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

Stem definition	Drug id	CAS RN
	4468	33643-46-8

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: spravato esketamine HCl esketamine hydrochloride esketamine l-Ketamine	Esketamine is the S-enantiomer of racemic ketamine. It is a non-selective, non-competitive, antagonist of the N-methyl-D-aspartate (NMDA) receptor, an ionotropic glutamate receptor. Through NMDA receptor antagonism, esketamine produces a transient increase in glutamate release leading to increases in alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor (AMPAR) stimulation and subsequently to increases in neurotrophic signalling which may contribute to the restoration of synaptic function in these brain regions involved with the regulation of mood and emotional behaviour. Restoration of dopaminergic neurotransmission in brain regions involved in the reward and motivation, and decreased stimulation of brain regions involved in anhedonia, may contribute to the rapid response. Molecular weight: 237.73 Formula: C13H16ClNO CLOGP: 2.93 LIPINSKI: 0 HAC: 2 HDO: 1 TPSA: 29.10 ALOGS: -3.71 ROTB: 2 Status: ONP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

spravato
esketamine HCl
esketamine hydrochloride
esketamine
l-Ketamine

Esketamine is the S-enantiomer of racemic ketamine. It is a non-selective, non-competitive, antagonist of the N-methyl-D-aspartate (NMDA) receptor, an ionotropic glutamate receptor. Through NMDA receptor antagonism, esketamine produces a transient increase in glutamate release leading to increases in alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor (AMPAR) stimulation and subsequently to increases in neurotrophic signalling which may contribute to the restoration of synaptic function in these brain regions involved with the regulation of mood and emotional behaviour. Restoration of dopaminergic neurotransmission in brain regions involved in the reward and motivation, and decreased stimulation of brain regions involved in anhedonia, may contribute to the rapid response.

Molecular weight: 237.73
Formula: C13H16ClNO
CLOGP: 2.93
LIPINSKI: 0
HAC: 2
HDO: 1
TPSA: 29.10
ALOGS: -3.71
ROTB: 2

Status: ONP

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

Drug dosage:

Dose	Unit	Route
8	mg	N

ADMET properties:

None

Approvals:

Date	Agency	Company	Orphan
Dec. 18, 2019	EMA	Janssen-Cilag International N.V.
May 3, 2019	FDA	JANSSEN PHARMS

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
Dissociation	2191.16	37.29	336	3792	2583	63482311
Sedation	664.23	37.29	196	3932	38613	63446281
Suicidal ideation	656.11	37.29	217	3911	62204	63422690
Suicide attempt	244.35	37.29	105	4023	60813	63424081
Anxiety	156.45	37.29	122	4006	217419	63267475
Dissociative disorder	154.56	37.29	26	4102	361	63484533
Blood pressure increased	93.30	37.29	80	4048	161982	63322912
Underdose	80.15	37.29	38	4090	27418	63457476
Panic attack	74.80	37.29	34	4094	22297	63462597
Euphoric mood	71.60	37.29	22	4106	4865	63480029

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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
Dissociation	875.07	55.42	136	1627	1522	34953646
Sedation	313.13	55.42	90	1673	20916	34934252
Suicidal ideation	306.09	55.42	103	1660	40285	34914883
Drug ineffective	80.84	55.42	106	1657	456645	34498523
Suicide attempt	79.75	55.42	39	1724	39077	34916091
Blood pressure increased	78.53	55.42	51	1712	88051	34867117
Hypertension	75.44	55.42	59	1704	136384	34818784
Anxiety	72.92	55.42	51	1712	99377	34855791

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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
Dissociation	2363.87	42.02	368	4177	3653	79736190
Sedation	896.09	42.02	256	4289	51639	79688204
Suicidal ideation	786.22	42.02	253	4292	76087	79663756
Suicide attempt	284.13	42.02	123	4422	82809	79657034
Dissociative disorder	177.05	42.02	32	4513	789	79739054
Anxiety	145.38	42.02	117	4428	248395	79491448
Blood pressure increased	135.35	42.02	105	4440	211255	79528588
Hypertension	114.61	42.02	116	4429	330876	79408967
Hospitalisation	100.34	42.02	64	4481	94172	79645671
Underdose	96.59	42.02	44	4501	33107	79706736

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	N01AX14	NERVOUS SYSTEM ANESTHETICS ANESTHETICS, GENERAL Other general anesthetics
ATC	N06AX27	NERVOUS SYSTEM PSYCHOANALEPTICS ANTIDEPRESSANTS Other antidepressants
CHEBI has role	CHEBI:38877	intravenous anesthetics
CHEBI has role	CHEBI:60643	N-methyl-D-aspartate receptor antagonists
MeSH PA	D000928	Antidepressive Agents
MeSH PA	D002491	Central Nervous System Agents
MeSH PA	D011619	Psychotropic Drugs

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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
Arteriovenous malformation	contraindication	24551003
Aneurysm	contraindication	432119003	DOID:178

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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	7.65	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 28MG BASE	SPRAVATO	JANSSEN PHARMS	N211243	March 5, 2019	RX	SPRAY	NASAL	9592207	March 20, 2027	TREATMENT OF TREATMENT-RESISTANT DEPRESSION IN ADULT IN CONJUNCTION WITH AN ORAL ANTIDEPRESSANT
EQ 28MG BASE	SPRAVATO	JANSSEN PHARMS	N211243	March 5, 2019	RX	SPRAY	NASAL	8785500	March 5, 2033	TREATMENT OF TREATMENT-RESISTANT DEPRESSION IN ADULT IN CONJUNCTION WITH AN ORAL ANTIDEPRESSANT
EQ 28MG BASE	SPRAVATO	JANSSEN PHARMS	N211243	March 5, 2019	RX	SPRAY	NASAL	11446260	March 14, 2034	TREATMENT OF DEPRESSIVE SYMPTOMS IN ADULTS WITH MDD WITH ACUTE SUICIDAL IDEATION OR BEHAVIOR BY NASALLY ADMINISTERING 56MG OR 84MG OF ESKETAMINE AS A PHARMACEUTICAL COMPOSITION TWICE PER WEEK IN CONJUNCTION WITH AN ORAL ANTIDEPRESSANT
EQ 28MG BASE	SPRAVATO	JANSSEN PHARMS	N211243	March 5, 2019	RX	SPRAY	NASAL	11446260	March 14, 2034	TREATMENT OF TREATMENT-RESISTANT DEPRESSION IN ADULTS BY NASALLY ADMINISTERING 56MG OR 84MG OF ESKETAMINE AS A PHARMACEUTICAL COMPOSITION IN CONJUNCTION WITH AN ORAL ANTIDEPRESSANT
EQ 28MG BASE	SPRAVATO	JANSSEN PHARMS	N211243	March 5, 2019	RX	SPRAY	NASAL	11446260	March 14, 2034	TREATMENT OF TREATMENT-RESISTANT DEPRESSION IN ADULTS BY NASALLY ADMINISTERING 56MG OR 84MG OF ESKETAMINE TWICE PER WEEK AS A PHARMACEUTICAL COMPOSITION IN CONJUNCTION WITH AN ORAL ANTIDEPRESSANT
EQ 28MG BASE	SPRAVATO	JANSSEN PHARMS	N211243	March 5, 2019	RX	SPRAY	NASAL	10869844	Sept. 10, 2035	TREATMENT OF DEPRESSIVE SYMPTOMS IN ADULTS WITH MDD WITH ACUTE SUICIDAL IDEATION OR BEHAVIOR BY NASALLY ADMINISTERING 56MG OR 84 MG OF ESKETAMINE 2X WEEKLY FOR 4 WEEKS IN CONJUNCTION WITH AN ORAL ANTIDEPRESSANT
EQ 28MG BASE	SPRAVATO	JANSSEN PHARMS	N211243	March 5, 2019	RX	SPRAY	NASAL	10869844	Sept. 10, 2035	TREATMENT OF TRD IN ADULTS BY NASALLY ADMINISTERING 56MG OR 84MG OF ESKETAMINE 2X WEEKLY FOR 4 WEEKS DURING THE INDUCTION PHASE FOLLOWED BY A MAINTENANCE PHASE OF 56MG OR 84 MG WEEKLY OR 1X EVERY TWO WEEKS IN CONJUNCTION WITH AN ORAL ANTIDEPRESSANT
EQ 28MG BASE	SPRAVATO	JANSSEN PHARMS	N211243	March 5, 2019	RX	SPRAY	NASAL	10869844	Sept. 10, 2035	TREATMENT OF TRD IN ADULTS BY NASALLY ADMINISTERING 56MG OR 84MG OF ESKETAMINE 2X WEEKLY FOR 4 WEEKS DURING THE INDUCTION PHASE IN CONJUNCTION WITH AN ORAL ANTIDEPRESSANT
EQ 28MG BASE	SPRAVATO	JANSSEN PHARMS	N211243	March 5, 2019	RX	SPRAY	NASAL	11173134	Sept. 10, 2035	TREATMENT OF DEPRESSION IN ADULTS WITH MOD AND ACUTE SUICIDAL IDEATION OR BEHAVIOR IN CONJUNCTION WITH AN ORAL ANTIDEPRESSANT BY NASALLY ADMINISTERING 56MG OR 84MG OF ESKETAMINE IN A MAINTENANCE PHASE WEEKLY OR LX EVERY 2 WEEKS AFTER INDUCTION PHASE
EQ 28MG BASE	SPRAVATO	JANSSEN PHARMS	N211243	March 5, 2019	RX	SPRAY	NASAL	11173134	Sept. 10, 2035	TREATMENT OF TRD IN CONJUNCTION WITH AN ORAL ANTIDEPRESSANT BY NASALLY ADMINISTERING 56MG OR 84MG OF ESKETAMINE IN A MAINTENANCE PHASE WEEKLY OR 1X EVERY TWO WEEKS TO ADULTS WHO HAVE BEEN ADMINISTERED ESKETAMINE IN A INDUCTION PHASE FOR ABOUT 4 WEEKS

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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
EQ 28MG BASE	SPRAVATO	JANSSEN PHARMS	N211243	March 5, 2019	RX	SPRAY	NASAL	July 31, 2023	TREATMENT OF SYMPTOMS IN ADULTS WITH MAJOR DEPRESSIVE DISORDER (MDD) WITH ACUTE SUICIDAL IDEATION OR BEHAVIOR.
EQ 28MG BASE	SPRAVATO	JANSSEN PHARMS	N211243	March 5, 2019	RX	SPRAY	NASAL	March 5, 2024	NEW CHEMICAL ENTITY (AN ENANTIOMER OF PREVIOUSLY APPROVED RACEMIC MIXTURE. SEE SECTION 505(U) OF THE FEDERAL FOOD AND DRUG COSMETIC ACT).

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Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Mechanism action	Bioact source	MoA source
Glutamate NMDA receptor	Ion channel		NMDZ1_RAT NMDE1_RAT NMDE2_RAT NMDE3_RAT NMDE4_RAT NMD3B_RAT NMD3A_RAT	ANTAGONIST	Ki	6.16		SCIENTIFIC LITERATURE

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External reference:

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ID	Source
JC9	PDB_CHEM_ID
015448	NDDF
015449	NDDF
1217154004	SNOMEDCT_US
182137	PUBCHEM_CID
2119365	RXNORM
309966	MMSL
33643-47-9	SECONDARY_CAS_RN
36280	MMSL
4038229	VANDF

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Spravato	HUMAN PRESCRIPTION DRUG LABEL	1	49396-0280	SPRAY	28 mg	NASAL	Export only	1 sections
Spravato	HUMAN PRESCRIPTION DRUG LABEL	1	50458-028	SOLUTION	28 mg	NASAL	NDA	38 sections
Spravato	HUMAN PRESCRIPTION DRUG LABEL	1	50458-028	SOLUTION	28 mg	NASAL	NDA	38 sections

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