Details of the Drug

General Information of Drug (ID: DMVU687)

Drug Name

Esketamine

Synonyms

(S)-Ketamine; l-Ketamine; (S)-(-)-Ketamine; 33643-46-8; S-Ketamine; UNII-50LFG02TXD; 50LFG02TXD; (S)-2-(o-chlorophenyl)-2-(methylamino)cyclohexanone; CHEBI:60799; esketamine HCl; (2S)-2-(2-chlorophenyl)-2-(methylamino)cyclohexanone; cyclohexanone, 2-(2-chlorophenyl)-2-(methylamino)-, (2S)-; 6740-88-1 (Parent); Esketamine [USAN:INN:BAN]; S-Ketamin; S-(-)-Ketamine; Esketamine (USAN/INN); AC1L4AD8; DSSTox_CID_27787; DSSTox_RID_82562; DSSTox_GSID_47810; SCHEMBL5512024; GTPL9152; CHEMBL395091; DTXSID6047810; YQEZ

Indication

Disease Entry	ICD 11	Status	REF
Depression	6A70-6A7Z	Phase 3	[1]
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Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

237.72

Logarithm of the Partition Coefficient (xlogp)

2.2

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Absorption Cmax: The maximum plasma concentration (Cmax) of drug is 3.79 mcg/L [2]
Absorption Tmax: The time to maximum plasma concentration (Tmax) is 2.77 h [2]
Bioavailability: The bioavailability of drug is 90% [2]
Clearance: The clearance of drug is 89 L/h []
Elimination: Less than 1% of drug is excreted in the urine as unchanged form []
Half-life: The concentration or amount of drug in body reduced by one-half in 7 - 12 hours []
Metabolism: The drug is metabolized via the cytochrome P450 (CYP) enzymes, CYP2B6 and CYP3A4, and to a lesser extent, CYP2C9 and CYP2C19 []
Vd: The volume of distribution (Vd) of drug is 709 L []

Chemical Identifiers

Formula: C13H16ClNO
IUPAC Name: (2S)-2-(2-chlorophenyl)-2-(methylamino)cyclohexan-1-one
Canonical SMILES: CN[C@@]1(CCCCC1=O)C2=CC=CC=C2Cl
InChI: 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
InChIKey: YQEZLKZALYSWHR-ZDUSSCGKSA-N

Cross-matching ID

PubChem CID: 182137
ChEBI ID: CHEBI:60799
CAS Number: 33643-46-8
DrugBank ID: DB11823
TTD ID: D0TP5H
INTEDE ID: DR0621

Combinatorial Drugs (CBD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
N-methyl-D-aspartate receptor (NMDAR)	TT9IK2Z	NOUNIPROTAC	Antagonist	[1]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 3A4 (CYP3A4)	DE4LYSA	CP3A4_HUMAN	Substrate	[3]
Cytochrome P450 2C9 (CYP2C9)	DE5IED8	CP2C9_HUMAN	Substrate	[3]
Mephenytoin 4-hydroxylase (CYP2C19)	DEGTFWK	CP2CJ_HUMAN	Substrate	[4]
Cytochrome P450 2B6 (CYP2B6)	DEPKLMQ	CP2B6_HUMAN	Substrate	[3]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Esketamine (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Oliceridine	DM6MDCF	Moderate	Additive CNS depression effects by the combination of Esketamine and Oliceridine.	Acute pain [MG31]	[5]
Eslicarbazepine	DMZREFQ	Moderate	Additive CNS depression effects by the combination of Esketamine and Eslicarbazepine.	Epilepsy/seizure [8A61-8A6Z]	[5]
Remimazolam	DMLVSYX	Moderate	Additive CNS depression effects by the combination of Esketamine and Remimazolam.	Labour/delivery anaesthesia complication [JB0C]	[5]
Allopregnanolone	DMNLHAC	Moderate	Additive CNS depression effects by the combination of Esketamine and Allopregnanolone.	Mental/behavioural/neurodevelopmental disorder [6E20-6E8Z]	[6]
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References

1	Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
2	A Phase I Study to Investigate the Absorption, Pharmacokinetics, and Excretion of [(14)C]Prucalopride After a Single Oral Dose in Healthy Volunteers. Clin Ther. 2016 Sep;38(9):2106-15. doi: 10.1016/j.clinthera.2016.08.003. Epub 2016 Sep 7.
3	Contribution of CYP3A4, CYP2B6, and CYP2C9 isoforms to N-demethylation of ketamine in human liver microsomes. Drug Metab Dispos. 2002 Jul;30(7):853-8.
4	Metabolism and metabolomics of ketamine: a toxicological approach. Forensic Sci Res. 2017 Feb 20;2(1):2-10.
5	Cerner Multum, Inc. "Australian Product Information.".
6	Product Information. Zulresso (brexanolone). Sage Therapeutics, Inc., Cambridge, MA.