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

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
Structure of ESKETAMINE

SMILES

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

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
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

1970
52
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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
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
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
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
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
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
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
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)
n = 11
Health Status: unhealthy
Condition: treatment resistant depression
Age Group: 41.8 years (range: 11 - 63 years)
Sex: M+F
Population Size: 11
Sources:
https://pubmed.ncbi.nlm.nih.gov/26707087
Other AEs: Vomiting...
Other AEs:
Vomiting (3%)
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)
n = 11
Health Status: unhealthy
Condition: treatment resistant depression
Age Group: 41.8 years (range: 11 - 63 years)
Sex: M+F
Population Size: 11
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
56 mg 2 times / week steady, intranasal (starting)
Recommended
Dose: 56 mg, 2 times / week
Route: intranasal
Route: steady
Dose: 56 mg, 2 times / week
Co-administed with::
antidepressant
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211243lbl.pdf
unhealthy, adult
Health Status: unhealthy
Condition: major depressive disorder
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
56 mg 2 times / week steady, intranasal (starting)
Recommended
Dose: 56 mg, 2 times / week
Route: intranasal
Route: steady
Dose: 56 mg, 2 times / week
Co-administed with::
antidepressant(oral)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211243lbl.pdf
unhealthy, adult
Health Status: unhealthy
Condition: major depressive disorder
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
10 mg 1 times / day multiple, oral (starting)
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
Condition: treatment resistant depression
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
Page: p. 43
unhealthy|healthy
n = 18
Health Status: unhealthy|healthy
Condition: treatment-resistant depression
Population Size: 18
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/211243Orig1s000ClinPharmR.pdf
Page: p. 43
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/211243Orig1s000ClinPharmR.pdf
Page: p. 43
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
Page: p. 43
unhealthy|healthy
n = 14
Health Status: unhealthy|healthy
Condition: treatment-resistant depression
Sex: M+F
Population Size: 14
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/211243Orig1s000ClinPharmR.pdf
Page: p. 43
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/211243Orig1s000ClinPharmR.pdf
Page: p. 43
AEs

AEs

AESignificanceDosePopulation
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)
n = 11
Health Status: unhealthy
Condition: treatment resistant depression
Age Group: 41.8 years (range: 11 - 63 years)
Sex: M+F
Population Size: 11
Sources:
https://pubmed.ncbi.nlm.nih.gov/26707087
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)
n = 11
Health Status: unhealthy
Condition: treatment resistant depression
Age Group: 41.8 years (range: 11 - 63 years)
Sex: M+F
Population Size: 11
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)
n = 11
Health Status: unhealthy
Condition: treatment resistant depression
Age Group: 41.8 years (range: 11 - 63 years)
Sex: M+F
Population Size: 11
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)
n = 11
Health Status: unhealthy
Condition: treatment resistant depression
Age Group: 41.8 years (range: 11 - 63 years)
Sex: M+F
Population Size: 11
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)
n = 11
Health Status: unhealthy
Condition: treatment resistant depression
Age Group: 41.8 years (range: 11 - 63 years)
Sex: M+F
Population Size: 11
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)
n = 11
Health Status: unhealthy
Condition: treatment resistant depression
Age Group: 41.8 years (range: 11 - 63 years)
Sex: M+F
Population Size: 11
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)
n = 11
Health Status: unhealthy
Condition: treatment resistant depression
Age Group: 41.8 years (range: 11 - 63 years)
Sex: M+F
Population Size: 11
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)
n = 11
Health Status: unhealthy
Condition: treatment resistant depression
Age Group: 41.8 years (range: 11 - 63 years)
Sex: M+F
Population Size: 11
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)
n = 11
Health Status: unhealthy
Condition: treatment resistant depression
Age Group: 41.8 years (range: 11 - 63 years)
Sex: M+F
Population Size: 11
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)
n = 11
Health Status: unhealthy
Condition: treatment resistant depression
Age Group: 41.8 years (range: 11 - 63 years)
Sex: M+F
Population Size: 11
Sources:
https://pubmed.ncbi.nlm.nih.gov/26707087
Hypertension 0.2%
Disc. AE
56 mg 2 times / week steady, intranasal (starting)
Recommended
Dose: 56 mg, 2 times / week
Route: intranasal
Route: steady
Dose: 56 mg, 2 times / week
Co-administed with::
antidepressant
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211243lbl.pdf
unhealthy, adult
Health Status: unhealthy
Condition: major depressive disorder
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 (starting)
Recommended
Dose: 56 mg, 2 times / week
Route: intranasal
Route: steady
Dose: 56 mg, 2 times / week
Co-administed with::
antidepressant
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211243lbl.pdf
unhealthy, adult
Health Status: unhealthy
Condition: major depressive disorder
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 (starting)
Recommended
Dose: 56 mg, 2 times / week
Route: intranasal
Route: steady
Dose: 56 mg, 2 times / week
Co-administed with::
antidepressant
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211243lbl.pdf
unhealthy, adult
Health Status: unhealthy
Condition: major depressive disorder
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 (starting)
Recommended
Dose: 56 mg, 2 times / week
Route: intranasal
Route: steady
Dose: 56 mg, 2 times / week
Co-administed with::
antidepressant
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211243lbl.pdf
unhealthy, adult
Health Status: unhealthy
Condition: major depressive disorder
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 (starting)
Recommended
Dose: 56 mg, 2 times / week
Route: intranasal
Route: steady
Dose: 56 mg, 2 times / week
Co-administed with::
antidepressant
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211243lbl.pdf
unhealthy, adult
Health Status: unhealthy
Condition: major depressive disorder
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 (starting)
Recommended
Dose: 56 mg, 2 times / week
Route: intranasal
Route: steady
Dose: 56 mg, 2 times / week
Co-administed with::
antidepressant
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211243lbl.pdf
unhealthy, adult
Health Status: unhealthy
Condition: major depressive disorder
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 (starting)
Recommended
Dose: 56 mg, 2 times / week
Route: intranasal
Route: steady
Dose: 56 mg, 2 times / week
Co-administed with::
antidepressant
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211243lbl.pdf
unhealthy, adult
Health Status: unhealthy
Condition: major depressive disorder
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 (starting)
Recommended
Dose: 56 mg, 2 times / week
Route: intranasal
Route: steady
Dose: 56 mg, 2 times / week
Co-administed with::
antidepressant
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211243lbl.pdf
unhealthy, adult
Health Status: unhealthy
Condition: major depressive disorder
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 (starting)
Recommended
Dose: 56 mg, 2 times / week
Route: intranasal
Route: steady
Dose: 56 mg, 2 times / week
Co-administed with::
antidepressant
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211243lbl.pdf
unhealthy, adult
Health Status: unhealthy
Condition: major depressive disorder
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 (starting)
Recommended
Dose: 56 mg, 2 times / week
Route: intranasal
Route: steady
Dose: 56 mg, 2 times / week
Co-administed with::
antidepressant
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211243lbl.pdf
unhealthy, adult
Health Status: unhealthy
Condition: major depressive disorder
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 (starting)
Recommended
Dose: 56 mg, 2 times / week
Route: intranasal
Route: steady
Dose: 56 mg, 2 times / week
Co-administed with::
antidepressant
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211243lbl.pdf
unhealthy, adult
Health Status: unhealthy
Condition: major depressive disorder
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 (starting)
Recommended
Dose: 56 mg, 2 times / week
Route: intranasal
Route: steady
Dose: 56 mg, 2 times / week
Co-administed with::
antidepressant
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211243lbl.pdf
unhealthy, adult
Health Status: unhealthy
Condition: major depressive disorder
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 (starting)
Recommended
Dose: 56 mg, 2 times / week
Route: intranasal
Route: steady
Dose: 56 mg, 2 times / week
Co-administed with::
antidepressant
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211243lbl.pdf
unhealthy, adult
Health Status: unhealthy
Condition: major depressive disorder
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211243lbl.pdf
Anxiety 1.2%
Disc. AE
56 mg 2 times / week steady, intranasal (starting)
Recommended
Dose: 56 mg, 2 times / week
Route: intranasal
Route: steady
Dose: 56 mg, 2 times / week
Co-administed with::
antidepressant(oral)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211243lbl.pdf
unhealthy, adult
Health Status: unhealthy
Condition: major depressive disorder
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211243lbl.pdf
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1709

inducer
768

inhibitor
1579
substrate
1010
inhibitor
1599

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP
110

UGT
34

P-gp
1437

BCRP
691

OATP1B1
781

OATP1B3
700

OAT1
595

OAT3
636

OCT2
638

MATE1
304

MATE2
261
CYP2B6
660

CYP2C19
985

P-gp
1527

BCRP
555

OATP1B1
403

OATP1B3
347

OAT1
320

OAT3
333

OCT1
322

OCT2
348
CYP2B6
538

CYP1A2
689
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP2B6
985
 modest
no (co-administration study)
Comment: administration with bupropion (substrate): activity of hepatic CYP2B6 was not altered
Page: 33,34
CYP3A4
1909
 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
765
 no
CYP
146
 no
CYP1A2
1673
 no
MATE1
306
 no
MATE2
261
 no
OAT1
599
 no
OAT3
638
 no
OATP1B1
796
 no
OATP1B3
709
 no
OCT2
639
 no
P-gp
1626
 no
UGT
58
 no
CYP3A4
1909
 yes [IC50 1.92 uM]
noresketamine
3
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP2B6
660
 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
1709
 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
985
 minor
CYP2C9
1010
 minor
BCRP
555
 no
OAT1
320
 no
noresketamine
3
OAT3
333
 no
noresketamine
3
OATP1B1
403
 no
OATP1B3
347
 no
OCT1
322
 no
noresketamine
3
OCT2
348
 no
noresketamine
3
P-gp
1527
 no
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
1632
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
Stereoselective interaction of ketamine with recombinant mu, kappa, and delta opioid receptors expressed in Chinese hamster ovary cells.
1999 Jan
Substance Class Chemical
Created
by admin
on Wed Jul 05 23:41:12 UTC 2023
Edited
by admin
on Wed Jul 05 23:41:12 UTC 2023
Record UNII
50LFG02TXD
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ESKETAMINE
INN   USAN   WHO-DD  
INN   USAN  
Official Name English
JNJ-54135419
Common Name English
KETAMINE, S-
Common Name English
(2S)-2-(2-Chlorophenyl)-2-(methylamino)cyclohexanone
Systematic Name English
CYCLOHEXANONE, 2-(O-CHLOROPHENYL)-2-(METHYLAMINO)-, (-)-
Common Name English
ESKETAMINE [USAN]
Common Name English
KETAVED
Brand Name English
S-KETAMINE
Common Name English
(-)-KETAMINE
Common Name English
Esketamine [WHO-DD]
Common Name English
L-KETAMINE
Common Name English
CYCLOHEXANONE, 2-(2-CHLOROPHENYL)-2-(METHYLAMINO)-, (2S)-
Systematic Name English
CYCLOHEXANONE, 2-(2-CHLOROPHENYL)-2-(METHYLAMINO)-, (S)-
Systematic Name English
S-(-)-KETAMINE
Common Name English
KETA-S
Brand Name English
esketamine [INN]
Common Name English
KETAMINE, (S)-
Common Name English
(S)-2-(O-CHLOROPHENYL)-2-(METHYLAMINO)CYCLOHEXANONE
Common Name English
Classification Tree Code System Code
WHO-ATC N01AX14
Created by admin on Wed Jul 05 23:41:12 UTC 2023 , Edited by admin on Wed Jul 05 23:41:12 UTC 2023
NCI_THESAURUS C245
Created by admin on Wed Jul 05 23:41:12 UTC 2023 , Edited by admin on Wed Jul 05 23:41:12 UTC 2023
WHO-VATC QN01AX14
Created by admin on Wed Jul 05 23:41:12 UTC 2023 , Edited by admin on Wed Jul 05 23:41:12 UTC 2023
Code System Code Type Description
CHEBI
60799
Created by admin on Wed Jul 05 23:41:12 UTC 2023 , Edited by admin on Wed Jul 05 23:41:12 UTC 2023
PRIMARY
WIKIPEDIA
ESKETAMINE
Created by admin on Wed Jul 05 23:41:12 UTC 2023 , Edited by admin on Wed Jul 05 23:41:12 UTC 2023
PRIMARY
LACTMED
Esketamine
Created by admin on Wed Jul 05 23:41:12 UTC 2023 , Edited by admin on Wed Jul 05 23:41:12 UTC 2023
PRIMARY
SMS_ID
100000089754
Created by admin on Wed Jul 05 23:41:12 UTC 2023 , Edited by admin on Wed Jul 05 23:41:12 UTC 2023
PRIMARY
DRUG CENTRAL
4468
Created by admin on Wed Jul 05 23:41:12 UTC 2023 , Edited by admin on Wed Jul 05 23:41:12 UTC 2023
PRIMARY
RXCUI
2119365
Created by admin on Wed Jul 05 23:41:12 UTC 2023 , Edited by admin on Wed Jul 05 23:41:12 UTC 2023
PRIMARY
INN
7884
Created by admin on Wed Jul 05 23:41:12 UTC 2023 , Edited by admin on Wed Jul 05 23:41:12 UTC 2023
PRIMARY
DRUG BANK
DB11823
Created by admin on Wed Jul 05 23:41:12 UTC 2023 , Edited by admin on Wed Jul 05 23:41:12 UTC 2023
PRIMARY
EVMPD
SUB25825
Created by admin on Wed Jul 05 23:41:12 UTC 2023 , Edited by admin on Wed Jul 05 23:41:12 UTC 2023
PRIMARY
EPA CompTox
DTXSID6047810
Created by admin on Wed Jul 05 23:41:12 UTC 2023 , Edited by admin on Wed Jul 05 23:41:12 UTC 2023
PRIMARY
FDA UNII
50LFG02TXD
Created by admin on Wed Jul 05 23:41:12 UTC 2023 , Edited by admin on Wed Jul 05 23:41:12 UTC 2023
PRIMARY
ChEMBL
CHEMBL395091
Created by admin on Wed Jul 05 23:41:12 UTC 2023 , Edited by admin on Wed Jul 05 23:41:12 UTC 2023
PRIMARY
CAS
33643-46-8
Created by admin on Wed Jul 05 23:41:12 UTC 2023 , Edited by admin on Wed Jul 05 23:41:12 UTC 2023
PRIMARY
DAILYMED
50LFG02TXD
Created by admin on Wed Jul 05 23:41:12 UTC 2023 , Edited by admin on Wed Jul 05 23:41:12 UTC 2023
PRIMARY
USAN
AB-57
Created by admin on Wed Jul 05 23:41:12 UTC 2023 , Edited by admin on Wed Jul 05 23:41:12 UTC 2023
PRIMARY
PUBCHEM
182137
Created by admin on Wed Jul 05 23:41:12 UTC 2023 , Edited by admin on Wed Jul 05 23:41:12 UTC 2023
PRIMARY
NCI_THESAURUS
C81400
Created by admin on Wed Jul 05 23:41:12 UTC 2023 , Edited by admin on Wed Jul 05 23:41:12 UTC 2023
PRIMARY
Related Record Type Details
Structure of ESKETAMINE HYDROCHLORIDE
SALT/SOLVATE -> PARENT
Structure of KETAMINE
RACEMATE -> ENANTIOMER
NMDA RECEPTOR
TARGET -> INHIBITOR
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.
ALLOSTERIC INHIBITOR
Ki
CYTOCHROME P450 3A4
METABOLIC ENZYME -> SUBSTRATE
Related Record Type Details
Structure of ESKETAMINE
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