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

Stem definitionDrug idCAS RN
4468 33643-46-8

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • spravato
  • esketamine HCl
  • esketamine hydrochloride
  • esketamine
  • l-Ketamine
  • 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:

DoseUnitRoute
8 mg N

ADMET properties:

None

Approvals:

DateAgencyCompanyOrphan
Dec. 18, 2019 EMA Janssen-Cilag International N.V.
May 3, 2019 FDA JANSSEN PHARMS

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Dissociation 915.09 48.24 138 1531 2096 53345301
Sedation 274.84 48.24 79 1590 29596 53317801
Suicidal ideation 230.87 48.24 82 1587 60429 53286968
Anxiety 90.68 48.24 63 1606 196641 53150756
Depression 89.97 48.24 61 1608 182991 53164406
Suicide attempt 82.77 48.24 39 1630 58129 53289268
Dissociative disorder 62.72 48.24 10 1659 213 53347184

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Dissociation 326.41 63.90 50 698 1160 32511618
Suicidal ideation 154.74 63.90 50 698 38033 32474745
Sedation 116.08 63.90 34 714 18492 32494286
Drug ineffective 73.76 63.90 64 684 383413 32129365
Depression 67.10 63.90 36 712 97024 32415754

Pharmacologic Action:

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

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Depressive disorder indication 35489007
Arteriovenous malformation contraindication 24551003
Aneurysm contraindication 432119003 DOID:178

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 7.65 Basic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent 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 July 9, 2031 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 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 ANTIDEPRESSENT
EQ 28MG BASE SPRAVATO JANSSEN PHARMS N211243 March 5, 2019 RX SPRAY NASAL 11173134 Sept. 14, 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

Orange Book exclusivity data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
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).

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Glutamate NMDA receptor Ion channel ANTAGONIST Ki 6.16 SCIENTIFIC LITERATURE

External reference:

IDSource
D07283 KEGG_DRUG
33643-47-9 SECONDARY_CAS_RN
4038229 VANDF
4038230 VANDF
CHEBI:60799 CHEBI
JC9 PDB_CHEM_ID
CHEMBL395091 ChEMBL_ID
CHEMBL2364609 ChEMBL_ID
DB11823 DRUGBANK_ID
C000629870 MESH_SUPPLEMENTAL_RECORD_UI
9152 IUPHAR_LIGAND_ID
7884 INN_ID
50LFG02TXD UNII
182137 PUBCHEM_CID
2119365 RXNORM
309966 MMSL
36280 MMSL
d09174 MMSL
015448 NDDF
015449 NDDF
785816006 SNOMEDCT_US
789486001 SNOMEDCT_US
C2825616 UMLSCUI

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
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