CAS 478296-72-9 Gabapentin Enacarbil (HCID 9883933)

개요

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.

이름 및 식별자

우선 이름: Gabapentin Enacarbil
IUPAC: 2-[1-[[1-(2-methylpropanoyloxy)ethoxycarbonylamino]methyl]cyclohexyl]acetic acid
현지명: 가바펜틴에나카르빌
영어명: Gabapentin enacarbil
분자식: C16H27NO6
분자량: 329.39

이름 및 동의어

Gabapentin enacarbil478296-72-9HorizantRegniteXP-13512XP13512ASP8825gabapentine enacarbilXP 13512gabapentina enacarbilogabapentinum enacarbilumGSK1838262

이름 더 보기

가바펜틴에나카르빌Gabapen 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

데이터베이스 식별자

CAS: 478296-72-9
PubChem CID: 9883933
DTXSID: DTXSID30870359
ChEMBL: CHEMBL1628502
ChEBI: CHEBI:68840
UNII: 75OCL1SPBQ
EC Number: 620-082-7
Nikkaji: J3.209.908D

물성

구조 계산 물성

XLogP: 3.1
극성 표면적: 102 Å²
수소 결합 공여자 수: 2
수소 결합 수용자 수: 6
회전 가능 결합 수: 9
무거운 원자 수: 23
형식 전하: 0
복잡도: 428

실험 및 물리화학적 성질

SolubilitySolubility of 0.5 mg/mL in water

Human Drugs · 2건

FDA approved drugs -> Active ingredient

Melting PointMelting onset of about 64°C.

Dissociation ConstantspKa 5.0

물리화학적 성질

녹는점: 65 °C · 65 °C
끓는 점: 482 · 482.0±20.0 °C(Predicted)
밀도: 1.134 · 1.134
저장 조건: -20 °C · Store at -20°C
용해도: 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)
물리적 상태: 가루
산도 계수 (pKa): 4.72 · 4.72±0.10(Predicted)
색상: 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
SMILES: C1(CNC(OC(OC(=O)C(C)C)C)=O)(CC(O)=O)CCCCC1

안전 및 규제

GHS 분류

GHS Classification · 3건

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.

유해성 정보

Hazard Classes and CategoriesNot Classified

독성 정보

Hepatotoxicity · 1건

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 · 6건

Drug Induced Liver Injury Rank (DILIrank 2.0)

Gabapentin enacarbil

vNo-DILI-concern

0

No match

DOI:10.1016/j.drudis.2016.02.015

안전 데이터

wgk: WGK 3
스토리지 클래스: 11 - Combustible Solids

화학 및 산업

약리 정보

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 · 2건

GABAPENTIN ENACARBIL

Decreased Central Nervous System Disorganized Electrical Activity [PE]

응용 분야 · 2건

개요Gabapentin 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.

용도Gabapentin enacarbil (HORIZANT GlaxoSmithKline/XenoPort) is a prodrug of gabapentin used as an anticonvulsant as well as a treatment for neurogenic pain, with the same mechanism of action as pregabalin.

공급사81 곳

Suzhou ARTK Medchem Co., Ltd.+86-18168183658 · [email protected]

江苏艾康生物医药研发有限公司025-025-66113011 15955137747 · [email protected]

Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]

Aladdin Scientific[email protected]

LGM Pharma1-(800)-881-8210 · [email protected]

추가 설명

정의ChEBI: 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.