Details of the Drug

General Information of Drug (ID: DMT5HA4)

Drug Name
Ketamine
Synonyms
Calypsol; Cetamina; Green; Ketaject; Ketalar; Ketaminum; Ketanest; Ketoject; Ketolar; Tekam; KETAMINE HCL; Ketalar base; Ketamine Base; Special K; Special K [street name]; CLSTA 20; T385; Cetamina [INN-Spanish]; Dl-Ketamine; Ketalar (TN); Ketamine (INN); Ketamine [INN:BAN]; Ketaminum [INN-Latin]; Ketanest (TN); Ketaset (TN); Tekam (TN); Cyclohexanone, 2-(2-chlorophenyl)-2-(methylamino)-(9CI); Cyclohexanone, 2-(2-chlorophenyl)-2-(methylamino)-, (+-)-(9CI); Cyclohexanone, 2-(o-chlorophenyl)-2-(methylamino)-, (+/-)-(8CI); (+/-)-2-(2-Chlorophenyl)-2-(methylamino)cyclohexanone; (+/-)-2-(o-Chlorophenyl)-2-(methylamino)cyclohexanone; 2-(2-Chlorophenyl)-2-(methylamino)cyclohexanone; 2-(2-chlorophenyl)-2-(methylamino)cyclohexan-1-one; 2-(Methylamino)-2-(2-chlorophenyl)cyclohexanone; 2-(o-Chlorophenyl)-2-(methylamino)-cyclohexanone; 2-(o-Chlorophenyl)-2-(methylamino)cyclohexanone
Indication
Disease Entry ICD 11 Status REF
Anaesthesia 9A78.6 Approved [1]
Anxiety N.A. Approved [2]
Bipolar disorder 6A60 Approved [2]
Depression 6A70-6A7Z Approved [2]
Traumatic brain injury NA07.Z Approved [2]
Coronavirus Disease 2019 (COVID-19) 1D6Y Phase 2 [3]
Chronic pain MG30 Investigative [2]
⏷ Show the Full List of Indication(s)
Therapeutic Class
Analgesics
Affected Organisms
Humans and other mammals
ATC Code
N01AX03: Ketamine
N01AX: Other general anesthetics
N01A: ANESTHETICS, GENERAL
N01: ANESTHETICS
N: NERVOUS SYSTEM
Drug Type
Small molecular drug
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) 2
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 2
ADMET Property
Absorption Cmax
The maximum plasma concentration (Cmax) of drug is 0.75 mg/L [4]
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [5]
Bioavailability
The bioavailability of drug is 93% [4]
Clearance
The clearance of drug is 1.36 L/h/kg [6]
Elimination
Pharmacokinetic studies have resulted in the recovery of 85-95% of the administered dose in urine mainly in the form of metabolites [7]
Half-life
The concentration or amount of drug in body reduced by one-half in 186 minutes [4]
Metabolism
The drug is metabolized via the hepatic [4]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 8.41285 micromolar/kg/day [8]
Unbound Fraction
The unbound fraction of drug in plasma is 0.47% [9]
Vd
The volume of distribution (Vd) of drug is 0.3713 L/kg [10]
Water Solubility
The ability of drug to dissolve in water is measured as 200 mg/mL [5]
Chemical Identifiers
Formula
C13H16ClNO
IUPAC Name
2-(2-chlorophenyl)-2-(methylamino)cyclohexan-1-one
Canonical SMILES
CNC1(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
InChIKey
YQEZLKZALYSWHR-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
3821
ChEBI ID
CHEMBL742
CAS Number
6740-88-1
UNII
690G0D6V8H
DrugBank ID
DB01221
TTD ID
D0UM7O
VARIDT ID
DR00685
INTEDE ID
DR0903
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

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 [11]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [12]
Cytochrome P450 2C9 (CYP2C9) DE5IED8 CP2C9_HUMAN Substrate [12]
Cytochrome P450 2B6 (CYP2B6) DEPKLMQ CP2B6_HUMAN Substrate [12]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Actin, aortic smooth muscle (ACTA2) OTEDLG8E ACTA_HUMAN Gene/Protein Processing [13]
Amyloid-beta precursor protein (APP) OTKFD7R4 A4_HUMAN Gene/Protein Processing [14]
Cadherin-1 (CDH1) OTFJMXPM CADH1_HUMAN Gene/Protein Processing [13]
DNA damage-inducible transcript 3 protein (DDIT3) OTI8YKKE DDIT3_HUMAN Gene/Protein Processing [15]
Protein S100-A4 (S100A4) OTLRGFSQ S10A4_HUMAN Gene/Protein Processing [13]
Renin (REN) OT52GZR2 RENI_HUMAN Gene/Protein Processing [16]
Sodium/hydrogen exchanger 6 (SLC9A6) OT5N47TC SL9A6_HUMAN Gene/Protein Processing [14]
Transforming growth factor beta-1 proprotein (TGFB1) OTV5XHVH TGFB1_HUMAN Gene/Protein Processing [13]
Twist-related protein 1 OTB3H60O TWST1_HUMAN Gene/Protein Processing [13]
Vimentin OTGZLW4J VIME_HUMAN Gene/Protein Processing [13]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Ketamine (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Pexidartinib DMS2J0Z Moderate Increased metabolism of Ketamine caused by Pexidartinib mediated induction of CYP450 enzyme. Bone/articular cartilage neoplasm [2F7B] [17]
Tucatinib DMBESUA Moderate Decreased metabolism of Ketamine caused by Tucatinib mediated inhibition of CYP450 enzyme. Breast cancer [2C60-2C6Y] [18]
Alpelisib DMEXMYK Moderate Increased metabolism of Ketamine caused by Alpelisib mediated induction of CYP450 enzyme. Breast cancer [2C60-2C6Y] [19]
MK-8228 DMOB58Q Moderate Decreased metabolism of Ketamine caused by MK-8228 mediated inhibition of CYP450 enzyme. Cytomegaloviral disease [1D82] [20]
Esketamine DMVU687 Moderate Additive CNS depression effects by the combination of Ketamine and Esketamine. Depression [6A70-6A7Z] [21]
Cenobamate DM8KLU9 Moderate Increased metabolism of Ketamine caused by Cenobamate mediated induction of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [22]
Darunavir DMN3GCH Moderate Decreased metabolism of Ketamine caused by Darunavir mediated inhibition of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [23]
PF-06463922 DMKM7EW Moderate Increased metabolism of Ketamine caused by PF-06463922 mediated induction of CYP450 enzyme. Lung cancer [2C25] [24]
Selpercatinib DMZR15V Moderate Decreased metabolism of Ketamine caused by Selpercatinib mediated inhibition of CYP450 enzyme. Lung cancer [2C25] [19]
Idelalisib DM602WT Moderate Decreased metabolism of Ketamine caused by Idelalisib mediated inhibition of CYP450 enzyme. Mature B-cell leukaemia [2A82] [25]
IPI-145 DMWA24P Moderate Decreased metabolism of Ketamine caused by IPI-145 mediated inhibition of CYP450 enzyme. Mature B-cell leukaemia [2A82] [26]
Dabrafenib DMX6OE3 Moderate Increased metabolism of Ketamine caused by Dabrafenib mediated induction of CYP450 enzyme. Melanoma [2C30] [19]
Flibanserin DM70DTN Moderate Additive CNS depression effects by the combination of Ketamine and Flibanserin. Mood disorder [6A60-6E23] [27]
Levomethadyl Acetate DM06HG5 Major Additive CNS depression effects by the combination of Ketamine and Levomethadyl Acetate. Opioid use disorder [6C43] [27]
Olaparib DM8QB1D Moderate Increased metabolism of Ketamine caused by Olaparib mediated induction of CYP450 enzyme. Ovarian cancer [2C73] [21]
Rucaparib DM9PVX8 Moderate Decreased metabolism of Ketamine caused by Rucaparib mediated inhibition of CYP450 enzyme. Ovarian cancer [2C73] [28]
Abametapir DM2RX0I Moderate Decreased metabolism of Ketamine caused by Abametapir mediated inhibition of CYP450 enzyme. Pediculosis [1G00] [29]
Lefamulin DME6G97 Moderate Decreased metabolism of Ketamine caused by Lefamulin mediated inhibition of CYP450 enzyme. Pneumonia [CA40] [30]
Lonafarnib DMGM2Z6 Moderate Decreased metabolism of Ketamine caused by Lonafarnib mediated inhibition of CYP450 enzyme. Premature ageing appearance [LD2B] [31]
Telotristat ethyl DMDIYFZ Moderate Increased metabolism of Ketamine caused by Telotristat ethyl mediated induction of CYP450 enzyme. Small intestine developmental anomaly [DA90] [19]
Larotrectinib DM26CQR Moderate Decreased metabolism of Ketamine caused by Larotrectinib mediated inhibition of CYP450 enzyme. Solid tumour/cancer [2A00-2F9Z] [21]
LEE011 DMMX75K Moderate Decreased metabolism of Ketamine caused by LEE011 mediated inhibition of CYP450 enzyme. Solid tumour/cancer [2A00-2F9Z] [32]
Fostamatinib DM6AUHV Moderate Decreased metabolism of Ketamine caused by Fostamatinib mediated inhibition of CYP450 enzyme. Thrombocytopenia [3B64] [33]
⏷ Show the Full List of 23 DDI Information of This Drug

References

1 FDA Approved Drug Products from FDA Official Website. 2019. Application Number: (ANDA) 076092.
2 Ketamine FDA Label
3 ClinicalTrials.gov (NCT04365985) Study of Immunomodulation Using Naltrexone and Ketamine for COVID-19. U.S. National Institutes of Health.
4 Bioavailability, pharmacokinetics, and analgesic activity of ketamine in humans. J Pharm Sci. 1982 May;71(5):539-42.
5 BDDCS applied to over 900 drugs
6 Fanta S, Kinnunen M, Backman JT, Kalso E: Population pharmacokinetics of S-ketamine and norketamine in healthy volunteers after intravenous and oral dosing. Eur J Clin Pharmacol. 2015 Apr;71(4):441-7. doi: 10.1007/s00228-015-1826-y. Epub 2015 Mar 1.
7 Ketamine monograph
8 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
9 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
10 Pypendop BH, Ilkiw JE: Pharmacokinetics of ketamine and its metabolite, norketamine, after intravenous administration of a bolus of ketamine to isoflurane-anesthetized dogs. Am J Vet Res. 2005 Dec;66(12):2034-8. doi: 10.2460/ajvr.2005.66.2034.
11 Ketamine modulates theta and gamma oscillations. J Cogn Neurosci. 2010 Jul;22(7):1452-64.
12 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.
13 Ketamine-induced bladder fibrosis involves epithelial-to-mesenchymal transition mediated by transforming growth factor-1. Am J Physiol Renal Physiol. 2017 Oct 1;313(4):F961-F972. doi: 10.1152/ajprenal.00686.2016. Epub 2017 Mar 22.
14 Ketamine promotes the amyloidogenic pathway by regulating endosomal pH. Toxicology. 2022 Apr 15;471:153163. doi: 10.1016/j.tox.2022.153163. Epub 2022 Apr 1.
15 Lipoxin A4 methyl ester attenuated ketamine-induced neurotoxicity in SH-SY5Y cells via regulating leptin pathway. Toxicol In Vitro. 2023 Jun;89:105581. doi: 10.1016/j.tiv.2023.105581. Epub 2023 Mar 11.
16 Ketamine hypertension and the renin-angiotensin system. Clin Exp Hypertens A. 1983;5(6):875-83. doi: 10.3109/10641968309081814.
17 Product Information. Turalio (pexidartinib). Daiichi Sankyo, Inc., Parsippany, NJ.
18 Product Information. Tukysa (tucatinib). Seattle Genetics Inc, Bothell, WA.
19 Cerner Multum, Inc. "UK Summary of Product Characteristics.".
20 Product Information. Prevymis (letermovir). Merck & Company Inc, Whitehouse Station, NJ.
21 Cerner Multum, Inc. "Australian Product Information.".
22 Product Information. Xcopri (cenobamate). SK Life Science, Inc., Paramus, NJ.
23 Product Information. Prezista (darunavir). Ortho Biotech Inc, Bridgewater, NJ.
24 Product Information. Lorbrena (lorlatinib). Pfizer U.S. Pharmaceuticals Group, New York, NY.
25 Product Information. Zydelig (idelalisib). Gilead Sciences, Foster City, CA.
26 Product Information. Copiktra (duvelisib). Verastem, Inc., Needham, MA.
27 Product Information. Addyi (flibanserin). Sprout Pharmaceuticals, Raleigh, NC.
28 EMA. European Medicines Agency. European Union "EMA - List of medicines under additional monitoring.".
29 Product Information. Xeglyze (abametapir topical). Dr. Reddy's Laboratories Inc, Upper Saddle River, NJ.
30 Product Information. Xenleta (lefamulin). Nabriva Therapeutics US, Inc., King of Prussia, PA.
31 Product Information. Zokinvy (lonafarnib). Eiger BioPharmaceuticals, Palo Alto, CA.
32 DSouza DL, Levasseur LM, Nezamis J, Robbins DK, Simms L, Koch KM "Effect of alosetron on the pharmacokinetics of alprazolam." J Clin Pharmacol 41 (2001): 452-4. [PMID: 11304902]
33 Product Information. Tavalisse (fostamatinib). Rigel Pharmaceuticals, South San Francisco, CA.