기본 정보
- CAS
290297-26-6- 표준 SMILES
Cc1ccccc1-c1cc(N2CCN(C)CC2)ncc1N(C)C(=O)C(C)(C)c1cc(C(F)(F)F)cc(C(F)(F)F)c1- InChIKey
WAXQNWCZJDTGBU-UHFFFAOYSA-N- 분자식
- C30H32F6N4O
- 평균 분자량
- 578.6 g/mol
- 단동위원소 질량
- 578.24803063
개요
Netupitant is a monocarboxylic acid amide obtained by formal condensation of the carboxy group of 2-[3,5-bis(trifluoromethyl)phenyl]-2-methylpropanoic acid with the secondary amino group of N-methyl-4-(2-methylphenyl)-6-(4-methylpiperazin-1-yl)pyridin-3-amine; an antiemetic used in combination with palonosetron hydrochloride (under the trade name Akynzeo) to treat nausea and vomiting in patients undergoing cancer chemotherapy. It has a role as an antiemetic and a neurokinin-1 receptor antagonist. It is a member of toluenes, a monocarboxylic acid amide, an organofluorine compound, an aminopyridine, a N-alkylpiperazine and a N-arylpiperazine.
이름 및 식별자
- 우선 이름
- Netupitant
- IUPAC
- 2-[3,5-bis(trifluoromethyl)phenyl]-N,2-dimethyl-N-[4-(2-methylphenyl)-6-(4-methylpiperazin-1-yl)-3-pyridinyl]propanamide
- 영어명
- 2-[3,5-bis(trifluoromethyl)phenyl]-N,2-dimethyl-N-[4-(2-methylphenyl)-6-(4-methylpiperazin-1-yl)pyridin-3-yl]propanamide
- 분자식
- C30H32F6N4O
- 분자량
- 578.59
이름 및 동의어
Netupitant290297-26-62-[3,5-bis(trifluoromethyl)phenyl]-N,2-dimethyl-N-[4-(2-methylphenyl)-6-(4-methylpiperazin-1-yl)pyridin-3-yl]propanamideRo 67-3189/000Ro-67-3189Ro-6731890007732P08TIRCHEBI:85155DTXSID50183271RO-67-3189/000AKYNZEO CAPSULE COMPONENT NETUPITANTNETUPITANT COMPONENT AKYNZEO CAPSULE
이름 더 보기
NETUPITANT (RO 67-31898)NetupitanCID-6451149CID 6451149Ro 67-31898NataipitideRo 67-31898/000Netupitant(CID-6451149)
D051522-(3,5-Bis(trifluoromethyl)phenyl)-N-methyl-N-(4-(2-methylphenyl)-6-(4-methylpiperazin-1-yl)pyridin-3-yl)-2-methylpropanamidenetupitantum2-(3,5-bis(trifluoromethyl)phenyl)-N,2-dimethyl-N-(4-(2-methylphenyl)-6-(4-methylpiperazin-1-yl)pyridin-3-yl)propanamideCID6451149RefChem:832394DTXCID60105762RO 673189000
데이터베이스 식별자
- CAS
물성
구조 계산 물성
- XLogP
- 6.8
- 극성 표면적
- 39.7 Ų
- 수소 결합 공여자 수
- 0
- 수소 결합 수용자 수
- 10
- 회전 가능 결합 수
- 5
- 무거운 원자 수
- 41
- 형식 전하
- 0
- 복잡도
- 865
실험 및 물리화학적 성질
Drugs
Pharmaceuticals -> Alimentary tract and metabolism -> Antiemetics and antinauseants
Pharmaceuticals -> Listed in ZINC15
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
물리화학적 성질
- 녹는점
- 156.2 · 156.2-160.0 °C
- 끓는 점
- 597.4 · 597.4±50.0 °C(Predicted)
- 밀도
- 1.255 · 1.255
- 저장 조건
- 2 · 2-8°C
- 용해도
- 클로로포름(약간 용해됨), DMSO(약간 용해됨), 메탄올(약간 용해됨)
- 산도 계수 (pKa)
- 7.89 · 7.89±0.38(Predicted)
- 물리적 상태
- 고체
- 색상
- 흰색에서 황백색까지
- InChIKey
- WAXQNWCZJDTGBU-UHFFFAOYSA-N
- SMILES
- C(N(C)C1=C(C2C=CC=CC=2C)C=C(N2CCN(C)CC2)N=C1)(=O)C(C1C=C(C(F)(F)F)C=C(C(F)(F)F)C=1)(C)C
안전 및 규제
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
GHS 분류
GHS Classification
Warning
H302 (50%): Harmful if swallowed [Warning Acute toxicity, oral]
P203, P264, P264+P265, P270, P280, P301+P317, P302+P352, P305+P351+P338, P318, P321, P330, P332+P317, P337+P317, P362+P364, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
유해성 정보
Hazard Classes and CategoriesAcute Tox. 4 (50%)
안전 데이터
- wgk
- WGK 3
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2
- 스토리지 클래스
- 11 - Combustible Solids
화학 및 산업
약리 정보
Protein Binding> 99.5% at drug concentrations ranging from 10-1300 ng/mL.
Mechanism of Action
Delayed emesis (vomiting) has been largely associated with the activation of tachykinin family neurokinin 1 (NK1) receptors (broadly distributed in the central and peripheral nervous systems) by substance P. As shown in in vitro and in vivo studies, netupitant inhibits substance P mediated responses.
Biological Half-Life96 hours with CV% of 61.
Metabolism/Metabolites
Once absorbed, netupitant is extensively metabolized to form three major metabolites: desmethyl derivative, M1; N-oxide derivative, M2; and OH-methyl derivative, M3. Metabolism is mediated primarily by CYP3A4 and to a lesser extent by CYP2C9 and CYP2D6. Metabolites M1, M2 and M3 were shown to bind to the substance P/neurokinin 1 (NK1) receptor.
FDA Pharmacological Classification
7732P08TIR
NETUPITANT
Mechanisms of Action [MoA] - Neurokinin 1 Antagonists
Established Pharmacologic Class [EPC] - Substance P/Neurokinin-1 Receptor Antagonist
Mechanisms of Action [MoA] - Cytochrome P450 3A4 Inhibitors
Mechanisms of Action [MoA] - P-Glycoprotein Inhibitors
Absorption, Distribution and Excretion
Upon oral administration of a single dose of netupitant, netupitant started to be measurable in plasma between 15 minutes and 3 hours after dosing. Plasma concentrations reached Cmax in approximately 5 hours. There was a greater than dose-proportional increase in the systemic exposure with the dose increase from 10 mg to 300 mg and a dose-proportional increase in systemic exposure with a dose increase from 300 mg to 450 mg.
Primarily fecal.
In cancer patients, Vz/F: 1982 ± 906 L (mean ± SD).
Estimated systemic clearance of 20.3 ± 9.2 L/h (mean ± SD).
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