Doxepin

Tricyclic Antidepressant — DERMATOLOGICALS

Key facts

Doxepin is an ofp drug in the Tricyclic Antidepressant class catalogued in DrugCentral. It was first approved by the FDA in 1969. DrugCentral lists 30 molecular targets, including Adra1a, HRH1 and ADRA1A. Recorded indications include Anxiety, Atopic dermatitis, Bipolar affective disorder, current episode depression and Depressive disorder.

• Approval status: ofp (first approved 1969 by the FDA).
• Drug class: Tricyclic Antidepressant.
• Molecular targets: Adra1a, HRH1, ADRA1A and SLC6A2 (30 listed in DrugCentral).
• Indications: Anxiety, Atopic dermatitis, Bipolar affective disorder, current episode depression, Depressive disorder and Insomnia and others.
• ATC code: D04AX01 (Other antipruritics).
• Molecular formula: C19H21NO; molecular weight 279.38 g/mol.

Indications & contraindications

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

Indications (8)

• Anxiety
• Atopic dermatitis
• Bipolar affective disorder, current episode depression
• Depressive disorder
• Insomnia
• Itching of skin
• Lichen simplex chronicus
• Severe major depression with psychotic features

Off-label uses (1)

• Cholestatic pruritus

Contraindications (21)

• Alcoholism
• Angle-closure glaucoma
• Benign prostatic hyperplasia
• Bipolar affective disorder, current episode manic
• Breastfeeding (mother)
• Chronic idiopathic constipation
• Conduction disorder of the heart
• Congenital long QT syndrome
• Epilepsy
• Hepatic failure
• Hyperthyroidism
• Myocardial infarction in recovery phase
• Open-angle glaucoma
• Orthostatic hypotension
• Prolonged QT interval
• Retention of urine
• Sleep apnea
• Sleep automatism
• Suicidal thoughts
• Syncope
• Torsades de pointes

Mechanism & targets

• Established pharmacologic class: Tricyclic Antidepressant

Molecular targets (30)

Target	Gene	Action	Activity
Alpha-1A adrenergic receptor	Adra1a	unknown	IC50 11.00
Histamine H1 receptor	HRH1	antagonist	Ki 9.75
Alpha-1A adrenergic receptor	ADRA1A	unknown	Ki 7.63
Sodium-dependent noradrenaline transporter	SLC6A2	inhibitor	Kd 7.53
Alpha-1B adrenergic receptor	Adra1b	unknown	Ki 7.48
5-hydroxytryptamine receptor 2A	HTR2A	unknown	EC50 7.45
Muscarinic acetylcholine receptor M1	CHRM1	unknown	Ki 7.42
Alpha-1D adrenergic receptor	ADRA1D	unknown	Ki 7.37
Muscarinic acetylcholine receptor M3	CHRM3	unknown	Ki 7.28
Alpha-2B adrenergic receptor	ADRA2B	unknown	IC50 7.21
5-hydroxytryptamine receptor 2B	HTR2B	unknown	EC50 7.20
Sodium-dependent serotonin transporter	SLC6A4	inhibitor	Kd 7.17
Muscarinic acetylcholine receptor M5	CHRM5	unknown	Ki 7.12
Muscarinic acetylcholine receptor M4	CHRM4	unknown	Ki 7.09
5-hydroxytryptamine receptor 2C	HTR2C	unknown	EC50 7.00
Alpha-2C adrenergic receptor	ADRA2C	unknown	IC50 7.00
5-hydroxytryptamine receptor 6	HTR6	unknown	Ki 6.98
Muscarinic acetylcholine receptor M2	CHRM2	unknown	Ki 6.80
Histamine H4 receptor	HRH4	unknown	EC50 6.79
Serotonin (5-HT) receptor	Htr2c|Htr2a|Htr1a|Htr1b|Htr1d|Htr1f|Htr2b|Htr6|Htr7|Htr5a|Htr5b|Htr3a|Htr4|Htr3b	unknown	IC50 6.70

Regulatory approvals (1)

Date	Agency	Marketed as	Applicant	Orphan
1969-09-23	FDA	—	—

ATC classification

ATC code	Therapeutic hierarchy
D04AX01	DERMATOLOGICALS › ANTIPRURITICS, INCL. ANTIHISTAMINES, ANESTHETICS, ETC. › ANTIPRURITICS, INCL. ANTIHISTAMINES, ANESTHETICS, ETC. › Other antipruritics
N06AA12	NERVOUS SYSTEM › PSYCHOANALEPTICS › ANTIDEPRESSANTS › Non-selective monoamine reuptake inhibitors

Pharmacogenomics

Drug-label and guideline annotations from PharmGKB and CPIC.

• FDA label: CYP2C19, CYP2D6 · Informative PGx
• HCSC label: CYP2C19, 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	1552.8
Toxicity to various agents	1032.0
Drug abuse	261.4
Respiratory depression	252.6
Needle fatigue	227.3
Gait spastic	209.7
Cardio-respiratory arrest	201.0
Relapsing-remitting multiple sclerosis	193.1
Hypertonic bladder	156.8
Monoparesis	156.1
Bezoar	141.1
Nocturia	132.4

Chemical structure

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

• Molecular formula: C₁₉H₂₁NO
• Molecular weight: 279.38 g/mol
• CAS number: —
• InChIKey: ODQWQRRAPPTVAG-UHFFFAOYSA-N
• PubChem CID: 3158

CN(C)CCC=C1C2=CC=CC=C2COC2=C1C=CC=C2

Frequently asked questions

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

What is Doxepin used for?

DrugCentral lists the following indications for Doxepin: Anxiety, Atopic dermatitis, Bipolar affective disorder, current episode depression, Depressive disorder, Insomnia, Itching of skin, Lichen simplex chronicus and Severe major depression with psychotic features.

How does Doxepin work?

Its molecular targets in DrugCentral include Adra1a, HRH1 (antagonist), ADRA1A and SLC6A2 (inhibitor).

When was Doxepin first approved?

Doxepin was first approved by the FDA in 1969.

What drug class does Doxepin belong to?

Doxepin is in the Tricyclic Antidepressant class.

What is the chemical formula of Doxepin?

Doxepin has the molecular formula C19H21NO and a molecular weight of 279.38 g/mol.

Sources

• DrugCentral drug card 956 — structure, indications, targets, approvals, pharmacologic classes (CC BY-SA 4.0)
• ChEMBL CHEMBL1628227 — compound record and bioactivity
• PubChem CID 3158 — chemical identifiers
• DrugBank DB01142 — drug record
• FDA UNII 5ASJ6HUZ7D — substance identity
• DailyMed: FDA labels for Doxepin — current prescribing information (label search)
• UniProt P35367 (HRH1) — target protein
• UniProt P35348 (ADRA1A) — target protein
• UniProt P23975 (SLC6A2) — target protein
• UniProt P28223 (HTR2A) — target protein
• UniProt P11229 (CHRM1) — target protein
• UniProt P25100 (ADRA1D) — 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.