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

Stem definition	Drug id	CAS RN
substances of the imipramine group	812	50-47-5

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: desipramine demethylimipramine desimipramine desipramin desmethylimipramine methylaminopropyliminodibenzyl monodemethylimipramine norimipramine desipramine hydrochloride desipramine HCl	A tricyclic dibenzazepine compound that potentiates neurotransmission. Desipramine selectively blocks reuptake of norepinephrine from the neural synapse, and also appears to impair serotonin transport. This compound also possesses minor anticholinergic activity, through its affinity to muscarinic receptors. Molecular weight: 266.39 Formula: C18H22N2 CLOGP: 4.47 LIPINSKI: 0 HAC: 2 HDO: 1 TPSA: 15.27 ALOGS: -3.83 ROTB: 4 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

desipramine
demethylimipramine
desimipramine
desipramin
desmethylimipramine
methylaminopropyliminodibenzyl
monodemethylimipramine
norimipramine
desipramine hydrochloride
desipramine HCl

A tricyclic dibenzazepine compound that potentiates neurotransmission. Desipramine selectively blocks reuptake of norepinephrine from the neural synapse, and also appears to impair serotonin transport. This compound also possesses minor anticholinergic activity, through its affinity to muscarinic receptors.

Molecular weight: 266.39
Formula: C18H22N2
CLOGP: 4.47
LIPINSKI: 0
HAC: 2
HDO: 1
TPSA: 15.27
ALOGS: -3.83
ROTB: 4

Status: OFP

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

Drug dosage:

Dose	Unit	Route
0.10	g	O

ADMET properties:

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Property	Value	Reference
BA (Bioavailability)	82.50 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
S (Water solubility)	30.28 mg/mL	Bocci G, Oprea TI, Benet LZ
t_half (Half-life)	22 hours	Lombardo F, Berellini G, Obach RS
EoM (Fraction excreted unchanged in urine)	2 %	Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose)	16.09 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
Vd (Volume of distribution)	15 L/kg	Lombardo F, Berellini G, Obach RS
CL (Clearance)	11 mL/min/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)	0.16 %	Lombardo F, Berellini G, Obach RS

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Approvals:

Date	Agency	Company	Orphan
Nov. 20, 1964	FDA	SANOFI AVENTIS US

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	146.73	33.67	68	1282	145605	63342067
Hyperkeratosis	112.54	33.67	26	1324	5992	63481680
Cardiac murmur	89.77	33.67	26	1324	14526	63473146
Immune thrombocytopenia	83.90	33.67	23	1327	10533	63477139
Angina pectoris	71.21	33.67	26	1324	30052	63457620
Dyspnoea exertional	59.89	33.67	28	1322	60274	63427398
Intestinal obstruction	49.11	33.67	20	1330	30879	63456793
Urinary retention	46.07	33.67	19	1331	30282	63457390
Ileus	43.43	33.67	15	1335	14710	63472962
Therapy non-responder	39.89	33.67	23	1327	75878	63411794

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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	62.98	32.82	31	544	98137	34858219

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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	198.91	28.14	101	1723	245666	79496898
Hyperkeratosis	74.70	28.14	20	1804	7770	79734794
Immune thrombocytopenia	70.33	28.14	23	1801	17782	79724782
Cardiac murmur	60.71	28.14	20	1804	15804	79726760
Toxicity to various agents	50.98	28.14	55	1769	421485	79321079
Intestinal obstruction	44.37	28.14	21	1803	42999	79699565
Angina pectoris	40.69	28.14	21	1803	51711	79690853
Therapy non-responder	39.05	28.14	25	1799	92280	79650284
Dyspnoea exertional	37.86	28.14	24	1800	87049	79655515
Ileus	33.95	28.14	15	1809	26196	79716368

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	N06AA01	NERVOUS SYSTEM PSYCHOANALEPTICS ANTIDEPRESSANTS Non-selective monoamine reuptake inhibitors
CHEBI has role	CHEBI:88188	allergenic drug
CHEBI has role	CHEBI:35469	antidepressants
CHEBI has role	CHEBI:35640	adrenergic uptake inhibitors
CHEBI has role	CHEBI:37890	alpha-adrenergic receptor blockaders
CHEBI has role	CHEBI:37955	H1 receptor antagonists
CHEBI has role	CHEBI:48873	acetylcholine receptor antagonist
CHEBI has role	CHEBI:50949	SSRI
CHEBI has role	CHEBI:76779	post-proline endopeptidase inhibitors
CHEBI has role	CHEBI:76811	sphingomyelin cholinephosphohydrolase inhibitors

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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
Depressive disorder	indication	35489007
Cataplexy	off-label use	46263000
Anxiety	off-label use	48694002
Bulimia nervosa	off-label use	78004001
Neuropathic pain	off-label use	247398009
Chronic idiopathic urticaria	off-label use	302162004
Panic disorder	off-label use	371631005	DOID:594
Attention deficit hyperactivity disorder	off-label use	406506008
Depressive Disorder following Traumatic Brain Injury	off-label use
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	9.83	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	9.08	WOMBAT-PK	CHEMBL
D(1A) dopamine receptor	GPCR	P21728	DRD1_HUMAN		Ki	5.26	PDSP
D(2) dopamine receptor	GPCR	P14416	DRD2_HUMAN		Ki	5.63	PDSP
Alpha-2A adrenergic receptor	GPCR	P08913	ADA2A_HUMAN		Ki	5.86	PDSP
Potassium voltage-gated channel subfamily H member 2	Ion channel	Q12809	KCNH2_HUMAN		Ki	5.86	WOMBAT-PK
Sodium-dependent serotonin transporter	Transporter	P31645	SC6A4_HUMAN		Kd	7.76	WOMBAT-PK
5-hydroxytryptamine receptor 1A	GPCR	P08908	5HT1A_HUMAN		Ki	5.19	PDSP
5-hydroxytryptamine receptor 2A	GPCR	P28223	5HT2A_HUMAN		Ki	6.80	WOMBAT-PK
5-hydroxytryptamine receptor 2B	GPCR	P41595	5HT2B_HUMAN		EC50	6.50	WOMBAT-PK
Alpha-1A adrenergic receptor	GPCR	P35348	ADA1A_HUMAN		Ki	7	WOMBAT-PK

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External reference:

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ID	Source
DSM	PDB_CHEM_ID
001503	NDDF
004602	NDDF
1064	MMSL
1500	INN_ID
203174	RXNORM
2399	IUPHAR_LIGAND_ID
26120001	SNOMEDCT_US
2995	PUBCHEM_CID
33378002	SNOMEDCT_US

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Desipramine Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0781-8218	TABLET, FILM COATED	10 mg	ORAL	ANDA	20 sections
Desipramine Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0781-8218	TABLET, FILM COATED	10 mg	ORAL	ANDA	20 sections
Desipramine Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0781-8972	TABLET, FILM COATED	25 mg	ORAL	ANDA	20 sections
Desipramine Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0781-8972	TABLET, FILM COATED	25 mg	ORAL	ANDA	20 sections
Desipramine Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0781-8973	TABLET, FILM COATED	50 mg	ORAL	ANDA	20 sections
Desipramine Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0781-8973	TABLET, FILM COATED	50 mg	ORAL	ANDA	20 sections
Desipramine Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0781-8974	TABLET, FILM COATED	75 mg	ORAL	ANDA	20 sections
Desipramine Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0781-8974	TABLET, FILM COATED	75 mg	ORAL	ANDA	20 sections
Desipramine Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0781-8975	TABLET, FILM COATED	100 mg	ORAL	ANDA	20 sections
Desipramine Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0781-8975	TABLET, FILM COATED	100 mg	ORAL	ANDA	20 sections

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