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Zuclopenthixol

HCID 5311507
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기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
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기본 정보

CAS
53772-83-1
표준 SMILES
OCCN1CCN(CC/C=C2/c3ccccc3Sc3ccc(Cl)cc32)CC1
InChIKey
WFPIAZLQTJBIFN-DVZOWYKESA-N
분자식
C22H25ClN2OS
평균 분자량
401 g/mol
단동위원소 질량
400.1376123

개요

Clopenthixol is a thioxanthene derivative having a chloro substituent at the 2-position and an alkylidene group at the 10-position with undefined double bond stereochemistry. It has a role as an alpha-adrenergic antagonist, a H1-receptor antagonist, a serotonergic antagonist, a dopaminergic antagonist and a first generation antipsychotic. It is a primary alcohol, a N-alkylpiperazine and a member of thioxanthenes.

이름 및 식별자

우선 이름
Zuclopenthixol
IUPAC
2-[4-[(3Z)-3-(2-chlorothioxanthen-9-ylidene)propyl]piperazin-1-yl]ethanol
영어명
Zuclopenthixol
분자식
C22H25ClN2OS
분자량
400.96

이름 및 동의어

Zuclopenthixol53772-83-1ClopixolZuclopentixolZuclopenthixolumClopentixol cis-(Z)-2-[4-[(3Z)-3-(2-chlorothioxanthen-9-ylidene)propyl]piperazin-1-yl]ethanol47ISU063SG(Z)-4-(3-(2-Chlorothioxanthen-9-ylidene)propyl)-1-piperazineethanolDTXSID3048233CHEBI:513642-(4-{3-[(9Z)-2-CHLORO-9H-THIOXANTHEN-9-YLIDENE]PROPYL}PIPERAZIN-1-YL)ETHAN-1-OL
이름 더 보기
Cisordinolcis(Z)-FormUnii-47isu063sgEinecs 258-758-5cis-Clopenthixol(Z)-Clopenthixol
zuclopentixolo2-(4-((3Z)-3-(2-chlorothioxanthen-9-ylidene)propyl)piperazin-1-yl)ethanol2-(4-(3-((9Z)-2-chloro-9H-thioxanthen-9-ylidene)propyl)piperazin-1-yl)ethan-1-olClopenthixol cis(z)-RefChem:196277DTXCID4028208N05AF05258-758-5

데이터베이스 식별자

CAS
53772-83-1、982-24-1
PubChem CID
5311507
DTXSID
DTXSID3048233

물성

구조 계산 물성보충 중

XLogP
4.3
극성 표면적
52 Ų
수소 결합 공여자 수
1
수소 결합 수용자 수
4
회전 가능 결합 수
5
무거운 원자 수
27
형식 전하
0
복잡도
509

실험 및 물리화학적 성질

Drugs · 3건

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals

Pharmaceuticals -> Antipsychotics

Solubility · 2건

slight

2.60e-03 g/L

Human Drugs · 2건

Breast Feeding; Lactation; Milk, Human; Antipsychotic Agents; Dopamine Antagonists

Pharmaceuticals

Melting Point~50
Physical DescriptionSolid

물리화학적 성질

녹는점
56 · 56-60°C
끓는 점
577.4 · 577.4±50.0 °C(Predicted)
밀도
1.289 · 1.289±0.06 g/cm3(Predicted)
저장 조건
-20 °C · -20°C Freezer, Under Inert Atmosphere
용해도
클로로포름(약간 용해됨), 메탄올(약간 용해됨)
물리적 상태
고체
산도 계수 (pKa)
14.96 · 14.96±0.10(Predicted)
색상
흰색에서 황백색까지

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 4건

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 3 reports by companies from 1 notifications to the ECHA C&L Inventory.

유해성 정보

Regulatory InformationREACH registered substance: Zuclopenthixol (EC: 258-758-5)
Hazard Classes and CategoriesAcute Tox. 4 (100%)

독성 정보

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

안전 데이터

wgk
WGK 3
Hazard Classifications
Acute Tox. 4 Oral
스토리지 클래스
11 - Combustible Solids

화학 및 산업

약리 정보

ATC Code · 3건

N05AF05

N - Nervous system

QN - Nervous system

Protein Binding98-99%
PharmacodynamicsZuclopenthixol is a thioxanthene with therapeutic actions similar to the phenothiazine antipsychotics. It is an antagonist at D1 and D2 dopamine receptors.
Mechanism of Action · 1건

Zuclopenthixol is a typical antipsychotic neuroleptic drug of the thioxanthene class. It mainly acts by antagonism of D1 and D2 dopamine receptors. Zuclopenthixol also has high affinity for alpha1-adrenergic and 5-HT2 receptors. It has weaker histamine H1 receptor blocking activity, and even lower affinity for muscarinic cholinergic and alpha2-adrenergic receptors.

Biological Half-Life20 hours (range 12-28 hours) for the tablet form, 19 days for the depot form.
Metabolism/MetabolitesThe metabolism of zuclopenthixol is mainly by sulphoxidation, side chain N-dealkylation and glucuronic acid conjugation. The metabolites are devoid of pharmacological activity.
MeSH Pharmacological Classification · 2건

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.

Drugs that bind to but do not activate DOPAMINE RECEPTORS, thereby blocking the actions of dopamine or exogenous agonists. Many drugs used in the treatment of psychotic disorders (ANTIPSYCHOTIC AGENTS) are dopamine antagonists, although their therapeutic effects may be due to long-term adjustments of the brain rather than to the acute effects of blocking dopamine receptors. Dopamine antagonists have been used for several other clinical purposes including as ANTIEMETICS, in the treatment of Tourette syndrome, and for hiccup. Dopamine receptor blockade is associated with NEUROLEPTIC MALIGNANT SYNDROME.

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화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
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새 노트새 반응견적 요청하기
ChEMBL
CHEMBL53904
ChEBI
CHEBI:59115
UNII
47ISU063SG
EC Number
258-758-5
Nikkaji
J32.497C、J9.475G
InChI
InChI=1S/C22H25ClN2OS/c23-17-7-8-22-20(16-17)18(19-4-1-2-6-21(19)27-22)5-3-9-24-10-12-25(13-11-24)14-15-26/h1-2,4-8,16,26H,3,9-15H2/b18-5-
InChIKey
WFPIAZLQTJBIFN-DVZOWYKESA-N
SMILES
S1c2c(cc(cc2)Cl)\C(=C/CCN4CCN(CC4)CCO)\c3c1cccc3

화학적 성질

Pale Yellow Low Melting Solid

Absorption, Distribution and Excretion · 4건

Upon reaching the body water phase, the decanoate ester is slowly released from the oil depot, which is resultantly hydrolyzed to the active substance, zuclopenthixol. The decanoate ester provides a means of slow release since zuclopenthixol itself is a short-acting drug.

Primarily in the feces with approximately 10% in the urine.

20 L/kg.

approximately 0.9 L/min.

Cellular LocationsMembrane

용도 및 제조

UsesUse (kg; approx.) in Germany (2009): >100
Use ClassificationPharmaceuticals
응용 분야 · 2건

개요Zuclopenthixol is a kind of antipsychotic agent. It is a thioxanthene-based neuroleptic with in vivo action similar to the phenothiazine antipsychotics through antagonizing D1 and D2 dopamine receptors. It has three major formulations form including zuclopenthixol decanoate, zuclopenthixol acetate, and zuclopenthixol dihydrochloride. It can be used for the treatment of schizophrenia and bipolar mania. Besides antagonizing the D1 and D2 dopamine receptors, Zuclopenthixol can also take effect through antagonizing alpha1-adrenergic and 5-HT2 receptors. It can also weakly block the histamine H1 receptor.

용도Zuclopenthixol is an anti-psychotic drug. It is an inhibitor of coxsackievirus B3. Also, it is an intermediate used in the synthesis of Zuclopenthixol Decanoate (Z701490), which is used in the maintenance treatment of chronic schizophrenic patients. It is one of the three distinct formulations of Zuclopenthixol namely, zuclopenthixol dihydrochloride, zuclopenthixol acetate or Acuphase and zuclopenthixol decanoate.

추가 설명

정의ChEBI: The (Z)-isomer of clopenthixol.