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This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry ABSOLUTE
Molecular Formula C13H16ClNO.ClH
Molecular Weight 274.186
Optical Activity ( + )
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Esketamine hydrochloride

SMILES

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

InChI

InChIKey=VCMGMSHEPQENPE-ZOWNYOTGSA-N
InChI=1S/C13H16ClNO.ClH/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;1H/t13-;/m0./s1

HIDE SMILES / InChI

Molecular Formula C13H16ClNO
Molecular Weight 237.725
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
128 ng/mL
0.35 mg/kg single, respiratory
dose: 0.35 mg/kg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
ESKETAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
180 ng/mL
0.5 mg/kg single, respiratory
dose: 0.5 mg/kg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
ESKETAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
227 ng/mL
0.7 mg/kg single, respiratory
dose: 0.7 mg/kg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
ESKETAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
52 ng/mL
0.35 mg/kg single, respiratory
dose: 0.35 mg/kg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
NORKETAMINE, (S)- plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
97 ng/mL
0.5 mg/kg single, respiratory
dose: 0.5 mg/kg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
NORKETAMINE, (S)- plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
153 ng/mL
0.7 mg/kg single, respiratory
dose: 0.7 mg/kg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
NORKETAMINE, (S)- plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
2277.6 ng/mL
0.5 mg/kg single, intramuscular
dose: 0.5 mg/kg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
ESKETAMINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
475.2 ng × h/mL
0.5 mg/kg single, intramuscular
dose: 0.5 mg/kg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
ESKETAMINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
287.5 min
0.5 mg/kg single, intramuscular
dose: 0.5 mg/kg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
ESKETAMINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
11.1 h
single, respiratory
ESKETAMINE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
7.5 h
single, respiratory
NORKETAMINE, (S)- plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
56%
ESKETAMINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
40 mg/kg 2 times / week multiple, intravenous
Dose: 40 mg/kg, 2 times / week
Route: intravenous
Route: multiple
Dose: 40 mg/kg, 2 times / week
Sources:
unhealthy, 41.8 years (range: 11 - 63 years)
Health Status: unhealthy
Age Group: 41.8 years (range: 11 - 63 years)
Sex: M+F
Sources:
Other AEs: Dissociation, Dizziness...
Other AEs:
Dissociation (17%)
Dizziness (3%)
Dry mouth (7%)
Headache (23%)
Nasopharyngitis (7%)
Nausea (10%)
Oropharyngeal pain (3%)
Paresthesia (7%)
Vertigo (7%)
Sources:
40 mg/kg 2 times / week multiple, intravenous
Dose: 40 mg/kg, 2 times / week
Route: intravenous
Route: multiple
Dose: 40 mg/kg, 2 times / week
Sources:
unhealthy, 41.8 years (range: 11 - 63 years)
Health Status: unhealthy
Age Group: 41.8 years (range: 11 - 63 years)
Sex: M+F
Sources:
Other AEs: Vomiting...
Other AEs:
Vomiting (3%)
Sources:
56 mg 2 times / week steady, intranasal
Recommended
Dose: 56 mg, 2 times / week
Route: intranasal
Route: steady
Dose: 56 mg, 2 times / week
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
Disc. AE: Anxiety...
AEs leading to
discontinuation/dose reduction:
Anxiety (1.2%)
Sources:
56 mg 2 times / week steady, intranasal
Recommended
Dose: 56 mg, 2 times / week
Route: intranasal
Route: steady
Dose: 56 mg, 2 times / week
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
Disc. AE: Depression, Blood pressure increased...
AEs leading to
discontinuation/dose reduction:
Depression (0.9%)
Blood pressure increased (0.6%)
Dizziness (0.6%)
Suicidal ideation (0.5%)
Dissociation (0.4%)
Nausea (0.4%)
Vomiting (0.4%)
Headache (0.3%)
Muscular weakness (0.3%)
Vertigo (0.2%)
Hypertension (0.2%)
Panic attack (0.2%)
Sedation (0.2%)
Sources:
10 mg 1 times / day multiple, oral
Dose: 10 mg, 1 times / day
Route: oral
Route: multiple
Dose: 10 mg, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
28 mg single, intravenous
Dose: 28 mg
Route: intravenous
Route: single
Dose: 28 mg
Sources:
unhealthy|healthy
84 mg single, oral
unhealthy|healthy
AEs

AEs

AESignificanceDosePopulation
Nausea 10%
40 mg/kg 2 times / week multiple, intravenous
Dose: 40 mg/kg, 2 times / week
Route: intravenous
Route: multiple
Dose: 40 mg/kg, 2 times / week
Sources:
unhealthy, 41.8 years (range: 11 - 63 years)
Health Status: unhealthy
Age Group: 41.8 years (range: 11 - 63 years)
Sex: M+F
Sources:
Dissociation 17%
40 mg/kg 2 times / week multiple, intravenous
Dose: 40 mg/kg, 2 times / week
Route: intravenous
Route: multiple
Dose: 40 mg/kg, 2 times / week
Sources:
unhealthy, 41.8 years (range: 11 - 63 years)
Health Status: unhealthy
Age Group: 41.8 years (range: 11 - 63 years)
Sex: M+F
Sources:
Headache 23%
40 mg/kg 2 times / week multiple, intravenous
Dose: 40 mg/kg, 2 times / week
Route: intravenous
Route: multiple
Dose: 40 mg/kg, 2 times / week
Sources:
unhealthy, 41.8 years (range: 11 - 63 years)
Health Status: unhealthy
Age Group: 41.8 years (range: 11 - 63 years)
Sex: M+F
Sources:
Dizziness 3%
40 mg/kg 2 times / week multiple, intravenous
Dose: 40 mg/kg, 2 times / week
Route: intravenous
Route: multiple
Dose: 40 mg/kg, 2 times / week
Sources:
unhealthy, 41.8 years (range: 11 - 63 years)
Health Status: unhealthy
Age Group: 41.8 years (range: 11 - 63 years)
Sex: M+F
Sources:
Oropharyngeal pain 3%
40 mg/kg 2 times / week multiple, intravenous
Dose: 40 mg/kg, 2 times / week
Route: intravenous
Route: multiple
Dose: 40 mg/kg, 2 times / week
Sources:
unhealthy, 41.8 years (range: 11 - 63 years)
Health Status: unhealthy
Age Group: 41.8 years (range: 11 - 63 years)
Sex: M+F
Sources:
Dry mouth 7%
40 mg/kg 2 times / week multiple, intravenous
Dose: 40 mg/kg, 2 times / week
Route: intravenous
Route: multiple
Dose: 40 mg/kg, 2 times / week
Sources:
unhealthy, 41.8 years (range: 11 - 63 years)
Health Status: unhealthy
Age Group: 41.8 years (range: 11 - 63 years)
Sex: M+F
Sources:
Nasopharyngitis 7%
40 mg/kg 2 times / week multiple, intravenous
Dose: 40 mg/kg, 2 times / week
Route: intravenous
Route: multiple
Dose: 40 mg/kg, 2 times / week
Sources:
unhealthy, 41.8 years (range: 11 - 63 years)
Health Status: unhealthy
Age Group: 41.8 years (range: 11 - 63 years)
Sex: M+F
Sources:
Paresthesia 7%
40 mg/kg 2 times / week multiple, intravenous
Dose: 40 mg/kg, 2 times / week
Route: intravenous
Route: multiple
Dose: 40 mg/kg, 2 times / week
Sources:
unhealthy, 41.8 years (range: 11 - 63 years)
Health Status: unhealthy
Age Group: 41.8 years (range: 11 - 63 years)
Sex: M+F
Sources:
Vertigo 7%
40 mg/kg 2 times / week multiple, intravenous
Dose: 40 mg/kg, 2 times / week
Route: intravenous
Route: multiple
Dose: 40 mg/kg, 2 times / week
Sources:
unhealthy, 41.8 years (range: 11 - 63 years)
Health Status: unhealthy
Age Group: 41.8 years (range: 11 - 63 years)
Sex: M+F
Sources:
Vomiting 3%
40 mg/kg 2 times / week multiple, intravenous
Dose: 40 mg/kg, 2 times / week
Route: intravenous
Route: multiple
Dose: 40 mg/kg, 2 times / week
Sources:
unhealthy, 41.8 years (range: 11 - 63 years)
Health Status: unhealthy
Age Group: 41.8 years (range: 11 - 63 years)
Sex: M+F
Sources:
Anxiety 1.2%
Disc. AE
56 mg 2 times / week steady, intranasal
Recommended
Dose: 56 mg, 2 times / week
Route: intranasal
Route: steady
Dose: 56 mg, 2 times / week
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
Hypertension 0.2%
Disc. AE
56 mg 2 times / week steady, intranasal
Recommended
Dose: 56 mg, 2 times / week
Route: intranasal
Route: steady
Dose: 56 mg, 2 times / week
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
Panic attack 0.2%
Disc. AE
56 mg 2 times / week steady, intranasal
Recommended
Dose: 56 mg, 2 times / week
Route: intranasal
Route: steady
Dose: 56 mg, 2 times / week
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
Sedation 0.2%
Disc. AE
56 mg 2 times / week steady, intranasal
Recommended
Dose: 56 mg, 2 times / week
Route: intranasal
Route: steady
Dose: 56 mg, 2 times / week
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
Vertigo 0.2%
Disc. AE
56 mg 2 times / week steady, intranasal
Recommended
Dose: 56 mg, 2 times / week
Route: intranasal
Route: steady
Dose: 56 mg, 2 times / week
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
Headache 0.3%
Disc. AE
56 mg 2 times / week steady, intranasal
Recommended
Dose: 56 mg, 2 times / week
Route: intranasal
Route: steady
Dose: 56 mg, 2 times / week
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
Muscular weakness 0.3%
Disc. AE
56 mg 2 times / week steady, intranasal
Recommended
Dose: 56 mg, 2 times / week
Route: intranasal
Route: steady
Dose: 56 mg, 2 times / week
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
Dissociation 0.4%
Disc. AE
56 mg 2 times / week steady, intranasal
Recommended
Dose: 56 mg, 2 times / week
Route: intranasal
Route: steady
Dose: 56 mg, 2 times / week
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
Nausea 0.4%
Disc. AE
56 mg 2 times / week steady, intranasal
Recommended
Dose: 56 mg, 2 times / week
Route: intranasal
Route: steady
Dose: 56 mg, 2 times / week
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
Vomiting 0.4%
Disc. AE
56 mg 2 times / week steady, intranasal
Recommended
Dose: 56 mg, 2 times / week
Route: intranasal
Route: steady
Dose: 56 mg, 2 times / week
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
Suicidal ideation 0.5%
Disc. AE
56 mg 2 times / week steady, intranasal
Recommended
Dose: 56 mg, 2 times / week
Route: intranasal
Route: steady
Dose: 56 mg, 2 times / week
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
Blood pressure increased 0.6%
Disc. AE
56 mg 2 times / week steady, intranasal
Recommended
Dose: 56 mg, 2 times / week
Route: intranasal
Route: steady
Dose: 56 mg, 2 times / week
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
Dizziness 0.6%
Disc. AE
56 mg 2 times / week steady, intranasal
Recommended
Dose: 56 mg, 2 times / week
Route: intranasal
Route: steady
Dose: 56 mg, 2 times / week
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
Depression 0.9%
Disc. AE
56 mg 2 times / week steady, intranasal
Recommended
Dose: 56 mg, 2 times / week
Route: intranasal
Route: steady
Dose: 56 mg, 2 times / week
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
modest
no (co-administration study)
Comment: administration with bupropion (substrate): activity of hepatic CYP2B6 was not altered
Page: 33,34
modest
weak (co-administration study)
Comment: twice-a-week dosing of nasal esketamine (84 mg) reduced the AUClast and AUC?? of probe CYP3A substrate Reference ID: 4397019 35 midazolam by a mean of 18% and 16%, respectively;
Page: 33,35
no
no
no
no
no
no
no
no
no
no
no
no
yes [IC50 1.92 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
major
weak (co-administration study)
Comment: pretreatment with ticlopidine (inhibitor) had no effect on the mean esketamine Cmax following a 56-mg nasal dose, whereas the AUC of esketamine was increased by 29%; Cmax, AUClast, and AUCinf of esketamine were approximately 17%, 31%, and 28% lower, respectively, when subjects were pretreated with rifampicin (inducer);
Page: 33,36,37
major
weak (co-administration study)
Comment: esketamine Cmax and AUCinf were increased by 11% and 4%, respectively, when coadministered with clarithromycin; Cmax, AUClast, and AUCinf of esketamine were approximately 17%, 31%, and 28% lower, respectively, when subjects were pretreated with rifampicin (inducer);
Page: 33,36,37
minor
minor
no
no
no
no
no
no
no
no
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Determination of absolute configuration of ketamine enantiomers by HPLC-CD-UV technique.
1999
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:56:23 GMT 2025
Edited
by admin
on Mon Mar 31 17:56:23 GMT 2025
Record UNII
L8P1H35P2Z
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
KETANEST S
Preferred Name English
Esketamine hydrochloride
EP   MART.   USAN   WHO-DD  
USAN  
Official Name English
Esketamine hydrochloride [MART.]
Common Name English
Esketamine hydrochloride [USAN]
Common Name English
Cyclohexanone, 2-(2-chlorophenyl)-2-(methylamino)-, hydrochloride (1:1), (2S)-
Systematic Name English
SPRAVATO
Brand Name English
Esketamine hydrochloride [EP MONOGRAPH]
Common Name English
Esketamine hydrochloride [JAN]
Common Name English
(S)-(+)-Ketamine hydrochloride
Common Name English
Esketamine hydrochloride [ORANGE BOOK]
Common Name English
Ketamine hydrochloride, S-
Common Name English
Esketamine hydrochloride [WHO-DD]
Common Name English
(+)-(S)-Ketamine hydrochloride
Common Name English
(2S)-2-(2-Chlorophenyl)-2-(methylamino)cyclohexanone hydrochloride
Systematic Name English
Ketamine hydrochloride, (S)-
Common Name English
AM-101
Code English
AM-101 (Esketamine hydrochloride gel)
Common Name English
Code System Code Type Description
DRUG BANK
DBSALT002086
Created by admin on Mon Mar 31 17:56:23 GMT 2025 , Edited by admin on Mon Mar 31 17:56:23 GMT 2025
PRIMARY
CAS
33643-47-9
Created by admin on Mon Mar 31 17:56:23 GMT 2025 , Edited by admin on Mon Mar 31 17:56:23 GMT 2025
PRIMARY
FDA UNII
L8P1H35P2Z
Created by admin on Mon Mar 31 17:56:23 GMT 2025 , Edited by admin on Mon Mar 31 17:56:23 GMT 2025
PRIMARY
PUBCHEM
44632368
Created by admin on Mon Mar 31 17:56:23 GMT 2025 , Edited by admin on Mon Mar 31 17:56:23 GMT 2025
PRIMARY
DAILYMED
L8P1H35P2Z
Created by admin on Mon Mar 31 17:56:23 GMT 2025 , Edited by admin on Mon Mar 31 17:56:23 GMT 2025
PRIMARY
SMS_ID
100000091708
Created by admin on Mon Mar 31 17:56:23 GMT 2025 , Edited by admin on Mon Mar 31 17:56:23 GMT 2025
PRIMARY
NCI_THESAURUS
C175718
Created by admin on Mon Mar 31 17:56:23 GMT 2025 , Edited by admin on Mon Mar 31 17:56:23 GMT 2025
PRIMARY
RXCUI
2119366
Created by admin on Mon Mar 31 17:56:23 GMT 2025 , Edited by admin on Mon Mar 31 17:56:23 GMT 2025
PRIMARY
EVMPD
SUB25811
Created by admin on Mon Mar 31 17:56:23 GMT 2025 , Edited by admin on Mon Mar 31 17:56:23 GMT 2025
PRIMARY
CHEBI
60800
Created by admin on Mon Mar 31 17:56:23 GMT 2025 , Edited by admin on Mon Mar 31 17:56:23 GMT 2025
PRIMARY
EPA CompTox
DTXSID601027734
Created by admin on Mon Mar 31 17:56:23 GMT 2025 , Edited by admin on Mon Mar 31 17:56:23 GMT 2025
PRIMARY
ChEMBL
CHEMBL395091
Created by admin on Mon Mar 31 17:56:23 GMT 2025 , Edited by admin on Mon Mar 31 17:56:23 GMT 2025
PRIMARY
USAN
AB-58
Created by admin on Mon Mar 31 17:56:23 GMT 2025 , Edited by admin on Mon Mar 31 17:56:23 GMT 2025
PRIMARY
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