Imipramine

Tricyclic Antidepressant — NERVOUS SYSTEM

Key facts

Imipramine is an ofp drug in the Tricyclic Antidepressant class catalogued in DrugCentral. It was first approved by the FDA in 1959. DrugCentral lists 48 molecular targets, including Hrh1, SLC6A4 and Adra1a. Recorded indications include Depressive disorder and Nocturnal enuresis.

• Approval status: ofp (first approved 1959 by the FDA).
• Drug class: Tricyclic Antidepressant.
• Molecular targets: Hrh1, SLC6A4, Adra1a and ADORA3 (48 listed in DrugCentral).
• Indications: Depressive disorder and Nocturnal enuresis.
• ATC code: N06AA02 (Non-selective monoamine reuptake inhibitors).
• Molecular formula: C19H24N2; molecular weight 280.42 g/mol.

Indications & contraindications

Drug–disease relationships curated by DrugCentral (OMOP / SNOMED concepts).

Indications (2)

• Depressive disorder
• Nocturnal enuresis

Off-label uses (8)

• Anxiety
• Attention deficit hyperactivity disorder
• Bulimia nervosa
• Cataplexy
• Narcolepsy
• Neuralgia
• Neuropathic pain
• Panic disorder

Contraindications (29)

• Alcohol intoxication
• Alcoholism
• Angle-closure glaucoma
• Benign prostatic hyperplasia
• Bipolar disorder
• Cerebrovascular accident
• Chronic heart failure
• Conduction disorder of the heart
• Disease of liver
• Disorder of cardiovascular system
• Disorder of coronary artery
• Electroconvulsive therapy
• Epilepsy
• Hyperthyroidism
• Hypomania
• Intestinal obstruction
• Kidney disease
• Mania
• Myocardial infarction in recovery phase
• Neutropenic disorder
• Ocular hypertension
• Paralytic ileus
• Retention of urine
• Schizophrenia
• Seizure disorder
• Suicidal thoughts
• Surgical procedure
• Syncope
• Thrombocytopenic disorder

Mechanism & targets

• Established pharmacologic class: Tricyclic Antidepressant

Molecular targets (48)

Target	Gene	Action	Activity
Histamine H1 receptor	Hrh1	unknown	IC50 10.22
Sodium-dependent serotonin transporter	SLC6A4	inhibitor	Kd 8.85
Alpha-1A adrenergic receptor	Adra1a	unknown	IC50 8.77
Adenosine receptor A3	ADORA3	unknown	IC50 8.36
Sodium-dependent serotonin transporter	Slc6a4	unknown	Ki 8.30
Muscarinic acetylcholine receptor M2	CHRM2	unknown	Ki 8.08
Transporter	Slc6a2	unknown	Ki 7.92
Sodium-dependent noradrenaline transporter	Slc6a2	unknown	Ki 7.92
Serotonin 2 (5-HT2) receptor	Htr2c|Htr2a|Htr2b	unknown	Ki 7.64
Histamine H1 receptor	HRH1	unknown	IC50 7.61
Alpha-1A adrenergic receptor	ADRA1A	unknown	IC50 7.50
Sodium-dependent noradrenaline transporter	SLC6A2	inhibitor	Kd 7.43
Sodium-dependent dopamine transporter	Slc6a3	unknown	Ki 7.38
Sodium-dependent serotonin transporter	Slc6a4	unknown	Ki 7.38
Muscarinic acetylcholine receptor M1	CHRM1	unknown	Ki 7.38
Serotonin (5-HT) receptor	Htr2c|Htr2a|Htr1a|Htr1b|Htr1d|Htr1f|Htr2b|Htr6|Htr7|Htr5a|Htr5b|Htr3a|Htr4|Htr3b	unknown	IC50 7.36
Adrenergic receptor alpha-1	Adra1b|Adra1d|Adra1a	unknown	Ki 7.34
Muscarinic acetylcholine receptor M3	CHRM3	unknown	Ki 7.22
Muscarinic acetylcholine receptor	Chrm1|Chrm3|Chrm4|Chrm5|Chrm2	unknown	Ki 7.19
Alpha-2B adrenergic receptor	ADRA2B	unknown	IC50 7.10

Regulatory approvals (1)

Date	Agency	Marketed as	Applicant	Orphan
1959-04-16	FDA	—	—

ATC classification

ATC code	Therapeutic hierarchy
N06AA02	NERVOUS SYSTEM › PSYCHOANALEPTICS › ANTIDEPRESSANTS › Non-selective monoamine reuptake inhibitors

Pharmacogenomics

Drug-label and guideline annotations from PharmGKB and CPIC.

• FDA label: CYP2D6 · Informative PGx
• HCSC label: CYP2D6 · Informative PGx

Reported adverse-event signals

Strongest FDA FAERS disproportionality signals (log-likelihood ratio). A signal is a statistical association in spontaneous reports, not proof that the drug causes the event.

MedDRA term	LLR
Completed suicide	198.0
Toxicity to various agents	138.7
Neuroleptic malignant syndrome	69.5
Paranoia	67.0
Antidepressant drug level above therapeutic	60.4
Hallucination, auditory	54.3
Overdose	51.8
Psychotic disorder	43.6
Depressed level of consciousness	42.9
Long QT syndrome	40.3
Drug interaction	37.7
Procedural hypotension	37.0

Chemical structure

Full physicochemical, ADMET and 3D-structure analysis of Imipramine is on its molecule page.

• Molecular formula: C₁₉H₂₄N₂
• Molecular weight: 280.42 g/mol
• CAS number: 50-49-7
• InChIKey: BCGWQEUPMDMJNV-UHFFFAOYSA-N
• PubChem CID: 3696

CN(C)CCCN1C2=CC=CC=C2CCC2=C1C=CC=C2

Frequently asked questions

Answers are generated from the structured data on this page, not written by hand.

What is Imipramine used for?

DrugCentral lists the following indications for Imipramine: Depressive disorder and Nocturnal enuresis.

How does Imipramine work?

Its molecular targets in DrugCentral include Hrh1, SLC6A4 (inhibitor), Adra1a and ADORA3.

When was Imipramine first approved?

Imipramine was first approved by the FDA in 1959.

What drug class does Imipramine belong to?

Imipramine is in the Tricyclic Antidepressant class.

What is the chemical formula of Imipramine?

Imipramine has the molecular formula C19H24N2 and a molecular weight of 280.42 g/mol.

Sources

• DrugCentral drug card 1427 — structure, indications, targets, approvals, pharmacologic classes (CC BY-SA 4.0)
• ChEMBL CHEMBL11 — compound record and bioactivity
• PubChem CID 3696 — chemical identifiers
• DrugBank DB00458 — drug record
• FDA UNII OGG85SX4E4 — substance identity
• DailyMed: FDA labels for Imipramine — current prescribing information (label search)
• UniProt P31645 (SLC6A4) — target protein
• UniProt P0DMS8 (ADORA3) — target protein
• UniProt P08172 (CHRM2) — target protein
• UniProt P35367 (HRH1) — target protein
• UniProt P35348 (ADRA1A) — target protein
• UniProt P23975 (SLC6A2) — target protein
• FDA Adverse Event Reporting System (openFDA FAERS) — adverse-event signals, as aggregated by DrugCentral
• PharmGKB / CPIC — pharmacogenomic label annotations

How this page is built: methodology · editorial policy & corrections.