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QuickView for Amitriptyline (compound)


PubChem
Name: Amitriptyline
PubChem Compound ID: 11065
Description: Tricyclic antidepressant with anticholinergic and sedative properties. It appears to prevent the re-uptake of norepinephrine and serotonin at nerve terminals, thus potentiating the action of these neurotransmitters. Amitriptyline also appears to antagonize cholinergic and alpha-1 adrenergic responses to bioactive amines.
Molecular formula: C20H24ClN
Molecular weight: 313.864 g/mol
Synonyms:
Elavil (TN); Levate; EU-0100112; Proheptadien monohydrochloride; Daprimen; 5-(3-Dimethylaminopropylidene)dibenzo(a,d)(1,4)cycloheptadiene hydrochloride; Tryptizol; Tryptanol; NIH 10794; Trepiline.
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DrugBank
Identification
Name: Amitriptyline
Name (isomeric): DB00321
Drug Type: small molecule
Description: Tricyclic antidepressant with anticholinergic and sedative properties. It appears to prevent the re-uptake of norepinephrine and serotonin at nerve terminals, thus potentiating the action of these neurotransmitters. Amitriptyline also appears to antagonize cholinergic and alpha-1 adrenergic responses to bioactive amines.
Synonyms:
Amitriptylin; Amitryptiline; Amitriptyline Hydrochloride; Amitriptyline HCL; Amitryptyline; Amytriptiline; Amitriprolidine
Brand: Hexathane, Saroten, Triptanol, Sylvemid, Horizon, Damilen, Adepril, Sarotex, Triptilin, Proheptadiene, Tryptizol, Elavil, Triptisol, Redomex, Laroxil, Flavyl, Amitid, Lentizol, Laroxyl, Elanil, Seroten, Damilan, Lantron, Tryptanol, Amitril, Endep, Adepress, dAmitriptyline
Brand name mixture:
Pms-Levazine 3/15 Tab(Amitriptyline Hydrochloride + Perphenazine), Proavil Tab(Amitriptyline Hydrochloride + Perphenazine), Etrafon F Tab(Amitriptyline Hydrochloride + Perphenazine), Etrafon a Tab(Amitriptyline Hydrochloride + Perphenazine), Etrafon D Tab(Amitriptyline Hydrochloride + Perphenazine), Etrafon 2 10(Amitriptyline Hydrochloride + Per...
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Category: Analgesics, Non-Narcotic, Adrenergic Uptake Inhibitors, Antidepressive Agents, Tricyclic
CAS number: 50-48-6
Pharmacology
Indication: For the treatment of depression, chronic pain, irritable bowel syndrome, sleep disorders, diabetic neuropathy, agitation and insomnia, and migraine prophylaxis.
Pharmacology:
Amitriptyline, a tertiary amine tricyclic antidepressant, is structurally related to both the skeletal muscle relaxant cyclobenzaprine and the thioxanthene antipsychotics such as thiothixene. It is extremely sedating, and thus improvement of sleep patterns can be the first benefit of treatment. Amitriptyline exhibits strong anticholinergic activity...
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Mechanism of Action:
Amitriptyline is metabolized to nortriptyline which inhibits the reuptake of norepinephrine and serotonin almost equally. Amitriptyline inhibits the membrane pump mechanism responsible for uptake of norepinephrine and serotonin in adrenergic and serotonergic neurons. Pharmacologically this action may potentiate or prolong neuronal activity since re...
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Absorption: Rapidly and well absorbed following oral administration (bioavailability is 30-60% due to first pass metabolism). Peak plasma concentrations occur 2-12 hours following oral or intramuscular administration.
Protein binding: Very highly protein bound (90% or more) in plasma and tissues
Biotransformation: Exclusively hepatic, with first pass effect. Amitriptyline is demethylated in the liver to its primary active metabolite, nortriptyline.
Route of elimination: Virtually the entire dose is excreted as glucuronide or sulfate conjugate of metabolites, with little unchanged drug appearing in the urine. 25-50% of a single orally administered dose is excreted in urine as inactive metabolites within 24 hours. Small amounts are excreted in feces via biliary elimination.
Half Life: 10 to 50 hours, with an average of 15 hours
Toxicity: LD50=350 mg/kg (in mice). Symptoms of overdose include abnormally low blood pressure, confusion, convulsions, dilated pupils and other eye problems, disturbed concentration, drowsiness, hallucinations, impaired heart function, rapid or irregular heartbeat, reduced body temperature, stupor, and unresponsiveness or coma. Side effects include: sedation, hypotension, blurred vision, dry mouth, constipation, urinary retention, postural hypotension, tachycardia, hypertension, ECG changes, heart failure, impaired memory and delirium, and precipitation of hypomanic or manic episodes in bipolar depression. Withdrawal symptoms include gastrointestinal disturbances, anxiety, and insomnia.
Affected organisms: Humans and other mammals
Interactions
Food interaction:
Avoid St.John's Wort.
Avoid alcohol.
Take with food to reduce irritation.
Avoid excessive quantities of coffee or tea (caffeine).
Drug interaction:
GrepafloxacinIncreased risk of cardiotoxicity and arrhythmias
DuloxetinePossible increase in the levels of this agent when used with duloxetine
SparfloxacinIncreased risk of cardiotoxicity and arrhythmias
TranylcypromineIncreased risk of serotonin syndrome. Concomitant therapy should be avoided. A significant washout period, dependent on the half-lives of the agents, should be employed between therapies.
OrciprenalineThe tricyclic antidepressant, amitriptyline, increases the sympathomimetic effect of orciprenaline.
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