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トリフルプロマジン

Triflupromazine

HCID 5568
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
146-54-3
標準SMILES
CN(C)CCCN1c2ccccc2Sc2ccc(C(F)(F)F)cc21
InChIKey
XSCGXQMFQXDFCW-UHFFFAOYSA-N
分子式
C18H19F3N2S
平均分子量
352.4 g/mol
単同位体質量
352.12210427

概要

Triflupromazine is a member of the class of phenothiazines that is 10H-phenothiazine having a trifluoromethyl subsitituent at the 2-position and a 3-(dimethylamino)propyl group at the N-10 position. It has a role as an anticoronaviral agent, a dopaminergic antagonist, an antiemetic and a first generation antipsychotic. It is a tertiary amine, an organofluorine compound and a member of phenothiazines. It derives from a hydride of a 10H-phenothiazine.

名称と識別子

優先名称
Triflupromazine
IUPAC
N,N-dimethyl-3-[2-(trifluoromethyl)phenothiazin-10-yl]propan-1-amine
現地名
トリフルプロマジン
英語名
triflupromazine
分子式
C18H19F3N2S
分子量
352.4170696

名称と別名

triflupromazineFluopromazineTrifluopromazine146-54-3VesprinPsyquilTriflupromazinaVetameTriflupromazinum2-(Trifluoromethyl)promazineNivoman10H-Phenothiazine-10-propanamine, N,N-dimethyl-2-(trifluoromethyl)-
名称をさらに表示
ベタムN,N-ジメチル-2-(トリフルオロメチル)-10H-フェノチアジン-10-プロパン-1-アミントリフルオプロマジントリフルプロマジンN,N-ジメチル-3-[2-(トリフルオロメチル)-10H-フェノチアジン-10-イル]プロパン-1-アミン10-[3-(ジメチルアミノ)プロピル]-2-(トリフルオロメチル)-10H-フェノチアジンN,N-ジメチル-2-トリフルオロメチル-10H-フェノチアジン-10-プロパン-1-アミンフルオプロマジンジメチル({3-[2-(トリフルオロメチル)-10H-フェノチアジン-10-イル]プロピル})アミンAdazineTRIFLUOROPROMAZINEtriflupromazine USP/EP/BPFluphenazine hydrochloride IHS Impurity Edimethyl(3-(2-trifluoromethylphenothiazin-10-yl)propyl)amine10-[3-(Dimethylamino)propyl]-2-(trifluoromethyl)-10H-phenothiazine
2-Trifluoromethyl-10-(gamma-dimethylaminopropyl)phenothiazine10-(3-(Dimethylamino)propyl)-2-(trifluoromethyl)phenothiazineRO16TQF95YDTXSID9023704dimethyl({3-[2-(trifluoromethyl)-10H-phenothiazin-10-yl]propyl})amineN,N-Dimethyl-2-(trifluoromethyl)-10H-phenothiazine-10-propanamineCHEBI:9711Phenothiazine, 10-(3-(dimethylamino)propyl)-2-(trifluoromethyl)-

物性

構造計算による物性

XLogP
5.2
極性表面積
31.8 Ų
水素結合供与体数
0
水素結合受容体数
6
回転可能結合数
4
重原子数
24
形式電荷
0
複雑度
416

実験および物理化学的性質

Drugs · 2 件

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Nervous system -> Antipsychotics

LogP · 2 件

5.2

5.17

Color/FormVISCOUS, LIGHT AMBER-COLORED, LIQ, WHICH CRYSTALLIZES ON PROLONGED STANDING INTO LARGE IRREGULAR CRYSTALS
Solubility · 3 件

SOL IN WATER, ALC, & ACETONE; INSOL IN ETHER /HCL/

PRACTICALLY INSOL IN WATER

1.80e-03 g/L

Human Drugs · 3 件

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Pharmaceuticals

Boiling Point176 °C @ 0.7 MM HG
Refractive IndexINDEX OF REFRACTION: 1.5780 @ 23 °C/D
Physical DescriptionSolid
Stability/Shelf LifeSOLN ARE SENSITIVE TO AIR & LIGHT /HYDROCHLORIDE/
Collision Cross Section174.51 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

安全と法規制

安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 4 件

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P203, P261, P262, P264, P270, P271, P280, P301+P316, P302+P352, P304+P340, P316, P318, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Other Safety InformationIMAP assessments - 10H-Phenothiazine-10-propanamine, N,N-dimethyl-2-(trifluoromethyl)-: Environment tier I assessment
Hazard Classes and CategoriesAcute Tox. 3 (100%)

毒性情報

Interactions · 5 件

...ANTIPSYCHOTIC DRUGS...MAY BLOCK ANTIHYPERTENSIVE EFFECTS OF GUANETHIDINE. PT BEING TREATED WITH PHENOTHIAZINES SHOULD BE ADVISED THAT THEIR SUSCEPTIBILITY TO ALCOHOL MAY BE INCR. /PHENOTHIAZINES/

ADDITIVE TO ACTION OF OTHER DEPRESSANTS & WILL POTENTIATE ANESTHETICS.

MAY INCR TOXICITY OF ORGANOPHOSPHORUS OR OTHER ACETYLCHOLINESTERASE INHIBITORS & PROCAINE. DO NOT USE EPINEPHRINE TO COMBAT ITS HYPOTENSIVE OR DEPRESSANT EFFECTS AS IT POTENTIATES THEM.

CONCURRENT ADMIN OF PHENOTHIAZINES & TRICYCLIC ANTIDEPRESSANTS MAY RESULT IN INCR IN SERUM LEVEL OF EITHER AGENT. /PHENOTHIAZINES/

For more Interactions (Complete) data for TRIFLUPROMAZINE (7 total), please visit the HSDB record page.

Exposure RoutesAbsorption may be erratic and peak plasma concentrations show large interindividual differences.
Toxicity Summary · 1 件

Triflupromazine binds to the dopamine D1 and dopamine D2 receptors and inhibits their activity. The mechanism of the anti-emetic effect is due predominantly to blockage of the dopamine D2 neurotransmitter receptors in the chemoreceptor trigger zone (CTZ) and vomiting centre. Triflupromazine blocks the neurotransmitter dopamine and the vagus nerve in the gastrointestinal tract. Triflupromazine also binds the muscarinic acetylcholine receptors (M1 and M2) and the tryptamine D receptors (5HT<sub>2B</sub>).

化学と産業

薬理情報

ATC Code · 2 件

N - Nervous system

QN - Nervous system

Protein BindingVery high (90% or more).
Pharmacodynamics · 1 件

Triflupromazine is a member of a class of drugs called phenthiazines, which are dopamine D1/D2 receptor antagonists. Phenothiazines are used to treat serious mental and emotional disorders, including schizophrenia and other psychotic disorders. It reduces anxiety, emotional withdrawal, hallucinations, disorganized thoughts, blunted mood, and suspiciousness. Triflupromazine is used particularly to control violent behavior during acute episodes of psychotic disorders. It can also be used to control severe nausea and vomiting, severe hiccups, and moderate to severe pain in some hospitalized patients. Triflupromazine acts on the central nervous system.

Mechanism of Action · 3 件

Triflupromazine binds to the dopamine D1 and dopamine D2 receptors and inhibits their activity. The mechanism of the anti-emetic effect is due predominantly to blockage of the dopamine D2 neurotransmitter receptors in the chemoreceptor trigger zone (CTZ) and vomiting centre. Triflupromazine blocks the neurotransmitter dopamine and the vagus nerve in the gastrointestinal tract. Triflupromazine also binds the muscarinic acetylcholine receptors (M1 and M2) and the tryptamine D receptors (5HT<sub>2B</sub>).

...PHENOTHIAZINES, BLOCK DOPAMINE RECEPTORS & INCR TURNOVER RATE OF DOPAMINE IN CORPUS STRIATUM. INCR TURNOVER RATE IS BELIEVED TO BE RESULT OF NEURONAL FEEDBACK MECHANISM. ...FIRING OF.../IDENTIFIED DOPAMINERGIC NEURONS IN SUBSTANTIA NIGRA & VENTRAL TEGMENTAL AREAS/ IS INCR BY ANTIPSYCHOTIC PHENOTHIAZINES. /PHENOTHIAZINES/

THERE IS AN ADENYLATE CYCLASE IN LIMBIC SYSTEM, AS WELL AS IN CAUDATE NUCLEUS, THAT IS SPECIFICALLY ACTIVATED BY DOPAMINE. ...ACTIVATION OF...ENZYME IS... BLOCKED BY...PHENOTHIAZINES. ...THERAPEUTIC EFFICACY & SIDE EFFECTS MAY RELATE TO INHIBITION OF DOPAMINE ACTIVATION OF ADENYLATE CYCLASE. /PHENOTHIAZINES/

Metabolism/Metabolites · 3 件

Hepatic.

...METAB...BY OXIDATIVE PROCESSES MEDIATED LARGELY BY HEPATIC MICROSOMAL & OTHER DRUG-METABOLIZING ENZYMES. CONJUGATION WITH GLUCURONIC ACID...PROMINENT ROUTE.../PRC: REACTIONS INCL HYDROXYLATION, DEMETHYLATION, SULFOXIDE FORMATION; METABOLIC ALTERATIONS IN SIDE CHAIN MAY ALSO OCCUR/. /PHENOTHIAZINES/

関連反応

0 件
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化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート

データベース識別子

CAS
146-54-3
PubChem CID
5568
DTXSID
DTXSID9023704
ChEMBL
CHEMBL570
ChEBI
CHEBI:9711
UNII
RO16TQF95Y
EC Number
205-673-6
Nikkaji
J2.957B
Other Experimental Properties · 4 件

SLIGHT, CHARACTERISTIC ODOR; MELTS BETWEEN 170 & 178 °C /HYDROCHLORIDE/

PH OF 2% AQ SOLN 4.1, IF PH IS RAISED TO 6.4, PPT OF FREE BASE RESULTS /HYDROCHLORIDE/

WHITE TO PALE TAN, CRYSTALLINE POWDER /HYDROCHLORIDE/

CRYSTALS FROM XYLENE /HYDROCHLORIDE/

物理化学的性質

融点
25 °C · 25°C
沸点
0.7 · bp0.7 176°; bp0.4 162-164°
比重(密度)
1.2198 · 1.2198 (estimate)
屈折率
23 · nD23 1.5780
酸解離定数(Pka)
9.41 · pKa 9.41(H2O (extrap) t = 24±1 I～0.002) (Uncertain)
水溶解度
1.762 mg/L · 1.762mg/L(24℃)
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.
Human Toxicity Excerpts · 5 件

MILD ELEVATION OF TEMP...IF...GIVEN PARENTERALLY. ...HYPOTHERMIA CAN OCCUR & MAY BE DUE BOTH TO ACTION ON HEAT-REGULATING CENTER & TO DIRECT PERIPHERAL VASODILATATION. SENSITIVITY & ADAPTATION TO ENVIRONMENTAL TEMP CHANGE ARE IMPAIRED...FATAL HYPERTHERMIA & HEAT STROKE ARE POSSIBLE COMPLICATIONS. /PHENOTHIAZINES/

...JAUNDICE FOLLOWING PHENOTHIAZINE ADMIN IS HYPERSENSITIVITY MANIFESTATION. ... LEUKOCYTOSIS, LEUKOPENIA, & EOSINOPHILIA OCCUR WITH PHENOTHIAZINE MEDICATION. /PHENOTHIAZINES/

...SKIN DISORDERS ARE ASSOC WITH USE OF PHENOTHIAZINES. FIRST IS HYPERSENSITIVITY REACTION THAT MAY BE URTICARIAL, MACULOPAPULAR, PETECHIAL, OR EDEMATOUS. ...PHOTOSENSITIVITY OCCURS... /PHENOTHIAZINES/

ABNORMAL PIGMENTATION INDUCED BY LONG-TERM ADMIN OF PHENOTHIAZINES IN HIGH DOSES TO CHRONIC SCHIZOPHRENICS HAS BEEN REPORTED. ... PIGMENTARY RETINOPATHY...MAY BE CLOSELY RELATED TOXIC EFFECT OF PHENOTHIAZINES... /PHENOTHIAZINES/

For more Human Toxicity Excerpts (Complete) data for TRIFLUPROMAZINE (9 total), please visit the HSDB record page.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Non-Human Toxicity ExcerptsAVOID RAPID IV (MAY CAUSE SEVERE HYPOTENSION & CV COLLAPSE), & INTRAARTERIAL INJECTIONS (DISORIENTATION, CONVULSIONS, & DEATHS MAY OCCUR) ESP IN HORSES.

安全データ

有毒物質データの
146-54-3(Hazardous Substances Data)

Hepatic.

MeSH Pharmacological Classification · 3 件

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.

Absorption, Distribution and Excretion · 2 件

Absorption may be erratic and peak plasma concentrations show large interindividual differences.

FATE OF SEVERAL (14)C QUATERNARY PHENOTHIAZINES, SUCH AS...TRIFLUPROMAZINE METHIODIDE...HAVE BEEN STUDIED IN RAT. ...MORE OF IP DOSE OF PHENOTHIAZINE WAS EXCRETED IN FECES (VIA BILE). WHERE EXAMINED, NO N-DEALKYLATION OF QUATERNARY NITROGEN WAS DETECTED. /METHIODIDE/

Cellular LocationsMembrane

用途と製造

Uses · 3 件

MEDICATION (VET)

MEDICATION

Used mainly in the management of psychoses. Also used to control nausea and vomiting.

Methods of ManufacturingYALE ET AL, J AM CHEM SOC 79, 4375 (1957); BRITISH PATENT 813,861 (1959 TO SK & F).
Formulations/Preparations · 3 件

TABLET-10, 25, 50 MG; SYRUP-50 MG/5 ML; VIAL-10 MG/ML IN 10 ML; SYRINGE-10 MG/ML.

ORAL SUSPENSION NF: 50 MG/5 ML (HYDROCHLORIDE EQUIVALENT).

ADAZINE, FLUOMAZINA, FLUOROFEN, NIVOMAN, PSYQUIL, SIQUIL, VESPRAL, VESPRIN. /HYDROCHLORIDE/

Use ClassificationPharmaceuticals

応用分野

使用In psychiatric practice, triflupromazine is used for psychomotor excitement in patients with schizophrenia for paranoid and manic-depressive conditions, and for neurosis.

上流・下流製品情報

上流原料

ナトリウムアミド2-(トリフルオロメチル)フェノチアジン

サプライヤー8 社

北京华美互利生物化工010-56205725 · [email protected]
陕西缔都医药化工有限公司029-81024372 17792795018 · [email protected]
Chongqing jooe co., ltd+86-15223382610 · [email protected]
青岛海智微元生物科技有限公司18317699790 18317699790 · [email protected]
天津阿尔塔科技有限公司022-6537-8550 15522853686 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
Shaanxi Didu New Materials Co. Ltd+86-86-17392712779 +86-13289823923 · [email protected]
TargetMol中国（陶术生物）15002134094 · [email protected]

補足説明

定義ChEBI: A member of the class of phenothiazines that is 10H-phenothiazine having a trifluoromethyl subsitituent at the 2-position and a 3-(dimethylamino)propyl group at the N-10 position.