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doxepin 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
tricyclic compounds	956	1668-19-5

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: P-3693A doxepin doxepine doxepin hydrochloride silenor doxepin HCl	A dibenzoxepin tricyclic compound. It displays a range of pharmacological actions including maintaining adrenergic innervation. Its mechanism of action is not fully understood, but it appears to block reuptake of monoaminergic neurotransmitters into presynaptic terminals. It also possesses anticholinergic activity and modulates antagonism of histamine H(1)- and H(2)-receptors. Molecular weight: 279.38 Formula: C19H21NO CLOGP: 4.09 LIPINSKI: 0 HAC: 2 HDO: 0 TPSA: 12.47 ALOGS: -3.94 ROTB: 3 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

P-3693A
doxepin
doxepine
doxepin hydrochloride
silenor
doxepin HCl

A dibenzoxepin tricyclic compound. It displays a range of pharmacological actions including maintaining adrenergic innervation. Its mechanism of action is not fully understood, but it appears to block reuptake of monoaminergic neurotransmitters into presynaptic terminals. It also possesses anticholinergic activity and modulates antagonism of histamine H(1)- and H(2)-receptors.

Molecular weight: 279.38
Formula: C19H21NO
CLOGP: 4.09
LIPINSKI: 0
HAC: 2
HDO: 0
TPSA: 12.47
ALOGS: -3.94
ROTB: 3

Status: OFP

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

Dose	Unit	Route
0.10	g	O
0.10	g	P

ADMET properties:

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Property	Value	Reference
BA (Bioavailability)	30 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
MRTD (Maximum Recommended Therapeutic Daily Dose)	17.90 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
t_half (Half-life)	15 hours	Lombardo F, Berellini G, Obach RS
CL (Clearance)	14 mL/min/kg	Lombardo F, Berellini G, Obach RS
Vd (Volume of distribution)	12 L/kg	Lombardo F, Berellini G, Obach RS
BDDCS (Biopharmaceutical Drug Disposition Classification System)	1	Benet LZ, Broccatelli F, Oprea TI
fu (Fraction unbound in plasma)	0.20 %	Lombardo F, Berellini G, Obach RS
EoM (Fraction excreted unchanged in urine)	0 %	Benet LZ, Broccatelli F, Oprea TI

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Approvals:

Date	Agency	Company	Orphan
Sept. 23, 1969	FDA

FDA Adverse Event Reporting System (Female)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Completed suicide	628.13	13.12	435	17871	145238	63325478
Toxicity to various agents	408.51	13.12	425	17881	246825	63223891
Respiratory depression	220.79	13.12	98	18208	13617	63457099
Cardio-respiratory arrest	158.07	13.12	134	18172	59825	63410891
Drug abuse	95.43	13.12	111	18195	72407	63398309
Respiratory arrest	86.06	13.12	73	18233	32572	63438144
Depressed level of consciousness	79.96	13.12	94	18212	61984	63408732
Chronic spontaneous urticaria	74.71	13.12	23	18283	1134	63469582
Urticaria	65.07	13.12	146	18160	165656	63305060
Cardiac arrest	62.96	13.12	103	18203	92442	63378274

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FDA Adverse Event Reporting System (Male)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Completed suicide	386.14	17.26	258	8140	97910	34850623
Toxicity to various agents	207.46	17.26	247	8151	200115	34748418
Needle fatigue	154.35	17.26	37	8361	844	34947689
Relapsing-remitting multiple sclerosis	147.90	17.26	37	8361	1013	34947520
Gait spastic	146.32	17.26	37	8361	1059	34947474
Drug abuse	136.24	17.26	142	8256	98954	34849579
Hypertonic bladder	126.86	17.26	37	8361	1827	34946706
Monoparesis	118.46	17.26	37	8361	2309	34946224
Muscle spasticity	85.26	17.26	37	8361	5851	34942682
Central nervous system lesion	81.95	17.26	37	8361	6426	34942107

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FDA Adverse Event Reporting System (Geriatric)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Completed suicide	1005.52	13.79	705	21896	245062	79476725
Toxicity to various agents	590.60	13.79	658	21943	420882	79300905
Drug abuse	207.85	13.79	243	22358	162448	79559339
Cardio-respiratory arrest	180.04	13.79	186	22415	108324	79613463
Respiratory depression	155.12	13.79	97	22504	27533	79694254
Needle fatigue	137.46	13.79	35	22566	867	79720920
Gait spastic	127.64	13.79	35	22566	1162	79720625
Relapsing-remitting multiple sclerosis	119.39	13.79	35	22566	1484	79720303
Hypertonic bladder	98.30	13.79	39	22562	4162	79717625
Respiratory arrest	95.99	13.79	99	22502	57451	79664336

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	D04AX01	DERMATOLOGICALS ANTIPRURITICS, INCL. ANTIHISTAMINES, ANESTHETICS, ETC. ANTIPRURITICS, INCL. ANTIHISTAMINES, ANESTHETICS, ETC. Other antipruritics
ATC	N06AA12	NERVOUS SYSTEM PSYCHOANALEPTICS ANTIDEPRESSANTS Non-selective monoamine reuptake inhibitors
CHEBI has role	CHEBI:35469	antidepressants
FDA EPC	N0000175752	Tricyclic Antidepressant
MeSH PA	D000928	Antidepressive Agents
MeSH PA	D000929	Antidepressive Agents, Tricyclic
MeSH PA	D002491	Central Nervous System Agents
MeSH PA	D002492	Central Nervous System Depressants
MeSH PA	D018494	Histamine Agents
MeSH PA	D006633	Histamine Antagonists

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Drug Use | Suggest Off label Use Form| |View source of the data|

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Disease	Relation	SNOMED_ID	DOID
Atopic dermatitis	indication	24079001	DOID:3310
Depressive disorder	indication	35489007
Anxiety	indication	48694002
Lichen simplex chronicus	indication	53891004
Severe major depression with psychotic features	indication	73867007
Bipolar affective disorder, current episode depression	indication	191627008	DOID:3312
Insomnia	indication	193462001
Itching of skin	indication	418363000
Cholestatic pruritus	off-label use	707150004
Suicidal thoughts	contraindication	6471006

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🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	8.66	Basic

Orange Book patent data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Patent number	Patent expiration date	Patent use
EQ 3MG BASE	SILENOR	CURRAX	N022036	March 17, 2010	RX	TABLET	ORAL	10238620	May 18, 2027	TREATMENT OF INSOMNIA
EQ 3MG BASE	SILENOR	CURRAX	N022036	March 17, 2010	RX	TABLET	ORAL	10653662	May 18, 2027	TREATMENT OF INSOMNIA
EQ 3MG BASE	SILENOR	CURRAX	N022036	March 17, 2010	RX	TABLET	ORAL	9486437	May 18, 2027	TREATMENT OF INSOMNIA
EQ 3MG BASE	SILENOR	CURRAX	N022036	March 17, 2010	RX	TABLET	ORAL	9861607	May 18, 2027	TREATMENT OF INSOMNIA
EQ 3MG BASE	SILENOR	CURRAX	N022036	March 17, 2010	RX	TABLET	ORAL	10653660	July 20, 2027	TREATMENT OF INSOMNIA
EQ 3MG BASE	SILENOR	CURRAX	N022036	March 17, 2010	RX	TABLET	ORAL	11110074	July 20, 2027	TREATMENT OF INSOMNIA
EQ 3MG BASE	SILENOR	CURRAX	N022036	March 17, 2010	RX	TABLET	ORAL	9572814	July 20, 2027	TREATMENT OF INSOMNIA
EQ 3MG BASE	SILENOR	CURRAX	N022036	March 17, 2010	RX	TABLET	ORAL	7915307	Aug. 24, 2027	TREATMENT OF INSOMNIA
EQ 3MG BASE	SILENOR	CURRAX	N022036	March 17, 2010	RX	TABLET	ORAL	11234954	Jan. 18, 2028	TREATMENT OF INSOMNIA
EQ 3MG BASE	SILENOR	CURRAX	N022036	March 17, 2010	RX	TABLET	ORAL	10548871	April 11, 2028	TREATMENT OF INSOMNIA

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Orange Book exclusivity data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Exclusivity date	Description
5%	DOXEPIN HYDROCHLORIDE	TEVA PHARMS	A215408	Feb. 17, 2023	RX	CREAM	TOPICAL	Aug. 16, 2023	COMPETITIVE GENERIC THERAPY

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Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Sodium-dependent noradrenaline transporter	Transporter	P23975	SC6A2_HUMAN	INHIBITOR	Kd	7.53	WOMBAT-PK	CHEMBL
Histamine H1 receptor	GPCR	P35367	HRH1_HUMAN	ANTAGONIST	Ki	9.75	WOMBAT-PK	DRUG LABEL
Alpha-2A adrenergic receptor	GPCR	P08913	ADA2A_HUMAN		Ki	6.30	DRUG MATRIX
Sigma non-opioid intracellular receptor 1	Membrane receptor	Q99720	SGMR1_HUMAN		Ki	6.58	DRUG MATRIX
Sodium-dependent serotonin transporter	Transporter	P31645	SC6A4_HUMAN	INHIBITOR	Kd	7.17	WOMBAT-PK
5-hydroxytryptamine receptor 1A	GPCR	P08908	5HT1A_HUMAN		Ki	6.54	WOMBAT-PK
5-hydroxytryptamine receptor 2A	GPCR	P28223	5HT2A_HUMAN		EC50	7.45	WOMBAT-PK
5-hydroxytryptamine receptor 2B	GPCR	P41595	5HT2B_HUMAN		EC50	7.20	WOMBAT-PK
5-hydroxytryptamine receptor 2C	GPCR	P28335	5HT2C_HUMAN		EC50	7	WOMBAT-PK
5-hydroxytryptamine receptor 6	GPCR	P50406	5HT6R_HUMAN		Ki	6.98	CHEMBL

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External reference:

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ID	Source
001509	NDDF
004607	NDDF
11841005	SNOMEDCT_US
1225	IUPHAR_LIGAND_ID
1229-29-4	SECONDARY_CAS_RN
172015	MMSL
1855	INN_ID
203179	RXNORM
239355	MMSL
27123	MMSL

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Doxepin	HUMAN PRESCRIPTION DRUG LABEL	1	0228-3315	TABLET, FILM COATED	3 mg	ORAL	ANDA	31 sections
Doxepin	HUMAN PRESCRIPTION DRUG LABEL	1	0228-3316	TABLET, FILM COATED	6 mg	ORAL	ANDA	31 sections
doxepin hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0093-9609	CREAM	50 mg	TOPICAL	ANDA	18 sections
Doxepin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0378-1049	CAPSULE	10 mg	ORAL	ANDA	17 sections
Doxepin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0378-1049	CAPSULE	10 mg	ORAL	ANDA	17 sections
Doxepin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0378-3125	CAPSULE	25 mg	ORAL	ANDA	17 sections
Doxepin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0378-3125	CAPSULE	25 mg	ORAL	ANDA	17 sections
Doxepin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0378-4250	CAPSULE	50 mg	ORAL	ANDA	17 sections
Doxepin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0378-4250	CAPSULE	50 mg	ORAL	ANDA	17 sections
Doxepin Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0378-4810	TABLET	3 mg	ORAL	NDA authorized generic	32 sections

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