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Details

Stereochemistry RACEMIC
Molecular Formula C13H16ClNO
Molecular Weight 237.725
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of KETAMINE

SMILES

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

InChI

InChIKey=YQEZLKZALYSWHR-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C13H16ClNO
Molecular Weight 237.725
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

Ketamine (brand name Ketalar) is a cyclohexanone derivative used for induction of anesthesia. Ketalar is indicated as the sole anesthetic agent for diagnostic and surgical procedures that do not require skeletal muscle relaxation; also, it is indicated for the induction of anesthesia prior to the administration of other general anesthetic agents. Ketamine blocks NMDA receptors through an interaction with sites thought to be located within the ion channel pore region. However, the complete pharmacology of ketamine is more complex, and it is known to directly interact with a variety of other sites to varying degrees. Recently, it was shown that inclusion of the NR3B subunit does not alter the ketamine sensitivity of recombinant NR1/NR2 receptors expressed in oocytes. Likewise, 100 μM ketamine produced only weak inhibition of the glycine-induced current of NR1/NR3A/NR3B receptors. The side effects of ketamine noted in clinical studies include psychedelic symptoms (hallucinations, memory defects, panic attacks), nausea/vomiting, somnolence, cardiovascular stimulation and, in a minority of patients, hepatoxicity. The recreational use of ketamine is increasing and comes with a variety of additional risks ranging from bladder and renal complications to persistent psychotypical behaviour and memory defects. Ketamine was first synthesized in 1962 by Calvin Stevens at Parke-Davis Co (now Pfizer) as an alternative anesthetic to phencyclidine. It was first used in humans in 1965 by Corssen and Domino and was introduced into clinical practice by 1970.

CNS Activity

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
KETALAR
PubMed

PubMed

TitleDatePubMed
The effects of ketamine and of Innovar anesthesia on digitalis tolerance in dogs.
1975 Jan-Feb
Ketamine-pancuronium-narcotic technic for cardiovascular surgery in infants--a comparative study.
1975 Nov-Dec
Intravenous midazolam significantly enhances the lethal effect of thiopental but not that of ketamine in mice.
2001 Dec
Precordial compression without airway management induces lung injury in the rodent cardiac arrest model with central apnea.
2001 Nov
Clonidine versus ketamine to prevent tourniquet pain during intravenous regional anesthesia with lidocaine.
2001 Nov-Dec
Interaction of intravenous anesthetics with recombinant human M1-M3 muscarinic receptors expressed in chinese hamster ovary cells.
2002 Dec
Concentration-effect relationships for intravenous alfentanil and ketamine infusions in human volunteers: effects on acute thresholds and capsaicin-evoked hyperpathia.
2002 Jan
Effects of subanesthetic doses of ketamine on sensorimotor information processing in healthy subjects.
2002 Mar-Apr
Search of antimicrobial activity of selected non-antibiotic drugs.
2002 Nov-Dec
Ketamine as an adjuvant to opioids for cancer pain.
2003
Schizophrenia, VIII: pharmacologic models.
2003 Dec
Ketamine for refractory status epilepticus: a case of possible ketamine-induced neurotoxicity.
2003 Feb
Cold allodynia and hyperalgesia in neuropathic pain: the effect of N-methyl-D-aspartate (NMDA) receptor antagonist ketamine--a double-blind, cross-over comparison with alfentanil and placebo.
2003 Feb
[Anaesthesia for caesarean section. Comparison of two general anaesthetic regimens and spinal anaesthesia].
2003 Jan
Angina pain precipitated by a continuous subcutaneous infusion of ketamine.
2003 Jan
Effects of the 5-HT2A agonist psilocybin on mismatch negativity generation and AX-continuous performance task: implications for the neuropharmacology of cognitive deficits in schizophrenia.
2003 Jan
Double-blind randomized placebo-controlled trial of the effect of ketamine on postoperative morphine consumption in children following appendicectomy.
2003 Jun
Pretreatment with intravenous ketamine reduces propofol injection pain.
2003 Nov
Preprocedural fasting state and adverse events in children undergoing procedural sedation and analgesia in a pediatric emergency department.
2003 Nov
Synergistic antinociceptive effects of ketamine and morphine in the orofacial capsaicin test in the rat.
2003 Oct
The effect of variable-dose diazepam on dreaming and emergence phenomena in 400 cases of ketamine-fentanyl anaesthesia.
2003 Sep
Acute effects of ketamine on memory systems and psychotic symptoms in healthy volunteers.
2004 Jan
The development and maintenance of human visceral pain hypersensitivity is dependent on the N-methyl-D-aspartate receptor.
2004 Mar
Ketamine impairs response inhibition and is positively reinforcing in healthy volunteers: a dose-response study.
2004 Mar
Normal spatial and contextual learning for ketamine-treated rats in the pilocarpine epilepsy model.
2004 May
Postanesthetic cerebellar dysfunction in cats.
2004 May-Jun
Preemptive ketamine during general anesthesia for postoperative analgesia in patients undergoing laparoscopic cholecystectomy.
2004 Oct
Intravenous ketamine infusion as an adjuvant to morphine in a 2-year-old with severe cancer pain from metastatic neuroblastoma.
2004 Oct
Caudal analgesia in children: S(+)-ketamine vs S(+)-ketamine plus clonidine.
2004 Oct
Ketamine reduces lidocaine-induced seizures in mice.
2005 Aug
Ketamine pretreatment with venous occlusion attenuates pain on injection with propofol.
2005 Jan
Comparison of ephedrine and ketamine in prevention of injection pain and hypotension due to propofol induction.
2005 Jan
Ketamine and postoperative pain--a quantitative systematic review of randomised trials.
2005 Jan
Participation of adenosine system in the ketamine-induced motor activity in mice.
2005 Jan-Feb
Remifentanil-induced postoperative hyperalgesia and its prevention with small-dose ketamine.
2005 Jul
Safety of mixture of morphine with ketamine for postoperative patient-controlled analgesia: an audit with 1026 patients.
2005 Jul
Naloxone increases ketamine-induced hyperactivity in the open field in female rats.
2005 Jul
Ketamine and amphetamine both enhance synaptic transmission in the amygdala-nucleus accumbens pathway but with different time-courses.
2005 Jul
Adverse events associated with procedural sedation and analgesia in a pediatric emergency department: a comparison of common parenteral drugs.
2005 Jun
The anesthetics nitrous oxide and ketamine are more neurotoxic to old than to young rat brain.
2005 Jun
Severe refractory status epilepticus owing to presumed encephalitis.
2005 Mar
Characterization of morphine-induced hyperalgesia in male and female rats.
2005 Mar
Effect of N-methyl-D-aspartate receptor epsilon1 subunit gene disruption of the action of general anesthetic drugs in mice.
2005 Mar
Ketamine inhibits LPS-induced tumour necrosis factor-alpha and interleukin-6 in an equine macrophage cell line.
2005 Mar-Apr
Peri-operative ketamine for acute post-operative pain: a quantitative and qualitative systematic review (Cochrane review).
2005 Nov
Cortical glutamate-dopamine interaction and ketamine-induced psychotic symptoms in man.
2005 Nov
[Comparison of the suppressive effects of tramadol and low-dose ketamine on the patients with postoperative hyperalgesia after remifentanil-based anaesthesia].
2005 Oct
Topical amitriptyline and ketamine in neuropathic pain syndromes: an open-label study.
2005 Oct
Ischemic brain damage after ketamine and xylazine treatment in a young laboratory monkey (Macaca fascicularis).
2005 Sep
Induction of rat hepatic cytochrome P-450 by ketamine and its toxicological implications.
2005 Sep
Patents

Sample Use Guides

In Vivo Use Guide
Intravenous Route: The initial dose of Ketalar (ketamine hydrochloride injection) administered intravenously may range from 1 mg/kg to 4.5 mg/kg (0.5 to 2 mg/lb). The average amount required to produce five to ten minutes of surgical anesthesia has been 2 mg/kg (1 mg/lb). Intramuscular Route: The initial dose of Ketalar administered intramuscularly may range from 6.5 to 13 mg/kg (3 to 6 mg/lb). A dose of 10 mg/kg (5 mg/lb) will usually produce 12 to 25 minutes of surgical anesthesia.
Route of Administration: intravenous; intramuscular
In Vitro Use Guide
Primary cultures of cortical neurons treated with ketamine (10 μM-10mM) at 3 days-in vitro (3 DIV) displayed a concentration-dependent decrease in expanded growth cones
Substance Class Chemical
Created
by admin
on Mon Oct 21 20:32:24 UTC 2019
Edited
by admin
on Mon Oct 21 20:32:24 UTC 2019
Record UNII
690G0D6V8H
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
KETAMINE
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
NSC-70151
Code English
PMI-150
Code English
KETAFOL COMPONENT KETAMINE
Brand Name English
VETAKET
Brand Name English
CALYPSOL
Brand Name English
TEKAM
Brand Name English
CYCLOHEXANONE, 2-(2-CHLOROPHENYL)-2-(METHYLAMINO)-, (+/-)-
Systematic Name English
(+/-)-2-(O-CHLOROPHENYL)-2-(METHYLAMINO)CYCLOHEXANONE
Common Name English
(+/-)-KETAMINE
Common Name English
IMALGENE 1000
Brand Name English
KETASOL 100
Brand Name English
ANAKET V
Brand Name English
KETAMINE [WHO-DD]
Common Name English
KETAMINE [VANDF]
Common Name English
NARKETAN
Brand Name English
CYCLOHEXANONE, 2-(2-CHLOROPHENYL)-2-(METHYLAMINO)-
Systematic Name English
KETAMINE [MI]
Common Name English
URSOTAMIN
Brand Name English
CLORKETAM 1000
Brand Name English
DL-KETAMINE
Common Name English
KETAMINE [INN]
Common Name English
KETAMINE [HSDB]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C245
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
CFR 21 CFR 522.1222A
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
NDF-RT N0000175681
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
FDA ORPHAN DRUG 288809
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
WHO-VATC QN01AX03
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 1.1.2
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
DEA NO. 7285
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
NDF-RT N0000175975
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
WHO-ATC N01AX03
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
LIVERTOX 531
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
Code System Code Type Description
HSDB
6740-88-1
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
PRIMARY
INN
2156
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
PRIMARY
DRUG BANK
DB01221
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
PRIMARY
PUBCHEM
3821
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
PRIMARY
EVMPD
SUB08365MIG
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
PRIMARY
CAS
6740-88-1
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
PRIMARY
ChEMBL
CHEMBL742
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
PRIMARY
ECHA (EC/EINECS)
229-804-1
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
PRIMARY
CAS
33643-45-7
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
SUPERSEDED
CAS
100477-72-3
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
SUPERSEDED
IUPHAR
4233
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
PRIMARY
RXCUI
6130
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
PRIMARY RxNorm
LactMed
6740-88-1
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
PRIMARY
CAS
79499-51-7
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
SUPERSEDED
NCI_THESAURUS
C61797
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
PRIMARY
MESH
D007649
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
PRIMARY
EPA CompTox
6740-88-1
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
PRIMARY
MERCK INDEX
M6613
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
PRIMARY Merck Index
WIKIPEDIA
KETAMINE
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
PRIMARY
Related Record Type Details
TARGET->PARTIAL AGONIST
ENANTIOMER -> RACEMATE
BINDER->LIGAND
TRANSPORTER -> INHIBITOR
ENANTIOMER -> RACEMATE
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
Related Record Type Details
METABOLITE LESS ACTIVE -> PARENT
METABOLITE LESS ACTIVE -> PARENT
NMDA receptor (rat brain) binding assay
IN-VITRO
Ki
METABOLITE ACTIVE -> PARENT
NMDA receptor (rat brain) binding assay
IN-VITRO
Ki
METABOLITE ACTIVE -> PARENT
METABOLITE ACTIVE -> PARENT
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC