기본 정보
- CAS
608137-33-3- 표준 SMILES
CS(=O)(=O)O.CS(=O)(=O)O.C[C@@H](Cc1ccccc1)NC(=O)[C@@H](N)CCCCN- InChIKey
CETWSOHVEGTIBR-FORAGAHYSA-N- 분자식
- C17H33N3O7S2
- 평균 분자량
- 455.6 g/mol
- 단동위원소 질량
- 455.1759924
개요
Lisdexamfetamine Dimesylate is the dimesylate form and prodrug of the d-isomer of amphetamine, a non-catecholamine sympathomimetic amine with central nervous system (CNS) stimulating activity. Upon administration, lisdexamphetamine is converted to dextroamphetamine through cleavage of the lysine group. Dextroamphetamine acts by facilitating the release of catecholamines, particularly noradrenaline and dopamine, from its storage sites in nerve terminals in the CNS, and inhibits their uptake within the mesocorticolimbic system, a major component of the brain reward system, resulting in measurable behavioral changes such as euphoria, mental alertness and excitement and appetite suppression. As a CNS stimulant, this agent may increase blood pressure.
이름 및 식별자
- 우선 이름
- Lisdexamfetamine Dimesylate
- IUPAC
- (2S)-2,6-diamino-N-[(2S)-1-phenylpropan-2-yl]hexanamide;methanesulfonic acid
- 영어명
- (2S)-2,6-Diamino-N-[(1S)-1-methyl-2-phenylethyl]hexanamide dimethanesulfonate
- 분자식
- C16H29N3O4S
- 분자량
- 359.49
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- CAS
608137-33-3- PubChem CID
- 11597697
- DTXSID
DTXSID60209653- ChEMBL
CHEMBL1201178- UNII
- SJT761GEGS
물성
구조 계산 물성
- 극성 표면적
- 207 Ų
- 수소 결합 공여자 수
- 5
- 수소 결합 수용자 수
- 9
- 회전 가능 결합 수
- 8
- 무거운 원자 수
- 29
- 형식 전하
- 0
- 복잡도
- 344
실험 및 물리화학적 성질
Human Drugs
Breast Feeding; Lactation; Milk, Human; Adrenergic Agents; Central Nervous System Stimulants; Dopamine Agents; Sympathomimetics; Wakefulness-Promoting Agents
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
물리화학적 성질
- 인화점
- 9 ℃ · 9℃
- 저장 조건
- -20 °C · -20°C
- 물리적 상태
- A neat solid
안전 및 규제
독성 정보
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Lisdexamfetamine dimesylate
Ambiguous-DILI-concern
3
Adverse reactions
DOI:10.1016/j.drudis.2016.02.015
안전 데이터
- wgk
- 1
- ridadr
- UN1230 - class 3 - PG 2 - Methanol, solution
- risk_code
- 11-23/24/25-39/23/24/25
- hazard_code
- F,T
- safety_code
- 7-16-36/37-45
화학 및 산업
약리 정보
FDA Pharmacological Classification
LISDEXAMFETAMINE DIMESYLATE
Central Nervous System Stimulant [EPC]; Central Nervous System Stimulation [PE]
LISDEXAMFETAMINE DIMESYLATE CAPSULES
Central Nervous System Stimulation [PE]; Central Nervous System Stimulant [EPC]
MeSH Pharmacological Classification
A loosely defined group of drugs that tend to increase behavioral alertness, agitation, or excitation. They work by a variety of mechanisms, but usually not by direct excitation of neurons. The many drugs that have such actions as side effects to their main therapeutic use are not included here.
Drugs that block the transport of DOPAMINE into axon terminals or into storage vesicles within terminals. Most of the ADRENERGIC UPTAKE INHIBITORS also inhibit dopamine uptake.
응용 분야
개요ADHD is a neurobehavioral disorder characterized by varying degrees of inattention, hyperactivity, and impulsivity. ADHD is typically diagnosed in childhood and affects 7–12% of the pediatric population in the United States with the condition often enduring into adulthood. While the precise mechanism of action of lisdexamfetamine in treating ADHD is not known, amphetamines are believed to inhibit the reuptake of the neurotransmitters dopamine and noradrenaline (norepinephrine), thereby increasing their presynaptic availability and release into extraneuronal space. The prodrug is constructed by the condensation of D-amphetamine with the activated ester (N-hydroxysuccinimide) of bis-tert-butoxycarbonylprotected L-lysine. Lisdexamfetamine is ultimately generated by treatment with hydrochloric acid in dioxane. The most common adverse events, comparable to other amphetamine formulations, were decreased appetite, insomnia, upper abdominal pain, and irritability. Lisdexamfetamine is contraindicated in patients with advanced arteriosclerosis, symptomatic cardiovascular disease, moderate-to-severe hypertension, hyperthyroidism, known hypersensitivity to the sympathomimetic amines, glaucoma, a predisposition to agitated states, and a history of drug abuse. In addition, the drug should not be administered during or within 14 days of treatment with monoamine oxidase inhibitors. It has also been noted that psychostimulants may exacerbate symptoms of pre-existing psychotic disorders, so caution and close observation are recommended in this patient population.
용도Treatment of atten tion deficit hyperactivity disorder (ADHD).
공급사31 곳
관련 반응
화합물 노트
불러오는 중…