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Details

Stereochemistry ACHIRAL
Molecular Formula C18H22N2
Molecular Weight 266.3807
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DESIPRAMINE

SMILES

CNCCCN1C2=C(CCC3=C1C=CC=C3)C=CC=C2

InChI

InChIKey=HCYAFALTSJYZDH-UHFFFAOYSA-N
InChI=1S/C18H22N2/c1-19-13-6-14-20-17-9-4-2-7-15(17)11-12-16-8-3-5-10-18(16)20/h2-5,7-10,19H,6,11-14H2,1H3

HIDE SMILES / InChI
Desipramine is a tricyclic antidepressant that was approved by the FDA in 1964. It was derived from imipramine, which was the first tricyclic antidepressant to be manufactured. Desipramine is one of many tricyclic antidepressants, and this type of antidepressant gets its name due to its three-ring chemical structure. Desipramine, a secondary amine tricyclic antidepressant, is structurally related to both the skeletal muscle relaxant cyclobenzaprine and the thioxanthene antipsychotics such as thiothixene. It is the active metabolite of imipramine, a tertiary amine TCA. The acute effects of desipramine include inhibition of noradrenaline re-uptake at noradrenergic nerve endings and inhibition of serotonin (5-hydroxy tryptamine, 5HT) re-uptake at the serotoninergic nerve endings in the central nervous system. Desipramine exhibits greater noradrenergic re-uptake inhibition compared to the tertiary amine TCA imipramine. In addition to inhibiting neurotransmitter re-uptake, desipramine down-regulates beta-adrenergic receptors in the cerebral cortex and sensitizes serotonergic receptors with chronic use. The overall effect is increased serotonergic transmission. Antidepressant effects are typically observed 2 - 4 weeks following the onset of therapy though some patients may require up to 8 weeks of therapy prior to symptom improvement. Patients experiencing more severe depressive episodes may respond quicker than those with mild depressive symptoms. Desipramine is marketed under the trade name Norpramin, indicated for the treatment of depression.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
NORPRAMIN

Approved Use

Desipramine hydrochloride tablets are indicated for the treatment of depression.

Launch Date

1964
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
21.8 ng/mL
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DESIPRAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
656 ng × h/mL
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DESIPRAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
21 h
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DESIPRAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
9.78%
DESIPRAMINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
2500 mg single, oral
Overdose
Dose: 2500 mg
Route: oral
Route: single
Dose: 2500 mg
Sources:
healthy, 2 years
n = 1
Health Status: healthy
Age Group: 2 years
Sex: F
Population Size: 1
Sources:
Other AEs: Coma, Seizures...
Other AEs:
Coma (grade 5, 1 patient)
Seizures (grade 5, 1 patient)
Hypotension (grade 5, 1 patient)
Sources:
300 mg 1 times / day multiple, oral
Highest studied dose
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy, adult
n = 1
Health Status: unhealthy
Age Group: adult
Population Size: 1
Sources:
25 mg 1 times / day multiple, oral
Recommended
Dose: 25 mg, 1 times / day
Route: oral
Route: multiple
Dose: 25 mg, 1 times / day
Sources:
unhealthy, children | adolescents | and young adults
Health Status: unhealthy
Condition: major depressive disorde
Age Group: children | adolescents | and young adults
Sources:
Other AEs: Suicidal ideation...
AEs

AEs

AESignificanceDosePopulation
Coma grade 5, 1 patient
2500 mg single, oral
Overdose
Dose: 2500 mg
Route: oral
Route: single
Dose: 2500 mg
Sources:
healthy, 2 years
n = 1
Health Status: healthy
Age Group: 2 years
Sex: F
Population Size: 1
Sources:
Hypotension grade 5, 1 patient
2500 mg single, oral
Overdose
Dose: 2500 mg
Route: oral
Route: single
Dose: 2500 mg
Sources:
healthy, 2 years
n = 1
Health Status: healthy
Age Group: 2 years
Sex: F
Population Size: 1
Sources:
Seizures grade 5, 1 patient
2500 mg single, oral
Overdose
Dose: 2500 mg
Route: oral
Route: single
Dose: 2500 mg
Sources:
healthy, 2 years
n = 1
Health Status: healthy
Age Group: 2 years
Sex: F
Population Size: 1
Sources:
Suicidal ideation
25 mg 1 times / day multiple, oral
Recommended
Dose: 25 mg, 1 times / day
Route: oral
Route: multiple
Dose: 25 mg, 1 times / day
Sources:
unhealthy, children | adolescents | and young adults
Health Status: unhealthy
Condition: major depressive disorde
Age Group: children | adolescents | and young adults
Sources:
Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer






Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
no (co-administration study)
Comment: Ketoconazole did not alter the pharmacokinetics of orally administered desipramine in healthy volunteers; Genetic deficiency in CYP2D6 activity results in a 85% lower oral clearance of desipramine, as shown by a single dose pharmacokinetic study in healthy volunteers
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Ascending catecholamine pathways and amphetamine-induced locomotor activity: importance of dopamine and apparent non-involvement of norepinephrine.
1975 Aug 15
Desipramine-induced oral-pharyngeal disturbances: stuttering and jaw myoclonus.
1992 Dec
Effect of tolcapone on the haemodynamic effects and tolerability of desipramine.
2000
Antidepressant drugs appear to enhance cocaine-induced toxicity.
2000 Feb
National Patterns of Medication Treatment for Depression, 1987 to 2001.
2001 Dec
Tricyclic antidepressants and the Brugada syndrome: an example of Brugada waves appearing after the administration of desipramine.
2002 Aug
[Effect of local and systemic desipramine administration on extracellular noradrenaline in the myocardium of rats].
2002 Dec
Acute treatment with the cyclic antidepressant desipramine, but not fluoxetine, increases membrane-associated G protein-coupled receptor kinases 2/3 in rat brain.
2002 Dec
Prediction of treatment outcome by baseline urine cocaine results and self-reported cocaine use for cocaine and opioid dependence.
2003
Effects of electroconvulsive seizures and antidepressant drugs on brain-derived neurotrophic factor protein in rat brain.
2003 Oct 1
[Effects of neurotensin microinjected into ventral tegmental area on spontaneous motor activity in neonatal 6-hydroxydopamine-treated rats].
2004 Apr
Inhibition of cytochrome P450 enzymes participating in p-nitrophenol hydroxylation by drugs known as CYP2E1 inhibitors.
2004 Apr 15
Ethnic differences in substance abuse treatment retention, compliance, and outcome from two clinical trials.
2004 Feb
Discovering modes of action for therapeutic compounds using a genome-wide screen of yeast heterozygotes.
2004 Jan 9
Clinical implications of genetic polymorphism of CYP2D6 in Mexican Americans.
2004 Jun 1
NO induced apoptosis of vascular smooth muscle cells accompanied by ceramide increase.
2004 May
Inhibition of G protein-activated inwardly rectifying K+ channels by various antidepressant drugs.
2004 Oct
Brain-derived tumor necrosis factor-alpha and its involvement in noradrenergic neuron functioning involved in the mechanism of action of an antidepressant.
2004 Sep
Coadministration of histone deacetylase inhibitors and perifosine synergistically induces apoptosis in human leukemia cells through Akt and ERK1/2 inactivation and the generation of ceramide and reactive oxygen species.
2005 Mar 15
Response to SSRI-induced enuresis: a case report.
2006 Feb
[Trazodone for the treatment of behavioral and psychological symptoms of dementia (BPSD) in Alzheimer's disease: a retrospective study focused on the aggression and negativism in caregiving situations].
2006 Jun
Reduced evoked fos expression in activity-related brain regions in animal models of behavioral depression.
2007 Aug 15
Desipramine activated Bcl-2 expression and inhibited lipopolysaccharide-induced apoptosis in hippocampus-derived adult neural stem cells.
2007 May
D-161, a novel pyran-based triple monoamine transporter blocker: behavioral pharmacological evidence for antidepressant-like action.
2008 Jul 28
Glucagon-like peptide 1 receptor stimulation reverses key deficits in distinct rodent models of Parkinson's disease.
2008 May 21
Community-based randomised controlled trial evaluating falls and osteoporosis risk management strategies.
2008 Nov 4
Reactivation of inflammatory bowel disease in a mouse model of depression.
2009 Jun
Antidepressants influence somatostatin levels and receptor pharmacology in brain.
2009 Mar
Patents

Sample Use Guides

Usual Adult Dose for Depression 100 to 200 mg orally per day Maximum dose: 300 mg orally per day Comments: -Dosage should be initiated at a lower level and increased according to tolerance and clinical response. -In severely ill patients, dosage may be further increased to 300 mg per day if needed. -Treatment of patients requiring as much as 300 mg should generally be initiated in hospitals. Usual Geriatric Dose for Depression 25 to 100 mg orally per day Maximum dose: 150 mg orally per day
Route of Administration: Oral
Neuronal uptake 1 inhibitor desipramine (100 nM) decreased NE in 60-min hypothermic ischemia in isolated perfused guinea pig hearts.
Name Type Language
DESIPRAMINE
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
Desipramine [WHO-DD]
Common Name English
10,11-DIHYDRO-5-(3-(METHYLAMINO)PROPYL)-5H-DIBENZ(B,F)AZEPINE
Systematic Name English
N-DESMETHYLIMIPRAMINE
Common Name English
5H-DIBENZ(B,F)AZEPINE-5-PROPANAMINE, 10,11-DIHYDRO-N-METHYL-
Systematic Name English
DESIPRAMINE [VANDF]
Common Name English
DESIPRAMINE [HSDB]
Common Name English
IMIPRAMINE, DEMETHYL-
Common Name English
MONODEMETHYLIMIPRAMINE
Common Name English
IMIPRAMINE HYDROCHLORIDE IMPURITY A [EP IMPURITY]
Common Name English
desipramine [INN]
Common Name English
NORIMIPRAMINE
Common Name English
DESIPRAMINE [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C94727
Created by admin on Fri Dec 15 15:16:05 GMT 2023 , Edited by admin on Fri Dec 15 15:16:05 GMT 2023
NDF-RT N0000175752
Created by admin on Fri Dec 15 15:16:05 GMT 2023 , Edited by admin on Fri Dec 15 15:16:05 GMT 2023
LIVERTOX NBK548233
Created by admin on Fri Dec 15 15:16:05 GMT 2023 , Edited by admin on Fri Dec 15 15:16:05 GMT 2023
WHO-ATC N06AA01
Created by admin on Fri Dec 15 15:16:05 GMT 2023 , Edited by admin on Fri Dec 15 15:16:05 GMT 2023
WHO-VATC QN06AA01
Created by admin on Fri Dec 15 15:16:05 GMT 2023 , Edited by admin on Fri Dec 15 15:16:05 GMT 2023
Code System Code Type Description
CAS
50-47-5
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PRIMARY
ChEMBL
CHEMBL72
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EPA CompTox
DTXSID6022896
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SMS_ID
100000083169
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PRIMARY
PUBCHEM
2995
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PRIMARY
EVMPD
SUB06995MIG
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PRIMARY
INN
1500
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PRIMARY
CHEBI
47781
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PRIMARY
ECHA (EC/EINECS)
200-040-0
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PRIMARY
HSDB
3052
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PRIMARY
DRUG CENTRAL
812
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PRIMARY
RXCUI
3247
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PRIMARY RxNorm
DRUG BANK
DB01151
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PRIMARY
MERCK INDEX
m4191
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PRIMARY Merck Index
IUPHAR
2399
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PRIMARY
WIKIPEDIA
DESIPRAMINE
Created by admin on Fri Dec 15 15:16:05 GMT 2023 , Edited by admin on Fri Dec 15 15:16:05 GMT 2023
PRIMARY
MESH
D003891
Created by admin on Fri Dec 15 15:16:05 GMT 2023 , Edited by admin on Fri Dec 15 15:16:05 GMT 2023
PRIMARY
NCI_THESAURUS
C61700
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PRIMARY
FDA UNII
TG537D343B
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PRIMARY
DAILYMED
TG537D343B
Created by admin on Fri Dec 15 15:16:05 GMT 2023 , Edited by admin on Fri Dec 15 15:16:05 GMT 2023
PRIMARY
LACTMED
Desipramine
Created by admin on Fri Dec 15 15:16:05 GMT 2023 , Edited by admin on Fri Dec 15 15:16:05 GMT 2023
PRIMARY