudis.2016.02.015
安全データ
- wgk
- WGK 3
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
Protein BindingGabapentin plasma protein binding is less than 3%.
PharmacodynamicsSince gabapentin enacarbil is a prodrug of gabapentin, it's physiological effects are the same as gabapentin. Concerning PHN, gabapentin prevents allodynia and hyperalgesia.
Mechanism of ActionAlthough the exact mechanism of action of gabapentin in RLS and PHN is unknown, it is presumed to involve the descending noradrenergic system, resulting in the activation of spinal alpha2-adrenergic receptors.
Biological Half-LifeThe elimination half-life of gabapentin is 5.1 to 6.0 hours.
Metabolism/MetabolitesGabapentin enacarbil does not interact with any of the major cytochrome P450 enzymes.
FDA Pharmacological Classification
GABAPENTIN ENACARBIL
Decreased Central Nervous System Disorganized Electrical Activity [PE]
Absorption, Distribution and Excretion
Gabapentin enacarbil is absorbed in the intestines by active transport through the proton-linked monocarboxylate transporter, MCT-1.
Gabapentin enacarbil is eliminated primarily in the urine (94%) and to a lesser extent in the feces (5%).
The volume of distribution is 76L.
Renal clearance of gabapentin is 5 to 7 L/hr.
応用分野
説明Gabapentin enacarbil (GEn) is an actively transported prodrug of gabapentin that provides sustained doseproportional exposure to gabapentin and predictable bioavailability. In April 2011, Gabapentin enacarbil is approved by the US Food and Drug Administration for the treatment of moderate-to-severe primary restless legssyndrome (RLS) in adults.Gabapentin enacarbil was designed to be recognized as a substrate for two high-capacity nutrient transports, monocarboxylate transporter type 1 and sodium-dependent multivitamin transporter, and to be efficiently cleaved after absorption to give gabapentin. The separated enantiomers of gabapentin enacarbil have similar cleavage rates in human tissues. Preclinical studies showed that gabapentin enacarbil provides good systemic exposure of gabapentin in rats and monkeys.
関連反応
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化合物ノート
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