Esketamine

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C13H16ClNO
Molecular Weight	237.725
Optical Activity	( + )
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

CN[C@@]1(CCCCC1=O)C2=CC=CC=C2Cl

InChI

InChIKey=YQEZLKZALYSWHR-ZDUSSCGKSA-N

InChI=1S/C13H16ClNO/c1-15-13(9-5-4-8-12(13)16)10-6-2-3-7-11(10)14/h2-3,6-7,15H,4-5,8-9H2,1H3/t13-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C13H16ClNO
Molecular Weight	237.725
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

Esketamine is an S(+)-enantiomer of ketamine. It is a nonselective, noncompetitive antagonist of N-methyl-D-aspartate (NMDA) receptor. A nasal spray, containing esketamine, was approved in 2019 for the treatment of treatment-resistant depression in adults, in conjunction with an oral antidepressant, and is marketed under tradename SPARAVATO. Esketamine is a schedule III drug product in the USA.

Approval Year

C_max

Value	Dose	Analyte	Population
128 ng/mL	0.35 mg/kg single, respiratory	ESKETAMINE plasma	Homo sapiens
180 ng/mL	0.5 mg/kg single, respiratory	ESKETAMINE plasma	Homo sapiens
227 ng/mL	0.7 mg/kg single, respiratory	ESKETAMINE plasma	Homo sapiens
52 ng/mL	0.35 mg/kg single, respiratory	NORKETAMINE, (S)- plasma	Homo sapiens
97 ng/mL	0.5 mg/kg single, respiratory	NORKETAMINE, (S)- plasma	Homo sapiens
153 ng/mL	0.7 mg/kg single, respiratory	NORKETAMINE, (S)- plasma	Homo sapiens
2277.6 ng/mL	0.5 mg/kg single, intramuscular	ESKETAMINE plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
475.2 ng × h/mL	0.5 mg/kg single, intramuscular		ESKETAMINE plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
287.5 min	0.5 mg/kg single, intramuscular	ESKETAMINE plasma	Homo sapiens
11.1 h	single, respiratory	ESKETAMINE plasma	Homo sapiens
7.5 h	single, respiratory	NORKETAMINE, (S)- plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
56%			ESKETAMINE plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
40 mg/kg 2 times / week multiple, intravenous	unhealthy, 41.8 years (range: 11 - 63 years)	Other AEs: Dissociation, Dizziness...
40 mg/kg 2 times / week multiple, intravenous	unhealthy, 41.8 years (range: 11 - 63 years)	Other AEs: Vomiting...
56 mg 2 times / week steady, intranasal Recommended	unhealthy, adult	Disc. AE: Anxiety...
56 mg 2 times / week steady, intranasal Recommended	unhealthy, adult	Disc. AE: Depression, Blood pressure increased...
10 mg 1 times / day multiple, oral	unhealthy, adult

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AEs

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AE	Significance	Dose	Population
Nausea	10%	40 mg/kg 2 times / week multiple, intravenous	unhealthy, 41.8 years (range: 11 - 63 years)
Dissociation	17%	40 mg/kg 2 times / week multiple, intravenous	unhealthy, 41.8 years (range: 11 - 63 years)
Headache	23%	40 mg/kg 2 times / week multiple, intravenous	unhealthy, 41.8 years (range: 11 - 63 years)
Dizziness	3%	40 mg/kg 2 times / week multiple, intravenous	unhealthy, 41.8 years (range: 11 - 63 years)
Oropharyngeal pain	3%	40 mg/kg 2 times / week multiple, intravenous	unhealthy, 41.8 years (range: 11 - 63 years)

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,946 inducer 1,087 inhibitor 2,252	substrate 1,193		inhibitor 2,217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP 110 UGT 45 P-gp 1,741 BCRP 910 OATP1B1 1,079 OATP1B3 961 OAT1 725 OAT3 747 OCT2 779 MATE1 415 MATE2 267	CYP2B6 776 CYP2C19 1,119 P-gp 2,052 BCRP 697 OATP1B1 503 OATP1B3 435 OAT1 395 OAT3 391 OCT1 393 OCT2 434	CYP2B6 669 CYP1A2 832

Drug as perpetrator

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Target	Modality	Activity	Clinical evidence
CYP2B6 1,160	inducer 1,966	modest	no (co-administration study)
CYP3A4 2,633	inducer 1,966	modest	weak (co-administration study)
BCRP 985	inhibitor 4,027	no
CYP 150	inhibitor 4,027	no
CYP1A2 2,333	inducer 1,966	no

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Drug as victim

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Target	Modality	Activity	Clinical evidence
CYP2B6 776	substrate 4,014	major	weak (co-administration study)
CYP3A4 1,946	substrate 4,014	major	weak (co-administration study)
CYP2C19 1,119	substrate 4,014	minor
CYP2C9 1,193	substrate 4,014	minor
BCRP 697	substrate 4,014	no

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Tox targets

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Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2,263	inhibitor 2,237

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ChEBI	CHEBI:60799	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:60799
ZINC	ZINC000035999642	http://zinc15.docking.org/substances/ZINC000035999642

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PubMed

PubMed

Title	Date	PubMed
No data available in table

Substance Class	Chemical
Record UNII	50LFG02TXD
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Esketamine

Official Name

English

KETA-S

Preferred Name

English

JNJ-54135419

Common Name

English

KETAMINE, (S)-

Common Name

English

KETAMINE, S-

Common Name

English

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Classification Tree

Code System

Code

Other general anesthetics

WHO-ATC

N01AX14

Agent Affecting Nervous System

NCI_THESAURUS

C245

Other general anesthetics

WHO-VATC

QN01AX14

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Code System

Code

Type

Description

CHEBI

60799

PRIMARY

WIKIPEDIA

ESKETAMINE

PRIMARY

LACTMED

Esketamine

PRIMARY

SMS_ID

100000089754

PRIMARY

DRUG CENTRAL

4468

PRIMARY

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Related Record

Type

Details


					L8P1H35P2Z

Esketamine hydrochloride

SALT/SOLVATE -> PARENT

Amount:


					690G0D6V8H

KETAMINE

RACEMATE -> ENANTIOMER

Amount:


					4R3XO922WS

NMDA RECEPTOR

TARGET -> INHIBITOR

Comments:

Noncompetitive antagonists at the NMDA receptor via binding to an allosteric site distinct from the glutamate-binding site.This receptor is a critical modulator of CNS neurotransmission, and excitability changes produced by ketamine antagonism may explain the drug’s anesthetic and analgesic properties.

Interaction Type:

ALLOSTERIC INHIBITOR

Qualification:

Ki

Amount:

300 NANOMOLAR (average)


					PUO0521HZV

CYTOCHROME P450 3A4

METABOLIC ENZYME -> SUBSTRATE

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Related Record

Type

Details


					50LFG02TXD

Esketamine

ACTIVE MOIETY

Amount:

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SMILES

InChI

Approval Year

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Tox targets

Sourcing

PubMed

C_max

T_1/2

F_unbound

Drug as perpetrator