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Details

Stereochemistry ACHIRAL
Molecular Formula C20H23N
Molecular Weight 277.4041
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMITRIPTYLINE

SMILES

CN(C)CCC=C1c2ccccc2CCc3ccccc31

InChI

InChIKey=KRMDCWKBEZIMAB-UHFFFAOYSA-N
InChI=1S/C20H23N/c1-21(2)15-7-12-20-18-10-5-3-8-16(18)13-14-17-9-4-6-11-19(17)20/h3-6,8-12H,7,13-15H2,1-2H3

HIDE SMILES / InChI

Molecular Formula C20H23N
Molecular Weight 277.4041
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment:: https://www.ncbi.nlm.nih.gov/pubmed/23235671; https://www.ncbi.nlm.nih.gov/pubmed/11157426; http://www.ncbi.nlm.nih.gov/pubmed/16871467; http://www.ncbi.nlm.nih.gov/pubmed/2578912; http://www.ncbi.nlm.nih.gov/pubmed/?term=15943846

Amitriptyline is a derivative of dibenzocycloheptadiene and a tricyclic antidepressant (TCA) and is mainly used to treat symptoms of depression. It works on the central nervous system (CNS) by inhibiting the membrane pump mechanism responsible for uptake of norepinephrine and serotonin in adrenergic and serotonergic neurons. Amitriptyline has been frequently used as an active comparator in clinical trials on newer antidepressants. It is rarely used as a first-line antidepressant nowadays due to its high degree of toxicity in overdose and generally poorer tolerability than the newer antidepressants.

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P23975
Gene ID: 6530
Gene Symbol: SLC6A2
Target Organism: Homo sapiens (Human)
3.45000000000000018 nM [IC50]
Target ID: P31645
Gene ID: 6532
Gene Symbol: SLC6A4
Target Organism: Homo sapiens (Human)
13.3000000000000007 nM [IC50]
Target ID: P28223
Gene ID: 3356
Gene Symbol: HTR2A
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
AMITRIPTYLINE HYDROCHLORIDE

Approved Use

For the relief of symptoms of depression. Endogenous depression is more likely to be alleviated than are other depressive states.

Launch Date

873936000000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
15.3 ng/mL
75 mg single, oral
dose: 75 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
AMITRIPTYLINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
593 ng × h/mL
75 mg single, oral
dose: 75 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
AMITRIPTYLINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
20.4 h
75 mg single, oral
dose: 75 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
AMITRIPTYLINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
7.7%
150 mg 1 times / day multiple, oral
dose: 150 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
AMITRIPTYLINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
100 mg 1 times / day single, intravenous
Studied dose
Dose: 100 mg, 1 times / day
Route: intravenous
Route: single
Dose: 100 mg, 1 times / day
Sources:
healthy, 21 to 70 years
Health Status: healthy
Age Group: 21 to 70 years
Sex: M+F
Sources:
Disc. AE: Bradycardia...
Other AEs: Agitation, Dry mouth...
AEs leading to
discontinuation/dose reduction:
Bradycardia (grade 3, 20%)
Other AEs:
Agitation (20%)
Dry mouth (20%)
Drowsiness (20%)
Language disorder (20%)
Sources:
10 % 1 times / day single, topical
Highest studied dose
Dose: 10 %, 1 times / day
Route: topical
Route: single
Dose: 10 %, 1 times / day
Sources:
unhealthy, 57 years
Health Status: unhealthy
Age Group: 57 years
Sex: M
Sources:
Other AEs: Thought disorder, Mental concentration difficult...
Other AEs:
Thought disorder
Mental concentration difficult
Sources:
520.3 mg 1 times / day single, oral
Studied dose
Dose: 520.3 mg, 1 times / day
Route: oral
Route: single
Dose: 520.3 mg, 1 times / day
Sources:
healthy, mean age 22.1 years
Health Status: healthy
Age Group: mean age 22.1 years
Sex: M+F
Sources:
Other AEs: Mental status changes...
Other AEs:
Mental status changes
Sources:
25 mg 1 times / day multiple, oral
Studied dose
Dose: 25 mg, 1 times / day
Route: oral
Route: multiple
Dose: 25 mg, 1 times / day
Sources:
unhealthy, mean age 43.2 years
Health Status: unhealthy
Age Group: mean age 43.2 years
Sex: M+F
Sources:
Other AEs: Dry mouth, Sleepiness...
Other AEs:
Dry mouth (75%)
Sleepiness (68.8%)
Dizziness (25%)
Constipation (18.8%)
Palpitations (6.3%)
Malaise (6.3%)
Sources:
75 mg 1 times / day multiple, oral
Recommended
Dose: 75 mg, 1 times / day
Route: oral
Route: multiple
Dose: 75 mg, 1 times / day
Sources:
unhealthy, mean age 55 years
Health Status: unhealthy
Age Group: mean age 55 years
Sex: M+F
Sources:
Disc. AE: Drowsiness, Dry mouth...
Other AEs: Drowsiness, Nausea...
AEs leading to
discontinuation/dose reduction:
Drowsiness (10%)
Dry mouth (10%)
Other AEs:
Drowsiness (51.8%)
Nausea (7.4%)
Headache (7.4%)
Dry mouth (63%)
Thirst (7.4%)
Tiredness (7.4%)
Bad taste (18.5%)
Attention concentration difficulty (7.4%)
Hyperglycaemia (3.7%)
Sources:
59 mg 1 times / day multiple, oral
Studied dose
Dose: 59 mg, 1 times / day
Route: oral
Route: multiple
Dose: 59 mg, 1 times / day
Sources:
unhealthy, mean age 60.4 years
Health Status: unhealthy
Age Group: mean age 60.4 years
Sex: M+F
Sources:
Disc. AE: Ankle edema, Dizziness...
Other AEs: Sedation, Dry mouth...
AEs leading to
discontinuation/dose reduction:
Ankle edema (4%)
Dizziness (4%)
Other AEs:
Sedation (32%)
Dry mouth (32%)
Postural hypotension (20%)
Weight gain (24%)
Ataxia (8%)
Constipation (12%)
Lethargy (20%)
Edema (8%)
Headache (12%)
Pruritus (12%)
Bad taste (4%)
Nausea (4%)
Diarrhea (4%)
Blurred vision (8%)
Sources:
520.3 mg 1 times / day single, oral
Studied dose
Dose: 520.3 mg, 1 times / day
Route: oral
Route: single
Dose: 520.3 mg, 1 times / day
Sources:
healthy
Health Status: healthy
Sex: M+F
Sources:
Other AEs: Tachycardia...
Other AEs:
Tachycardia
Sources:
AEs

AEs

AESignificanceDosePopulation
Agitation 20%
100 mg 1 times / day single, intravenous
Studied dose
Dose: 100 mg, 1 times / day
Route: intravenous
Route: single
Dose: 100 mg, 1 times / day
Sources:
healthy, 21 to 70 years
Health Status: healthy
Age Group: 21 to 70 years
Sex: M+F
Sources:
Drowsiness 20%
100 mg 1 times / day single, intravenous
Studied dose
Dose: 100 mg, 1 times / day
Route: intravenous
Route: single
Dose: 100 mg, 1 times / day
Sources:
healthy, 21 to 70 years
Health Status: healthy
Age Group: 21 to 70 years
Sex: M+F
Sources:
Dry mouth 20%
100 mg 1 times / day single, intravenous
Studied dose
Dose: 100 mg, 1 times / day
Route: intravenous
Route: single
Dose: 100 mg, 1 times / day
Sources:
healthy, 21 to 70 years
Health Status: healthy
Age Group: 21 to 70 years
Sex: M+F
Sources:
Language disorder 20%
100 mg 1 times / day single, intravenous
Studied dose
Dose: 100 mg, 1 times / day
Route: intravenous
Route: single
Dose: 100 mg, 1 times / day
Sources:
healthy, 21 to 70 years
Health Status: healthy
Age Group: 21 to 70 years
Sex: M+F
Sources:
Bradycardia grade 3, 20%
Disc. AE
100 mg 1 times / day single, intravenous
Studied dose
Dose: 100 mg, 1 times / day
Route: intravenous
Route: single
Dose: 100 mg, 1 times / day
Sources:
healthy, 21 to 70 years
Health Status: healthy
Age Group: 21 to 70 years
Sex: M+F
Sources:
Mental concentration difficult
10 % 1 times / day single, topical
Highest studied dose
Dose: 10 %, 1 times / day
Route: topical
Route: single
Dose: 10 %, 1 times / day
Sources:
unhealthy, 57 years
Health Status: unhealthy
Age Group: 57 years
Sex: M
Sources:
Thought disorder
10 % 1 times / day single, topical
Highest studied dose
Dose: 10 %, 1 times / day
Route: topical
Route: single
Dose: 10 %, 1 times / day
Sources:
unhealthy, 57 years
Health Status: unhealthy
Age Group: 57 years
Sex: M
Sources:
Mental status changes
520.3 mg 1 times / day single, oral
Studied dose
Dose: 520.3 mg, 1 times / day
Route: oral
Route: single
Dose: 520.3 mg, 1 times / day
Sources:
healthy, mean age 22.1 years
Health Status: healthy
Age Group: mean age 22.1 years
Sex: M+F
Sources:
Constipation 18.8%
25 mg 1 times / day multiple, oral
Studied dose
Dose: 25 mg, 1 times / day
Route: oral
Route: multiple
Dose: 25 mg, 1 times / day
Sources:
unhealthy, mean age 43.2 years
Health Status: unhealthy
Age Group: mean age 43.2 years
Sex: M+F
Sources:
Dizziness 25%
25 mg 1 times / day multiple, oral
Studied dose
Dose: 25 mg, 1 times / day
Route: oral
Route: multiple
Dose: 25 mg, 1 times / day
Sources:
unhealthy, mean age 43.2 years
Health Status: unhealthy
Age Group: mean age 43.2 years
Sex: M+F
Sources:
Malaise 6.3%
25 mg 1 times / day multiple, oral
Studied dose
Dose: 25 mg, 1 times / day
Route: oral
Route: multiple
Dose: 25 mg, 1 times / day
Sources:
unhealthy, mean age 43.2 years
Health Status: unhealthy
Age Group: mean age 43.2 years
Sex: M+F
Sources:
Palpitations 6.3%
25 mg 1 times / day multiple, oral
Studied dose
Dose: 25 mg, 1 times / day
Route: oral
Route: multiple
Dose: 25 mg, 1 times / day
Sources:
unhealthy, mean age 43.2 years
Health Status: unhealthy
Age Group: mean age 43.2 years
Sex: M+F
Sources:
Sleepiness 68.8%
25 mg 1 times / day multiple, oral
Studied dose
Dose: 25 mg, 1 times / day
Route: oral
Route: multiple
Dose: 25 mg, 1 times / day
Sources:
unhealthy, mean age 43.2 years
Health Status: unhealthy
Age Group: mean age 43.2 years
Sex: M+F
Sources:
Dry mouth 75%
25 mg 1 times / day multiple, oral
Studied dose
Dose: 25 mg, 1 times / day
Route: oral
Route: multiple
Dose: 25 mg, 1 times / day
Sources:
unhealthy, mean age 43.2 years
Health Status: unhealthy
Age Group: mean age 43.2 years
Sex: M+F
Sources:
Drowsiness 10%
Disc. AE
75 mg 1 times / day multiple, oral
Recommended
Dose: 75 mg, 1 times / day
Route: oral
Route: multiple
Dose: 75 mg, 1 times / day
Sources:
unhealthy, mean age 55 years
Health Status: unhealthy
Age Group: mean age 55 years
Sex: M+F
Sources:
Dry mouth 10%
Disc. AE
75 mg 1 times / day multiple, oral
Recommended
Dose: 75 mg, 1 times / day
Route: oral
Route: multiple
Dose: 75 mg, 1 times / day
Sources:
unhealthy, mean age 55 years
Health Status: unhealthy
Age Group: mean age 55 years
Sex: M+F
Sources:
Bad taste 18.5%
75 mg 1 times / day multiple, oral
Recommended
Dose: 75 mg, 1 times / day
Route: oral
Route: multiple
Dose: 75 mg, 1 times / day
Sources:
unhealthy, mean age 55 years
Health Status: unhealthy
Age Group: mean age 55 years
Sex: M+F
Sources:
Hyperglycaemia 3.7%
75 mg 1 times / day multiple, oral
Recommended
Dose: 75 mg, 1 times / day
Route: oral
Route: multiple
Dose: 75 mg, 1 times / day
Sources:
unhealthy, mean age 55 years
Health Status: unhealthy
Age Group: mean age 55 years
Sex: M+F
Sources:
Drowsiness 51.8%
75 mg 1 times / day multiple, oral
Recommended
Dose: 75 mg, 1 times / day
Route: oral
Route: multiple
Dose: 75 mg, 1 times / day
Sources:
unhealthy, mean age 55 years
Health Status: unhealthy
Age Group: mean age 55 years
Sex: M+F
Sources:
Dry mouth 63%
75 mg 1 times / day multiple, oral
Recommended
Dose: 75 mg, 1 times / day
Route: oral
Route: multiple
Dose: 75 mg, 1 times / day
Sources:
unhealthy, mean age 55 years
Health Status: unhealthy
Age Group: mean age 55 years
Sex: M+F
Sources:
Attention concentration difficulty 7.4%
75 mg 1 times / day multiple, oral
Recommended
Dose: 75 mg, 1 times / day
Route: oral
Route: multiple
Dose: 75 mg, 1 times / day
Sources:
unhealthy, mean age 55 years
Health Status: unhealthy
Age Group: mean age 55 years
Sex: M+F
Sources:
Headache 7.4%
75 mg 1 times / day multiple, oral
Recommended
Dose: 75 mg, 1 times / day
Route: oral
Route: multiple
Dose: 75 mg, 1 times / day
Sources:
unhealthy, mean age 55 years
Health Status: unhealthy
Age Group: mean age 55 years
Sex: M+F
Sources:
Nausea 7.4%
75 mg 1 times / day multiple, oral
Recommended
Dose: 75 mg, 1 times / day
Route: oral
Route: multiple
Dose: 75 mg, 1 times / day
Sources:
unhealthy, mean age 55 years
Health Status: unhealthy
Age Group: mean age 55 years
Sex: M+F
Sources:
Thirst 7.4%
75 mg 1 times / day multiple, oral
Recommended
Dose: 75 mg, 1 times / day
Route: oral
Route: multiple
Dose: 75 mg, 1 times / day
Sources:
unhealthy, mean age 55 years
Health Status: unhealthy
Age Group: mean age 55 years
Sex: M+F
Sources:
Tiredness 7.4%
75 mg 1 times / day multiple, oral
Recommended
Dose: 75 mg, 1 times / day
Route: oral
Route: multiple
Dose: 75 mg, 1 times / day
Sources:
unhealthy, mean age 55 years
Health Status: unhealthy
Age Group: mean age 55 years
Sex: M+F
Sources:
Constipation 12%
59 mg 1 times / day multiple, oral
Studied dose
Dose: 59 mg, 1 times / day
Route: oral
Route: multiple
Dose: 59 mg, 1 times / day
Sources:
unhealthy, mean age 60.4 years
Health Status: unhealthy
Age Group: mean age 60.4 years
Sex: M+F
Sources:
Headache 12%
59 mg 1 times / day multiple, oral
Studied dose
Dose: 59 mg, 1 times / day
Route: oral
Route: multiple
Dose: 59 mg, 1 times / day
Sources:
unhealthy, mean age 60.4 years
Health Status: unhealthy
Age Group: mean age 60.4 years
Sex: M+F
Sources:
Pruritus 12%
59 mg 1 times / day multiple, oral
Studied dose
Dose: 59 mg, 1 times / day
Route: oral
Route: multiple
Dose: 59 mg, 1 times / day
Sources:
unhealthy, mean age 60.4 years
Health Status: unhealthy
Age Group: mean age 60.4 years
Sex: M+F
Sources:
Lethargy 20%
59 mg 1 times / day multiple, oral
Studied dose
Dose: 59 mg, 1 times / day
Route: oral
Route: multiple
Dose: 59 mg, 1 times / day
Sources:
unhealthy, mean age 60.4 years
Health Status: unhealthy
Age Group: mean age 60.4 years
Sex: M+F
Sources:
Postural hypotension 20%
59 mg 1 times / day multiple, oral
Studied dose
Dose: 59 mg, 1 times / day
Route: oral
Route: multiple
Dose: 59 mg, 1 times / day
Sources:
unhealthy, mean age 60.4 years
Health Status: unhealthy
Age Group: mean age 60.4 years
Sex: M+F
Sources:
Weight gain 24%
59 mg 1 times / day multiple, oral
Studied dose
Dose: 59 mg, 1 times / day
Route: oral
Route: multiple
Dose: 59 mg, 1 times / day
Sources:
unhealthy, mean age 60.4 years
Health Status: unhealthy
Age Group: mean age 60.4 years
Sex: M+F
Sources:
Dry mouth 32%
59 mg 1 times / day multiple, oral
Studied dose
Dose: 59 mg, 1 times / day
Route: oral
Route: multiple
Dose: 59 mg, 1 times / day
Sources:
unhealthy, mean age 60.4 years
Health Status: unhealthy
Age Group: mean age 60.4 years
Sex: M+F
Sources:
Sedation 32%
59 mg 1 times / day multiple, oral
Studied dose
Dose: 59 mg, 1 times / day
Route: oral
Route: multiple
Dose: 59 mg, 1 times / day
Sources:
unhealthy, mean age 60.4 years
Health Status: unhealthy
Age Group: mean age 60.4 years
Sex: M+F
Sources:
Bad taste 4%
59 mg 1 times / day multiple, oral
Studied dose
Dose: 59 mg, 1 times / day
Route: oral
Route: multiple
Dose: 59 mg, 1 times / day
Sources:
unhealthy, mean age 60.4 years
Health Status: unhealthy
Age Group: mean age 60.4 years
Sex: M+F
Sources:
Diarrhea 4%
59 mg 1 times / day multiple, oral
Studied dose
Dose: 59 mg, 1 times / day
Route: oral
Route: multiple
Dose: 59 mg, 1 times / day
Sources:
unhealthy, mean age 60.4 years
Health Status: unhealthy
Age Group: mean age 60.4 years
Sex: M+F
Sources:
Nausea 4%
59 mg 1 times / day multiple, oral
Studied dose
Dose: 59 mg, 1 times / day
Route: oral
Route: multiple
Dose: 59 mg, 1 times / day
Sources:
unhealthy, mean age 60.4 years
Health Status: unhealthy
Age Group: mean age 60.4 years
Sex: M+F
Sources:
Ankle edema 4%
Disc. AE
59 mg 1 times / day multiple, oral
Studied dose
Dose: 59 mg, 1 times / day
Route: oral
Route: multiple
Dose: 59 mg, 1 times / day
Sources:
unhealthy, mean age 60.4 years
Health Status: unhealthy
Age Group: mean age 60.4 years
Sex: M+F
Sources:
Dizziness 4%
Disc. AE
59 mg 1 times / day multiple, oral
Studied dose
Dose: 59 mg, 1 times / day
Route: oral
Route: multiple
Dose: 59 mg, 1 times / day
Sources:
unhealthy, mean age 60.4 years
Health Status: unhealthy
Age Group: mean age 60.4 years
Sex: M+F
Sources:
Ataxia 8%
59 mg 1 times / day multiple, oral
Studied dose
Dose: 59 mg, 1 times / day
Route: oral
Route: multiple
Dose: 59 mg, 1 times / day
Sources:
unhealthy, mean age 60.4 years
Health Status: unhealthy
Age Group: mean age 60.4 years
Sex: M+F
Sources:
Blurred vision 8%
59 mg 1 times / day multiple, oral
Studied dose
Dose: 59 mg, 1 times / day
Route: oral
Route: multiple
Dose: 59 mg, 1 times / day
Sources:
unhealthy, mean age 60.4 years
Health Status: unhealthy
Age Group: mean age 60.4 years
Sex: M+F
Sources:
Edema 8%
59 mg 1 times / day multiple, oral
Studied dose
Dose: 59 mg, 1 times / day
Route: oral
Route: multiple
Dose: 59 mg, 1 times / day
Sources:
unhealthy, mean age 60.4 years
Health Status: unhealthy
Age Group: mean age 60.4 years
Sex: M+F
Sources:
Tachycardia
520.3 mg 1 times / day single, oral
Studied dose
Dose: 520.3 mg, 1 times / day
Route: oral
Route: single
Dose: 520.3 mg, 1 times / day
Sources:
healthy
Health Status: healthy
Sex: M+F
Sources:
Overview

OverviewOther

Drug as perpetrator​Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Seizures during lithium-amitriptyline therapy.
1979 Sep
Syncope associated with concurrent amitriptyline and fluconazole therapy.
2000 Dec
Fatal cholestatic jaundice associated with amitriptyline.
2000 Jul-Aug
Amitriptyline and somnambulism.
2000 Oct
Near fatal case of atrio-ventricular block induced by amitriptyline at therapeutic dose.
2000 Sep
A randomized trial of fluoxetine versus amitriptyline in musculo-skeletal pain.
2001
Long-term effects of tricyclic antidepressants on norepinephrine kinetics in humans.
2001
The concentration of three anti-seizure medications in hair: the effects of hair color, controlling for dose and age.
2001
Involvement of potassium channels in amitriptyline and clomipramine analgesia.
2001
Amitriptyline versus bupivacaine in rat sciatic nerve blockade.
2001 Apr
Evidence for the use of gabapentin in the treatment of diabetic peripheral neuropathy.
2001 Apr
The effects of amitriptyline, citalopram and reboxetine on autonomic nervous system. A randomised placebo-controlled study on healthy volunteers.
2001 Apr
Noradrenergic dysfunction and antidepressant treatment response.
2001 Apr
Changes in quantitatively assessed tremor during treatment of major depression with lithium augmented by paroxetine or amitriptyline.
2001 Apr
[Sensory neuropathy in HIV infection: pathogenesis and therapy].
2001 Apr 14
Controlling phantom limb pain in Sierra Leone.
2001 Apr 21
Combined pharmacotherapy for nocturnal enuresis.
2001 Aug
Interaction of psychotropic drugs with monoamine oxidase in rat brain.
2001 Aug
Serum levels and cardiovascular effects of tricyclic antidepressants and selective serotonin reuptake inhibitors in depressed patients.
2001 Aug
Regional potassium distribution in the brain in forensic relevant types of intoxication preliminary morphometric evaluation using a histochemical method.
2001 Feb
Preventive therapy in pediatric migraine.
2001 Feb
Capillary electrochromatography of hydrophobic amines on continuous beds.
2001 Feb
Antidepressant treatment and global tests of coagulation and fibrinolysis.
2001 Feb
Transplacental transfer of amitriptyline and nortriptyline in isolated perfused human placenta.
2001 Feb
Prolonged coma and loss of brainstem reflexes following amitriptyline overdose.
2001 Feb
Cromolyn cream for recalcitrant idiopathic vulvar vestibulitis: results of a placebo controlled study.
2001 Feb
Amitriptyline v. the rest: still the leading antidepressant after 40 years of randomised controlled trials.
2001 Feb
The effect of polyelectrolyte counterion specificity, charge density, and conformation on polyelectrolyte-amphiphile interaction: the carrageenan/furcellaran-amitriptyline system.
2001 Feb
Salmon calcitonin potentiates the analgesia induced by antidepressants.
2001 Jan
Amitriptyline enhances the central component of physiological tremor.
2001 Jan
Mirtazepine: heir apparent to amitriptyline?
2001 Jan-Feb
Isolated sural neuropathy presenting as lateral ankle pain.
2001 Jul
Antinociception by tricyclic antidepressants in the rat formalin test: differential effects on different behaviours following systemic and spinal administration.
2001 Jul
[Ciguatera: clinical relevance of a marine neurotoxin].
2001 Jul 13
The effect of amitriptyline on pain intensity and perception of stress in bruxers.
2001 Jun
Acute eosinophilic pneumonia associated with amitriptyline in a hemodialysis patient.
2001 Jun
Involvement of adenosine in the effect of antidepressants on glutamate and aspartate release in the rat prefrontal cortex.
2001 Jun
Pharmacological modulation of SK3 channels.
2001 Jun
Corticotropin-releasing hormone perturbations in interstitial cystitis patients: evidence for abnormal sympathetic activity.
2001 Jun
Ring flexibility within tricyclic antidepressant drugs.
2001 Jun
Bipolar disorder after mefloquine treatment.
2001 May
Treatment of neuropathic pain with venlafaxine.
2001 May
Advances in the management of neuropathic pain.
2001 May
Patterns of response to repeated total sleep deprivations in depression.
2001 May
Combining psychotherapy and antidepressants in the treatment of depression.
2001 May
[St. John's wort: a pharmaceutical with potentially dangerous interactions].
2001 May 10
Management of chronic tension-type headache with tricyclic antidepressant medication, stress management therapy, and their combination: a randomized controlled trial.
2001 May 2
Efficacy of spinal manipulation for chronic headache: a systematic review.
2001 Sep
Drug use and five-year incidence of age-related cataracts: The Beaver Dam Eye Study.
2001 Sep
Antidepressants as risk factor for ischaemic heart disease: case-control study in primary care.
2001 Sep 22
Patents

Sample Use Guides

For outpatients, 75 mg of amitriptyline HCl a day in divided doses. If necessary, this may be increased to a total of 150 mg per day. An alternate method of initiating therapy in outpatients is to begin with 50 to 100 mg amitriptyline HCl at bedtime. This may be increased by 25 or 50 mg as necessary in the bedtime dose to a total of 150 mg per day. Hospitalized patients may require 100 mg a day initially. This can be increased gradually to 200 mg a day if necessary up to 300 mg a day. Not recommended for patients under 12 years of age
Route of Administration: Oral
In Vitro Use Guide
Amitriptyline was used at 40 uM in isolated rat hepatocytes for 60,120,180 min.
Substance Class Chemical
Created
by admin
on Sat Jun 26 09:26:22 UTC 2021
Edited
by admin
on Sat Jun 26 09:26:22 UTC 2021
Record UNII
1806D8D52K
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AMITRIPTYLINE
INN   MART.   MI   VANDF   WHO-DD  
INN  
Official Name English
AMITRIPTYLINE [USP]
Common Name English
1-PROPANAMINE, 3-(10,11-DIHYDRO-5H-DIBENZO(A,D)CYCLOHEPTEN-5-YLIDENE)-N,N-DIMETHYL-
Systematic Name English
LAROXYL
Brand Name English
3-(10,11-DIHYDRO-5H-DIBENZO(A,D)CYCLOHEPTEN-5-YLIDENE)-N,N-DIMETHYL-1-PROPANAMINE
Systematic Name English
NORTRIPTYLINE HYDROCHLORIDE IMPURITY F [EP]
Common Name English
AMITRIPTYLINE [MI]
Common Name English
AMITRIPTYLINE [VANDF]
Common Name English
AMITRIPTYLINE [INN]
Common Name English
AMITRIPTYLINE [MART.]
Common Name English
SEROTEN
Common Name English
AMITRIPTYLINE [WHO-DD]
Common Name English
PROHEPTADIENE
Common Name English
TRIPTANOL
Common Name English
DAMITRIPTYLINE
Common Name English
FLAVYL
Common Name English
Classification Tree Code System Code
WHO-ATC N06CA01
Created by admin on Sat Jun 26 09:26:23 UTC 2021 , Edited by admin on Sat Jun 26 09:26:23 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 24.2.1
Created by admin on Sat Jun 26 09:26:23 UTC 2021 , Edited by admin on Sat Jun 26 09:26:23 UTC 2021
FDA ORPHAN DRUG 288809
Created by admin on Sat Jun 26 09:26:23 UTC 2021 , Edited by admin on Sat Jun 26 09:26:23 UTC 2021
WHO-VATC QN06AA09
Created by admin on Sat Jun 26 09:26:23 UTC 2021 , Edited by admin on Sat Jun 26 09:26:23 UTC 2021
LIVERTOX 44
Created by admin on Sat Jun 26 09:26:23 UTC 2021 , Edited by admin on Sat Jun 26 09:26:23 UTC 2021
NDF-RT N0000175752
Created by admin on Sat Jun 26 09:26:23 UTC 2021 , Edited by admin on Sat Jun 26 09:26:23 UTC 2021
FDA ORPHAN DRUG 739620
Created by admin on Sat Jun 26 09:26:23 UTC 2021 , Edited by admin on Sat Jun 26 09:26:23 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 8.4
Created by admin on Sat Jun 26 09:26:23 UTC 2021 , Edited by admin on Sat Jun 26 09:26:23 UTC 2021
NCI_THESAURUS C94727
Created by admin on Sat Jun 26 09:26:23 UTC 2021 , Edited by admin on Sat Jun 26 09:26:23 UTC 2021
WHO-VATC QN06CA01
Created by admin on Sat Jun 26 09:26:23 UTC 2021 , Edited by admin on Sat Jun 26 09:26:23 UTC 2021
WHO-ATC N06AA09
Created by admin on Sat Jun 26 09:26:23 UTC 2021 , Edited by admin on Sat Jun 26 09:26:23 UTC 2021
Code System Code Type Description
MESH
D000639
Created by admin on Sat Jun 26 09:26:23 UTC 2021 , Edited by admin on Sat Jun 26 09:26:23 UTC 2021
PRIMARY
LACTMED
Amitriptyline
Created by admin on Sat Jun 26 09:26:23 UTC 2021 , Edited by admin on Sat Jun 26 09:26:23 UTC 2021
PRIMARY
WIKIPEDIA
AMITRIPTYLINE
Created by admin on Sat Jun 26 09:26:23 UTC 2021 , Edited by admin on Sat Jun 26 09:26:23 UTC 2021
PRIMARY
HSDB
3007
Created by admin on Sat Jun 26 09:26:23 UTC 2021 , Edited by admin on Sat Jun 26 09:26:23 UTC 2021
PRIMARY
INN
976
Created by admin on Sat Jun 26 09:26:23 UTC 2021 , Edited by admin on Sat Jun 26 09:26:23 UTC 2021
PRIMARY
PUBCHEM
2160
Created by admin on Sat Jun 26 09:26:23 UTC 2021 , Edited by admin on Sat Jun 26 09:26:23 UTC 2021
PRIMARY
IUPHAR
200
Created by admin on Sat Jun 26 09:26:23 UTC 2021 , Edited by admin on Sat Jun 26 09:26:23 UTC 2021
PRIMARY
CAS
50-48-6
Created by admin on Sat Jun 26 09:26:23 UTC 2021 , Edited by admin on Sat Jun 26 09:26:23 UTC 2021
PRIMARY
EVMPD
SUB05462MIG
Created by admin on Sat Jun 26 09:26:23 UTC 2021 , Edited by admin on Sat Jun 26 09:26:23 UTC 2021
PRIMARY
MERCK INDEX
M1753
Created by admin on Sat Jun 26 09:26:23 UTC 2021 , Edited by admin on Sat Jun 26 09:26:23 UTC 2021
PRIMARY Merck Index
NCI_THESAURUS
C62005
Created by admin on Sat Jun 26 09:26:23 UTC 2021 , Edited by admin on Sat Jun 26 09:26:23 UTC 2021
PRIMARY
RXCUI
704
Created by admin on Sat Jun 26 09:26:23 UTC 2021 , Edited by admin on Sat Jun 26 09:26:23 UTC 2021
PRIMARY RxNorm
ChEMBL
CHEMBL629
Created by admin on Sat Jun 26 09:26:23 UTC 2021 , Edited by admin on Sat Jun 26 09:26:23 UTC 2021
PRIMARY
FDA UNII
1806D8D52K
Created by admin on Sat Jun 26 09:26:23 UTC 2021 , Edited by admin on Sat Jun 26 09:26:23 UTC 2021
PRIMARY
EPA CompTox
50-48-6
Created by admin on Sat Jun 26 09:26:23 UTC 2021 , Edited by admin on Sat Jun 26 09:26:23 UTC 2021
PRIMARY
DRUG BANK
DB00321
Created by admin on Sat Jun 26 09:26:23 UTC 2021 , Edited by admin on Sat Jun 26 09:26:23 UTC 2021
PRIMARY
DRUG CENTRAL
180
Created by admin on Sat Jun 26 09:26:23 UTC 2021 , Edited by admin on Sat Jun 26 09:26:23 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-041-6
Created by admin on Sat Jun 26 09:26:23 UTC 2021 , Edited by admin on Sat Jun 26 09:26:23 UTC 2021
PRIMARY
Related Record Type Details
METABOLIC ENZYME -> SUBSTRATE
Metabolizing reaction by CYP2D6: N-demethylation
BINDER->LIGAND
BINDING
TARGET -> INHIBITOR
TRANSPORTER -> INHIBITOR
METABOLIC ENZYME -> SUBSTRATE
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
METABOLIC ENZYME -> INHIBITOR
IC50
BINDING PROTEIN->LIGAND
Amitriptyline displayed an approximately 2:1 [drug:AGP] binding stoichiometry; DETERMINED BY ITC
BINDING
Kd
TARGET -> INHIBITOR
TARGET -> INHIBITOR
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> INHIBITOR
METABOLIC ENZYME -> SUBSTRATE
Related Record Type Details
METABOLITE -> PARENT
METABOLITE -> PARENT
URINE
METABOLITE ACTIVE -> PARENT
MAJOR
METABOLITE -> PARENT
METABOLITE -> PARENT
URINE
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
PARENT -> IMPURITY
UNSPECIFIED
EP
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC
MAXIMUM TOLERATED DOSE TOXICITY DEPRESSION, INPATIENTS: 300 MG/DAY

Route of Elimination PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC