Ketamine

Identification

Summary

Ketamine is a rapid-acting general anesthetic and NMDA receptor antagonist used for induction of anesthesia diagnostic and surgical procedures typically in combination with a muscle relaxant.

Brand Names
Ketalar
Generic Name
Ketamine
DrugBank Accession Number
DB01221
Background

Ketamine is an NMDA receptor antagonist with a potent anesthetic effect.6 It was developed in 1963 as a replacement for phencyclidine (PCP) by Calvin Stevens at Parke Davis Laboratories. It started being used for veterinary purposes in Belgium and in 1964 was proven that compared to PCP, it produced minor hallucinogenic effects and shorter psychotomimetic effects. It was FDA approved in 1970, and from there, it has been used as an anesthetic for children or patients undergoing minor surgeries but mainly for veterinary purposes.14

Type
Small Molecule
Groups
Approved, Vet approved
Structure
Weight
Average: 237.725
Monoisotopic: 237.092041846
Chemical Formula
C13H16ClNO
Synonyms
  • (+-)-Ketamine
  • (±)-ketamine
  • 2-(2-Chloro-phenyl)-2-methylamino-cyclohexanone
  • 2-(methylamino)-2-(2-chlorophenyl)cyclohexanone
  • 2-(o-chlorophenyl)-2-(methylamino)-cyclohexanone
  • DL-ketamine
  • Ketamina
  • Kétamine
  • Ketamine
  • Ketaminum
  • NMDA
  • Special K
External IDs
  • 100477-72-3
  • NSC-70151

Pharmacology

Indication

Ketamine is indicated as an anesthetic agent for recommended diagnostic and surgical procedures. If skeletal muscle relaxation is needed, it should be combined with a muscle relaxant. If the surgical procedure involves visceral pain, it should be supplemented with an agent that obtunds visceral pain. Ketamine can be used for induction of anesthesia prior other general anesthetic agents and as a supplement of low potency agents.15,Label

Reports have indicated a potential use of ketamine as a therapeutic tool for the management of depression when administered in lower doses.7 These reports have increased the interest for ketamine in this area and several clinical trials are launched for this indication.16,8

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Associated Therapies
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Pharmacodynamics

Ketamine is a rapid-acting general anesthetic producing an anesthetic state characterized by profound analgesia, normal pharyngeal-laryngeal reflexes, normal or slightly enhanced skeletal muscle tone, cardiovascular and respiratory stimulation, and occasionally a transient and minimal respiratory depression. The anesthetic state produced by Ketamine has been termed as "dissociative anesthesia" in that it appears to selectively interrupt association pathways of the brain before producing somesthetic sensory blockade. It may selectively depress the thalamoneocortical system before significantly obtunding the more ancient cerebral centers and pathways (reticular-activating and limbic systems).2

Ketamine enhances descending inhibiting serotoninergic pathways and can exert antidepressive effects. These effects are seen in concentrations ten times lower than the needed concentration for anesthetic proposes. The effect of ketamine can be described as analgesic by the prevention of central sensitization in dorsal horn neurons as well as by the inhibition on the synthesis of nitric oxide. Ketamine can present cardiovascular changes and bronchodilatation.9

Mechanism of action

Ketamine interacts with N-methyl-D-aspartate (NMDA) receptors, opioid receptors, monoaminergic receptors, muscarinic receptors and voltage sensitive Ca ion channels. Unlike other general anaesthetic agents, ketamine does not interact with GABA receptors.5

TargetActionsOrganism
AGlutamate receptor ionotropic, NMDA 3A
antagonist
Humans
A5-hydroxytryptamine receptor 3A
potentiator
Humans
ANeuronal acetylcholine receptor subunit alpha-7
antagonist
Humans
ACholinesterase
inhibitor
Humans
ANitric oxide synthase, brain
inhibitor
Humans
UNeurokinin 1 receptor
antagonist
Humans
UDopamine D2 receptor
agonist
partial agonist
Humans
UDelta-type opioid receptor
binder
Humans
USodium-dependent noradrenaline transporter
inhibitor
Humans
UKappa-type opioid receptor
agonist
Humans
UMu-type opioid receptor
binder
Humans
UMuscarinic acetylcholine receptor
binder
Humans
U5-hydroxytryptamine receptor 2
antagonist
Humans
U5-hydroxytryptamine receptor 1
antagonist
Humans
Absorption

Ketamine absorption is very rapid and the bioavailability is around 93%. After the first pass metabolism, only 17% of the administered dose is absorbed.10 It distributes very rapidly and presents a distribution half-life of 1.95 min.12 The Cmax levels at peak reach 0.75 mcg/ml in plasma and 0.2 mcg/ml in cerebrospinal fluid.15

Volume of distribution

The apparent volume of distribution of the central compartment and at steady-state are 371.3 ml/kg and 4060.3 ml/kg, respectively.13

Protein binding

The plasma protein binding of ketamine accounts for 53.5% of the administered dose.12

Metabolism

Ketamine presents a mainly hepatic metabolism and its major metabolite is norketamine. The biotransformation of ketamine corresponds to N-dealkylation, hydroxylation of the cyclohexone ring, conjugation to glucuronic acid and dehydration of the hydroxylated metabolites for the formation of cyclohexene derivatives.10

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Route of elimination

Pharmacokinetic studies have resulted in the recovery of 85-95% of the administered dose in urine mainly in the form of metabolites. Some other routes of elimination of ketamine are bile and feces. When administered intravenously the resultant recovery is distributed by 91% of the administered dose in urine and 3% in feces.15

Half-life

The reported half-life in preclinical studies for ketamine is 186 min.10

Clearance

The clearance rate of ketamine is high and of around 95 L/h/70kg.11

Adverse Effects
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Toxicity

Preclinical studies related to the blocking of NMDA receptors have shown an increase in apoptosis in the developing brain which results in cognitive deficits when used for longer than 3 hours. Toxicity studies regarding carcinogenesis have not been performed. Regarding mutagenesis and fertility, ketamine showed to be clastogenic and to not have effects on fertility.Label

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when Ketamine is combined with 1,2-Benzodiazepine.
AbacavirAbacavir may decrease the excretion rate of Ketamine which could result in a higher serum level.
AbametapirThe serum concentration of Ketamine can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Ketamine can be increased when combined with Abatacept.
AbirateroneThe metabolism of Ketamine can be decreased when combined with Abiraterone.
Food Interactions
  • Avoid alcohol.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Ketamine hydrochlorideO18YUO0I831867-66-9VCMGMSHEPQENPE-UHFFFAOYSA-N
International/Other Brands
Ketaject (Bristol-Myers Squibb) / Ketanest (Parke Davis)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
KetalarInjection50 mg/1mLIntramuscular; IntravenousPar Pharmaceutical, Inc.2007-10-01Not applicableUS flag
KetalarInjection50 mg/1mLIntramuscular; IntravenousMonarch Pharmaceuticals, Inc.1970-02-192007-10-01US flag
KetalarInjection10 mg/1mLIntramuscular; IntravenousGeneral Injectables & Vaccines, Inc2012-10-172025-02-28US flag
KetalarInjection10 mg/1mLIntramuscular; IntravenousPar Pharmaceutical, Inc.2007-10-01Not applicableUS flag
KetalarInjection10 mg/1mLIntramuscular; IntravenousMonarch Pharmaceuticals, Inc.1970-02-192007-10-01US flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Ketamine HydrochlorideInjection50 mg/1mLIntramuscular; IntravenousPar Pharmaceutical2012-06-012018-04-29US flag
Ketamine HydrochlorideInjection, solution50 mg/1mLIntramuscular; IntravenousSagent Pharmaceuticals2023-07-15Not applicableUS flag
Ketamine HydrochlorideInjection, solution, concentrate50 mg/1mLIntramuscular; IntravenousHenry Schein, Inc.2022-01-11Not applicableUS flag
Ketamine HydrochlorideInjection, solution, concentrate100 mg/1mLIntramuscular; IntravenousPhysicians Total Care, Inc.2004-06-162011-06-30US flag
Ketamine HydrochlorideInjection, solution50 mg/1mLIntramuscular; IntravenousGland Pharma Limited2023-01-24Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
MKH Dose PackKetamine hydrochloride (25 mg/1) + Hydroxyzine hydrochloride (10 mg/1) + Midazolam (3 mg/1)TrocheSublingualImprimis Njof, Llc2019-03-04Not applicableUS flag
MKO MeltKetamine hydrochloride (25 mg/1) + Midazolam (3 mg/1) + Ondansetron hydrochloride dihydrate (2 mg/1)TrocheSublingualImprimis Njof, Llc2018-12-012019-03-04US flag
MKO Melt Dose PackKetamine hydrochloride (25 mg/1) + Midazolam (3 mg/1) + Ondansetron hydrochloride (2 mg/1)TrocheSublingualImprimis Njof, Llc2019-03-04Not applicableUS flag
Topical Nerve PainKetamine (0.1 g/100mL) + Diazepam (0.1 g/100mL) + Diclofenac sodium (0.1 g/100mL) + Gabapentin (0.1 g/100mL)CreamTopicalDr Marc's Manufacturing And Sales2016-02-232018-04-17US flag

Categories

ATC Codes
N01AX03 — Ketamine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as chlorobenzenes. These are compounds containing one or more chlorine atoms attached to a benzene moiety.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Halobenzenes
Direct Parent
Chlorobenzenes
Alternative Parents
Aralkylamines / Aryl chlorides / Cyclic ketones / Dialkylamines / Organopnictogen compounds / Organochlorides / Organic oxides / Hydrocarbon derivatives
Substituents
Amine / Aralkylamine / Aromatic homomonocyclic compound / Aryl chloride / Aryl halide / Carbonyl group / Chlorobenzene / Cyclic ketone / Hydrocarbon derivative / Ketone
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
secondary amino compound, monochlorobenzenes, cyclohexanones (CHEBI:6121)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
690G0D6V8H
CAS number
6740-88-1
InChI Key
YQEZLKZALYSWHR-UHFFFAOYSA-N
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
IUPAC Name
2-(2-chlorophenyl)-2-(methylamino)cyclohexan-1-one
SMILES
CNC1(CCCCC1=O)C1=CC=CC=C1Cl

References

Synthesis Reference

John A. Flores, Kenton L. Crowley, "Process for the preparation of ketamine ointment." U.S. Patent US5817699, issued June, 1995.

US5817699
General References
  1. Harrison NL, Simmonds MA: Quantitative studies on some antagonists of N-methyl D-aspartate in slices of rat cerebral cortex. Br J Pharmacol. 1985 Feb;84(2):381-91. [Article]
  2. Bergman SA: Ketamine: review of its pharmacology and its use in pediatric anesthesia. Anesth Prog. 1999 Winter;46(1):10-20. [Article]
  3. Bonanno FG: Ketamine in war/tropical surgery (a final tribute to the racemic mixture). Injury. 2002 May;33(4):323-7. [Article]
  4. Lankenau SE, Sanders B, Bloom JJ, Hathazi D, Alarcon E, Tortu S, Clatts MC: First injection of ketamine among young injection drug users (IDUs) in three U.S. cities. Drug Alcohol Depend. 2007 Mar 16;87(2-3):183-93. Epub 2006 Sep 18. [Article]
  5. Reboso Morales JA, Gonzalez Miranda F: [Ketamine]. Rev Esp Anestesiol Reanim. 1999 Mar;46(3):111-22. [Article]
  6. Ivani G, Vercellino C, Tonetti F: Ketamine: a new look to an old drug. Minerva Anestesiol. 2003 May;69(5):468-71. [Article]
  7. Yang Y, Cui Y, Sang K, Dong Y, Ni Z, Ma S, Hu H: Ketamine blocks bursting in the lateral habenula to rapidly relieve depression. Nature. 2018 Feb 14;554(7692):317-322. doi: 10.1038/nature25509. [Article]
  8. Kirby T: Ketamine for depression: the highs and lows. Lancet Psychiatry. 2015 Sep;2(9):783-4. doi: 10.1016/S2215-0366(15)00392-2. [Article]
  9. Xu J, Lei H: Ketamine-an update on its clinical uses and abuses. CNS Neurosci Ther. 2014 Dec;20(12):1015-20. doi: 10.1111/cns.12363. [Article]
  10. Clements JA, Nimmo WS, Grant IS: Bioavailability, pharmacokinetics, and analgesic activity of ketamine in humans. J Pharm Sci. 1982 May;71(5):539-42. [Article]
  11. 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. [Article]
  12. Kaka JS, Hayton WL: Pharmacokinetics of ketamine and two metabolites in the dog. J Pharmacokinet Biopharm. 1980 Apr;8(2):193-202. [Article]
  13. 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. [Article]
  14. Ketamine [Link]
  15. Ketamine monograph [Link]
  16. Time magazine [Link]
Human Metabolome Database
HMDB0015352
KEGG Drug
D08098
KEGG Compound
C07525
PubChem Compound
3821
PubChem Substance
46508295
ChemSpider
3689
BindingDB
50044140
RxNav
6130
ChEBI
6121
ChEMBL
CHEMBL742
Therapeutic Targets Database
DAP001148
PharmGKB
PA450144
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Ketamine
FDA label
Download (228 KB)
MSDS
Download (67.5 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingPreventionPain / Postpartum Depression1
4Active Not RecruitingTreatmentAcute Pain / Coronary Artery Disease (CAD) / Postoperative pain / Valvular Heart Diseases1
4Active Not RecruitingTreatmentCoronavirus Disease 2019 (COVID‑19) / Stress Disorder, Acute1
4Active Not RecruitingTreatmentCritically Ill Patients / Postoperative pain1
4Active Not RecruitingTreatmentDepression, Bipolar / Suicidal Thoughts / Unipolar Depression1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Bedford Labs
  • Ben Venue Laboratories Inc.
  • Bioniche Pharma
  • Hospira Inc.
  • JHP Pharmaceuticals LLC
  • Medisca Inc.
  • Monarch Pharmacy
  • Pharmedium
  • Physicians Total Care Inc.
Dosage Forms
FormRouteStrength
InjectionIntramuscular
InjectionIntramuscular; Intravenous
InjectionIntramuscular50 MG/ML
InjectionIntramuscular; Intravenous10 mg/1mL
InjectionIntramuscular; Intravenous100 mg/1mL
InjectionIntramuscular; Intravenous50 mg/1mL
InjectionIntravenous
SolutionIntramuscular; Intravenous50 mg / mL
Injection500 mg
InjectionIntramuscular; Intravenous500 mg
Injection, solution10 mg/ml
Injection, solutionParenteral10 mg/ml
Injection, solution50 mg/ml
SolutionIntramuscular; Intravenous500 mg
Injection, solutionParenteral50 MG/ML
Injection57.677 mg/ml
Injection, solutionIntramuscular; Intravenous50 MG
Injection, solutionIntramuscular; Intravenous10 mg/1mL
Injection, solutionIntramuscular; Intravenous100 mg/1mL
Injection, solutionIntramuscular; Intravenous50 mg/1mL
Injection, solution, concentrateIntramuscular; Intravenous100 mg/1mL
Injection, solution, concentrateIntramuscular; Intravenous50 mg/1mL
PowderNot applicable1 g/1g
InjectionIntramuscular; Intravenous50 mg/ml
SolutionIntramuscular; Intravenous10 mg / mL
SolutionIntramuscular; Intravenous100 mg / 2 mL
SolutionIntramuscular; Intravenous500 mg / 10 mL
TrocheSublingual
CreamTopical
Prices
Unit descriptionCostUnit
Ketamine hcl powder7.22USD g
Ketamine hcl-ns 50 mg/5 ml syr2.82USD ml
Ketamine 100 mg/ml vial2.36USD ml
Ketalar 100 mg/ml vial1.95USD ml
Ketamine hcl-ns 100 mg/10 ml1.95USD ml
Ketamine HCl 50 mg/ml Solution1.77USD ml
Ketalar 10 mg/ml vial0.99USD ml
Ketamine 10 mg/ml vial0.99USD ml
Ketalar 50 mg/ml vial0.75USD ml
Ketamine 50 mg/ml vial0.61USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)92.5ºCMedical toxicology of drug abuse. (2012)
water solubilitySoluble'MSDS'
logP3.120Medical toxicology of drug abuse. (2012)
pKa7.5Ketamine monograph
Predicted Properties
PropertyValueSource
Water Solubility0.0464 mg/mLALOGPS
logP2.69ALOGPS
logP3.35Chemaxon
logS-3.7ALOGPS
pKa (Strongest Acidic)19.77Chemaxon
pKa (Strongest Basic)7.16Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area29.1 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity65.55 m3·mol-1Chemaxon
Polarizability24.97 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9974
Blood Brain Barrier+0.9826
Caco-2 permeable+0.6326
P-glycoprotein substrateSubstrate0.5753
P-glycoprotein inhibitor INon-inhibitor0.5948
P-glycoprotein inhibitor IINon-inhibitor0.8383
Renal organic cation transporterNon-inhibitor0.6737
CYP450 2C9 substrateNon-substrate0.6363
CYP450 2D6 substrateSubstrate0.8918
CYP450 3A4 substrateSubstrate0.7407
CYP450 1A2 substrateNon-inhibitor0.7323
CYP450 2C9 inhibitorNon-inhibitor0.7985
CYP450 2D6 inhibitorNon-inhibitor0.6912
CYP450 2C19 inhibitorNon-inhibitor0.5347
CYP450 3A4 inhibitorNon-inhibitor0.8253
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5426
Ames testNon AMES toxic0.7223
CarcinogenicityNon-carcinogens0.8878
BiodegradationNot ready biodegradable0.9937
Rat acute toxicity2.3939 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8859
hERG inhibition (predictor II)Inhibitor0.6047
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0ue9-1900000000-137b9855ffed670aa9f4
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-004i-0930000000-8216e02922628a5070cf
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0090000000-7704dbbfa717abc4bab2
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0090000000-aff2b684d97275321043
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0290000000-1707dec51cc3e89964c9
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0940000000-59871faec16835eb1b3a
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0900000000-ca62e82b4a1dfb81b3b0
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0900000000-6c243d7b1c2e8cf69efa
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0900000000-441a423105753e2c8b9c
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0090000000-24585e7c2431b3b9319e
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0290000000-c9d734b085ec94dabd9a
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0940000000-054d77385726d4e35e20
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0900000000-8c263bb521fb6ebe6cac
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0900000000-702873d66ce0d419711d
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0900000000-e23ba411aa96df9b5d6f
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0090000000-5f14196db213c95f3e71
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-000i-0090000000-85385cf96aa2ac05921a
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-05br-0390000000-9177663a5915fac51aa7
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-004i-0910000000-d00d242dae695dc5aff9
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-004i-0900000000-95c2a8805f1587266fea
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-004i-1900000000-9e61adc80771178de9d3
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-00di-0190000000-686c139c454aea662d84
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0980000000-bded2bdf9853c6184bf1
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0090000000-f329d25c0537015062fc
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-052u-0890000000-7934d3aa418dfbf17488
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-052r-2290000000-f29c223b2da48a50baf6
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0avr-1910000000-c2a25e54634de389a8a5
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-000w-9110000000-3c59d084c31e14c73fad
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-152.3173949
predicted
DarkChem Lite v0.1.0
[M-H]-149.78523
predicted
DeepCCS 1.0 (2019)
[M+H]+152.3352949
predicted
DarkChem Lite v0.1.0
[M+H]+152.14323
predicted
DeepCCS 1.0 (2019)
[M+Na]+152.3356949
predicted
DarkChem Lite v0.1.0
[M+Na]+159.28464
predicted
DeepCCS 1.0 (2019)

Targets

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Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
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Learn more
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Protein phosphatase 2a binding
Specific Function
NMDA receptor subtype of glutamate-gated ion channels with reduced single-channel conductance, low calcium permeability and low voltage-dependent sensitivity to magnesium. Mediated by glycine. May ...
Gene Name
GRIN3A
Uniprot ID
Q8TCU5
Uniprot Name
Glutamate receptor ionotropic, NMDA 3A
Molecular Weight
125464.07 Da
References
  1. Smothers CT, Woodward JJ: Pharmacological characterization of glycine-activated currents in HEK 293 cells expressing N-methyl-D-aspartate NR1 and NR3 subunits. J Pharmacol Exp Ther. 2007 Aug;322(2):739-48. Epub 2007 May 14. [Article]
  2. Harrison NL, Simmonds MA: Quantitative studies on some antagonists of N-methyl D-aspartate in slices of rat cerebral cortex. Br J Pharmacol. 1985 Feb;84(2):381-91. [Article]
  3. Sinner B, Graf BM: Ketamine. Handb Exp Pharmacol. 2008;(182):313-33. doi: 10.1007/978-3-540-74806-9_15. [Article]
  4. Radovanovic D, Pjevic M: [Ketamine: the past 30 years and its future]. Med Pregl. 2003 Sep-Oct;56(9-10):439-45. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Potentiator
General Function
Voltage-gated potassium channel activity
Specific Function
This is one of the several different receptors for 5-hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor is a ligand-gate...
Gene Name
HTR3A
Uniprot ID
P46098
Uniprot Name
5-hydroxytryptamine receptor 3A
Molecular Weight
55279.835 Da
References
  1. Appadu BL, Lambert DG: Interaction of i.v. anaesthetic agents with 5-HT3 receptors. Br J Anaesth. 1996 Feb;76(2):271-3. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Toxic substance binding
Specific Function
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane. The cha...
Gene Name
CHRNA7
Uniprot ID
P36544
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-7
Molecular Weight
56448.925 Da
References
  1. Kohrs R, Durieux ME: Ketamine: teaching an old drug new tricks. Anesth Analg. 1998 Nov;87(5):1186-93. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Identical protein binding
Specific Function
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name
BCHE
Uniprot ID
P06276
Uniprot Name
Cholinesterase
Molecular Weight
68417.575 Da
References
  1. Kohrs R, Durieux ME: Ketamine: teaching an old drug new tricks. Anesth Analg. 1998 Nov;87(5):1186-93. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Tetrahydrobiopterin binding
Specific Function
Produces nitric oxide (NO) which is a messenger molecule with diverse functions throughout the body. In the brain and peripheral nervous system, NO displays many properties of a neurotransmitter. P...
Gene Name
NOS1
Uniprot ID
P29475
Uniprot Name
Nitric oxide synthase, brain
Molecular Weight
160969.095 Da
References
  1. Kohrs R, Durieux ME: Ketamine: teaching an old drug new tricks. Anesth Analg. 1998 Nov;87(5):1186-93. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Tachykinin receptor activity
Specific Function
This is a receptor for the tachykinin neuropeptide substance P. It is probably associated with G proteins that activate a phosphatidylinositol-calcium second messenger system. The rank order of aff...
Gene Name
TACR1
Uniprot ID
P25103
Uniprot Name
Substance-P receptor
Molecular Weight
46250.5 Da
References
  1. Okamoto T, Minami K, Uezono Y, Ogata J, Shiraishi M, Shigematsu A, Ueta Y: The inhibitory effects of ketamine and pentobarbital on substance p receptors expressed in Xenopus oocytes. Anesth Analg. 2003 Jul;97(1):104-10, table of contents. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
Partial agonist
General Function
Potassium channel regulator activity
Specific Function
Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase.
Gene Name
DRD2
Uniprot ID
P14416
Uniprot Name
D(2) dopamine receptor
Molecular Weight
50618.91 Da
References
  1. Seeman P, Guan HC, Hirbec H: Dopamine D2High receptors stimulated by phencyclidines, lysergic acid diethylamide, salvinorin A, and modafinil. Synapse. 2009 Aug;63(8):698-704. doi: 10.1002/syn.20647. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Opioid receptor activity
Specific Function
G-protein coupled receptor that functions as receptor for endogenous enkephalins and for a subset of other opioids. Ligand binding causes a conformation change that triggers signaling via guanine n...
Gene Name
OPRD1
Uniprot ID
P41143
Uniprot Name
Delta-type opioid receptor
Molecular Weight
40368.235 Da
References
  1. Smith DJ, Pekoe GM, Martin LL, Coalgate B: The interaction of ketamine with the opiate receptor. Life Sci. 1980 Mar 10;26(10):789-95. [Article]
  2. Hustveit O, Maurset A, Oye I: Interaction of the chiral forms of ketamine with opioid, phencyclidine, sigma and muscarinic receptors. Pharmacol Toxicol. 1995 Dec;77(6):355-9. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Norepinephrine:sodium symporter activity
Specific Function
Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name
SLC6A2
Uniprot ID
P23975
Uniprot Name
Sodium-dependent noradrenaline transporter
Molecular Weight
69331.42 Da
References
  1. Salt PJ, Barnes PK, Beswick FJ: Inhibition of neuronal and extraneuronal uptake of noradrenaline by ketamine in the isolated perfused rat heart. Br J Anaesth. 1979 Sep;51(9):835-8. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Opioid receptor activity
Specific Function
G-protein coupled opioid receptor that functions as receptor for endogenous alpha-neoendorphins and dynorphins, but has low affinity for beta-endorphins. Also functions as receptor for various synt...
Gene Name
OPRK1
Uniprot ID
P41145
Uniprot Name
Kappa-type opioid receptor
Molecular Weight
42644.665 Da
References
  1. Smith DJ, Pekoe GM, Martin LL, Coalgate B: The interaction of ketamine with the opiate receptor. Life Sci. 1980 Mar 10;26(10):789-95. [Article]
  2. Hustveit O, Maurset A, Oye I: Interaction of the chiral forms of ketamine with opioid, phencyclidine, sigma and muscarinic receptors. Pharmacol Toxicol. 1995 Dec;77(6):355-9. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Voltage-gated calcium channel activity
Specific Function
Receptor for endogenous opioids such as beta-endorphin and endomorphin. Receptor for natural and synthetic opioids including morphine, heroin, DAMGO, fentanyl, etorphine, buprenorphin and methadone...
Gene Name
OPRM1
Uniprot ID
P35372
Uniprot Name
Mu-type opioid receptor
Molecular Weight
44778.855 Da
References
  1. Smith DJ, Pekoe GM, Martin LL, Coalgate B: The interaction of ketamine with the opiate receptor. Life Sci. 1980 Mar 10;26(10):789-95. [Article]
  2. Hustveit O, Maurset A, Oye I: Interaction of the chiral forms of ketamine with opioid, phencyclidine, sigma and muscarinic receptors. Pharmacol Toxicol. 1995 Dec;77(6):355-9. [Article]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Phosphatidylinositol phospholipase c activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...

Components:
References
  1. Hustveit O, Maurset A, Oye I: Interaction of the chiral forms of ketamine with opioid, phencyclidine, sigma and muscarinic receptors. Pharmacol Toxicol. 1995 Dec;77(6):355-9. [Article]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Virus receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodop...

Components:
References
  1. Martin LL, Bouchal RL, Smith DJ: Ketamine inhibits serotonin uptake in vivo. Neuropharmacology. 1982 Feb;21(2):113-8. [Article]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances. Ligand binding causes a conformation change that triggers...

Components:
References
  1. Martin LL, Bouchal RL, Smith DJ: Ketamine inhibits serotonin uptake in vivo. Neuropharmacology. 1982 Feb;21(2):113-8. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gas...
Gene Name
PTGS1
Uniprot ID
P23219
Uniprot Name
Prostaglandin G/H synthase 1
Molecular Weight
68685.82 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Desta Z, Moaddel R, Ogburn ET, Xu C, Ramamoorthy A, Venkata SL, Sanghvi M, Goldberg ME, Torjman MC, Wainer IW: Stereoselective and regiospecific hydroxylation of ketamine and norketamine. Xenobiotica. 2012 Nov;42(11):1076-87. doi: 10.3109/00498254.2012.685777. Epub 2012 May 21. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
Molecular Weight
56277.81 Da
References
  1. Hijazi Y, Boulieu R: 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. [Article]
  2. Yanagihara Y, Kariya S, Ohtani M, Uchino K, Aoyama T, Yamamura Y, Iga T: Involvement of CYP2B6 in n-demethylation of ketamine in human liver microsomes. Drug Metab Dispos. 2001 Jun;29(6):887-90. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Curator comments
One in vivo study in rats demonstrated the induction of CYP3A4 by ketamine. Several other studies indicate that ketamine is a CYP3A4 substrate.
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Lin F, He Y, Zhang L, Zhang M, Zhang Y, Wen C: Assessment of the effect of ketamine on cytochrome P450 isoforms activity in rats by cocktail method. Int J Clin Exp Med. 2015 Mar 15;8(3):4335-41. eCollection 2015. [Article]
  2. Mossner LD, Schmitz A, Theurillat R, Thormann W, Mevissen M: Inhibition of cytochrome P450 enzymes involved in ketamine metabolism by use of liver microsomes and specific cytochrome P450 enzymes from horses, dogs, and humans. Am J Vet Res. 2011 Nov;72(11):1505-13. doi: 10.2460/ajvr.72.11.1505. [Article]
  3. Yanagihara Y, Kariya S, Ohtani M, Uchino K, Aoyama T, Yamamura Y, Iga T: Involvement of CYP2B6 in n-demethylation of ketamine in human liver microsomes. Drug Metab Dispos. 2001 Jun;29(6):887-90. [Article]
  4. Hijazi Y, Boulieu R: 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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inducer
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Lin F, He Y, Zhang L, Zhang M, Zhang Y, Wen C: Assessment of the effect of ketamine on cytochrome P450 isoforms activity in rats by cocktail method. Int J Clin Exp Med. 2015 Mar 15;8(3):4335-41. eCollection 2015. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 18, 2024 16:48