基本情報
- 標準SMILES
Cl.Fc1ccc([C@@H]2CCNC[C@H]2COc2ccc3c(c2)OCO3)cc1- InChIKey
GELRVIPPMNMYGS-RVXRQPKJSA-N- 分子式
- C19H21ClFNO3
- 平均分子量
- 365.8 g/mol
- 単同位体質量
- 365.11939943
概要
Paroxetine hydrochloride is the hydrochloride salt of paroxetine. It is an antidepressant drug. It has a role as an antidepressant, an anxiolytic drug, a P450 inhibitor, a hepatotoxic agent and a serotonin uptake inhibitor. It contains a paroxetinium(1+).
名称と識別子
- 優先名称
- Paroxetine Hydrochloride
- IUPAC
- (3S,4R)-3-(1,3-benzodioxol-5-yloxymethyl)-4-(4-fluorophenyl)piperidine;hydrochloride
名称と別名
名称をさらに表示
データベース識別子
- CAS
130855-16-2、78246-49-8- PubChem CID
- 62878
- DTXSID
DTXSID50228914- ChEMBL
CHEMBL1708、CHEMBL6067650- ChEBI
CHEBI:7944- UNII
- 3I3T11UD2S、5V22ESA4MA
- EC Number
- 616-601-1
物性
構造計算による物性
- 極性表面積
- 39.7 Ų
- 水素結合供与体数
- 2
- 水素結合受容体数
- 5
- 回転可能結合数
- 4
- 重原子数
- 25
- 形式電荷
- 0
- 複雑度
- 402
実験および物理化学的性質
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
安全と法規制
GHS分類
GHS Classification
Danger
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P304+P340, P305+P354+P338, P317, P319, P330, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 58 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
危険有害性情報
毒性情報
Treatment
Treatment should consist of those general measures employed in the management of overdosage with any drugs effective in the treatment of major depressive disorder. Ensure an adequate airway, oxygenation, and ventilation. Monitor cardiac rhythm and vital signs. General supportive and symptomatic measures are also recommended. Induction of emesis is not recommended. Gastric lavage with a large-bore orogastric tube with appropriate airway protection, if needed, may be indicated if performed soon after ingestion, or in symptomatic patients. Activated charcoal should be administered. Due to the large volume of distribution of this drug, forced diuresis, dialysis, hemoperfusion, and exchange transfusion are unlikely to be of benefit. No specific antidotes for paroxetine are known. (L1712)
Exposure Routes
Paroxetine hydrochloride is slowly, but completely absorbed following oral administration. Paroxetine mesylate salt is also completely absorbed after oral dosing. The oral bioavailability appears to be low due to extensive first-pass metabolism. Paroxetine hydrochloride oral tablets and suspension are reportedly bioequivalent. Absorption of either salt form is not substantially affected by food. Peak concentrations of Brisbelle (mesylate salt) were reached at 6 hours (3 to 8 hours range). Steady state Cmax was 13.10 ng/mL. The steady state AUC (0-last) was 237 hr*ng/mL. Paroxetine mesylate generally follows non-linear pharmacokinetics because CYP2D6, the enzyme that is part responisible for paroxetine metabolism, is readily saturable.
Toxicity Summary
Paroxetine is a potent and highly selective inhibitor of neuronal serotonin reuptake. Paroxetine likely inhibits the reuptake of serotonin at the neuronal membrane, enhances serotonergic neurotransmission by reducing turnover of the neurotransmitter, therefore it prolongs its activity at synaptic receptor sites and potentiates 5-HT in the CNS; paroxetine is more potent than both sertraline and fluoxetine in its ability to inhibit 5-HT reuptake. Compared to the tricyclic antidepressants, SSRIs have dramatically decreased binding to histamine, acetylcholine, and norepinephrine receptors. The mechanism of action for the treatment of vasomotor symptoms is unknown.
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Paroxetine hydrochloride
vLess-DILI-concern
8
Adverse reactions
DOI:10.1016/j.drudis.2016.02.015
化学と産業
薬理情報
Metabolism/Metabolites
Paroxetine is extensively metabolized after oral administration, likely in the liver. The main metabolites are polar and conjugated products of oxidation and methylation, which are readily eliminated by the body. The predominant metabolites are glucuronic acid and sulfate conjugates. Paroxetine metabolites do not possess significant pharmacologic activity (less than 2% that of parent compound). Paroxetine is metabolized by cytochrome P450 (CYP) 2D6. Enzyme saturation appears to account for the nonlinear pharmacokinetics observed with increasing dose and duration of therapy. Route of Elimination: Approximately 64% of a 30 mg oral solution of paroxetine was excreted in the urine with 2% as the parent compound and 62% as metabolites. Approximately 36% of the dose was excreted in the feces (via bile), mostly as metabolites and less than 1% as parent compound. Half Life: 21-24 hours
FDA Pharmacological Classification
PAROXETINE HYDROCHLORIDE
Serotonin Uptake Inhibitors [MoA]; Serotonin Reuptake Inhibitor [EPC]
MeSH Pharmacological Classification
A structurally and mechanistically diverse group of drugs that are not tricyclics or monoamine oxidase inhibitors. The most clinically important appear to act selectively on serotonergic systems, especially by inhibiting serotonin reuptake.
Compounds that specifically inhibit the reuptake of serotonin in the brain.
Drugs and compounds which inhibit or antagonize the biosynthesis or actions of CYTOCHROME P-450 CYP2D6.
用途と製造
Uses
Labeled indications include: major depressive disorder (MDD), panic disorder with or without agoraphobia, obsessive-compulsive disorder (OCD), social anxiety disorder (social phobia), generalized anxiety disorder (GAD), post-traumatic stress disorder (PTSD), and premenstrual dysphoric disorder (PMDD). Unlabeled indications include: eating disorders, impulse control disorders, vasomotor symptoms of menopause, obsessive-compulsive disorder (OCD) in children, and mild dementia-associated agitation in nonpsychotic individuals. Brisdelle, which consists of paroxetine mesylate is indicated for the treatment of moderate to severe vasomotor symptoms (like hot flashes) associated with menopause.
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関連ノート
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