U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
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

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

1970
61
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
128 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/28100533/
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/28100533/
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/28100533/
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/28100533/
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/28100533/
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/28100533/
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/31827320/
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/31827320/
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/31827320/
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
OTHER GOV
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/211243Orig1s000ClinPharmR.pdf
single, respiratory
 ESKETAMINE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
7.5 h
OTHER GOV
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/211243Orig1s000ClinPharmR.pdf
single, respiratory
 NORKETAMINE, (S)- plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
56%
REVIEW
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/211243Orig1s000ClinPharmR.pdf
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:
https://pubmed.ncbi.nlm.nih.gov/26707087
unhealthy, 41.8 years (range: 11 - 63 years)
Health Status: unhealthy
Age Group: 41.8 years (range: 11 - 63 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/26707087
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:
https://pubmed.ncbi.nlm.nih.gov/26707087
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:
https://pubmed.ncbi.nlm.nih.gov/26707087
unhealthy, 41.8 years (range: 11 - 63 years)
Health Status: unhealthy
Age Group: 41.8 years (range: 11 - 63 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/26707087
Other AEs: Vomiting...
Other AEs:
Vomiting (3%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/26707087
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211243lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211243lbl.pdf
Disc. AE: Anxiety...
AEs leading to
discontinuation/dose reduction:
Anxiety (1.2%)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211243lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211243lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211243lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211243lbl.pdf
10 mg 1 times / day multiple, oral
Dose: 10 mg, 1 times / day
Route: oral
Route: multiple
Dose: 10 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/31783823
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/31783823
Sources:
https://pubmed.ncbi.nlm.nih.gov/31783823
28 mg single, intravenous
Dose: 28 mg
Route: intravenous
Route: single
Dose: 28 mg
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/211243Orig1s000ClinPharmR.pdf
unhealthy|healthy
Health Status: unhealthy|healthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/211243Orig1s000ClinPharmR.pdf
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/211243Orig1s000ClinPharmR.pdf
84 mg single, oral
Dose: 84 mg
Route: oral
Route: single
Dose: 84 mg
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/211243Orig1s000ClinPharmR.pdf
unhealthy|healthy
Health Status: unhealthy|healthy
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/211243Orig1s000ClinPharmR.pdf
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/211243Orig1s000ClinPharmR.pdf
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:
https://pubmed.ncbi.nlm.nih.gov/26707087
unhealthy, 41.8 years (range: 11 - 63 years)
Health Status: unhealthy
Age Group: 41.8 years (range: 11 - 63 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/26707087
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:
https://pubmed.ncbi.nlm.nih.gov/26707087
unhealthy, 41.8 years (range: 11 - 63 years)
Health Status: unhealthy
Age Group: 41.8 years (range: 11 - 63 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/26707087
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:
https://pubmed.ncbi.nlm.nih.gov/26707087
unhealthy, 41.8 years (range: 11 - 63 years)
Health Status: unhealthy
Age Group: 41.8 years (range: 11 - 63 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/26707087
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:
https://pubmed.ncbi.nlm.nih.gov/26707087
unhealthy, 41.8 years (range: 11 - 63 years)
Health Status: unhealthy
Age Group: 41.8 years (range: 11 - 63 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/26707087
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:
https://pubmed.ncbi.nlm.nih.gov/26707087
unhealthy, 41.8 years (range: 11 - 63 years)
Health Status: unhealthy
Age Group: 41.8 years (range: 11 - 63 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/26707087
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:
https://pubmed.ncbi.nlm.nih.gov/26707087
unhealthy, 41.8 years (range: 11 - 63 years)
Health Status: unhealthy
Age Group: 41.8 years (range: 11 - 63 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/26707087
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:
https://pubmed.ncbi.nlm.nih.gov/26707087
unhealthy, 41.8 years (range: 11 - 63 years)
Health Status: unhealthy
Age Group: 41.8 years (range: 11 - 63 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/26707087
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:
https://pubmed.ncbi.nlm.nih.gov/26707087
unhealthy, 41.8 years (range: 11 - 63 years)
Health Status: unhealthy
Age Group: 41.8 years (range: 11 - 63 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/26707087
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:
https://pubmed.ncbi.nlm.nih.gov/26707087
unhealthy, 41.8 years (range: 11 - 63 years)
Health Status: unhealthy
Age Group: 41.8 years (range: 11 - 63 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/26707087
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:
https://pubmed.ncbi.nlm.nih.gov/26707087
unhealthy, 41.8 years (range: 11 - 63 years)
Health Status: unhealthy
Age Group: 41.8 years (range: 11 - 63 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/26707087
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211243lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211243lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211243lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211243lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211243lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211243lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211243lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211243lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211243lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211243lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211243lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211243lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211243lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211243lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211243lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211243lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211243lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211243lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211243lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211243lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211243lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211243lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211243lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211243lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211243lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211243lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211243lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211243lbl.pdf
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1946

inducer
1087

inhibitor
2252
substrate
1193
inhibitor
2217

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP
110

UGT
45

P-gp
1741

BCRP
910

OATP1B1
1079

OATP1B3
961

OAT1
725

OAT3
747

OCT2
779

MATE1
415

MATE2
267
CYP2B6
776

CYP2C19
1119

P-gp
2052

BCRP
697

OATP1B1
503

OATP1B3
435

OAT1
395

OAT3
391

OCT1
393

OCT2
434
CYP2B6
669

CYP1A2
832
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP2B6
1160
 modest
no (co-administration study)
Comment: administration with bupropion (substrate): activity of hepatic CYP2B6 was not altered
Page: 33,34
CYP3A4
2633
 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
BCRP
985
 no
CYP
150
 no
CYP1A2
2333
 no
MATE1
416
 no
MATE2
267
 no
OAT1
730
 no
OAT3
749
 no
OATP1B1
1095
 no
OATP1B3
970
 no
OCT2
782
 no
P-gp
1932
 no
UGT
70
 no
CYP3A4
2633
 yes [IC50 1.92 uM]
noresketamine
3
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP2B6
776
 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
CYP3A4
1946
 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
CYP2C19
1119
 minor
CYP2C9
1193
 minor
BCRP
697
 no
OAT1
395
 no
noresketamine
3
OAT3
391
 no
noresketamine
3
OATP1B1
503
 no
OATP1B3
435
 no
OCT1
393
 no
noresketamine
3
OCT2
434
 no
noresketamine
3
P-gp
2052
 no
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
2263
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:60799
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:60799
ZINC
ZINC000035999642
http://zinc15.docking.org/substances/ZINC000035999642
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
Related Record Type Details
Structure of Esketamine
PARENT -> SALT/SOLVATE
Structure of KETAMINE HYDROCHLORIDE
RACEMATE -> ENANTIOMER
Related Record Type Details
Structure of 3-Chlorobenzonitrile
IMPURITY -> PARENT
Structure of (2-Chlorophenyl) (1-hydroxycyclopentyl) ketone
IMPURITY -> PARENT
Structure of N-Nitroso-esketamine
IMPURITY -> PARENT
Structure of Chlorocyclopentane
IMPURITY -> PARENT
Structure of N-nitroso-ketamine
IMPURITY -> PARENT
Structure of CYCLOPENTANE
IMPURITY -> PARENT
Structure of O-CHLOROBENZALDEHYDE
IMPURITY -> PARENT
Structure of 2-Chlorobenzonitrile
IMPURITY -> PARENT
Structure of 3-CHLOROBENZALDEHYDE
IMPURITY -> PARENT
Structure of CYCLOPENTANOL
IMPURITY -> PARENT
Structure of CYCLOPENTANOL
PARENT -> IMPURITY
Structure of 4-CHLOROBENZONITRILE
IMPURITY -> PARENT
Structure of Bromocyclopentane
IMPURITY -> PARENT
Related Record Type Details
Structure of Esketamine
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