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
63
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
1737

inducer
781

inhibitor
1587
substrate
1037
inhibitor
1612

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP
111

UGT
35

P-gp
1461

BCRP
699

OATP1B1
788

OATP1B3
706

OAT1
599

OAT3
642

OCT2
647

MATE1
306

MATE2
263
CYP2B6
664

CYP2C19
991

P-gp
1537

BCRP
561

OATP1B1
406

OATP1B3
350

OAT1
326

OAT3
339

OCT1
327

OCT2
355
CYP2B6
547

CYP1A2
701
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP2B6
1001
 modest
no (co-administration study)
Comment: administration with bupropion (substrate): activity of hepatic CYP2B6 was not altered
Page: 33,34
CYP3A4
1925
 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
773
 no
CYP
147
 no
CYP1A2
1692
 no
MATE1
308
 no
MATE2
263
 no
OAT1
603
 no
OAT3
644
 no
OATP1B1
803
 no
OATP1B3
715
 no
OCT2
648
 no
P-gp
1650
 no
UGT
59
 no
CYP3A4
1925
 yes [IC50 1.92 uM]
noresketamine
3
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP2B6
664
 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
1737
 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
991
 minor
CYP2C9
1037
 minor
BCRP
561
 no
OAT1
326
 no
noresketamine
3
OAT3
339
 no
noresketamine
3
OATP1B1
406
 no
OATP1B3
350
 no
OCT1
327
 no
noresketamine
3
OCT2
355
 no
noresketamine
3
P-gp
1537
 no
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
1647
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
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:13:49 GMT 2023
Edited
by admin
on Fri Dec 15 16:13:49 GMT 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
KETAMINE, S-
Common Name English
(2S)-2-(2-Chlorophenyl)-2-(methylamino)cyclohexanone
Systematic Name English
ESKETAMINE [USAN]
Common Name English
KETAVED
Brand Name English
S-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
KETA-S
Brand Name English
esketamine [INN]
Common Name English
KETAMINE S-ISOMER
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 Fri Dec 15 16:13:49 GMT 2023 , Edited by admin on Fri Dec 15 16:13:49 GMT 2023
NCI_THESAURUS C245
Created by admin on Fri Dec 15 16:13:49 GMT 2023 , Edited by admin on Fri Dec 15 16:13:49 GMT 2023
WHO-VATC QN01AX14
Created by admin on Fri Dec 15 16:13:49 GMT 2023 , Edited by admin on Fri Dec 15 16:13:49 GMT 2023
Code System Code Type Description
CHEBI
60799
Created by admin on Fri Dec 15 16:13:49 GMT 2023 , Edited by admin on Fri Dec 15 16:13:49 GMT 2023
PRIMARY
WIKIPEDIA
ESKETAMINE
Created by admin on Fri Dec 15 16:13:49 GMT 2023 , Edited by admin on Fri Dec 15 16:13:49 GMT 2023
PRIMARY
LACTMED
Esketamine
Created by admin on Fri Dec 15 16:13:49 GMT 2023 , Edited by admin on Fri Dec 15 16:13:49 GMT 2023
PRIMARY
SMS_ID
100000089754
Created by admin on Fri Dec 15 16:13:49 GMT 2023 , Edited by admin on Fri Dec 15 16:13:49 GMT 2023
PRIMARY
DRUG CENTRAL
4468
Created by admin on Fri Dec 15 16:13:49 GMT 2023 , Edited by admin on Fri Dec 15 16:13:49 GMT 2023
PRIMARY
RXCUI
2119365
Created by admin on Fri Dec 15 16:13:49 GMT 2023 , Edited by admin on Fri Dec 15 16:13:49 GMT 2023
PRIMARY
INN
7884
Created by admin on Fri Dec 15 16:13:49 GMT 2023 , Edited by admin on Fri Dec 15 16:13:49 GMT 2023
PRIMARY
DRUG BANK
DB11823
Created by admin on Fri Dec 15 16:13:49 GMT 2023 , Edited by admin on Fri Dec 15 16:13:49 GMT 2023
PRIMARY
EVMPD
SUB25825
Created by admin on Fri Dec 15 16:13:49 GMT 2023 , Edited by admin on Fri Dec 15 16:13:49 GMT 2023
PRIMARY
EPA CompTox
DTXSID6047810
Created by admin on Fri Dec 15 16:13:49 GMT 2023 , Edited by admin on Fri Dec 15 16:13:49 GMT 2023
PRIMARY
FDA UNII
50LFG02TXD
Created by admin on Fri Dec 15 16:13:49 GMT 2023 , Edited by admin on Fri Dec 15 16:13:49 GMT 2023
PRIMARY
ChEMBL
CHEMBL395091
Created by admin on Fri Dec 15 16:13:49 GMT 2023 , Edited by admin on Fri Dec 15 16:13:49 GMT 2023
PRIMARY
CAS
33643-46-8
Created by admin on Fri Dec 15 16:13:49 GMT 2023 , Edited by admin on Fri Dec 15 16:13:49 GMT 2023
PRIMARY
DAILYMED
50LFG02TXD
Created by admin on Fri Dec 15 16:13:49 GMT 2023 , Edited by admin on Fri Dec 15 16:13:49 GMT 2023
PRIMARY
USAN
AB-57
Created by admin on Fri Dec 15 16:13:49 GMT 2023 , Edited by admin on Fri Dec 15 16:13:49 GMT 2023
PRIMARY
PUBCHEM
182137
Created by admin on Fri Dec 15 16:13:49 GMT 2023 , Edited by admin on Fri Dec 15 16:13:49 GMT 2023
PRIMARY
NCI_THESAURUS
C81400
Created by admin on Fri Dec 15 16:13:49 GMT 2023 , Edited by admin on Fri Dec 15 16:13:49 GMT 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
ACTIVE MOIETY
NIH
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