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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
Structure for Ketamine (DB01221)
- 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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- Contraindications & Blackbox Warnings
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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
Target Actions Organism AGlutamate receptor ionotropic, NMDA 3A antagonistHumans A5-hydroxytryptamine receptor 3A potentiatorHumans ANeuronal acetylcholine receptor subunit alpha-7 antagonistHumans ACholinesterase inhibitorHumans ANitric oxide synthase 1 inhibitorHumans USubstance-P receptor antagonistHumans UD(2) dopamine receptor agonistpartial agonistHumans UDelta-type opioid receptor binderHumans USodium-dependent noradrenaline transporter inhibitorHumans UKappa-type opioid receptor agonistHumans UMu-type opioid receptor binderHumans UMuscarinic acetylcholine receptor binderHumans U5-hydroxytryptamine receptor 2 antagonistHumans U5-hydroxytryptamine receptor 1 antagonistHumans - 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
Hover over products below to view reaction partners
- 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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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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Ketamine is combined with 1,2-Benzodiazepine. Abacavir Abacavir may decrease the excretion rate of Ketamine which could result in a higher serum level. Abametapir The serum concentration of Ketamine can be increased when it is combined with Abametapir. Abatacept The metabolism of Ketamine can be increased when combined with Abatacept. Abiraterone The metabolism of Ketamine can be decreased when combined with Abiraterone. - Food Interactions
- Avoid alcohol.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Ketamine hydrochloride O18YUO0I83 1867-66-9 VCMGMSHEPQENPE-UHFFFAOYSA-N - International/Other Brands
- Ketaject (Bristol-Myers Squibb) / Ketanest (Parke Davis)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Ketalar Injection 50 mg/1mL Intramuscular; Intravenous Monarch Pharmaceuticals, Inc. 1970-02-19 2007-10-01 US 
Ketalar Injection 10 mg/1mL Intramuscular; Intravenous ENDO USA, Inc. 2007-10-01 Not applicable US Ketalar Injection 100 mg/1mL Intramuscular; Intravenous ENDO USA, Inc. 2007-10-01 Not applicable US Ketalar Injection 10 mg/1mL Intramuscular; Intravenous Monarch Pharmaceuticals, Inc. 1970-02-19 2007-10-01 US Ketalar Solution 50 mg / mL Intramuscular; Intravenous Searchlight Pharma Inc 1972-12-31 Not applicable Canada 
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Ketamine Hydrochloride Injection 100 mg/1mL Intramuscular; Intravenous Eugia US LLC 2021-03-15 Not applicable US Ketamine Hydrochloride Injection, solution, concentrate 100 mg/1mL Intramuscular; Intravenous Physicians Total Care, Inc. 2004-06-16 2011-06-30 US Ketamine Hydrochloride Injection 50 mg/1mL Intramuscular; Intravenous Hikma Pharmaceuticals USA Inc. 1996-07-01 Not applicable US Ketamine Hydrochloride Injection 100 mg/1mL Intramuscular; Intravenous Civica, Inc. 2019-12-05 Not applicable US Ketamine Hydrochloride Injection 10 mg/1mL Intramuscular; Intravenous Par Pharmaceutical 2012-06-01 2018-05-06 US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image MKH Dose Pack Ketamine hydrochloride (25 mg/1) + Hydroxyzine hydrochloride (10 mg/1) + Midazolam (3 mg/1) Troche Sublingual Imprimis Njof, Llc 2019-03-04 Not applicable US MKO Melt Ketamine hydrochloride (25 mg/1) + Midazolam (3 mg/1) + Ondansetron hydrochloride dihydrate (2 mg/1) Troche Sublingual Imprimis Njof, Llc 2018-12-01 2019-03-04 US MKO Melt Dose Pack Ketamine hydrochloride (25 mg/1) + Midazolam (3 mg/1) + Ondansetron hydrochloride (2 mg/1) Troche Sublingual Imprimis Njof, Llc 2019-03-04 Not applicable US Topical Nerve Pain Ketamine (0.1 g/100mL) + Diazepam (0.1 g/100mL) + Diclofenac sodium (0.1 g/100mL) + Gabapentin (0.1 g/100mL) Cream Topical Dr Marc's Manufacturing And Sales 2016-02-23 2018-04-17 US
Categories
- ATC Codes
- N01AX03 — Ketamine
- Drug Categories
- Agents producing tachycardia
- Amino Acids
- Amino Acids, Acidic
- Amino Acids, Dicarboxylic
- Amino Acids, Peptides, and Proteins
- Analgesics
- Anesthetics
- Anesthetics, Dissociative
- Anesthetics, General
- Anesthetics, Intravenous
- Central Nervous System Agents
- Central Nervous System Depressants
- Cholinesterase Inhibitors
- Cyclohexanes
- Cycloparaffins
- Cytochrome P-450 CYP2B6 Substrates
- Cytochrome P-450 CYP2C8 Substrates
- Cytochrome P-450 CYP2C9 Substrates
- Cytochrome P-450 CYP3A Inducers
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Inducers
- Cytochrome P-450 CYP3A4 Inducers (strength unknown)
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Enzyme Inducers
- Cytochrome P-450 Substrates
- Drugs that are Mainly Renally Excreted
- Excitatory Amino Acid Agents
- Excitatory Amino Acid Agonists
- Excitatory Amino Acid Antagonists
- Miscellaneous General Anesthetics
- N-Methylaspartate, agonists
- Nervous System
- Neurotransmitter Agents
- NMDA Receptor Antagonists
- Peripheral Nervous System Agents
- Sensory System Agents
- Vasodilating Agents
- 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
- 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]
- Bergman SA: Ketamine: review of its pharmacology and its use in pediatric anesthesia. Anesth Prog. 1999 Winter;46(1):10-20. [Article]
- Bonanno FG: Ketamine in war/tropical surgery (a final tribute to the racemic mixture). Injury. 2002 May;33(4):323-7. [Article]
- 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]
- Reboso Morales JA, Gonzalez Miranda F: [Ketamine]. Rev Esp Anestesiol Reanim. 1999 Mar;46(3):111-22. [Article]
- Ivani G, Vercellino C, Tonetti F: Ketamine: a new look to an old drug. Minerva Anestesiol. 2003 May;69(5):468-71. [Article]
- 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]
- 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]
- 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]
- 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]
- 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]
- Kaka JS, Hayton WL: Pharmacokinetics of ketamine and two metabolites in the dog. J Pharmacokinet Biopharm. 1980 Apr;8(2):193-202. [Article]
- 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]
- Ketamine [Link]
- Ketamine monograph [Link]
- Time magazine [Link]
- External Links
- Human Metabolome Database
- HMDB0015352
- KEGG Drug
- D08098
- KEGG Compound
- C07525
- PubChem Compound
- 3821
- PubChem Substance
- 46508295
- ChemSpider
- 3689
- BindingDB
- 50044140
- 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
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Active Not Recruiting Prevention Acute Pain / Analgesia / Chronic Pain / Morphine / Neuropathic Pain / Postoperative pain / S-ketamine 1 somestatus stop reason just information to hide Not Available Active Not Recruiting Treatment Hospital Inpatient Trauma Injury / Pain Management 1 somestatus stop reason just information to hide Not Available Completed Not Available Abdominal Pain 1 somestatus stop reason just information to hide Not Available Completed Not Available Acute Pain 1 somestatus stop reason just information to hide Not Available Completed Not Available Acute Pain / Analgesia / Post Traumatic Stress Disorder (PTSD) / Traumas, Brain / Traumatic Amputations 1 somestatus stop reason just information to hide
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
Form Route Strength Injection Intramuscular Injection Intramuscular; Intravenous 100 MG/ML Injection Intramuscular 50 MG/ML Injection Intramuscular; Intravenous 10 mg/1mL Injection Intramuscular; Intravenous 100 mg/1mL Injection Intramuscular; Intravenous 50 mg/1mL Injection Intravenous 50 MG/ML Solution Intramuscular; Intravenous 50 mg / mL Injection 500 mg Injection Intramuscular; Intravenous 500 mg Injection, solution 10 mg/ml Injection, solution Parenteral 10 mg/ml Injection, solution 50 mg/ml Solution Intramuscular; Intravenous 500 mg Injection, solution Parenteral 50 MG/ML Injection 57.677 mg/ml Injection, solution Intramuscular; Intravenous 50 MG Injection Intramuscular; Intravenous 118.8 mg Injection, solution Intramuscular; Intravenous 10 mg/1mL Injection, solution Intramuscular; Intravenous 100 mg/1mL Injection, solution Intramuscular; Intravenous 50 mg/1mL Injection, solution, concentrate Intramuscular; Intravenous 100 mg/1mL Injection, solution, concentrate Intramuscular; Intravenous 50 mg/1mL Powder Not applicable 1 g/1g Injection Intramuscular; Intravenous 50 mg/ml Solution Intramuscular; Intravenous 10 mg / mL Solution Intramuscular; Intravenous 100 mg / 2 mL Solution Intramuscular; Intravenous 500 mg / 10 mL Injection Intramuscular; Intravenous Troche Sublingual Solution Intramuscular 576.000 mg Cream Topical - Prices
Unit description Cost Unit Ketamine hcl powder 7.22USD g Ketamine hcl-ns 50 mg/5 ml syr 2.82USD ml Ketamine 100 mg/ml vial 2.36USD ml Ketalar 100 mg/ml vial 1.95USD ml Ketamine hcl-ns 100 mg/10 ml 1.95USD ml Ketamine HCl 50 mg/ml Solution 1.77USD ml Ketalar 10 mg/ml vial 0.99USD ml Ketamine 10 mg/ml vial 0.99USD ml Ketalar 50 mg/ml vial 0.75USD ml Ketamine 50 mg/ml vial 0.61USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 92.5ºC Medical toxicology of drug abuse. (2012) water solubility Soluble 'MSDS' logP 3.120 Medical toxicology of drug abuse. (2012) pKa 7.5 Ketamine monograph - Predicted Properties
Property Value Source Water Solubility 0.0464 mg/mL ALOGPS logP 2.69 ALOGPS logP 3.35 Chemaxon logS -3.7 ALOGPS pKa (Strongest Acidic) 19.77 Chemaxon pKa (Strongest Basic) 7.16 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 29.1 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 65.55 m3·mol-1 Chemaxon Polarizability 24.97 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9974 Blood Brain Barrier + 0.9826 Caco-2 permeable + 0.6326 P-glycoprotein substrate Substrate 0.5753 P-glycoprotein inhibitor I Non-inhibitor 0.5948 P-glycoprotein inhibitor II Non-inhibitor 0.8383 Renal organic cation transporter Non-inhibitor 0.6737 CYP450 2C9 substrate Non-substrate 0.6363 CYP450 2D6 substrate Substrate 0.8918 CYP450 3A4 substrate Substrate 0.7407 CYP450 1A2 substrate Non-inhibitor 0.7323 CYP450 2C9 inhibitor Non-inhibitor 0.7985 CYP450 2D6 inhibitor Non-inhibitor 0.6912 CYP450 2C19 inhibitor Non-inhibitor 0.5347 CYP450 3A4 inhibitor Non-inhibitor 0.8253 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.5426 Ames test Non AMES toxic 0.7223 Carcinogenicity Non-carcinogens 0.8878 Biodegradation Not ready biodegradable 0.9937 Rat acute toxicity 2.3939 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8859 hERG inhibition (predictor II) Inhibitor 0.6047
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 152.3173949 predictedDarkChem Lite v0.1.0 [M-H]- 149.78523 predictedDeepCCS 1.0 (2019) [M+H]+ 152.3352949 predictedDarkChem Lite v0.1.0 [M+H]+ 152.14323 predictedDeepCCS 1.0 (2019) [M+Na]+ 152.3356949 predictedDarkChem Lite v0.1.0 [M+Na]+ 159.28464 predictedDeepCCS 1.0 (2019)
Targets
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Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General 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. During the development of neural circuits, plays a role in the synaptic refinement period, restricting spine maturation and growth. By competing with GIT1 interaction with ARHGEF7/beta-PIX, may reduce GIT1/ARHGEF7-regulated local activation of RAC1, hence affecting signaling and limiting the maturation and growth of inactive synapses. May also play a role in PPP2CB-NMDAR mediated signaling mechanism
- Specific Function
- Calcium channel activity
- Gene Name
- GRIN3A
- Uniprot ID
- Q8TCU5
- Uniprot Name
- Glutamate receptor ionotropic, NMDA 3A
- Molecular Weight
- 125464.07 Da
References
- 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]
- 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]
- Sinner B, Graf BM: Ketamine. Handb Exp Pharmacol. 2008;(182):313-33. doi: 10.1007/978-3-540-74806-9_15. [Article]
- 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
- Forms serotonin (5-hydroxytryptamine/5-HT3)-activated cation-selective channel complexes, which when activated cause fast, depolarizing responses in neurons
- Specific Function
- Excitatory extracellular ligand-gated monoatomic ion channel activity
- Gene Name
- HTR3A
- Uniprot ID
- P46098
- Uniprot Name
- 5-hydroxytryptamine receptor 3A
- Molecular Weight
- 55279.835 Da
References
- 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
- 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 channel is blocked by alpha-bungarotoxin
- Specific Function
- Acetylcholine binding
- Gene Name
- CHRNA7
- Uniprot ID
- P36544
- Uniprot Name
- Neuronal acetylcholine receptor subunit alpha-7
- Molecular Weight
- 56448.925 Da
References
- 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
- Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters
- Specific Function
- Acetylcholinesterase activity
- Gene Name
- BCHE
- Uniprot ID
- P06276
- Uniprot Name
- Cholinesterase
- Molecular Weight
- 68417.575 Da
References
- 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
- 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. Probably has nitrosylase activity and mediates cysteine S-nitrosylation of cytoplasmic target proteins such SRR
- Specific Function
- Arginine binding
- Gene Name
- NOS1
- Uniprot ID
- P29475
- Uniprot Name
- Nitric oxide synthase 1
- Molecular Weight
- 160969.095 Da
References
- 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
- 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 affinity of this receptor to tachykinins is: substance P > substance K > neuromedin-K
- Specific Function
- Substance p receptor activity
- Gene Name
- TACR1
- Uniprot ID
- P25103
- Uniprot Name
- Substance-P receptor
- Molecular Weight
- 46250.5 Da
References
- 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
- AgonistPartial agonist
- General Function
- Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase (PubMed:21645528). Positively regulates postnatal regression of retinal hyaloid vessels via suppression of VEGFR2/KDR activity, downstream of OPN5 (By similarity)
- Specific Function
- Dopamine binding
- Gene Name
- DRD2
- Uniprot ID
- P14416
- Uniprot Name
- D(2) dopamine receptor
- Molecular Weight
- 50618.91 Da
References
- 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
- G-protein coupled receptor that functions as a receptor for endogenous enkephalins and for a subset of other opioids. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate cyclase. Signaling leads to the inhibition of adenylate cyclase activity. Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Plays a role in the perception of pain and in opiate-mediated analgesia. Plays a role in developing analgesic tolerance to morphine
- Specific Function
- G protein-coupled enkephalin receptor activity
- Gene Name
- OPRD1
- Uniprot ID
- P41143
- Uniprot Name
- Delta-type opioid receptor
- Molecular Weight
- 40368.235 Da
References
- 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]
- 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
- Mediates sodium- and chloride-dependent transport of norepinephrine (also known as noradrenaline) (PubMed:2008212, PubMed:8125921). Can also mediate sodium- and chloride-dependent transport of dopamine (PubMed:11093780, PubMed:8125921)
- Specific Function
- Actin binding
- Gene Name
- SLC6A2
- Uniprot ID
- P23975
- Uniprot Name
- Sodium-dependent noradrenaline transporter
- Molecular Weight
- 69331.42 Da
References
- 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
- G-protein coupled opioid receptor that functions as a receptor for endogenous alpha-neoendorphins and dynorphins, but has low affinity for beta-endorphins. Also functions as a receptor for various synthetic opioids and for the psychoactive diterpene salvinorin A. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate cyclase. Signaling leads to the inhibition of adenylate cyclase activity. Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Plays a role in the perception of pain. Plays a role in mediating reduced physical activity upon treatment with synthetic opioids. Plays a role in the regulation of salivation in response to synthetic opioids. May play a role in arousal and regulation of autonomic and neuroendocrine functions
- Specific Function
- Dynorphin receptor activity
- Gene Name
- OPRK1
- Uniprot ID
- P41145
- Uniprot Name
- Kappa-type opioid receptor
- Molecular Weight
- 42644.665 Da
References
- 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]
- 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
- Receptor for endogenous opioids such as beta-endorphin and endomorphin (PubMed:10529478, PubMed:12589820, PubMed:7891175, PubMed:7905839, PubMed:7957926, PubMed:9689128). Receptor for natural and synthetic opioids including morphine, heroin, DAMGO, fentanyl, etorphine, buprenorphin and methadone (PubMed:10529478, PubMed:10836142, PubMed:12589820, PubMed:19300905, PubMed:7891175, PubMed:7905839, PubMed:7957926, PubMed:9689128). Also activated by enkephalin peptides, such as Met-enkephalin or Met-enkephalin-Arg-Phe, with higher affinity for Met-enkephalin-Arg-Phe (By similarity). Agonist binding to the receptor induces coupling to an inactive GDP-bound heterotrimeric G-protein complex and subsequent exchange of GDP for GTP in the G-protein alpha subunit leading to dissociation of the G-protein complex with the free GTP-bound G-protein alpha and the G-protein beta-gamma dimer activating downstream cellular effectors (PubMed:7905839). The agonist- and cell type-specific activity is predominantly coupled to pertussis toxin-sensitive G(i) and G(o) G alpha proteins, GNAI1, GNAI2, GNAI3 and GNAO1 isoforms Alpha-1 and Alpha-2, and to a lesser extent to pertussis toxin-insensitive G alpha proteins GNAZ and GNA15 (PubMed:12068084). They mediate an array of downstream cellular responses, including inhibition of adenylate cyclase activity and both N-type and L-type calcium channels, activation of inward rectifying potassium channels, mitogen-activated protein kinase (MAPK), phospholipase C (PLC), phosphoinositide/protein kinase (PKC), phosphoinositide 3-kinase (PI3K) and regulation of NF-kappa-B (By similarity). Also couples to adenylate cyclase stimulatory G alpha proteins (By similarity). The selective temporal coupling to G-proteins and subsequent signaling can be regulated by RGSZ proteins, such as RGS9, RGS17 and RGS4 (By similarity). Phosphorylation by members of the GPRK subfamily of Ser/Thr protein kinases and association with beta-arrestins is involved in short-term receptor desensitization (By similarity). Beta-arrestins associate with the GPRK-phosphorylated receptor and uncouple it from the G-protein thus terminating signal transduction (By similarity). The phosphorylated receptor is internalized through endocytosis via clathrin-coated pits which involves beta-arrestins (By similarity). The activation of the ERK pathway occurs either in a G-protein-dependent or a beta-arrestin-dependent manner and is regulated by agonist-specific receptor phosphorylation (By similarity). Acts as a class A G-protein coupled receptor (GPCR) which dissociates from beta-arrestin at or near the plasma membrane and undergoes rapid recycling (By similarity). Receptor down-regulation pathways are varying with the agonist and occur dependent or independent of G-protein coupling (By similarity). Endogenous ligands induce rapid desensitization, endocytosis and recycling (By similarity). Heterooligomerization with other GPCRs can modulate agonist binding, signaling and trafficking properties (By similarity)
- Specific Function
- Beta-endorphin receptor activity
- Gene Name
- OPRM1
- Uniprot ID
- P35372
- Uniprot Name
- Mu-type opioid receptor
- Molecular Weight
- 44778.855 Da
References
- 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]
- 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
- The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
- Specific Function
- G protein-coupled acetylcholine receptor activity
Components:
References
- 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
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin) (PubMed:1330647, PubMed:18703043, PubMed:19057895). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane (DOI) and lysergic acid diethylamide (LSD) (PubMed:28129538). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors (PubMed:28129538). Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways (PubMed:28129538). Signaling activates phospholipase C and a phosphatidylinositol-calcium second messenger system that modulates the activity of phosphatidylinositol 3-kinase and promotes the release of Ca(2+) ions from intracellular stores (PubMed:18703043, PubMed:28129538). Affects neural activity, perception, cognition and mood (PubMed:18297054). Plays a role in the regulation of behavior, including responses to anxiogenic situations and psychoactive substances. Plays a role in intestinal smooth muscle contraction, and may play a role in arterial vasoconstriction
- Specific Function
- 1-(4-iodo-2,5-dimethoxyphenyl)propan-2-amine binding
Components:
| Name | UniProt ID |
|---|---|
| 5-hydroxytryptamine receptor 2A | P28223 |
| 5-hydroxytryptamine receptor 2B | P41595 |
| 5-hydroxytryptamine receptor 2C | P28335 |
References
- 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
- 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 signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate cyclase. Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways. Signaling inhibits adenylate cyclase activity and activates a phosphatidylinositol-calcium second messenger system that regulates the release of Ca(2+) ions from intracellular stores. Plays a role in the regulation of 5-hydroxytryptamine release and in the regulation of dopamine and 5-hydroxytryptamine metabolism. Plays a role in the regulation of dopamine and 5-hydroxytryptamine levels in the brain, and thereby affects neural activity, mood and behavior. Plays a role in the response to anxiogenic stimuli
- Specific Function
- G protein-coupled serotonin receptor activity
Components:
| Name | UniProt ID |
|---|---|
| 5-hydroxytryptamine receptor 1A | P08908 |
| 5-hydroxytryptamine receptor 1B | P28222 |
| 5-hydroxytryptamine receptor 1D | P28221 |
| 5-hydroxytryptamine receptor 1E | P28566 |
| 5-hydroxytryptamine receptor 1F | P30939 |
References
- 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
- Dual cyclooxygenase and peroxidase that plays an important role in the biosynthesis pathway of prostanoids, a class of C20 oxylipins mainly derived from arachidonate ((5Z,8Z,11Z,14Z)-eicosatetraenoate, AA, C20:4(n-6)), with a particular role in the inflammatory response. The cyclooxygenase activity oxygenates AA to the hydroperoxy endoperoxide prostaglandin G2 (PGG2), and the peroxidase activity reduces PGG2 to the hydroxy endoperoxide prostaglandin H2 (PGH2), the precursor of all 2-series prostaglandins and thromboxanes. This complex transformation is initiated by abstraction of hydrogen at carbon 13 (with S-stereochemistry), followed by insertion of molecular O2 to form the endoperoxide bridge between carbon 9 and 11 that defines prostaglandins. The insertion of a second molecule of O2 (bis-oxygenase activity) yields a hydroperoxy group in PGG2 that is then reduced to PGH2 by two electrons (PubMed:7947975). Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gastric epithelial cells, it is a key step in the generation of prostaglandins, such as prostaglandin E2 (PGE2), which plays an important role in cytoprotection. In platelets, it is involved in the generation of thromboxane A2 (TXA2), which promotes platelet activation and aggregation, vasoconstriction and proliferation of vascular smooth muscle cells (Probable). Can also use linoleate (LA, (9Z,12Z)-octadecadienoate, C18:2(n-6)) as substrate and produce hydroxyoctadecadienoates (HODEs) in a regio- and stereospecific manner, being (9R)-HODE ((9R)-hydroxy-(10E,12Z)-octadecadienoate) and (13S)-HODE ((13S)-hydroxy-(9Z,11E)-octadecadienoate) its major products (By similarity)
- Specific Function
- Heme binding
- Gene Name
- PTGS1
- Uniprot ID
- P23219
- Uniprot Name
- Prostaglandin G/H synthase 1
- Molecular Weight
- 68685.82 Da
References
- 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
- A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:11093772, PubMed:14559847, PubMed:15766564, PubMed:19965576, PubMed:7574697). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:11093772, PubMed:14559847, PubMed:15766564, PubMed:19965576, PubMed:7574697). Primarily catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) with a preference for the last double bond (PubMed:15766564, PubMed:19965576, PubMed:7574697). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes all trans-retinoic acid toward its 4-hydroxylated form (PubMed:11093772). Displays 16-alpha hydroxylase activity toward estrogen steroid hormones, 17beta-estradiol (E2) and estrone (E1) (PubMed:14559847). Plays a role in the oxidative metabolism of xenobiotics. It is the principal enzyme responsible for the metabolism of the anti-cancer drug paclitaxel (taxol) (PubMed:26427316)
- Specific Function
- Arachidonic acid epoxygenase activity
- Gene Name
- CYP2C8
- Uniprot ID
- P10632
- Uniprot Name
- Cytochrome P450 2C8
- Molecular Weight
- 55824.275 Da
References
- 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
- A cytochrome P450 monooxygenase involved in the metabolism of endocannabinoids and steroids (PubMed:12865317, PubMed:21289075). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the epoxidation of double bonds of arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:21289075). Hydroxylates steroid hormones, including testosterone at C-16 and estrogens at C-2 (PubMed:12865317, PubMed:21289075). Plays a role in the oxidative metabolism of xenobiotics, including plant lipids and drugs (PubMed:11695850, PubMed:22909231). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850)
- Specific Function
- Anandamide 11,12 epoxidase activity
- Gene Name
- CYP2B6
- Uniprot ID
- P20813
- Uniprot Name
- Cytochrome P450 2B6
- Molecular Weight
- 56277.81 Da
References
- 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]
- 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
- A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids and steroids (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:15766564, PubMed:19965576, PubMed:7574697, PubMed:9866708). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Exhibits low catalytic activity for the formation of catechol estrogens from 17beta-estradiol (E2) and estrone (E1), namely 2-hydroxy E1 and E2 (PubMed:12865317). Catalyzes bisallylic hydroxylation and hydroxylation with double-bond migration of polyunsaturated fatty acids (PUFA) (PubMed:9435160, PubMed:9866708). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). Contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan (PubMed:25994031)
- Specific Function
- (r)-limonene 6-monooxygenase activity
- Gene Name
- CYP2C9
- Uniprot ID
- P11712
- Uniprot Name
- Cytochrome P450 2C9
- Molecular Weight
- 55627.365 Da
References
- 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]
- 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]
- 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]
- 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
- SubstrateInducer
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of sterols, steroid hormones, retinoids and fatty acids (PubMed:10681376, PubMed:11093772, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:19965576, PubMed:20702771, PubMed:21490593, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:21490593, PubMed:21576599, PubMed:2732228). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C-16 position (PubMed:11555828, PubMed:12865317, PubMed:14559847). Plays a role in the metabolism of androgens, particularly in oxidative deactivation of testosterone (PubMed:15373842, PubMed:15764715, PubMed:22773874, PubMed:2732228). Metabolizes testosterone to less biologically active 2beta- and 6beta-hydroxytestosterones (PubMed:15373842, PubMed:15764715, PubMed:2732228). Contributes to the formation of hydroxycholesterols (oxysterols), particularly A-ring hydroxylated cholesterol at the C-4beta position, and side chain hydroxylated cholesterol at the C-25 position, likely contributing to cholesterol degradation and bile acid biosynthesis (PubMed:21576599). Catalyzes bisallylic hydroxylation of polyunsaturated fatty acids (PUFA) (PubMed:9435160). Catalyzes the epoxidation of double bonds of PUFA with a preference for the last double bond (PubMed:19965576). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:20702771). Plays a role in the metabolism of retinoids. Displays high catalytic activity for oxidation of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes atRA toward 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Responsible for oxidative metabolism of xenobiotics. Acts as a 2-exo-monooxygenase for plant lipid 1,8-cineole (eucalyptol) (PubMed:11159812). Metabolizes the majority of the administered drugs. Catalyzes sulfoxidation of the anthelmintics albendazole and fenbendazole (PubMed:10759686). Hydroxylates antimalarial drug quinine (PubMed:8968357). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850). Also involved in vitamin D catabolism and calcium homeostasis. Catalyzes the inactivation of the active hormone calcitriol (1-alpha,25-dihydroxyvitamin D(3)) (PubMed:29461981)
- Specific Function
- 1,8-cineole 2-exo-monooxygenase activity
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- 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 September 15, 2024 04:52