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
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
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C19H21N |
| Molecular Weight | 263.3767 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL222 |
6.3 nM [Ki] | ||
Target ID: CHEMBL229 |
0.04 nM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Preventing | AVENTYL HYDROCHLORIDE Approved UseNortriptyline hydrochloride capsules are indicated for the relief of symptoms of depression. Endogenous depressions are more likely to be alleviated than are other depressive states. Launch Date1964 |
|||
| Primary | AVENTYL HYDROCHLORIDE Approved UseNortriptyline hydrochloride capsules are indicated for the relief of symptoms of depression. Endogenous depressions are more likely to be alleviated than are other depressive states. Launch Date1964 |
|||
| Primary | AVENTYL HYDROCHLORIDE Approved UseNortriptyline hydrochloride capsules are indicated for the relief of symptoms of depression. Endogenous depressions are more likely to be alleviated than are other depressive states. Launch Date1964 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
36 nM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12814461 |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
NORTRIPTYLINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
16.91 ng/mL OTHER GOV https://pdf.hres.ca/dpd_pm/00001266.PDF |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
NORTRIPTYLINE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1591 nM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12814461 |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
NORTRIPTYLINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
767.28 ng × h/mL OTHER GOV https://pdf.hres.ca/dpd_pm/00001266.PDF |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
NORTRIPTYLINE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
29.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12814461 |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
NORTRIPTYLINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
32.75 h OTHER GOV https://pdf.hres.ca/dpd_pm/00001266.PDF |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
NORTRIPTYLINE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
8.35% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7094510 |
NORTRIPTYLINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Page: 7.0 |
yes [Ki 450 uM] |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| major | likely (co-administration study) Comment: Concomitant use of tricyclic antidepressants with drugs that can inhibit cytochrome P450 2D6 may require lower doses than usually prescribed for either the tricyclic antidepressant or the other drug |
|||
| minor | ||||
| minor | ||||
| yes |
Tox targets
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| Amitriptyline and heart block. | 1967 Jul 29 |
|
| Ophthalmological effects of nortriptyline--relationship to plasma level. | 1972 |
|
| [Double blind clinical study of mianserin and nortriptyline (author's transl)]. | 1978 Sep-Oct |
|
| Cardiovascular side effects of long-term therapy with tricyclic antidepressants in the aged. | 1979 May |
|
| Slow tricyclic antidepressant metabolism, polypharmacy, and cardiac arrest. | 1980 Jan |
|
| Hoarseness and tricyclic antidepressants. | 1980 May |
|
| Atrial flutter with amoxapine: a case report. | 1981 Nov |
|
| Comparison of imipramine- and nortriptyline-induced orthostatic hypotension: a meaningful difference. | 1981 Sep |
|
| The clinical efficacy and side-effects of mianserin and nortriptyline in depressed out-patients: a double-blind randomized trial. | 1982 |
|
| Marked sinus tachycardia resulting from the synergistic effects of marijuana and nortriptyline. | 1983 May |
|
| Psychosis after discontinuation of nortriptyline. | 1984 Apr |
|
| The effects of mood changes and antidepressants on the cognitive capacity of elderly depressed patients. | 1989 Fall |
|
| Use of yohimbine to counteract nortriptyline-induced orthostatic hypotension. | 1989 Feb |
|
| Naproxen reversal of nortriptyline-induced orthostatic hypotension. | 1989 Sep |
|
| Myoclonus caused by a tricyclic antidepressant. | 1990 Apr |
|
| Low dose tricyclic tachycardia. | 1991 Jan |
|
| Tricyclics and heart failure. | 1991 Nov |
|
| Cognitive decline with nortriptyline use in a patient with dementia of the Alzheimer's type. | 1992 Jan |
|
| Midodrine for TCA-induced orthostatic hypotension. | 1993 Nov |
|
| Nortriptyline-induced fulminant hepatic failure. | 1995 Jan |
|
| Depression following smoking cessation in women. | 1996 |
|
| Nortriptyline-induced hepatic failure. | 1996 Feb |
|
| Spasmodic dysphonia, a rare form of tardive dystonia, induced by low-dose risperidone? | 2004 Mar |
|
| Interactions of cyclobenzaprine and tricyclic antidepressants. | 2005 Jan |
|
| Determination of the dissociation constants (pKa) of secondary and tertiary amines in organic media by capillary electrophoresis and their role in the electrophoretic mobility order inversion. | 2005 Mar 11 |
|
| The adsorption mechanism of nortryptiline on C18-bonded Discovery. | 2005 Nov 18 |
|
| [A case of Brugada syndrome with convulsive seizure during antidepressant administration: relation of antidepressant agents and arrhythmia leading to sudden death]. | 2006 |
|
| Gabapentin versus nortriptyline in post-herpetic neuralgia patients: a randomized, double-blind clinical trial--the GONIP Trial. | 2006 Aug |
|
| Photoinduced chemiluminescence of pharmaceuticals. | 2006 May 3 |
|
| Monoamine transporter gene polymorphisms and antidepressant response in koreans with late-life depression. | 2006 Oct 4 |
|
| Nortriptyline delays disease onset in models of chronic neurodegeneration. | 2007 Aug |
|
| Comparative metabolic capabilities and inhibitory profiles of CYP2D6.1, CYP2D6.10, and CYP2D6.17. | 2007 Aug |
|
| Inhibition of astroglial inwardly rectifying Kir4.1 channels by a tricyclic antidepressant, nortriptyline. | 2007 Feb |
|
| In silico prediction of pregnane X receptor activators by machine learning approaches. | 2007 Jan |
|
| Nortriptyline protects mitochondria and reduces cerebral ischemia/hypoxia injury. | 2008 Feb |
|
| Tako-tsubo syndrome following nortriptyline overdose. | 2008 Jun |
|
| Possession states precipitated by nortriptyline. | 2008 May |
|
| Bioactivation of the tricyclic antidepressant amitriptyline and its metabolite nortriptyline to arene oxide intermediates in human liver microsomes and recombinant P450s. | 2008 May 9 |
|
| Community-based randomised controlled trial evaluating falls and osteoporosis risk management strategies. | 2008 Nov 4 |
|
| Trifluoperazine: a rynodine receptor agonist. | 2009 Aug |
|
| Synergistic drug-cytokine induction of hepatocellular death as an in vitro approach for the study of inflammation-associated idiosyncratic drug hepatotoxicity. | 2009 Jun 15 |
|
| Adverse reactions to antidepressants. | 2009 Sep |
|
| Spontaneous hypothermia on intensive care unit admission is a predictor of unfavorable neurological outcome in patients after resuscitation: an observational cohort study. | 2010 |
|
| 3D-QSAR design of new escitalopram derivatives for the treatment of major depressive disorders. | 2010 Apr-Jun |
|
| Early-life stress and antidepressants modulate peripheral biomarkers in a gene-environment rat model of depression. | 2010 Aug 16 |
|
| Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method. | 2010 Dec |
|
| Current treatment options in smoking cessation. | 2010 Feb |
|
| An overview of Indian research in anxiety disorders. | 2010 Jan |
|
| Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. | 2011 Jul 14 |
|
| Palmitate increases the susceptibility of cells to drug-induced toxicity: an in vitro method to identify drugs with potential contraindications in patients with metabolic disease. | 2012 Oct |
Sample Use Guides
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.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 05:10:51 GMT 2023
by
admin
on
Sat Dec 16 05:10:51 GMT 2023
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| Record UNII |
00FN6IH15D
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| Record Status |
Validated (UNII)
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| Record Version |
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NCI_THESAURUS |
C94727
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169453
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C704
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CHEMBL445
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1474005
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DTXSID2045109
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m8074
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DBSALT000641
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212-973-0
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00FN6IH15D
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13468
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894-71-3
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00FN6IH15D
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100000085743
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203130
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SUB03464MIG
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1001637-77-9
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NO STRUCTURE GIVEN |
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ASSAY (TITRATION)
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IMPURITY -> PARENT |
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CHROMATOGRAPHIC PURITY (HPLC/UV)
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