기본 정보
- CAS
106516-24-9- 표준 SMILES
O=C1NCCN1CCN1CCC(c2cn(-c3ccc(F)cc3)c3ccc(Cl)cc23)CC1- InChIKey
GZKLJWGUPQBVJQ-UHFFFAOYSA-N- 분자식
- C24H26ClFN4O
- 평균 분자량
- 440.9 g/mol
- 단동위원소 질량
- 440.17791735
개요
Sertindole is a phenylindole that is 1H-indole which is substituted on the nitrogen by a p-chlorophenyl group, at position 5 by chlorine, and at position 3 by a piperidin-4-yl group, which is itself substituted on the nitrogen by a 2-(2-oxoimidazolidin-1-yl)ethyl group. It has a role as an alpha-adrenergic antagonist, a H1-receptor antagonist, a serotonergic antagonist and a second generation antipsychotic. It is an organochlorine compound, an organofluorine compound, a phenylindole, a heteroarylpiperidine and an imidazolidinone.
이름 및 식별자
- 우선 이름
- Sertindole
- IUPAC
- 1-[2-[4-[5-chloro-1-(4-fluorophenyl)indol-3-yl]piperidin-1-yl]ethyl]imidazolidin-2-one
- 영어명
- Sertindole
- 분자식
- C24H26ClFN4O
- 분자량
- 440.94
이름 및 동의어
SERTINDOLE106516-24-9SerLectSerdolectSertindolSertindolumLu 23-174zerdolLu-23-1741-[2-[4-[5-chloro-1-(4-fluorophenyl)indol-3-yl]piperidin-1-yl]ethyl]imidazolidin-2-oneDTXSID60489671-(2-{4-[5-chloro-1-(4-fluorophenyl)-1H-indol-3-yl]piperidin-1-yl}ethyl)imidazolidin-2-one
이름 더 보기
S-1991SerdoleetSertindole>SUBSTANCE 5364890SERTINDOLE USP/EP/BP
GVV4Z879SP1-(2-(4-(5-Chloro-1-(4-fluorophenyl)-1H-indol-3-yl)piperidin-1-yl)ethyl)imidazolidin-2-oneCHEBI:9122DTXCID30288931-(2-(4-(5-chloro-1-(4-fluorophenyl)-1H-indol-3-yl)-1-piperidinyl)ethyl)-2-imidazolidinone1-[2-[4-[5-chloro-1-(4-fluorophenyl)-indol-3-yl]-1-piperidyl]ethyl]imidazolidin-2-one1-[2-[4-[5-chloro-1-(4-fluorophenyl)-1h-indol-3-yl]-1-piperidinyl]ethyl]-2-imidazolidinone1-(2-(4-(5-chloro-1-(4-fluorophenyl)-indol-3-yl)-1-piperidyl)ethyl)imidazolidin-2-one
데이터베이스 식별자
- CAS
106516-24-9- PubChem CID
- 60149
- DTXSID
DTXSID6048967- ChEMBL
CHEMBL12713- ChEBI
CHEBI:9122- UNII
- GVV4Z879SP
- EC Number
- 634-595-9
- Nikkaji
- J380.356B
물성
구조 계산 물성
- XLogP
- 4.1
- 극성 표면적
- 40.5 Ų
- 수소 결합 공여자 수
- 1
- 수소 결합 수용자 수
- 3
- 회전 가능 결합 수
- 5
- 무거운 원자 수
- 31
- 형식 전하
- 0
- 복잡도
- 623
실험 및 물리화학적 성질
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Antipsychotics
Pharmaceuticals -> Nervous system -> Antipsychotics
Solubility9.63e-03 g/L
Physical DescriptionSolid
Collision Cross Section215.9 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]
물리화학적 성질
- 녹는점
- 95 · 95-100°C
- 끓는 점
- 592.1 · 592.1±50.0 °C(Predicted)
- 밀도
- 1.36 · 1.36
- 저장 조건
- 2 · Sealed in dry,2-8°C
- 용해도
- 10 mg/mL · DMSO: >10mg/mL
- 물리적 상태
- 고체
- 산도 계수 (pKa)
- 14.53 · 14.53±0.20(Predicted)
- 색상
- 회백색
- Merck
- 14 · 14,8466
- InChI
- InChI=1S/C24H26ClFN4O/c25-18-1-6-23-21(15-18)22(16-30(23)20-4-2-19(26)3-5-20)17-7-10-28(11-8-17)13-14-29-12-9-27-24(29)31/h1-6,15-17H,7-14H2,(H,27,31)
- InChIKey
- GZKLJWGUPQBVJQ-UHFFFAOYSA-N
- SMILES
- C1(=O)N(CCN2CCC(C3C4=C(N(C5=CC=C(F)C=C5)C=3)C=CC(Cl)=C4)CC2)CCN1
화학적 성질
Off-White to Pale Yellow Solid
안전 및 규제
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
GHS 분류
GHS Classification
Warning
H315 (95.2%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 42 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
유해성 정보
Hazard Classes and CategoriesSkin Irrit. 2 (95.2%)
안전 데이터
- wgk
- 3
- rtecs
- NJ0621100
- HS 번호
- 2933.99.6100
- risk_code
- 36/37/38
- hazard_code
- Xi
- safety_code
- 26
화학 및 산업
약리 정보
ATC Code
N - Nervous system
QN - Nervous system
Pharmacodynamics
Sertindole is an atypical antipsychotic at least as effective as haloperidol and risperidone in the treatment of neuroleptic-responsive schizophrenia. Sertindole improves negative symptoms, and is also effective for the treatment of neuroleptic-resistant schizophrenia. Sertindole is generally well tolerated and is associated with a low rate of extrapyramidal symptoms (EPS).
Mechanism of Action
Sertindole is an antipsychotic drug with affinity for dopamine D2, serotonin 5-HT2A and 5-HT2C, and alpha1-adrenoreceptors. Preclinical studies suggest that sertindole acts preferentially on limbic and cortical dopaminergic neurons and clinical trials have confirmed that sertindole is effective at a low dopamine D2 occupancy level.
Biological Half-Life3 days
Metabolism/Metabolites
Hepatic. Sertindole is metabolized by cytochrome P450 isoenzymes CYP 2D6 and CYP 3A4.
Sertindole has known human metabolites that include 1-[2-[4-[5-Chloro-1-(4-fluorophenyl)indol-3-yl]piperidin-1-yl]ethyl]-4-hydroxyimidazolidin-2-one and 5-Chloro-1-(4-fluorophenyl)-3-(piperidin-4-yl)-1H-indole.
MeSH Pharmacological Classification
Agents that control agitated psychotic behavior, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect. They are used in SCHIZOPHRENIA; senile dementia; transient psychosis following surgery; or MYOCARDIAL INFARCTION; etc. These drugs are often referred to as neuroleptics alluding to the tendency to produce neurological side effects, but not all antipsychotics are likely to produce such effects. Many of these drugs may also be effective against nausea, emesis, and pruritus.
Absorption, Distribution and ExcretionOrally available.
Cellular LocationsMembrane
응용 분야
개요Serdolect was launched in the UK for acute and chronic schizophrenia and schizoaffective psychoses. It is synthetically available in three steps from 5chloro-l- (4-fluorophenyl)-l H-indole. Sertindole is selective for the limbic areas of the brain and has a high affinity for the serotinin 5-HT2 receptor where it behaves as an antagonist. It has weak affinity for the α1-adrenergic receptor and no affinity for dopamine D2 receptors. It is as effective as haloperidol but without the extrapyramidal symptoms. This may be a consequence of the fact that it expresses the c-fos protein in a manner different for haloperidol but similar to clozapine. It is non-sedating, long lasting (several days after a single dose) and has an atypical mode of action.
용도Antipsychotic used in the treatment of schizophrenia.
상·하류 제품 정보
상류 원료
공급사94 곳
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추가 설명
정의ChEBI: A phenylindole that is 1H-indole which is substituted on the nitrogen by a p-chlorophenyl group, at position 5 by chlorine, and at position 3 by a piperidin-4-yl group, which is itself substituted on the nitrogen by a 2-(2-o oimidazolidin-1-yl)ethyl group.
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