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Details

Stereochemistry ACHIRAL
Molecular Formula C19H21N.ClH
Molecular Weight 299.838
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NORTRIPTYLINE HYDROCHLORIDE

SMILES

Cl.CNCCC=C1C2=C(CCC3=C1C=CC=C3)C=CC=C2

InChI

InChIKey=SHAYBENGXDALFF-UHFFFAOYSA-N
InChI=1S/C19H21N.ClH/c1-20-14-6-11-19-17-9-4-2-7-15(17)12-13-16-8-3-5-10-18(16)19;/h2-5,7-11,20H,6,12-14H2,1H3;1H

HIDE SMILES / InChI

Description

Nortriptyline is a second-generation tricyclic antidepressant (TCA) marketed as the hydrochloride salt under the trade names Sensoval, Aventyl, Pamelor, Norpress, Allegron, Noritren and Nortrilen. Nortriptyline is used in the treatment of depression and childhood nocturnal enuresis. Its off-label uses include treatment of postherpetic neuralgia, angioedema and smoking Cessation, and attention deficit hyperactivity disorder in some neurological disorders. It is believed that nortriptyline either inhibits the reuptake of the neurotransmitter serotonin at the neuronal membrane or acts at beta-adrenergic receptors. Nortriptyline is US FDA-approved for the treatment of major depression. In the United Kingdom, it may also be used for treating nocturnal enuresis, with courses of treatment lasting no more than three months. The most common side effects include dry mouth, sedation, constipation, and increased appetite, mild blurred vision, tinnitus, occasionally hypomania or mania. An occasional side effect is a rapid or irregular heartbeat. Alcohol may exacerbate some of its side effects. However, fewer and milder side effects occur with nortriptyline than tertiary tricyclic antidepressants such as imipramine and amitriptyline. For this reason, nortriptyline is preferred to other tricyclic antidepressants, particularly with older adults, which also improves compliance.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
6.3 nM [Ki]
0.04 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
AVENTYL HYDROCHLORIDE
Primary
AVENTYL HYDROCHLORIDE
Primary
AVENTYL HYDROCHLORIDE

Cmax

ValueDoseCo-administeredAnalytePopulation
16.91 ng/mL
25 mg single, oral
NORTRIPTYLINE plasma
Homo sapiens
36 nM
25 mg single, oral
NORTRIPTYLINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
767.28 ng × h/mL
25 mg single, oral
NORTRIPTYLINE plasma
Homo sapiens
1591 nM × h
25 mg single, oral
NORTRIPTYLINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
32.75 h
25 mg single, oral
NORTRIPTYLINE plasma
Homo sapiens
29.3 h
25 mg single, oral
NORTRIPTYLINE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
8.35%
NORTRIPTYLINE plasma
Homo sapiens

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
25mg PO q6-8hr. No more than 150 mg/day
Route of Administration: Oral
In Vitro Use Guide
Two cell lines and eight primary cell cultures from metastatic melanoma deposits were exposed to three tricyclic drugs, amitriptyline, nortriptyline and clomipramine, at concentrations ranging from 200 to 6.25 µmol/l in the ATP-based tumour chemosensitivity assay. All three drugs showed activity, although nortriptyline was more active than clomipramine or amitriptyline in both cell lines and primary cell cultures, with an IC50 of 9, 27 and 33 µmol/l, respectively.