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

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=C(Cl)C=CC=C2

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
51
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
1670

inducer
753

inhibitor
1532
substrate
985
inhibitor
1570

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP
107

UGT
32

P-gp
1401

BCRP
678

OATP1B1
770

OATP1B3
691

OAT1
584

OAT3
625

OCT2
630

MATE1
302

MATE2
259
CYP2B6
648

CYP2C19
955

P-gp
1491

BCRP
545

OATP1B1
389

OATP1B3
333

OAT1
314

OAT3
328

OCT1
317

OCT2
336
CYP2B6
521

CYP1A2
671
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP2B6
946
 modest
no (co-administration study)
Comment: administration with bupropion (substrate): activity of hepatic CYP2B6 was not altered
Page: 33,34
CYP3A4
1857
 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
751
 no
CYP
143
 no
CYP1A2
1620
 no
MATE1
304
 no
MATE2
259
 no
OAT1
588
 no
OAT3
627
 no
OATP1B1
785
 no
OATP1B3
700
 no
OCT2
631
 no
P-gp
1588
 no
UGT
55
 no
CYP3A4
1857
 yes [IC50 1.92 uM]
noresketamine
2
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP2B6
648
 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
1670
 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
955
 minor
CYP2C9
985
 minor
BCRP
545
 no
OAT1
314
 no
noresketamine
2
OAT3
328
 no
noresketamine
2
OATP1B1
389
 no
OATP1B3
333
 no
OCT1
317
 no
noresketamine
2
OCT2
336
 no
noresketamine
2
P-gp
1491
 no
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
1603
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
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 Fri Dec 16 16:59:40 UTC 2022
Edited
by admin
on Fri Dec 16 16:59:40 UTC 2022
Record UNII
L8P1H35P2Z
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
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
KETANEST S
Brand 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 Fri Dec 16 16:59:40 UTC 2022 , Edited by admin on Fri Dec 16 16:59:40 UTC 2022
PRIMARY
CAS
33643-47-9
Created by admin on Fri Dec 16 16:59:40 UTC 2022 , Edited by admin on Fri Dec 16 16:59:40 UTC 2022
PRIMARY
FDA UNII
L8P1H35P2Z
Created by admin on Fri Dec 16 16:59:40 UTC 2022 , Edited by admin on Fri Dec 16 16:59:40 UTC 2022
PRIMARY
PUBCHEM
44632368
Created by admin on Fri Dec 16 16:59:40 UTC 2022 , Edited by admin on Fri Dec 16 16:59:40 UTC 2022
PRIMARY
DAILYMED
L8P1H35P2Z
Created by admin on Fri Dec 16 16:59:40 UTC 2022 , Edited by admin on Fri Dec 16 16:59:40 UTC 2022
PRIMARY
NCI_THESAURUS
C175718
Created by admin on Fri Dec 16 16:59:40 UTC 2022 , Edited by admin on Fri Dec 16 16:59:40 UTC 2022
PRIMARY
RXCUI
2119366
Created by admin on Fri Dec 16 16:59:40 UTC 2022 , Edited by admin on Fri Dec 16 16:59:40 UTC 2022
PRIMARY
EVMPD
SUB25811
Created by admin on Fri Dec 16 16:59:40 UTC 2022 , Edited by admin on Fri Dec 16 16:59:40 UTC 2022
PRIMARY
CHEBI
60800
Created by admin on Fri Dec 16 16:59:40 UTC 2022 , Edited by admin on Fri Dec 16 16:59:40 UTC 2022
PRIMARY
EPA CompTox
DTXSID601027734
Created by admin on Fri Dec 16 16:59:40 UTC 2022 , Edited by admin on Fri Dec 16 16:59:40 UTC 2022
PRIMARY
ChEMBL
CHEMBL395091
Created by admin on Fri Dec 16 16:59:40 UTC 2022 , Edited by admin on Fri Dec 16 16:59:40 UTC 2022
PRIMARY
USAN
AB-58
Created by admin on Fri Dec 16 16:59:40 UTC 2022 , Edited by admin on Fri Dec 16 16:59:40 UTC 2022
PRIMARY
Related Record Type Details
Structure of ESKETAMINE
PARENT -> SALT/SOLVATE
Structure of KETAMINE HYDROCHLORIDE
RACEMATE -> ENANTIOMER
Related Record Type Details
Structure of ESKETAMINE
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966