- Molecular NameAmitriptyline
- SynonymAmitriprolidine; Amitriptylin; Amitriptyline HCL; Amitriptyline Hydrochloride; Amitryptiline; Amitryptyline; Amytriptiline
- Weight277.411
- Drugbank_IDDB00321
- ACS_NO50-48-6
- Show 3D model
- LogP (experiment)5.04
- LogP (predicted, AB/LogP v2.0)4.79
- pka9.4
- LogD (pH=7, predicted)3.01
- Solubility (experiment)0.0097 mg/ml
- LogS (predicted, ACD/Labs)(ph=7)-1.91
- LogSw (predicted, AB/LogsW2.0)0.01
- Sw (mg/ml) (predicted, ACD/Labs)0.04
- No.of HBond Donors0
- No.of HBond Acceptors1
- No.of Rotatable Bonds3
- TPSA3.24
- StatusFDA approved
- AdministrationN/A
- PharmacologyA psychoactive drug and pharmaceutical of the tricyclic antidepressant (TCA) chemical class which is used primarily as an antidepressant and anxiolytic agent. It is the most widely prescribed TCA and perhaps also the most efficient against depressive symptoms.
- Absorption_value95.0
- Absorption (description)Readily absorbed after oral administration and rapidly taken up by the tissues.
- Caco_2N/A
- Bioavailability48.0
- Protein binding94.8
- Volume of distribution (VD)15 L/kg
- Blood/Plasma Partitioning ratio (D_blood)Plasma:whole blood ratio, 1.2.
- MetabollsmHepatic CYP2C19, CYP1A2, CYP2D6. The main metabolic reaction, demethylation to form the major active metabolite, nortriptyline, is catalysed by CYP2C19 and CYP3A4 isoenzymes; hydroxylation is catalysed by CYP2D6; N-oxidation and conjugation also occur; other metabolites include didesmethylamitriptyline, 10-hydroxy- derivatives, conjugates, and amitriptyline N-oxide; the 10-hydroxy- metabolites may also have some activity.
- Half life21 h
- Excretiont is mainly excreted in the urine as free and conjugated metabolites, up to about 35% of a single dose being excreted in 24 h. About 50% of the excreted material is 10-hydroxynortriptyline and its glucuronide conjugate; up to 27% is 10-hydroxyamitriptyline (mainly conjugated); unchanged drug and nortriptyline each account for less than 5% of the excreted material. About 8% of a dose may be eliminated in the faeces as unchanged drug.
- Urinary Excretion<2
- Clerance11.5 ml/min/kg.
- ToxicityModerate intoxication is associated with plasma concentrations of 0.05 to 0.43 mg/L (mean 0.17) and severe toxic symptoms with concentrations greater than 0.3 mg/L. The fatal blood concentration range is 0.55 to 16.1 mg/L (mean 3.3). Corresponding toxic doses are greater than 1 g (moderate intoxication) and greater than 2 g (severe or fatal). 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.
- LD50 (rat)N/A
- LD50 (mouse)N/A