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Ketamine

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Also known as Anaket vCalypsolClorketam 1000Dl-ketamineImalgene 1000KetalarKetaminaKetamine component of ketafolKetasol 100NarketanNSC-70151PMI-150TekamUrsotaminVetaketSID29215438SID56424156SID144205256(+/-)-Ketamine

Summary

Ketamine (CHEMBL742) is an approved small-molecule intravenous anaesthetic (ATC N01AX03) targeting GRIN2A, GRIN2B, and GRIN2C; indicated across 75 conditions including injury and epilepsy.

At a glance

  • Status: Approved (max clinical phase 4)
  • Modality: Small molecule
  • ATC class: N01AX03
  • Targets: 4 (GRIN2A, GRIN2B, GRIN2C…)
  • Indications: 75 conditions
  • Clinical trials: 917
  • Chemistry: 237.72 Da · C13H16ClNO

Identifiers

Drug identity and classification

FieldValue
ChEMBL IDCHEMBL742
NameKetamine
TypeSmall molecule
Max phase4
FDA approvedyes
PubChem CID3821
ChEBICHEBI:6121
ATCN01AX03
Molecular formulaC13H16ClNO
Molecular weight237.72
InChIKeyYQEZLKZALYSWHR-UHFFFAOYSA-N

SMILES: CNC1(CCCCC1=O)C2=CC=CC=C2Cl

IUPAC name: 2-(2-chlorophenyl)-2-(methylamino)cyclohexan-1-one

ChEBI definition: A member of the class of cyclohexanones in which one of the hydrogens at position 2 is substituted by a 2-chlorophenyl group, while the other is substituted by a methylamino group.

Pharmacological roles (ChEBI): intravenous anaesthetic, NMDA receptor antagonist, analgesic, neurotoxin.

Other ChEBI roles (chemical / environmental): environmental contaminant, xenobiotic.

Also known as: Anaket v, Calypsol, Clorketam 1000, Dl-ketamine, Imalgene 1000, Ketalar, Ketamina, Ketamine, Ketamine component of ketafol, Ketasol 100, Narketan, NSC-70151

Parent form; salt/anhydrous children: CHEMBL1714

Patent coverage: 28,739 distinct patent families (101,983 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 101,420 (99%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

GeneTargetActionpAffinityCancer dependencyUniProt
GRIN2AGluN2A0.4%Q12879
GRIN2BGluN2B0%Q13224
GRIN2CGluN2C6.180.2%Q14957
GRIN2DGluN2D0.2%O15399

Broader ChEMBL bioactivity targets: 13 (assay-derived). Sample: Prelamin-A/C, Glutamate NMDA receptor; GRIN1/GRIN2B, Glutamate NMDA receptor; GRIN1/GRIN2A, Glutamate NMDA receptor, Voltage-dependent L-type calcium channel subunit alpha-1C, Glutamate [NMDA] receptor, Glutamate NMDA receptor; Grin1/Grin2b, Glutamate NMDA receptor; Grin1/Grin2a, Sodium-dependent serotonin transporter, Mu-type opioid receptor.

Bioactivity

ChEMBL activities: 40 potent at pChembl ≥ 5 of 46 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

TargetpChemblTypeValueUnitActivity ID
P354396.75Ki180nMCHEMBL_ACT_22482168
P354396.75Ki180nMCHEMBL_ACT_22482172
P354396.75Ki180nMCHEMBL_ACT_22482173
P354396.75Ki180nMCHEMBL_ACT_22482187
P354396.75Ki180nMCHEMBL_ACT_22482202
P354396.75Ki180nMCHEMBL_ACT_22482203
GRIN2D6.75Ki180nMCHEMBL_ACT_22482204
P354396.75Ki180nMCHEMBL_ACT_22482205
P354396.75Ki180nMCHEMBL_ACT_22482210
P354396.75Ki180nMCHEMBL_ACT_22482211
P354396.75Ki180nMCHEMBL_ACT_22482212
P354396.75Ki180nMCHEMBL_ACT_22482213
P354396.75Ki180nMCHEMBL_ACT_22482214
P354396.75Ki180nMCHEMBL_ACT_22482215
P354396.75Ki180nMCHEMBL_ACT_22482216
GRIN2D6.75Ki180nMCHEMBL_ACT_22482217
GRIN16.75Ki180nMCHEMBL_ACT_22482218
P354396.75Ki180nMCHEMBL_ACT_22482219
GRIN2D6.38Ki420nMCHEMBL_ACT_844199
GRIN16.3IC50500nMCHEMBL_ACT_29100833
GRIN16.29IC50510nMCHEMBL_ACT_29100839
P354396.21IC50610nMCHEMBL_ACT_385662
P354396.21IC50610nMCHEMBL_ACT_417213
P354396.16IC50700nMCHEMBL_ACT_19252436
P354396.07IC50860nMCHEMBL_ACT_213208
P354396IC501000nMCHEMBL_ACT_24920113
GRIN15.9IC501259nMCHEMBL_ACT_6155997
CACNA1C5.75IC501800nMCHEMBL_ACT_15777534
GRIN2D5.72Ki1900nMCHEMBL_ACT_19252414
GRIN15.5IC503200nMCHEMBL_ACT_3274050

Target pathways

Aggregated over 4 target gene(s): GRIN2A, GRIN2B, GRIN2C, GRIN2D.

Top Reactome pathways

11 total, by targets touching each:

PathwayTargetsGenes
Unblocking of NMDA receptors, glutamate binding and activation4GRIN2A, GRIN2B, GRIN2C, GRIN2D
Neurexins and neuroligins4GRIN2A, GRIN2B, GRIN2C, GRIN2D
Synaptic adhesion-like molecules4GRIN2A, GRIN2B, GRIN2C, GRIN2D
Assembly and cell surface presentation of NMDA receptors4GRIN2A, GRIN2B, GRIN2C, GRIN2D
Negative regulation of NMDA receptor-mediated neuronal transmission4GRIN2A, GRIN2B, GRIN2C, GRIN2D
Long-term potentiation4GRIN2A, GRIN2B, GRIN2C, GRIN2D
Ras activation upon Ca2+ influx through NMDA receptor2GRIN2B, GRIN2D
RAF/MAP kinase cascade2GRIN2B, GRIN2D
MECP2 regulates neuronal receptors and channels2GRIN2A, GRIN2B
EPHB-mediated forward signaling1GRIN2B
Activated NTRK2 signals through FYN1GRIN2B

Dominant GO biological processes

GO termTargets
brain development4
ionotropic glutamate receptor signaling pathway4
synaptic transmission, glutamatergic4
regulation of synaptic plasticity4
regulation of neuronal synaptic plasticity4
positive regulation of synaptic transmission, glutamatergic4
excitatory postsynaptic potential4
long-term synaptic potentiation4
calcium ion transmembrane import into cytosol4
monoatomic cation transmembrane transport4
excitatory chemical synaptic transmission4
regulation of monoatomic cation transmembrane transport4
positive regulation of excitatory postsynaptic potential4
monoatomic ion transport4
monoatomic ion transmembrane transport4

Indications & clinical

Indications

75 indications (0 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

IndicationTrial phaseMONDOEFO
injury3MONDO:0021178EFO:0000546
epilepsy3MONDO:0005027EFO:0000474
morbid obesity3MONDO:0005139EFO:0001074
bone fracture3MONDO:0005315EFO:0003931
neuralgia3MONDO:0021667EFO:0005762
toxic shock syndrome3MONDO:0001881EFO:0006834
mucositis3MONDO:0020579EFO:1001898
status asthmaticus3MONDO:0004766EFO:0008590
delirium3MONDO:0045057EFO:0009267
postpartum depression3MONDO:0005929EFO:0007453
major depressive disorder3MONDO:0002009MONDO:0002009
depressive disorder3MONDO:0002050MONDO:0002050
pharyngitis3MONDO:0002258MONDO:0002258
alcohol abuse3MONDO:0002046MONDO:0007079
sickle cell disease3MONDO:0011382MONDO:0011382
bipolar disorder3MONDO:0004985MONDO:0004985
neoplasm3MONDO:0005070MONDO:0004992
lung disorder3MONDO:0005275EFO:0003818
spinal stenosis3MONDO:0005965EFO:0007490
post-traumatic stress disorder2MONDO:0005146EFO:0001358
obsessive-compulsive disorder2MONDO:0008114EFO:0004242
cocaine dependence2MONDO:0005186EFO:0002610
subarachnoid hemorrhage2MONDO:0005099EFO:0000713
autism spectrum disorder2MONDO:0005258EFO:0003756
reproductive system disorder2MONDO:0005039EFO:0000512
borderline personality disorder2MONDO:0001156HP:0012076
strabismus2MONDO:0003432HP:0000486
severe acute respiratory syndrome2MONDO:0005091EFO:0000694
acute respiratory distress syndrome2MONDO:0006502EFO:1000637
complex regional pain syndrome2MONDO:0019369EFO:1001998
breast neoplasm2MONDO:0021100MONDO:0007254
lung neoplasm2MONDO:0021117MONDO:0008903
brain injury2MONDO:0043510MONDO:0043510
temporomandibular joint disorder2MONDO:0005473EFO:0005279
ventricular septal defect2MONDO:0002070MONDO:0002070
cataract2MONDO:0005129MONDO:0005129
Rett syndrome2MONDO:0010726MONDO:0010726
Parkinson disease2MONDO:0005180MONDO:0005180
opiate dependence1MONDO:0005530EFO:0005611
stroke disorder1MONDO:0005098EFO:0000712
drug dependence1MONDO:0005303EFO:0003890
mental disorder1MONDO:0005084EFO:0000677
nicotine dependence1MONDO:0008575EFO:0003768
cannabis dependence1MONDO:0005689EFO:0007191
perceptual disorders1MONDO:0024417MONDO:0024417
cardiac arrest1MONDO:0000745EFO:0009492
respiratory failure1MONDO:0021113EFO:0009686
tethered spinal cord syndrome1MONDO:0006995EFO:1001210
social phobia0MONDO:0001247EFO:1001917
radius fracture0MONDO:0005325EFO:0003957
hemorrhoid0MONDO:0004872EFO:0009552
appendicitis0MONDO:0005649EFO:0007149
multiple sclerosis0MONDO:0005301MONDO:0005301

22 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 917.

Phase distribution

PhaseTrials
PHASE4269
Not specified229
PHASE2130
PHASE186
PHASE382
PHASE2/PHASE345
EARLY_PHASE140
PHASE1/PHASE236

Top trials by phase / activity

NCTPhaseStatusTitle
NCT03272698PHASE4RECRUITINGECT with Ketamine Anesthesia Vs High Intensity Ketamine with ECT Rescue for Treatment-Resistant Depression
NCT03735563PHASE4RECRUITINGPremedication for Less Invasive Surfactant Administration
NCT04119180PHASE4RECRUITINGSedation Versus Protective Stabilization for Pediatric Dental Treatment
NCT04248205PHASE4RECRUITINGKetamine for Post-operative Analgesia in Hemorrhoidectomy
NCT04578938PHASE4ACTIVE_NOT_RECRUITINGKetamine + Cognitive Training for Suicidality in the Medical Setting
NCT04781673PHASE4ACTIVE_NOT_RECRUITINGKetamine vs Lidocaine in Traumatic Rib Fractures
NCT04933149PHASE4ENROLLING_BY_INVITATIONKetamine Infusion for Neuropathic Pain in Brachial Plexus Injuries
NCT05097261PHASE4RECRUITINGKetamine in Acute Brain Injury Patients.
NCT05268562PHASE4ACTIVE_NOT_RECRUITINGKetamine and Kidney Injury in Cardiac Surgery
NCT05450432PHASE4RECRUITINGLong-Term Maintenance With Ketamine and Esketamine for Reduction of Suicide in High-Risk Patients With Depression
NCT05821972PHASE4RECRUITINGNebulized Dexmedetomidine Combined With Ketamine Versus Nebulized Dexmedetomidine for Cleft Palate
NCT05934669PHASE4RECRUITINGIN Midazolam vs IN Dexmedetomidine vs IN Ketamine During Minimal Procedures in Pediatric ED
NCT06213324PHASE4RECRUITINGNeural Circuit Effects of Ketamine in Depression
NCT06278779PHASE4RECRUITINGComparative Effectiveness Study of Two Forms of Ketamine for Treatment-resistant Depression
NCT06284473PHASE4RECRUITINGKetamine as a Supplement to Local Anesthesia for Minor Procedures
NCT06317636PHASE4ACTIVE_NOT_RECRUITINGPropofol-Enhanced Assessment of Ketamine for Chronic Pain and Depression
NCT06364540PHASE4RECRUITINGNebulized Ketamine to Nebulized Fentanyl for Treating Acute Painful Conditions in the ED
NCT06408974PHASE4NOT_YET_RECRUITINGComparison Between Ketamine Intrathecal and iv Dexamethasone for Post Cesarean Analgesia
NCT06414356PHASE4RECRUITINGThe Effect of Outpatient Ketamine Infusion on Chronic Neuropathic Pain and PTSD
NCT06506565PHASE4RECRUITINGLow-Dose Ketamine Infusion During Burn Wound Care
NCT06745388PHASE4RECRUITINGMagnesium and Cramping
NCT06774274PHASE4RECRUITINGAnalgesic Efficacy of Intravenous Ketamine as a Continuous Infusion vs PCA in the Management of Acute Postoperative Pain in Major Orthopedic Surgery.
NCT06868589PHASE4ACTIVE_NOT_RECRUITINGReducing Pain With Methadone and Ketamine in Liver Transplant
NCT06903819PHASE4RECRUITINGKetamine for Pain, Opioid Use, and Mental Health in Orthopedic Trauma Patients
NCT06951802PHASE4RECRUITINGEndometriosis and Pain Treatment by Intraoperative Administration of Low-dose Ketamine
NCT06968624PHASE4NOT_YET_RECRUITINGKetamine for Postherpetic Neuralgia With Depression
NCT07022821PHASE4RECRUITINGComparison of Dexmedetomidine + Ketamine for Postoperative Pain in C-Section
NCT07139106PHASE4NOT_YET_RECRUITINGUnderstanding the Role of the Kappa Opioid Receptor in Ketamine’s Attenuation of Suicidal Thoughts
NCT07177235PHASE4NOT_YET_RECRUITINGKetamine for the Treatment of Refractory Status Epilepticus
NCT07190612PHASE4NOT_YET_RECRUITINGEfficacy of Propofol Combination With Either Ketamine, Dexmedetomidine or Midazolam for Sedation During Upper Gastrointestinal Endoscopic Procedures
NCT07214701PHASE4NOT_YET_RECRUITINGSedative and Analgesic Effects of Dexmedetomidine Versus Ketamine in Patients Undergoing Varicocelectomy Under Spinal Anaesthesia: A Prospective Randomized Comparative Trial
NCT07427446PHASE4RECRUITINGDexmedetomidine-Midazolam vs. Ketamine-Midazolam on Emergence Delirium
NCT00129597PHASE4UNKNOWNEffect of Ketalar to Prevent Postoperative Chronic Pain After Mastectomy
NCT00163969PHASE4COMPLETEDThe Use of Ketamine as Rescue Analgesia in the Recovery Room Following Opioid Administration. A Double-blind Randomised Trial in Postoperative Patients
NCT00200564PHASE4UNKNOWNKetamine and Postoperative Analgesia in Children
NCT00205712PHASE4COMPLETEDPrevention of N-methyl-D-aspartate (NMDA) Antagonist-induced Psychosis in Kids
NCT00232492PHASE4COMPLETEDKetamine on Acute Pain in Females and Males
NCT00236223PHASE4TERMINATEDThe Effect of Gabapentin, Ketamine and Dexamethasone on Pain and Opioid Requirements After Hip Surgery
NCT00252122PHASE4TERMINATEDPilot Study on the Effects of Intravenous Ketamine on Acute Pain Crisis in Patients With Sickle Cell Disease
NCT00300794PHASE4COMPLETEDEffects of Ketamine On Precipitated Opioid Withdrawal Under General Anaesthesia

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline, but PharmGKB curates 1 clinical and 7 variant annotation(s) for this drug (gene-keyed; see PharmGKB).

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

40 molecules share ≥1 primary target. Top 40 by shared-target count:

MoleculeSourceStatusShared targets
AMANTADINEChEMBL + PubChemPhase 4 (approved)GRIN2A, GRIN2B, GRIN2C, GRIN2D
CHLORPROMAZINEChEMBL + PubChemPhase 4 (approved)GRIN2A, GRIN2B, GRIN2C, GRIN2D
DEXTROMETHORPHANChEMBL + PubChemPhase 4 (approved)GRIN2A, GRIN2B, GRIN2C, GRIN2D
LEVORPHANOLChEMBL + PubChemPhase 4 (approved)GRIN2A, GRIN2B, GRIN2C, GRIN2D
MEMANTINEChEMBL + PubChemPhase 4 (approved)GRIN2A, GRIN2B, GRIN2C, GRIN2D
ORPHENADRINEChEMBL + PubChemPhase 4 (approved)GRIN2A, GRIN2B, GRIN2C, GRIN2D
CYCLOSERINEChEMBLPhase 4 (approved)GRIN2A, GRIN2B, GRIN2C, GRIN2D
PROCYCLIDINEChEMBLPhase 4 (approved)GRIN2A, GRIN2B, GRIN2C, GRIN2D
GLUTAMIC ACIDChEMBL + PubChemPhase 3 (approved)GRIN2A, GRIN2B, GRIN2C, GRIN2D
DALZANEMDORChEMBLPhase 3GRIN2A, GRIN2B, GRIN2C, GRIN2D
ESMETHADONEChEMBLPhase 3GRIN2A, GRIN2B, GRIN2C, GRIN2D
ALPHAMETHADOLChEMBLPhase 2GRIN2A, GRIN2B, GRIN2C, GRIN2D
BUDIPINEChEMBLPhase 2GRIN2A, GRIN2B, GRIN2C, GRIN2D
DEXTRORPHANChEMBLPhase 2GRIN2A, GRIN2B, GRIN2C, GRIN2D
DIZOCILPINEChEMBLPhase 2GRIN2A, GRIN2B, GRIN2C, GRIN2D
IFENPRODILChEMBLPhase 2GRIN2A, GRIN2B, GRIN2C, GRIN2D
LANICEMINEChEMBLPhase 2GRIN2A, GRIN2B, GRIN2C, GRIN2D
LEVOMETHADONEChEMBLPhase 2GRIN2A, GRIN2B, GRIN2C, GRIN2D
LICOSTINELChEMBLPhase 2GRIN2A, GRIN2B, GRIN2C, GRIN2D
PERZINFOTELChEMBLPhase 2GRIN2A, GRIN2B, GRIN2C, GRIN2D
PHENCYCLIDINEChEMBLPhase 2GRIN2A, GRIN2B, GRIN2C, GRIN2D
RACEMETHORPHANChEMBLPhase 2GRIN2A, GRIN2B, GRIN2C, GRIN2D
RADIPRODILChEMBLPhase 2GRIN2A, GRIN2B, GRIN2C, GRIN2D
SELFOTELChEMBLPhase 2GRIN2A, GRIN2B, GRIN2C, GRIN2D
TEZAMPANELChEMBLPhase 2GRIN2A, GRIN2B, GRIN2C, GRIN2D
TRAXOPRODILChEMBLPhase 2GRIN2A, GRIN2B, GRIN2C, GRIN2D
BETAMETHADOLChEMBLPhase 2GRIN2A, GRIN2C, GRIN2D
TACRINEChEMBLPhase 4 (approved)GRIN2A, GRIN2B
LATREPIRDINEChEMBLPhase 3GRIN2A, GRIN2B
ZELQUISTINELChEMBLPhase 2GRIN2B, GRIN2C
NimodipinePubChemApprovedGRIN2C, GRIN2D
ESKETAMINEChEMBL + PubChemPhase 4 (approved)GRIN2A
HALOPERIDOLChEMBLPhase 4 (approved)GRIN2B
PENTAMIDINEChEMBLPhase 4 (approved)GRIN2A
DEXOXADROLChEMBLPhase 2GRIN2A
DIMEMORFANChEMBLPhase 2GRIN2A
ELIPRODILChEMBLPhase 2GRIN2B
ETOXADROLChEMBLPhase 2GRIN2A
EVT-101 FREE BASEChEMBLPhase 2GRIN2B
ONFASPRODILChEMBLPhase 2GRIN2B

About this page

Generated deterministically by Sugi Atlas from primary biomedical databases via BioBTree. Every record on this page traces to a primary source.

Generated
Atlas version
v1.1.2
BioBTree
v2.0.2

Sources 30

This page pulls from 30 datasets indexed by BioBTree:

chebichembl_activitychembl_moleculechembl_targetcivic_evidenceclingen_dosageclinical_trialsdepmapefoensemblentrezgogoparentgtopdbgtopdb_interactiongtopdb_ligandhgncmeshmondomsigdbpatent_compoundpharmgkbpharmgkb_guidelinepubchempubchem_activityreactomereactomeparentrefseqtranscriptuniprot