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트리플루오페라진 디하이드로클로라이드

Trifluoperazine Hydrochloride

HCID 66064
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
440-17-5
표준 SMILES
CN1CCN(CCCN2c3ccccc3Sc3ccc(C(F)(F)F)cc32)CC1.Cl.Cl
InChIKey
BXDAOUXDMHXPDI-UHFFFAOYSA-N
분자식
C21H26Cl2F3N3S
평균 분자량
480.4 g/mol
단동위원소 질량
479.1176589

개요

Trifluoperazine Hydrochloride is the hydrochloride salt of trifluoperazine, a phenothiazine derivative and a dopamine, alpha-adrenergic, and anticholinergic antagonist with antipsychotic, anxiolytic, and antiemetic activities. Trifluoperazine blocks central dopamine receptors, which may prevent or mitigate delusions and hallucinations caused by an excess of dopamine; dopamine blockade in the chemoreceptor trigger zone (CTZ) may result in an antiemetic effect. This agent binds to central adrenergic receptors, which may result in anxiolytic effects. Trifluoperazine also functions as a calmodulin inhibitor, elevating cytosolic calcium.

이름 및 식별자

우선 이름
Trifluoperazine Hydrochloride
IUPAC
10-[3-(4-methylpiperazin-1-yl)propyl]-2-(trifluoromethyl)phenothiazine;dihydrochloride
현지명
트리플루오페라진 디하이드로클로라이드
영어명
Trifluoperazine dihydrochloride
분자식
C21H26Cl2F3N3S
분자량
480.42

이름 및 동의어

Trifluoperazine dihydrochloride440-17-5Trifluoperazine hydrochlorideTrifluoperazine HClEskazineTrifluoroperazine dihydrochlorideDTXSID1045085SKF 5019Trifluperazine dihydrochloride6P1Y2SNF5V10-(3-(4-methylpiperazin-1-yl)propyl)-2-(trifluoromethyl)-10H-phenothiazine dihydrochloride10-[3-(4-Methylpiperazin-1-yl)propyl]-2-(trifluoromethyl)-10H-phenothiazine dihydrochloride
이름 더 보기
트리플루오페라진디하이드로클로라이드트라이플루오퍼아진 하이드로클로라이드Trifluoperazine dihydrochloride, 10-[3-(4-Methylpiperazin-1-yl)propyl]-2-(trifluoromethyl)-10H-phenothiazine dihydrochlorideUrinoxskf5019StelazinSTELAZINEEskazinylAi3-50137
NSC-75736910H-Phenothiazine, 10-(3-(4-methyl-1-piperazinyl)propyl)-2-(trifluoromethyl)-, dihydrochlorideDTXCID902508510-(3-(4-Methyl-1-piperazinyl)propyl)-2-(trifluoromethyl)phenothiazine dihydrochloride2-Trifluoromethyl-10-(3'-(1-methyl-4-piperazinyl)propyl)phenothiazine dihydrochloride10H-phenothiazine, 10-[3-(4-methyl-1-piperazinyl)propyl]-2-(trifluoromethyl)-, dihydrochlorideCHEBI:9710NSC17474

데이터베이스 식별자

CAS
440-17-5
PubChem CID
66064
DTXSID
DTXSID1045085
ChEMBL
CHEMBL1257040
UNII
6P1Y2SNF5V
EC Number
207-123-0

물성

구조 계산 물성

극성 표면적
35 Ų
수소 결합 공여자 수
2
수소 결합 수용자 수
7
회전 가능 결합 수
4
무거운 원자 수
30
형식 전하
0
복잡도
510

실험 및 물리화학적 성질

Human Drugs · 2건

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Collision Cross Section188.5 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

물리화학적 성질

녹는점
243 °C · 243 °C (dec.)(lit.)
인화점
9 ℃ · 9℃
저장 조건
-20 °C · -20°C
용해도
5 mg/mL · 에탄올: 용해성5mg/mL
산도 계수 (pKa)
1 · pK1 3.9, pK2 8.1(at 25℃)
물리적 상태
가루
색상
흰색에서 황백색까지
수용성
50 g/L, · water: 50g/L, clear
Merck
14 · 14,9680
BRN
3820024 · 3820024
안정성
흡습성
InChI
1S/C21H24F3N3S.2ClH/c1-25-11-13-26(14-12-25)9-4-10-27-17-5-2-3-6-19(17)28-20-8-7-16(15-18(20)27)21(22,23)24;;/h2-3,5-8,15H,4,9-14H2,1H3;2*1H
InChIKey
BXDAOUXDMHXPDI-UHFFFAOYSA-N
SMILES
Cl[H].Cl[H].CN1CCN(CCCN2c3ccccc3Sc4ccc(cc24)C(F)(F)F)CC1
EPA
10 H-Phenothiazine, · 10H-Phenothiazine, 10-[3-(4-methyl-1-piperazinyl)propyl]-2-(trifluoromethyl)-, dihydrochloride (440-17-5)

화학적 성질

Cream Fine Powder

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 42 reports by companies from 3 notifications to the ECHA C&L Inventory.

유해성 정보

Regulatory InformationHazard Traits - Bioaccumulation; Environmental Persistence
Other Safety InformationIMAP assessments - 10H-Phenothiazine, 10-[3-(4-methyl-1-piperazinyl)propyl]-2-(trifluoromethyl)-, dihydrochloride: Environment tier I assessment
Hazard Classes and CategoriesAcute Tox. 4 (100%)

독성 정보

Treatment · 1건

Treatment is essentially symptomatic and supportive. Early gastric lavage is helpful. Keep patient under observation and maintain an open airway, since involvement of the extrapyramidal mechanism may produce dysphagia and respiratory difficulty in severe overdosage. Do not attempt to induce emesis because a dystonic reaction of the head or neck may develop that could result in aspiration of vomitus. Extrapyramidal symptoms may be treated with anti-parkinsonism drugs, barbiturates or Benadryl. See prescribing information for these products. Care should be taken to avoid increasing respiratory depression. If administration of a stimulant is desirable, amphetamine, dextroamphetamine or caffeine with sodium benzoate is recommended. Stimulants that may cause convulsions (e.g., picrotoxin or pentylenetetrazol) should be avoided. If hypotension occurs, the standard measures for managing circulatory shock should be initiated. If it is desirable to administer a vasoconstrictor, Levophed and Neo-Synephrine are most suitable. Other pressor agents, including epinephrine, are not recommended because phenothiazine derivatives may reverse the usual elevating action of these agents and cause a further lowering of blood pressure. (L1712)

Exposure RoutesOral
Toxicity Summary · 1건

Trifluoperazine blocks postsynaptic mesolimbic dopaminergic D1 and D2 receptors in the brain; depresses the release of hypothalamic and hypophyseal hormones and is believed to depress the reticular activating system thus affecting basal metabolism, body temperature, wakefulness, vasomotor tone, and emesis.

Signs and SymptomsSymptoms of overdose include agitation, coma, convulsions, difficulty breathing, difficulty swallowing, dry mouth, extreme sleepiness, fever, intestinal blockage, irregular heart rate, low blood pressure, and restlessness.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver Injury · 6건

Drug Induced Liver Injury Rank (DILIrank 2.0)

Trifluoperazine hydrochloride

vLess-DILI-concern

2

Warnings & precautions

DOI:10.1016/j.drudis.2016.02.015

안전 데이터

wgk
3
tsca
TSCA listed
rtecs
SP1750000
ridadr
UN1230 - class 3 - PG 2 - Methanol, solution
HS 번호
29343000
risk_code
22
hazard_code
Xn
safety_code
36
위험 등급
9
F 고인화성물질
3-10
Hazard Classifications
Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Eye Irrit. 2Muta. 2STOT RE 1STOT SE 3
스토리지 클래스
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects

화학 및 산업

약리 정보

Metabolism/MetabolitesHepatic. Half Life: 10-20 hours
FDA Pharmacological Classification · 2건

TRIFLUOPERAZINE HYDROCHLORIDE

Phenothiazines [CS]; Phenothiazine [EPC]

MeSH Pharmacological Classification · 3건

Drugs used to prevent NAUSEA or VOMITING.

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.

용도 및 제조

UsesFor the treatment of anxiety disorders, depressive symptoms secondary to anxiety and agitation.
General Manufacturing Information10H-Phenothiazine, 10-[3-(4-methyl-1-piperazinyl)propyl]-2-(trifluoromethyl)-, hydrochloride (1:2): ACTIVE
응용 분야 · 3건

개요Trifluoperazine (TFP) is a phenothiazine compound with anti-adrenergic and anti-dopaminergic actions typical of antipsychotic agents. It antagonizes adrenergic receptors, with selectivity for α1 over the α2 subtypes (Kis = 24, 653, 163, and 391 nM for α1A, α2A, α2B, and α2C, respectively). TFP binds with much higher affinity to the dopamine D2-like receptor (Kd = 0.96 nM) compared to the dopamine D4-like and the serotonin 5-HT2A receptors (Kds = 44 and 135 nM, respectively). Furthermore, TFP antagonizes calmodulin (CaM) and alters the calcium-binding properties of calsequestrin (CSQ). TFP has been shown to activate type-2 ryanodine receptors independently of its CaM and CSQ activity.

용도Trifluoperazine dihydrochloride has been used as a calmodulin kinase antagonist in cultured Aplysia californica neurons. Trifluoperazine dihydrochloride has also been used as a PMCA inhibitor in mouse duodenal tissues to block the transcellular active calcium flux.

일반 설명Trifluoperazinehydrochloride, 10-[3-(4-Methyl-1-piperazinyl)propyl-[2-(trifluoromethyl)phenothiazine dihydrochloride (Stelazine).The absorption of trifluoperazine is erratic and variable andit is widely distributed into tissues. The excretion of trifluoperazineoccurs 50% via kidneys and the other 50% isthrough enterohepatic circulation. The metabolism and druginteractions of trifluoperazine are the same as with the otherphenothiazines. Trifluoperazine does not show any specificdrug interactions. Trifluoperazine is indicated for the managementof schizophrenia and short-term treatment ofnonpsychotic anxiety.

상·하류 제품 정보

상류 원료

1-(3-클로로프로필)-4-메틸피페라진2-(트리플루오로메틸)페노티아진나트륨아미드

하류 제품

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