U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C18H22N2.ClH
Molecular Weight 302.8422
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DESIPRAMINE HYDROCHLORIDE

SMILES

CNCCCN1c2ccccc2CCc3ccccc31.Cl

InChI

InChIKey=XAEWZDYWZHIUCT-UHFFFAOYSA-N
InChI=1S/C18H22N2.ClH/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;1H

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.4609
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Low dose tricyclic tachycardia.
1991 Jan
Repeated administration of desmethylimipramine blocks the reserpine-induced increase in tyrosine hydroxylase mRNA in locus coeruleus neurons of the rat.
1991 Jul
Changes in convulsion susceptibility of lidocaine by alteration of brain catecholaminergic functions.
1991 May
Regulation of serotonin type 2 (5-HT2) and beta-adrenergic receptors in rat cerebral cortex following novel and classical antidepressant treatment.
1991 Nov
Sudden self-harm while taking fluoxetine.
1992 Aug
Control of depression with fluoxetine and antiseizure medication in a brain-injured patient.
1992 Feb
Increased pulse and blood pressure associated with desipramine treatment of bulimia nervosa.
1992 Jun
The involvement of norepinephrine and microglia in hypothalamic and splenic IL-1beta responses to stress.
2006 Apr
Nigrostriatal damage with 6-OHDA: validation of routinely applied procedures.
2006 Aug
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
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
Rhesus monkey trace amine-associated receptor 1 signaling: enhancement by monoamine transporters and attenuation by the D2 autoreceptor in vitro.
2007 Apr
Reduced evoked fos expression in activity-related brain regions in animal models of behavioral depression.
2007 Aug 15
Pharmacokinetics of desipramine HCl when administered with cinacalcet HCl.
2007 Feb
Desipramine activated Bcl-2 expression and inhibited lipopolysaccharide-induced apoptosis in hippocampus-derived adult neural stem cells.
2007 May
Reduction of high-affinity beta2-adrenergic receptor binding by hyperforin and hyperoside on rat C6 glioblastoma cells measured by fluorescence correlation spectroscopy.
2007 May 1
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
A possible role for the endocannabinoid system in the neurobiology of depression.
2007 Nov 19
The role of the entorhinal cortex in extinction: influences of aging.
2008
Desipramine induces apoptotic cell death through nonmitochondrial and mitochondrial pathways in different types of human colon carcinoma cells.
2008
The role of NMDA receptor antagonists in nicotine tolerance, sensitization, and physical dependence: a preclinical review.
2008 Apr 30
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
Comparison of the effects of desmethylimipramine on behavior in the forced swim test in peripubertal and adult rats.
2008 Feb
An anti-immobility effect of exogenous corticosterone in mice.
2008 Feb 2
A novel approach for predicting antidepressant-induced sexual dysfunction in rats.
2008 Jan
Photophysics and photochemistry of imipramine, desimipramine, and clomipramine in several solvents: a fluorescence, 266 nm laser flash, and theoretical study.
2008 Jan 10
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
Impaired parasympathetic function increases susceptibility to inflammatory bowel disease in a mouse model of depression.
2008 Jun
Glucagon-like peptide 1 receptor stimulation reverses key deficits in distinct rodent models of Parkinson's disease.
2008 May 21
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 Fri Jun 25 21:11:41 UTC 2021
Edited
by admin
on Fri Jun 25 21:11:41 UTC 2021
Record UNII
1Y58DO4MY1
Record Status Validated (UNII)
Record Version
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Name Type Language
DESIPRAMINE HYDROCHLORIDE
EP   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN  
Official Name English
DESIPRAMINE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
RMI 9,384A
Code English
RMI-9384A
Code English
5H-DIBENZ(B,F)AZEPINE-5-PROPANAMINE, 10,11-DIHYDRO-N-METHYL-, MONOHYDROCHLORIDE
Common Name English
JB-8181
Code English
EX-4355
Code English
PERTOFRANE
Brand Name English
EX 4355
Code English
DESIPRAMINE HYDROCHLORIDE [MI]
Common Name English
NSC-114901
Code English
DESIPRAMINE HCL
Common Name English
DESIPRAMINE HYDROCHLORIDE [USP-RS]
Common Name English
DESIPRAMINE HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
DESIPRAMINE HYDROCHLORIDE [WHO-DD]
Common Name English
G-35020
Code English
10,11-DIHYDRO-5-(3-(METHYLAMINO)PROPYL)-5H-DIBENZ(B,F)AZEPINE MONOHYDROCHLORIDE
Systematic Name English
DESIPRAMINE HYDROCHLORIDE [MART.]
Common Name English
NORPRAMIN
Brand Name English
DMI
Common Name English
DESIPRAMINE HYDROCHLORIDE [USAN]
Common Name English
DESIPRAMINE HYDROCHLORIDE [VANDF]
Common Name English
DESIPRAMINE HYDROCHLORIDE [JAN]
Common Name English
DESIPRAMINE HYDROCHLORIDE [USP]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C94727
Created by admin on Fri Jun 25 21:11:41 UTC 2021 , Edited by admin on Fri Jun 25 21:11:41 UTC 2021
Code System Code Type Description
CAS
58-28-6
Created by admin on Fri Jun 25 21:11:41 UTC 2021 , Edited by admin on Fri Jun 25 21:11:41 UTC 2021
PRIMARY
NCI_THESAURUS
C28979
Created by admin on Fri Jun 25 21:11:41 UTC 2021 , Edited by admin on Fri Jun 25 21:11:41 UTC 2021
PRIMARY
RXCUI
203174
Created by admin on Fri Jun 25 21:11:41 UTC 2021 , Edited by admin on Fri Jun 25 21:11:41 UTC 2021
PRIMARY RxNorm
USP_CATALOG
1172006
Created by admin on Fri Jun 25 21:11:41 UTC 2021 , Edited by admin on Fri Jun 25 21:11:41 UTC 2021
PRIMARY USP-RS
EVMPD
SUB01595MIG
Created by admin on Fri Jun 25 21:11:41 UTC 2021 , Edited by admin on Fri Jun 25 21:11:41 UTC 2021
PRIMARY
MERCK INDEX
M4191
Created by admin on Fri Jun 25 21:11:41 UTC 2021 , Edited by admin on Fri Jun 25 21:11:41 UTC 2021
PRIMARY Merck Index
DRUG BANK
DBSALT000042
Created by admin on Fri Jun 25 21:11:41 UTC 2021 , Edited by admin on Fri Jun 25 21:11:41 UTC 2021
PRIMARY
EPA CompTox
58-28-6
Created by admin on Fri Jun 25 21:11:41 UTC 2021 , Edited by admin on Fri Jun 25 21:11:41 UTC 2021
PRIMARY
PUBCHEM
65327
Created by admin on Fri Jun 25 21:11:41 UTC 2021 , Edited by admin on Fri Jun 25 21:11:41 UTC 2021
PRIMARY
ChEMBL
CHEMBL72
Created by admin on Fri Jun 25 21:11:41 UTC 2021 , Edited by admin on Fri Jun 25 21:11:41 UTC 2021
PRIMARY
FDA UNII
1Y58DO4MY1
Created by admin on Fri Jun 25 21:11:41 UTC 2021 , Edited by admin on Fri Jun 25 21:11:41 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-373-1
Created by admin on Fri Jun 25 21:11:41 UTC 2021 , Edited by admin on Fri Jun 25 21:11:41 UTC 2021
PRIMARY
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