All FDA-approved EMA-approved PMDA-approved
Target Card Uniprot Example: P23975

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

Drug dosage:

Dose	Unit	Route
0.10	g	O
0.10	g	P

ADMET properties:

Property	Value	Reference
BDDCS (Biopharmaceutical Drug Disposition Classification System)	1	Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine)	1.50 %	Benet LZ, Broccatelli F, Oprea TI
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
Vd (Volume of distribution)	12 L/kg	Lombardo F, Berellini G, Obach RS
CL (Clearance)	13 mL/min/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.08 %	Lombardo F, Berellini G, Obach RS
t_half (Half-life)	16 hours	Lombardo F, Berellini G, Obach RS
S (Water solubility)	50 mg/mL	Bocci G, Oprea TI, Benet LZ

Approvals:

Date	Agency	Company	Orphan
April 16, 1959	FDA

FDA Adverse Event Reporting System (Female)

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
Decreased activity	20.85	18.91	9	3401	6311	63479301
Limb mass	19.06	18.91	7	3403	3225	63482387

FDA Adverse Event Reporting System (Male)

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
Brain oedema	25.51	24.72	13	1789	13808	34941321

FDA Adverse Event Reporting System (Geriatric)

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
Stress cardiomyopathy	32.66	18.10	15	4659	11151	79728563
Dystonia	28.59	18.10	17	4657	21382	79718332
Trismus	28.23	18.10	11	4663	5456	79734258
Procedural hypotension	25.82	18.10	8	4666	2015	79737699
Skin hyperpigmentation	25.15	18.10	11	4663	7292	79732422
Muscle rigidity	24.51	18.10	15	4659	19867	79719847
Electrocardiogram QT prolonged	23.97	18.10	28	4646	90358	79649356
Respiratory depression	22.29	18.10	16	4658	27614	79712100
Drug interaction	20.47	18.10	62	4612	415121	79324593
Withdrawal syndrome	20.41	18.10	15	4659	26839	79712875
Suicide attempt	19.22	18.10	24	4650	82908	79656806
Parkinsonism	19.14	18.10	12	4662	16572	79723142
Electrocardiogram abnormal	19.04	18.10	12	4662	16725	79722989
Iris hyperpigmentation	18.95	18.10	3	4671	31	79739683
Speech disorder	18.12	18.10	19	4655	54426	79685288

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

Source	Code	Description
ATC	N06AA02	NERVOUS SYSTEM PSYCHOANALEPTICS ANTIDEPRESSANTS Non-selective monoamine reuptake inhibitors
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
MeSH PA	D049990	Membrane Transport Modulators
MeSH PA	D018377	Neurotransmitter Agents
MeSH PA	D014179	Neurotransmitter Uptake Inhibitors
MeSH PA	D011619	Psychotropic Drugs
CHEBI has role	CHEBI:35469	antidepressants
FDA EPC	N0000175752	Tricyclic Antidepressant
CHEBI has role	CHEBI:35640	adrenergic uptake inhibitors
CHEBI has role	CHEBI:76779	post-proline endopeptidase inhibitors

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

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
Ocular hypertension	contraindication	4210003	DOID:9282
Suicidal thoughts	contraindication	6471006
Alcoholism	contraindication	7200002
Bipolar disorder	contraindication	13746004	DOID:3312
Electroconvulsive therapy	contraindication	23835007
Alcohol intoxication	contraindication	25702006
Hyperthyroidism	contraindication	34486009	DOID:7998
Conduction disorder of the heart	contraindication	44808001
Chronic heart failure	contraindication	48447003
Disorder of cardiovascular system	contraindication	49601007	DOID:1287
Paralytic ileus	contraindication	55525008	DOID:8442
Schizophrenia	contraindication	58214004	DOID:5419
Intestinal obstruction	contraindication	81060008	DOID:8437
Epilepsy	contraindication	84757009	DOID:1826
Kidney disease	contraindication	90708001	DOID:557
Seizure disorder	contraindication	128613002
Cerebrovascular accident	contraindication	230690007
Mania	contraindication	231494001
Hypomania	contraindication	231496004
Disease of liver	contraindication	235856003	DOID:409
Benign prostatic hyperplasia	contraindication	266569009
Retention of urine	contraindication	267064002
Syncope	contraindication	271594007
Thrombocytopenic disorder	contraindication	302215000	DOID:1588
Neutropenic disorder	contraindication	303011007	DOID:1227
Surgical procedure	contraindication	387713003
Angle-closure glaucoma	contraindication	392291006	DOID:13550
Disorder of coronary artery	contraindication	414024009
Myocardial infarction in recovery phase	contraindication	418044006

🐶 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:

Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Mechanism action	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
Muscarinic acetylcholine receptor M1	GPCR	P11229	ACM1_HUMAN		Ki	7.38		WOMBAT-PK
Muscarinic acetylcholine receptor M2	GPCR	P08172	ACM2_HUMAN		Ki	8.08		WOMBAT-PK
Muscarinic acetylcholine receptor M3	GPCR	P20309	ACM3_HUMAN		Ki	7.22		WOMBAT-PK
Muscarinic acetylcholine receptor M4	GPCR	P08173	ACM4_HUMAN		Ki	6.95		WOMBAT-PK
Muscarinic acetylcholine receptor M5	GPCR	P08912	ACM5_HUMAN		Ki	7.08		WOMBAT-PK
Sodium-dependent dopamine transporter	Transporter	Q01959	SC6A3_HUMAN		Ki	5.07		PDSP
Adenosine receptor A3	GPCR	P0DMS8	AA3R_HUMAN		IC50	8.36		CHEMBL
Voltage-dependent N-type calcium channel subunit alpha-1B	Ion channel	Q00975	CAC1B_HUMAN		IC50	4.66		CHEMBL
Major prion protein	Surface antigen	P04156	PRIO_HUMAN		EC50	5		CHEMBL
Solute carrier family 22 member 1	Transporter	O15245	S22A1_HUMAN		IC50	4.77		CHEMBL
Potassium voltage-gated channel subfamily H member 1	Ion channel	O95259	KCNH1_HUMAN	BLOCKER	IC50	5.70		IUPHAR
Solute carrier family 22 member 2	Transporter	O15244	S22A2_HUMAN		IC50	5.22		WOMBAT-PK
Sodium channel alpha subunits; brain (Types I, II, III)	Ion channel	P35498 Q99250 Q9NY46	SCN1A_HUMAN SCN2A_HUMAN SCN3A_HUMAN		IC50	5.44		CHEMBL
Sphingomyelin phosphodiesterase	Enzyme	P17405	ASM_HUMAN		IC50	5.30		CHEMBL
D(2) dopamine receptor	GPCR	P14416	DRD2_HUMAN		Ki	6.17		WOMBAT-PK
Sigma non-opioid intracellular receptor 1	Membrane receptor	Q99720	SGMR1_HUMAN		Ki	6.28		WOMBAT-PK
Alpha-1A adrenergic receptor	GPCR		ADA1A_RAT		IC50	8.77		CHEMBL
Sodium-dependent serotonin transporter	Transporter		SC6A4_RAT		Ki	7.38		CHEMBL
Sigma non-opioid intracellular receptor 1	Membrane receptor		SGMR1_RAT		Ki	6.46		CHEMBL
Transporter	Transporter		Q9WTR4_RAT		Ki	7.92		CHEMBL
Sodium-dependent dopamine transporter	Transporter		SC6A3_MOUSE		Ki	7.38		CHEMBL
Sodium-dependent noradrenaline transporter	Transporter		SC6A2_MOUSE		Ki	7.92		CHEMBL
5-hydroxytryptamine receptor 2C	GPCR		5HT2C_MOUSE		Ki	6.80		CHEMBL
D(2) dopamine receptor	GPCR		DRD2_MOUSE		Ki	6.14		CHEMBL
Sodium-dependent serotonin transporter	Transporter		SC6A4_MOUSE		Ki	8.30		CHEMBL
Histamine H1 receptor	GPCR		HRH1_RAT		IC50	10.22		CHEMBL
Muscarinic acetylcholine receptor M5	GPCR		ACM5_RAT		IC50	6.52		CHEMBL
Pleiotropic ABC efflux transporter of multiple drugs	Transporter		PDR5_YEAST		IC50	4.66		CHEMBL
Glutamate NMDA receptor	Ion channel		NMDZ1_RAT NMDE1_RAT NMDE2_RAT NMDE3_RAT NMDE4_RAT NMD3B_RAT NMD3A_RAT		IC50	4.85		CHEMBL
Muscarinic acetylcholine receptor	GPCR		ACM1_RAT ACM3_RAT ACM4_RAT ACM5_RAT ACM2_RAT		Ki	7.19		CHEMBL
Serotonin (5-HT) receptor	GPCR		5HT2C_RAT 5HT2A_RAT 5HT1A_RAT 5HT1B_RAT 5HT1D_RAT 5HT1F_RAT 5HT2B_RAT 5HT6R_RAT 5HT7R_RAT 5HT5A_RAT 5HT5B_RAT 5HT3A_RAT 5HT4R_RAT 5HT3B_RAT		IC50	7.36		CHEMBL
Adrenergic receptor alpha-2	GPCR		ADA2B_RAT ADA2C_RAT ADA2A_RAT		Ki	6.59		CHEMBL
Dopamine receptor	GPCR		DRD1_RAT DRD3_RAT DRD5_RAT DRD4_RAT DRD2_RAT		IC50	6.19		CHEMBL
Adrenergic receptor alpha-1	GPCR		ADA1B_RAT ADA1D_RAT ADA1A_RAT		Ki	7.34		CHEMBL
Serotonin 2 (5-HT2) receptor	GPCR		5HT2C_RAT 5HT2A_RAT 5HT2B_RAT		Ki	7.64		CHEMBL
G protein-activated inward rectifier potassium channel 4	Ion channel		KCNJ5_MOUSE	BLOCKER	EC50	4.50		IUPHAR
G protein-activated inward rectifier potassium channel 2	Ion channel		KCNJ6_MOUSE	BLOCKER	IC50	4.30		IUPHAR
Sigma intracellular receptor 2	Unclassified		SGMR2_RAT		Ki	5.68		CHEMBL

External reference:

ID	Source
4019785	VUID
N0000147875	NUI
D00815	KEGG_DRUG
73-07-4	SECONDARY_CAS_RN
113-52-0	SECONDARY_CAS_RN
10075-24-8	SECONDARY_CAS_RN
4017862	VANDF
4017863	VANDF
4019785	VANDF
C0020934	UMLSCUI
CHEBI:47499	CHEBI
IXX	PDB_CHEM_ID
CHEMBL11	ChEMBL_ID
DB00458	DRUGBANK_ID
CHEMBL2105257	ChEMBL_ID
CHEMBL1692	ChEMBL_ID
CHEMBL3989845	ChEMBL_ID
D007099	MESH_DESCRIPTOR_UI
3696	PUBCHEM_CID
357	IUPHAR_LIGAND_ID
793	INN_ID
OGG85SX4E4	UNII
150816	RXNORM
2328	MMSL
4870	MMSL
4871	MMSL
81685	MMSL
d00259	MMSL
001498	NDDF
001499	NDDF
001500	NDDF
3378009	SNOMEDCT_US
36113004	SNOMEDCT_US
372718005	SNOMEDCT_US
4203009	SNOMEDCT_US
1916	INN_ID

Pharmaceutical products:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Imipramine Pamoate	HUMAN PRESCRIPTION DRUG LABEL	1	0054-0273	CAPSULE	75 mg	ORAL	ANDA	20 sections
Imipramine Pamoate	HUMAN PRESCRIPTION DRUG LABEL	1	0054-0273	CAPSULE	75 mg	ORAL	ANDA	20 sections
Imipramine Pamoate	HUMAN PRESCRIPTION DRUG LABEL	1	0054-0274	CAPSULE	100 mg	ORAL	ANDA	20 sections
Imipramine Pamoate	HUMAN PRESCRIPTION DRUG LABEL	1	0054-0274	CAPSULE	100 mg	ORAL	ANDA	20 sections
Imipramine Pamoate	HUMAN PRESCRIPTION DRUG LABEL	1	0054-0275	CAPSULE	125 mg	ORAL	ANDA	20 sections
Imipramine Pamoate	HUMAN PRESCRIPTION DRUG LABEL	1	0054-0275	CAPSULE	125 mg	ORAL	ANDA	20 sections
Imipramine Pamoate	HUMAN PRESCRIPTION DRUG LABEL	1	0054-0276	CAPSULE	150 mg	ORAL	ANDA	20 sections
Imipramine Pamoate	HUMAN PRESCRIPTION DRUG LABEL	1	0054-0276	CAPSULE	150 mg	ORAL	ANDA	20 sections
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 PAMOATE	HUMAN PRESCRIPTION DRUG LABEL	1	16590-963	CAPSULE	75 mg	ORAL	NDA	22 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
Imipramine Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	50090-3148	TABLET, FILM COATED	25 mg	ORAL	ANDA	21 sections
Imipramine Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	50090-3148	TABLET, FILM COATED	25 mg	ORAL	ANDA	21 sections
Imipramine Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	50436-2022	TABLET, FILM COATED	25 mg	ORAL	ANDA	21 sections
IMIPRAMINE HYDROCHLORIDE	HUMAN PRESCRIPTION DRUG LABEL	1	51655-455	TABLET, FILM COATED	50 mg	ORAL	ANDA	12 sections
Imipramine Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	54868-1344	TABLET, FILM COATED	25 mg	ORAL	ANDA	20 sections
Imipramine Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	54868-2221	TABLET, FILM COATED	50 mg	ORAL	ANDA	20 sections
Imipramine Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	54868-2571	TABLET, FILM COATED	10 mg	ORAL	ANDA	20 sections
Imipramine Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	55289-144	TABLET, FILM COATED	25 mg	ORAL	ANDA	19 sections
Imipramine Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	55700-709	TABLET, FILM COATED	10 mg	ORAL	ANDA	20 sections
Imipramine Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	55700-709	TABLET, FILM COATED	10 mg	ORAL	ANDA	20 sections
Imipramine Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	55700-710	TABLET, FILM COATED	25 mg	ORAL	ANDA	20 sections