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

Stem definition	Drug id	CAS RN
substances of the imipramine group	1427	50-49-7

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: imipramine prazepine melipramine imipramine hydrochloride imipramine pamoate imipramine HCl	The prototypical tricyclic antidepressant. It has been used in major depression, dysthymia, bipolar depression, attention-deficit disorders, agoraphobia, and panic disorders. It has less sedative effect than some other members of this therapeutic group. Molecular weight: 280.42 Formula: C19H24N2 CLOGP: 5.04 LIPINSKI: 1 HAC: 2 HDO: 0 TPSA: 6.48 ALOGS: -3.63 ROTB: 4 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

imipramine
prazepine
melipramine
imipramine hydrochloride
imipramine pamoate
imipramine HCl

The prototypical tricyclic antidepressant. It has been used in major depression, dysthymia, bipolar depression, attention-deficit disorders, agoraphobia, and panic disorders. It has less sedative effect than some other members of this therapeutic group.

Molecular weight: 280.42
Formula: C19H24N2
CLOGP: 5.04
LIPINSKI: 1
HAC: 2
HDO: 0
TPSA: 6.48
ALOGS: -3.63
ROTB: 4

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
S (Water solubility)	50 mg/mL	Bocci G, Oprea TI, Benet LZ
MRTD (Maximum Recommended Therapeutic Daily Dose)	5.09 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability)	42 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
t_half (Half-life)	16 hours	Lombardo F, Berellini G, Obach RS
CL (Clearance)	13 mL/min/kg	Lombardo F, Berellini G, Obach RS
Vd (Volume of distribution)	12 L/kg	Lombardo F, Berellini G, Obach RS
EoM (Fraction excreted unchanged in urine)	1.50 %	Benet LZ, Broccatelli F, Oprea TI
BDDCS (Biopharmaceutical Drug Disposition Classification System)	1	Benet LZ, Broccatelli F, Oprea TI
fu (Fraction unbound in plasma)	0.08 %	Lombardo F, Berellini G, Obach RS

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Approvals:

Date	Agency	Company	Orphan
April 16, 1959	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
Paranoia	67.85	18.91	25	3385	11654	63473958
Hallucination, auditory	65.57	18.91	25	3385	12799	63472813
Completed suicide	64.37	18.91	57	3353	145616	63339996
Psychotic disorder	51.79	18.91	26	3384	25686	63459926
Toxicity to various agents	45.62	18.91	61	3349	247189	63238423
Stress cardiomyopathy	36.33	18.91	15	3395	9435	63476177
Procedural hypotension	30.71	18.91	8	3402	1182	63484430
Skin hyperpigmentation	28.31	18.91	11	3399	5910	63479702
Iris hyperpigmentation	25.65	18.91	4	3406	41	63485571
Urinary hesitation	21.39	18.91	7	3403	2293	63483319

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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
Blepharospasm	57.32	24.72	13	1789	1125	34954004
Toxicity to various agents	56.59	24.72	60	1742	200302	34754827
Completed suicide	50.20	24.72	41	1761	98127	34857002
Long QT syndrome	45.68	24.72	13	1789	2790	34952339
Neuroleptic malignant syndrome	42.51	24.72	20	1782	17914	34937215
Pyelitis	42.36	24.72	7	1795	111	34955018
Muscle rigidity	38.76	24.72	16	1786	10502	34944627
Dystonia	38.29	24.72	16	1786	10829	34944300
Trismus	38.10	24.72	11	1791	2484	34952645
Delusion	26.61	24.72	13	1789	12622	34942507

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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	103.13	18.10	97	4577	245670	79494044
Toxicity to various agents	65.13	18.10	100	4574	421440	79318274
Paranoia	62.88	18.10	28	4646	19404	79720310
Neuroleptic malignant syndrome	59.35	18.10	30	4644	27529	79712185
Hallucination, auditory	48.91	18.10	24	4650	20669	79719045
Overdose	45.55	18.10	55	4619	184151	79555563
Psychotic disorder	38.15	18.10	26	4648	41376	79698338
Blepharospasm	34.62	18.10	13	4661	5838	79733876
Long QT syndrome	34.39	18.10	13	4661	5942	79733772
Pyelitis	34.00	18.10	7	4667	336	79739378

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	N06AA02	NERVOUS SYSTEM PSYCHOANALEPTICS ANTIDEPRESSANTS Non-selective monoamine reuptake inhibitors
CHEBI has role	CHEBI:35469	antidepressants
CHEBI has role	CHEBI:35640	adrenergic uptake inhibitors
CHEBI has role	CHEBI:76779	post-proline endopeptidase inhibitors
FDA EPC	N0000175752	Tricyclic Antidepressant
MeSH PA	D018663	Adrenergic Agents
MeSH PA	D018759	Adrenergic Uptake Inhibitors
MeSH PA	D000928	Antidepressive Agents
MeSH PA	D000929	Antidepressive Agents, Tricyclic
MeSH PA	D002491	Central Nervous System Agents

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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
Nocturnal enuresis	indication	8009008
Depressive disorder	indication	35489007
Neuralgia	off-label use	16269008
Cataplexy	off-label use	46263000
Anxiety	off-label use	48694002
Narcolepsy	off-label use	60380001	DOID:8986
Bulimia nervosa	off-label use	78004001
Neuropathic pain	off-label use	247398009
Panic disorder	off-label use	371631005	DOID:594
Attention deficit hyperactivity disorder	off-label use	406506008

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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	9.04	Basic
pKa2	5.01	Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

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	7.43	WOMBAT-PK	CHEMBL
Sodium-dependent serotonin transporter	Transporter	P31645	SC6A4_HUMAN	INHIBITOR	Kd	8.85	WOMBAT-PK	CHEMBL
Potassium voltage-gated channel subfamily H member 2	Ion channel	Q12809	KCNH2_HUMAN		IC50	5.90	WOMBAT-PK
5-hydroxytryptamine receptor 1A	GPCR	P08908	5HT1A_HUMAN		Ki	5.24	PDSP
5-hydroxytryptamine receptor 2A	GPCR	P28223	5HT2A_HUMAN		Ki	6.83	WOMBAT-PK
5-hydroxytryptamine receptor 2C	GPCR	P28335	5HT2C_HUMAN		Ki	6.80	WOMBAT-PK
Alpha-1A adrenergic receptor	GPCR	P35348	ADA1A_HUMAN		IC50	7.50	WOMBAT-PK
Alpha-2B adrenergic receptor	GPCR	P18089	ADA2B_HUMAN		IC50	7.10	WOMBAT-PK
D(3) dopamine receptor	GPCR	P35462	DRD3_HUMAN		Ki	6.41	WOMBAT-PK
Histamine H1 receptor	GPCR	P35367	HRH1_HUMAN		IC50	7.61	WOMBAT-PK

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External reference:

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ID	Source
001498	NDDF
001499	NDDF
001500	NDDF
10075-24-8	SECONDARY_CAS_RN
113-52-0	SECONDARY_CAS_RN
150816	RXNORM
1916	INN_ID
2328	MMSL
3378009	SNOMEDCT_US
357	IUPHAR_LIGAND_ID

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Imipramine Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0781-1762	TABLET, FILM COATED	10 mg	ORAL	ANDA	19 sections
Imipramine Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0781-1764	TABLET, FILM COATED	25 mg	ORAL	ANDA	19 sections
Imipramine Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0781-1766	TABLET, FILM COATED	50 mg	ORAL	ANDA	19 sections
Imipramine Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	42291-345	TABLET, FILM COATED	10 mg	ORAL	ANDA	24 sections
Imipramine Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	42291-346	TABLET, FILM COATED	25 mg	ORAL	ANDA	24 sections
Imipramine Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	42291-347	TABLET, FILM COATED	50 mg	ORAL	ANDA	24 sections
Imipramine Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	49884-054	TABLET	10 mg	ORAL	ANDA	20 sections
Imipramine Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	49884-055	TABLET	25 mg	ORAL	ANDA	20 sections
Imipramine Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	49884-056	TABLET	50 mg	ORAL	ANDA	20 sections
Imipramine Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	50090-0035	TABLET, FILM COATED	25 mg	ORAL	ANDA	21 sections

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