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 302.842
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DESIPRAMINE HYDROCHLORIDE

SMILES

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

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 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C18H22N2
Molecular Weight 266.3807
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
Sudden self-harm while taking fluoxetine.
1992 Aug
Desipramine-induced oral-pharyngeal disturbances: stuttering and jaw myoclonus.
1992 Dec
Reversal of desipramine toxicity in rats using drug-specific antibody Fab' fragment: effects on hypotension and interaction with sodium bicarbonate.
1992 Mar
Trazodone induction of migraine headache through mCPP.
1992 May
Effects of catecholamine uptake blockers in the caudate-putamen and subregions of the medial prefrontal cortex of the rat.
2002 May 17
Utility of crossover designs in clinical trials: efficacy of desipramine vs. placebo in opioid-dependent cocaine abusers.
2002 Spring
Validation of a simple, ethologically relevant paradigm for assessing anxiety in mice.
2003 Sep 1
Inhibition of cytochrome P450 enzymes participating in p-nitrophenol hydroxylation by drugs known as CYP2E1 inhibitors.
2004 Apr 15
Discovering modes of action for therapeutic compounds using a genome-wide screen of yeast heterozygotes.
2004 Jan 9
Reboxetine for the treatment of patients with Cocaine Dependence Disorder.
2005 Apr
Desipramine treatment for cocaine dependence in buprenorphine- or methadone-treated patients: baseline urine results as predictor of response.
2005 Jan-Feb
Desipramine treatment of cocaine-dependent patients with depression: a placebo-controlled trial.
2005 Nov 1
[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
A possible role for the endocannabinoid system in the neurobiology of depression.
2007 Nov 19
Desipramine induces apoptotic cell death through nonmitochondrial and mitochondrial pathways in different types of human colon carcinoma cells.
2008
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-induced Ca-independent apoptosis in Mg63 human osteosarcoma cells: dependence on P38 mitogen-activated protein kinase-regulated activation of caspase 3.
2009 Mar
Time course and dose response of alpha tocopherol on oxidative stress in haemodialysis patients.
2009 Oct 22
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 Wed Jul 05 22:48:16 UTC 2023
Edited
by admin
on Wed Jul 05 22:48:16 UTC 2023
Record UNII
1Y58DO4MY1
Record Status Validated (UNII)
Record Version
  • Download
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
Desipramine hydrochloride [WHO-DD]
Common Name English
EX-4355
Code English
DESIPRAMINE HYDROCHLORIDE [USP MONOGRAPH]
Common Name 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
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
Classification Tree Code System Code
NCI_THESAURUS C94727
Created by admin on Wed Jul 05 22:48:16 UTC 2023 , Edited by admin on Wed Jul 05 22:48:16 UTC 2023
Code System Code Type Description
CHEBI
4449
Created by admin on Wed Jul 05 22:48:16 UTC 2023 , Edited by admin on Wed Jul 05 22:48:16 UTC 2023
PRIMARY
CAS
58-28-6
Created by admin on Wed Jul 05 22:48:16 UTC 2023 , Edited by admin on Wed Jul 05 22:48:16 UTC 2023
PRIMARY
NCI_THESAURUS
C28979
Created by admin on Wed Jul 05 22:48:16 UTC 2023 , Edited by admin on Wed Jul 05 22:48:16 UTC 2023
PRIMARY
RXCUI
203174
Created by admin on Wed Jul 05 22:48:16 UTC 2023 , Edited by admin on Wed Jul 05 22:48:16 UTC 2023
PRIMARY RxNorm
NSC
114901
Created by admin on Wed Jul 05 22:48:16 UTC 2023 , Edited by admin on Wed Jul 05 22:48:16 UTC 2023
PRIMARY
EVMPD
SUB01595MIG
Created by admin on Wed Jul 05 22:48:16 UTC 2023 , Edited by admin on Wed Jul 05 22:48:16 UTC 2023
PRIMARY
SMS_ID
100000092164
Created by admin on Wed Jul 05 22:48:16 UTC 2023 , Edited by admin on Wed Jul 05 22:48:16 UTC 2023
PRIMARY
MERCK INDEX
M4191
Created by admin on Wed Jul 05 22:48:16 UTC 2023 , Edited by admin on Wed Jul 05 22:48:16 UTC 2023
PRIMARY Merck Index
DAILYMED
1Y58DO4MY1
Created by admin on Wed Jul 05 22:48:16 UTC 2023 , Edited by admin on Wed Jul 05 22:48:16 UTC 2023
PRIMARY
DRUG BANK
DBSALT000042
Created by admin on Wed Jul 05 22:48:16 UTC 2023 , Edited by admin on Wed Jul 05 22:48:16 UTC 2023
PRIMARY
EPA CompTox
DTXSID9046942
Created by admin on Wed Jul 05 22:48:16 UTC 2023 , Edited by admin on Wed Jul 05 22:48:16 UTC 2023
PRIMARY
PUBCHEM
65327
Created by admin on Wed Jul 05 22:48:16 UTC 2023 , Edited by admin on Wed Jul 05 22:48:16 UTC 2023
PRIMARY
ChEMBL
CHEMBL72
Created by admin on Wed Jul 05 22:48:16 UTC 2023 , Edited by admin on Wed Jul 05 22:48:16 UTC 2023
PRIMARY
RS_ITEM_NUM
1172006
Created by admin on Wed Jul 05 22:48:16 UTC 2023 , Edited by admin on Wed Jul 05 22:48:16 UTC 2023
PRIMARY
FDA UNII
1Y58DO4MY1
Created by admin on Wed Jul 05 22:48:16 UTC 2023 , Edited by admin on Wed Jul 05 22:48:16 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-373-1
Created by admin on Wed Jul 05 22:48:16 UTC 2023 , Edited by admin on Wed Jul 05 22:48:16 UTC 2023
PRIMARY
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ACTIVE MOIETY