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Details

Stereochemistry ACHIRAL
Molecular Formula C18H22N2
Molecular Weight 266.3813
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DESIPRAMINE

SMILES

CNCCCN1c2ccccc2CCc3ccccc31

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

Molecular Formula C18H22N2
Molecular Weight 266.3813
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

-1.61395196E11
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
Low dose desipramine treatment of cocaine-related panic attacks.
1991 Dec
Changes in convulsion susceptibility of lidocaine by alteration of brain catecholaminergic functions.
1991 May
Increased pulse and blood pressure associated with desipramine treatment of bulimia nervosa.
1992 Jun
Oral contraceptives and panic disorder.
1992 May
Bupropion-induced carbohydrate craving and weight gain.
1992 Oct
National Patterns of Medication Treatment for Depression, 1987 to 2001.
2001 Dec
[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
Chronic treatment with desipramine and fluoxetine modulate BDNF, CaMKKalpha and CaMKKbeta mRNA levels in the hippocampus of transgenic mice expressing antisense RNA against the glucocorticoid receptor.
2004 Dec
Ethnic differences in substance abuse treatment retention, compliance, and outcome from two clinical trials.
2004 Feb
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
Norepinephrine-deficient mice lack responses to antidepressant drugs, including selective serotonin reuptake inhibitors.
2004 May 25
Evaluation of fresh and cryopreserved hepatocytes as in vitro drug metabolism tools for the prediction of metabolic clearance.
2004 Nov
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
Reboxetine for the treatment of patients with Cocaine Dependence Disorder.
2005 Apr
Blood pressure changes associated with medication treatment of adults with attention-deficit/hyperactivity disorder.
2005 Feb
Brugada syndrome precipitated by a tricyclic antidepressant.
2005 May
Selective cortical VGLUT1 increase as a marker for antidepressant activity.
2005 Nov
Interaction of organic cations with a newly identified plasma membrane monoamine transporter.
2005 Nov
Desipramine treatment of cocaine-dependent patients with depression: a placebo-controlled trial.
2005 Nov 1
A selective test for antidepressant treatments using rats bred for stress-induced reduction of motor activity in the swim test.
2005 Oct
The effects of desmethylimipramine on cyclic AMP-stimulated gene transcription in a model cell system.
2005 Sep 1
Nigrostriatal damage with 6-OHDA: validation of routinely applied procedures.
2006 Aug
Enhanced neurally evoked responses and inhibition of norepinephrine reuptake in rat mesenteric arteries after spinal transection.
2006 Jan
[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
Frequency of high-risk use of QT-prolonging medications.
2006 Jun
Down-regulation of norepinephrine transporter function induced by chronic administration of desipramine linking to the alteration of sensitivity of local-anesthetics-induced convulsions and the counteraction by co-administration with local anesthetics.
2006 Jun 22
Anti-inflammatory properties of desipramine and fluoxetine.
2007 May 3
CRE/CREB-driven up-regulation of gene expression by chronic social stress in CRE-luciferase transgenic mice: reversal by antidepressant treatment.
2007 May 9
Desipramine-induced apoptosis in human PC3 prostate cancer cells: activation of JNK kinase and caspase-3 pathways and a protective role of [Ca2+]i elevation.
2008 Aug 19
Do desipramine [10,11-dihydro-5-[3-(methylamino) propyl]-5H-dibenz[b,f]azepine monohydrochloride] and fluoxetine [N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]-propan-1-amine] ameliorate the extent of colonic damage induced by acetic acid in rats?
2008 Dec
The 5-hydroxytryptamine2A receptor antagonist R-(+)-alpha-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl-4-piperidinemethanol (M100907) attenuates impulsivity after both drug-induced disruption (dizocilpine) and enhancement (antidepressant drugs) of differential-reinforcement-of-low-rate 72-s behavior in the rat.
2008 Dec
D-161, a novel pyran-based triple monoamine transporter blocker: behavioral pharmacological evidence for antidepressant-like action.
2008 Jul 28
Narcolepsy: current treatment options and future approaches.
2008 Jun
Evaluation of the repeated open-space swim model of depression in the mouse.
2008 Nov
Community-based randomised controlled trial evaluating falls and osteoporosis risk management strategies.
2008 Nov 4
Desipramine potentiation of the acute depressant effects of ethanol: modulation by alpha2-adrenoreceptors and stress.
2008 Oct
Assessing the neuronal serotonergic target-based antidepressant stratagem: impact of in vivo interaction studies and knockout models.
2008 Sep
Neuronal damage and protection in the pathophysiology and treatment of psychiatric illness: stress and depression.
2009
Tetrabenazine as anti-chorea therapy in Huntington disease: an open-label continuation study. Huntington Study Group/TETRA-HD Investigators.
2009 Dec 18
Behavioral sensitization to cocaine: cooperation between glucocorticoids and epinephrine.
2009 Jul
Reactivation of inflammatory bowel disease in a mouse model of depression.
2009 Jun
Desipramine-induced Ca-independent apoptosis in Mg63 human osteosarcoma cells: dependence on P38 mitogen-activated protein kinase-regulated activation of caspase 3.
2009 Mar
Antidepressants influence somatostatin levels and receptor pharmacology in brain.
2009 Mar
Association of changes in norepinephrine and serotonin transporter expression with the long-term behavioral effects of antidepressant drugs.
2009 May
MPTP-induced neuroblast apoptosis in the subventricular zone is not regulated by dopamine or other monoamine transporters.
2009 Nov
Time course and dose response of alpha tocopherol on oxidative stress in haemodialysis patients.
2009 Oct 22
Transient supersensitivity to alpha-adrenoceptor agonists, and distinct hyper-reactivity to vasopressin and angiotensin II after denervation of rat tail artery.
2010 Jan
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.
Substance Class Chemical
Created
by admin
on Sat Jun 26 12:09:22 UTC 2021
Edited
by admin
on Sat Jun 26 12:09:22 UTC 2021
Record UNII
TG537D343B
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DESIPRAMINE
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official 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 [WHO-DD]
Common Name English
DESIPRAMINE [HSDB]
Common Name English
IMIPRAMINE, DEMETHYL-
Common Name English
MONODEMETHYLIMIPRAMINE
Common Name English
IMIPRAMINE HYDROCHLORIDE IMPURITY A [EP]
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 Sat Jun 26 12:09:23 UTC 2021 , Edited by admin on Sat Jun 26 12:09:23 UTC 2021
NDF-RT N0000175752
Created by admin on Sat Jun 26 12:09:23 UTC 2021 , Edited by admin on Sat Jun 26 12:09:23 UTC 2021
LIVERTOX 283
Created by admin on Sat Jun 26 12:09:23 UTC 2021 , Edited by admin on Sat Jun 26 12:09:23 UTC 2021
WHO-ATC N06AA01
Created by admin on Sat Jun 26 12:09:23 UTC 2021 , Edited by admin on Sat Jun 26 12:09:23 UTC 2021
WHO-VATC QN06AA01
Created by admin on Sat Jun 26 12:09:23 UTC 2021 , Edited by admin on Sat Jun 26 12:09:23 UTC 2021
Code System Code Type Description
CAS
50-47-5
Created by admin on Sat Jun 26 12:09:23 UTC 2021 , Edited by admin on Sat Jun 26 12:09:23 UTC 2021
PRIMARY
ChEMBL
CHEMBL72
Created by admin on Sat Jun 26 12:09:23 UTC 2021 , Edited by admin on Sat Jun 26 12:09:23 UTC 2021
PRIMARY
EPA CompTox
50-47-5
Created by admin on Sat Jun 26 12:09:23 UTC 2021 , Edited by admin on Sat Jun 26 12:09:23 UTC 2021
PRIMARY
PUBCHEM
2995
Created by admin on Sat Jun 26 12:09:23 UTC 2021 , Edited by admin on Sat Jun 26 12:09:23 UTC 2021
PRIMARY
EVMPD
SUB06995MIG
Created by admin on Sat Jun 26 12:09:23 UTC 2021 , Edited by admin on Sat Jun 26 12:09:23 UTC 2021
PRIMARY
INN
1500
Created by admin on Sat Jun 26 12:09:23 UTC 2021 , Edited by admin on Sat Jun 26 12:09:23 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-040-0
Created by admin on Sat Jun 26 12:09:23 UTC 2021 , Edited by admin on Sat Jun 26 12:09:23 UTC 2021
PRIMARY
HSDB
3052
Created by admin on Sat Jun 26 12:09:23 UTC 2021 , Edited by admin on Sat Jun 26 12:09:23 UTC 2021
PRIMARY
DRUG CENTRAL
812
Created by admin on Sat Jun 26 12:09:23 UTC 2021 , Edited by admin on Sat Jun 26 12:09:23 UTC 2021
PRIMARY
RXCUI
3247
Created by admin on Sat Jun 26 12:09:23 UTC 2021 , Edited by admin on Sat Jun 26 12:09:23 UTC 2021
PRIMARY RxNorm
DRUG BANK
DB01151
Created by admin on Sat Jun 26 12:09:23 UTC 2021 , Edited by admin on Sat Jun 26 12:09:23 UTC 2021
PRIMARY
MERCK INDEX
M4191
Created by admin on Sat Jun 26 12:09:23 UTC 2021 , Edited by admin on Sat Jun 26 12:09:23 UTC 2021
PRIMARY Merck Index
IUPHAR
2399
Created by admin on Sat Jun 26 12:09:23 UTC 2021 , Edited by admin on Sat Jun 26 12:09:23 UTC 2021
PRIMARY
WIKIPEDIA
DESIPRAMINE
Created by admin on Sat Jun 26 12:09:23 UTC 2021 , Edited by admin on Sat Jun 26 12:09:23 UTC 2021
PRIMARY
MESH
D003891
Created by admin on Sat Jun 26 12:09:23 UTC 2021 , Edited by admin on Sat Jun 26 12:09:23 UTC 2021
PRIMARY
NCI_THESAURUS
C61700
Created by admin on Sat Jun 26 12:09:23 UTC 2021 , Edited by admin on Sat Jun 26 12:09:23 UTC 2021
PRIMARY
FDA UNII
TG537D343B
Created by admin on Sat Jun 26 12:09:23 UTC 2021 , Edited by admin on Sat Jun 26 12:09:23 UTC 2021
PRIMARY
LACTMED
Desipramine
Created by admin on Sat Jun 26 12:09:23 UTC 2021 , Edited by admin on Sat Jun 26 12:09:23 UTC 2021
PRIMARY
Related Record Type Details
TRANSPORTER -> SUBSTRATE
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
METABOLIC ENZYME -> SUBSTRATE
Metabolizing reaction by CYP2D6: Hydroxylation
TRANSPORTER -> INHIBITOR
TARGET -> INHIBITOR
TRANSPORTER -> INHIBITOR
METABOLIC ENZYME -> SUBSTRATE
Pharmacological action: Tricyclic antidepressant drug (TCA)
BINDER->LIGAND
TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
Related Record Type Details
PARENT -> METABOLITE ACTIVE
Imipramine has activities at both the serotonin and norepeinephrine transporters with greater affinity for the serotonin transporter while desipramine and 2-hydroxydesipramine have greater affinities for the norepinephrine transporter (Owens et al., 1997).
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
ACTIVE MOIETY