기본 정보
- CAS
56995-20-1- 표준 SMILES
CCOC(=O)Nc1ccc(NCc2ccc(F)cc2)nc1N- InChIKey
JUUFBMODXQKSTD-UHFFFAOYSA-N- 분자식
- C15H17FN4O2
- 평균 분자량
- 304.32 g/mol
- 단동위원소 질량
- 304.13355396
개요
N-[2-amino-6-[(4-fluorophenyl)methylamino]-3-pyridinyl]carbamic acid ethyl ester is an aminopyridine.
이름 및 식별자
- 우선 이름
- Flupirtine
- IUPAC
- ethyl N-[2-amino-6-[(4-fluorophenyl)methylamino]-3-pyridinyl]carbamate
- 현지명
- 플루피르틴
- 영어명
- Flupirtine
- 분자식
- C15H17FN4O2
- 분자량
- 304.32
이름 및 동의어
Flupirtine56995-20-1Flupirtinumethyl N-[2-amino-6-[(4-fluorophenyl)methylamino]pyridin-3-yl]carbamateflupirtinaFlupirtinteMOH3ET196HDTXSID4048436W-2964ethyl 2-amino-6-((p-fluorobenzyl)amino)-3-pyridinecarbamateflupirtin maleateethyl N-(2-amino-6-((4-fluorophenyl)methylamino)pyridin-3-yl)carbamate
이름 더 보기
플루피르틴W2964D-9998W 2964KatadolonFlupirtinTrancopal DoloFLUPIRITNE MALEATE
RefChem:141020DTXCID4028410N02BG07ethyl N-(2-amino-6-(((4-fluorophenyl)methyl)amino)pyridin-3-yl)carbamate260-503-8Flupirtine (INN)D 9998FLUPIRTINE [INN]
데이터베이스 식별자
- CAS
56995-20-1- PubChem CID
- 53276
- DTXSID
DTXSID4048436- ChEMBL
물성
구조 계산 물성
- XLogP
- 2.4
- 극성 표면적
- 89.3 Ų
- 수소 결합 공여자 수
- 3
- 수소 결합 수용자 수
- 6
- 회전 가능 결합 수
- 6
- 무거운 원자 수
- 22
- 형식 전하
- 0
- 복잡도
- 350
실험 및 물리화학적 성질
Drugs
Pharmaceuticals
Pharmaceuticals -> Nervous system -> Analgesics
Pharmaceuticals -> Listed in ZINC15
LogP2.57
Human DrugsPharmaceuticals
물리화학적 성질
- 녹는점
- 115 · 115-116°
- 끓는 점
- 445.15 °C · 445.15°C (rough estimate)
- 밀도
- 1.35 · 1.350±0.06 g/cm3(Predicted)
- 저장 조건
- 2 · under inert gas (nitrogen or Argon) at 2–8 °C
- 용해도
- DMSO에 용해됨
- 물리적 상태
- 가루
- 산도 계수 (pKa)
- 12.19 · 12.19±0.70(Predicted)
- 수용성
- 1 g/L · 1g/L(온도 미표시)
- 주요 응용
- 법의학 및 독성학수의사
- InChI
- 1S/C15H17FN4O2/c1-2-22-15(21)19-12-7-8-13(20-14(12)17)18-9-10-3-5-11(16)6-4-10/h3-8H,2,9H2,1H3,(H,19,21)(H3,17,18,20)
- InChIKey
- JUUFBMODXQKSTD-UHFFFAOYSA-N
- SMILES
- FC1=CC=C(CNC2=NC(N)=C(NC(OCC)=O)C=C2)C=C1
안전 및 규제
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
GHS 분류
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P270, P271, P301+P317, P304+P340, P317, P330, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
유해성 정보
Hazard Classes and CategoriesAcute Tox. 4 (100%)
독성 정보
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
Flupirtine
DILI Positive
DOI:10.1016/j.drudis.2019.09.022
안전 데이터
- wgk
- WGK 3
- 독성
- LD50 orally in mice, rats: 617, 1660 mg/kg (Jakovlev)
- 스토리지 클래스
- 13 - Non Combustible Solids
화학 및 산업
약리 정보
ATC Code
N - Nervous system
QN - Nervous system
Mechanism of Action
Flupirtine upregulates Bcl-2, increases glutathione levels, activates an inwardly rectifying potassium channel, and delays loss of intermitochondrial membrane calcium retention capacity. Flupirtine acts like a NMDA receptor antagonists, but does not bind to the receptor. One study concluded that the discriminative effects of flupirtine are neither of opioid nor of alpha-1 adrenergic type, but are primarily mediated through alpha-2 adrenergic mechanisms [PMID: 2901483].
Biological Half-Life6.5 hrs (average), 11.2-16.8 hrs (average 14 hrs) (elderly), 8.7-10.9 hrs (average 9.8 hrs) (in those with moderate-level renal impairment).
Metabolism/MetabolitesHepatic to 2-amino-3-acetylamino-6-(para-fluorobenzylamino) pyridine (which has 20-30% the analgesic potential of its parent compound) and Para-fluorohippuric acid.
MeSH Pharmacological ClassificationCompounds capable of relieving pain without the loss of CONSCIOUSNESS.
Absorption, Distribution and Excretion
Bioavailability: 90% (oral), 70% (rectal)
72% of flupirtine and its metabolites appear in urine and 18% appear in faeces.
용도 및 제조
UsesUse (kg; approx.) in Germany (2009): >10000
Use ClassificationPharmaceuticals
응용 분야
용도Therapeutic use of Flupirtine was discontinued due to drug induced liver injury (DILI). Since the mechanism of action is not related to its adverse effects, it is important to focus on chemical modifications.
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