Esketamine

Identification

Summary

Esketamine is a NMDA receptor antagonist used for treatment-resistant depression.

Brand Names

Spravato

Generic Name

Esketamine

DrugBank Accession Number

DB11823

Background

Major depressive disorder (MDD) is a significant cause of disability worldwide and the most common illness preceding suicide.^5,3 On March 5, 2019, the nasal spray drug, esketamine, also known as Spravato (by Janssen Pharmaceuticals), was approved by the FDA for treatment-resistant major depression.

Esketamine is the s-enantiomer of Ketamine. Ketamine is a mixture of two enantiomers (mirror image molecules). This is the first time that the FDA has approved esketamine for any use. The FDA approved ketamine (Ketalar) in 1970.⁴

Esketamine may prove to be a promising treatment for patients diagnosed with major depressive disorder who have not experienced an improvement in symptoms despite treatment with various medications and therapies. The intranasal route of administration for this drug allows for easy administration and a fast onset of action, which sets it apart from many other antidepressant agents that may take several weeks to take effect.

Type

Small Molecule

Groups

Approved, Investigational

Structure

Similar Structures

Weight: Average: 237.73
Monoisotopic: 237.0920418
Chemical Formula: C₁₃H₁₆ClNO

Synonyms

(-)-Ketamine
(−)-ketamine
(S)-(−)-ketamine
(S)-2-(o-chlorophenyl)-2-(methylamino)cyclohexanone
(S)-ketamine
Esketamine
L-ketamine
S-(-)-Ketamine
S-ketamine

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Pharmacology

Indication

Esketamine is indicated in combination with an oral antidepressant for the treatment of treatment-resistant depression in adults.⁶ It is also indicated for the treatment of depressive symptoms in adults with major depressive disorder experiencing acute suicidal ideation or behaviour.⁶

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Associated Conditions

Indication Type	Indication	Approval Level	Age Group	Patient Characteristics	Dose Form
Used in combination for symptomatic treatment of	Major depressive disorder (mdd)	••••••••••••	•••••	•••••••• •••••••• ••• •••••••••	•••••
Symptomatic treatment of	Pain	••••••••••••			•••••••••
Used in combination to treat	Treatment resistant depression (trd)	••••••••••••	•••••		•••••

Associated Therapies

Intubation

Contraindications & Blackbox Warnings

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Pharmacodynamics

General effects

Esketamine is considered a central nervous system (CNS) depressant agent. It may cause sedation, dizziness, and lethargy, among other symptoms.⁶ This drug has dissociative and antidepressant properties.⁶ Acutely, esketamine may impair attention, judgment, thinking, reaction speed, and motor skills. Two placebo-controlled studies were performed to evaluate the effects of ketamine on the ability to drive. The effects of esketamine 84 mg were comparable to placebo at 6 hours and 18 hours post-ingestion.⁶

Effects on cardiac electrophysiology

The effect of esketamine (84 mg nasal spray and 0.8 mg/kg esketamine intravenously infused over 40 minutes) on the QTc interval was studied in a randomized, double-blind, placebo-, and positive-controlled (moxifloxacin 400 mg), 4-period, crossover study in 60 healthy volunteers. A marked increase in heart rate (higher than 10 bpm) was measured in subjects receiving intranasal and intravenous esketamine. Summative evidence from both nonclinical and clinical data suggests a lack of clinically relevant QTc prolongation at the normal therapeutic dose of esketamine.⁶

Effects on blood pressure

Eskestamine causes increases in systolic and/or diastolic blood pressure at all therapeutic doses. Peak blood pressure elevation after esketamine administration occurs about 40 minutes after administration and lasts approximately 4 hours.⁶

Cognitive effects

In a study of healthy volunteers, one dose of this agent caused decline in cognitive performance 40 minutes after administration. Compared to subjects ingesting a placebo, esketamine-treated subjects required a higher level of effort to complete assigned cognitive tests at 40 minutes after administration. Cognitive performance and mental effort were found to be similar between esketamine and placebo at 2 hours after administration.⁶

Reports of long-term memory or cognitive impairment have been made following repeated ketamine misuse or abuse. No adverse effects of esketamine nasal spray on cognitive function were seen in a one-year open-label safety study. The long-term cognitive effects of esketamine have not been studied for more than a 1 year period, therefore, the risk of cognitive decline with long-term use is not yet confirmed.⁶

Mechanism of action

Esketamine, the S-enantiomer of racemic ketamine, is a non-selective, non-competitive antagonist of the N-methyl-D-aspartate (NMDA) receptor, an ionotropic glutamate receptor. The exact mechanism by which esketamine acts as an antidepressant is unknown. The primary circulating metabolite of esketamine (noresketamine) shows activity at the same receptor with a weaker affinity.⁶

Target	Actions	Organism
UNMDA receptor	antagonist	Humans
UGlutamate receptor ionotropic, NMDA 2B	antagonist	Humans
UElongation factor 2	inhibitor	Humans
UBrain-derived neurotrophic factor	agonist	Humans
UBDNF/NT-3 growth factors receptor	Not Available	Humans

Absorption

Due to the fact that this drug is administered via nasal spray, absorption is rapid. The mean absolute bioavailability is approximately 48% after esketamine nasal spray administration. The time to achieve peak esketamine plasma concentration is 20 to 40 minutes after the last nasal spray of esketamine. Inter-subject variability of esketamine ranges from 27% to 66% for Cmax (maximum concentration) and 18% to 45% for AUC (area under the curve). The intra-subject variability of esketamine is about 15% for Cmax and 10% for AUC.⁶

Volume of distribution

The average steady-state volume of distribution of esketamine administered by the intravenous route is 709 L.⁶

Protein binding

The protein binding of esketamine is about 43% to 45%.⁶

Metabolism

Esketamine is mainly metabolized to the noresketamine metabolite by cytochrome P450 (CYP) enzymes, CYP2B6 and CYP3A4, and to a lesser extent, CYP2C9 and CYP2C19. Noresketamine is metabolized by cytochrome-dependent metabolic pathways followed by subsequent glucuronidation of metabolites.⁶

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Esketamine
- Noresketamine

Route of elimination

Less than 1% of a dose of nasal esketamine is measured as unchanged drug, excreted in the urine. Following intravenous (IV) or oral (PO) administration, esketamine-derived metabolites were mainly recovered in urine (≥ 78% of a radiolabeled dose), and a smaller percentage was measured in the feces (≤ 2% of a radiolabeled dose).⁶

Half-life

The mean terminal half-life (t1/2) ranges from 7 to 12 hours.⁶

Clearance

The average clearance of esketamine is approximately 89 L/hour following intravenous administration.⁶

Elimination of the major esketamine metabolite, noresketamine, from plasma is slower than esketamine. The decrease of noresketamine plasma concentrations occurs in a biphasic fashion, with a more rapid decline for the first 4 hours post-administration, and an average terminal t1/2 of approximately 8 hours.⁶

Adverse Effects

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Toxicity

Ketamine hydrochloride LD50: 447 mg/kg, Rat (oral) ^MSDS

Neurotoxicity

In a one-dose neuronal toxicity study with esketamine intranasal administration to adult female rats, no finding of neuronal vacuolation in the brain occurred with doses up to the equivalent of the maximum recommended human dose of 84 mg/day. In a second single dose neurotoxicity study performed with intranasal esketamine administration in adult female rats, no observation of neuronal necrosis up to a dose equivalent to the maximum recommended human dose was made. Neuronal vacuolation was not evaluated in this study.⁶ The relevance of these findings in humans is unknown at this time.⁶

A note on dependence and tolerance

Reports of physical dependence have been made following prolonged use of ketamine. Withdrawal signs and symptoms after abrupt discontinuation or significant dosage reduction of a drug is a common manifestation of drug dependence. There were no withdrawal symptoms observed up to 4 weeks in subjects after stopping esketamine treatment. Withdrawal symptoms have been observed after the discontinuation of frequently used (more than weekly) high doses of ketamine for a longer duration. These symptoms of withdrawal have a higher chance of occurring if esketamine was similarly abused.⁶

Symptoms of withdrawal reported to be associated with daily intake of high ketamine doses include craving, fatigue, poor appetite, and anxiety. Therefore, monitor esketamine-treated patients for symptoms and signs of physical dependence upon the discontinuation of the drug. Tolerance has been reported with prolonged use of ketamine. Tolerance is characterized by a decreased response to a drug following repeated doses (i.e., a higher dose of a drug is required to produce the same effect that was previously achieved at a lower dose). Comparable tolerance would be expected to occur with long-term use of esketamine.⁶

Use in pregnancy

This drug may cause fetal harm, based on the findings of animal studies. Pregnancy planning and prevention in females of reproductive potential should occur before the initiation of esketamine treatment.⁶ There is a pregnancy registry for women who exposed to esketamine during pregnancy. The goal of the registry is to gather data about the health of women and infants exposed to esketamine.

Use in lactation

Esketamine is present in human milk. No safety data on the effects of esketamine on the breastfed infant or on milk production are available. Studies in young animals report neurotoxicity. Due to the risk of neurotoxicity, advise patients that breastfeeding is not recommended during treatment with this drug.⁶

Pathways

Not Available

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Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">

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
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1,2-Benzodiazepine	The risk or severity of adverse effects can be increased when 1,2-Benzodiazepine is combined with Esketamine.
Abametapir	The serum concentration of Esketamine can be increased when it is combined with Abametapir.
Abatacept	The metabolism of Esketamine can be increased when combined with Abatacept.
Abemaciclib	The metabolism of Abemaciclib can be increased when combined with Esketamine.
Abrocitinib	The metabolism of Abrocitinib can be decreased when combined with Esketamine.

Food Interactions

Avoid alcohol. Ingesting alcohol may increase the sedative effects of esketamine.
Take separate from meals. Avoid eating for at least 2 hours, and drinking for at least 30 minutes before taking esketamine.

Products

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Esketamine hydrochloride	L8P1H35P2Z	33643-47-9	VCMGMSHEPQENPE-ZOWNYOTGSA-N

International/Other Brands

Keta-S / Ketanest S / Ketaved

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Spravato		28 mg		Janssen Cilag International Nv	2021-03-16	Not applicable
Spravato		28 mg		Janssen Cilag International Nv	2020-12-16	Not applicable
Spravato	Spray	28 mg/1	Nasal	Renaissance Lakewood LLC	2019-12-18	Not applicable
Spravato		28 mg		Janssen Cilag International Nv	2020-12-16	Not applicable
Spravato		28 mg		Janssen Cilag International Nv	2020-12-16	Not applicable

Chemical Identifiers

UNII: 50LFG02TXD
CAS number: 33643-46-8
InChI Key: YQEZLKZALYSWHR-ZDUSSCGKSA-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/t13-/m0/s1
IUPAC Name: (2S)-2-(2-chlorophenyl)-2-(methylamino)cyclohexan-1-one
SMILES: CN[C@@]1(CCCCC1=O)C1=CC=CC=C1Cl

References

General References

Morrison RL, Fedgchin M, Singh J, Van Gerven J, Zuiker R, Lim KS, van der Ark P, Wajs E, Xi L, Zannikos P, Drevets WC: Effect of intranasal esketamine on cognitive functioning in healthy participants: a randomized, double-blind, placebo-controlled study. Psychopharmacology (Berl). 2018 Apr;235(4):1107-1119. doi: 10.1007/s00213-018-4828-5. Epub 2018 Feb 1. [Article]
Jonkman K, Duma A, Olofsen E, Henthorn T, van Velzen M, Mooren R, Siebers L, van den Beukel J, Aarts L, Niesters M, Dahan A: Pharmacokinetics and Bioavailability of Inhaled Esketamine in Healthy Volunteers. Anesthesiology. 2017 Oct;127(4):675-683. doi: 10.1097/ALN.0000000000001798. [Article]
Turecki G, Brent DA: Suicide and suicidal behaviour. Lancet. 2016 Mar 19;387(10024):1227-39. doi: 10.1016/S0140-6736(15)00234-2. Epub 2015 Sep 15. [Article]
FDA approves new nasal spray medication for treatment-resistant depression; available only at a certified doctor’s office or clinic [Link]
WHO International fact sheet [Link]
FDA Approved Drug Products: Spravato (esketamine) nasal spray [Link]
Janssen slides, esketamine [File]

External Links

KEGG Drug: D07283
PubChem Compound: 182137
PubChem Substance: 347828170
ChemSpider: 158414
RxNav: 2119365
ChEBI: 60799
ChEMBL: CHEMBL395091
ZINC: ZINC000035999642
PDBe Ligand: JC9
Wikipedia: Esketamine

PDB Entries

7eu7 / 7eu8 / 7sac

MSDS

Download (36.8 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Active Not Recruiting	Prevention	Chronic Postoperative Pain / Dexmedetomidine / Esketamine / Postoperative Analgesia / Scoliosis Correction	1
4	Active Not Recruiting	Prevention	Ketamine / Postpartum Depression / Prenatal Depression	1
4	Active Not Recruiting	Treatment	Major Depressive Disorder (MDD)	1
4	Active Not Recruiting	Treatment	Treatment Resistant Depressive Disorder	1
4	Completed	Basic Science	Anesthesia therapy / Loss of Consciousness	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Injection, solution	Parenteral	25 mg/ml
Injection	Parenteral	25 mg/ml
Injection, solution	Parenteral	5 mg/ml
Injection	Parenteral	5 mg/ml
Injection, solution	Intramuscular; Intravenous	25 mg/ml
Injection, solution	Intramuscular; Intravenous	5 mg/ml
Solution	Nasal	28 mg / 2 act
Solution	Nasal	28 mg/0.2mL
Solution	Nasal	32.300 mg
Spray	Nasal	28 mg/1
Spray	Nasal	28 mg

Prices

Not Available

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
US8785500	No	2014-07-22	2031-07-09
US9592207	No	2017-03-14	2027-03-20
US10869844	No	2020-12-22	2035-09-10
US11173134	No	2021-11-16	2035-09-14
US11311500	No	2015-09-10	2035-09-10
US11446260	No	2014-03-14	2034-03-14

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	92.5	http://pharmacycode.com/Esketamine.html
boiling point (°C)	363.8ºC at 760mmHg	https://www.chemsrc.com/en/cas/33643-46-8_146615.html
water solubility	Freely soluble in water	https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/211243s004lbl.pdf
logP	3.28870	https://www.chemsrc.com/en/cas/33643-46-8_146615.html
pKa	7.5	https://edoc.unibas.ch/1310/1/20110314_1408_DissCB_e_version.pdf

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

Not Available

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-000i-0980000000-bded2bdf9853c6184bf1
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-000i-0090000000-f329d25c0537015062fc
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-052u-0890000000-7934d3aa418dfbf17488
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-052r-2290000000-f29c223b2da48a50baf6
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-000w-9110000000-3c59d084c31e14c73fad
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0avr-1910000000-c2a25e54634de389a8a5
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	150.71709	predicted	DeepCCS 1.0 (2019)
[M+H]+	153.11266	predicted	DeepCCS 1.0 (2019)
[M+Na]+	159.05582	predicted	DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.

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Details1. NMDA receptor (Protein Group)

Kind: Protein group
Organism: Humans
Pharmacological action: Unknown
Actions: Antagonist

General Function: Voltage-gated cation channel activity
Specific Function: NMDA receptor subtype of glutamate-gated ion channels with high calcium permeability and voltage-dependent sensitivity to magnesium. Mediated by glycine. This protein plays a key role in synaptic p...

Components:

Name	UniProt ID
Glutamate receptor ionotropic, NMDA 1	Q05586
Glutamate receptor ionotropic, NMDA 2A	Q12879
Glutamate receptor ionotropic, NMDA 2B	Q13224
Glutamate receptor ionotropic, NMDA 2C	Q14957
Glutamate receptor ionotropic, NMDA 2D	O15399
Glutamate receptor ionotropic, NMDA 3A	Q8TCU5
Glutamate receptor ionotropic, NMDA 3B	O60391

References

Morrison RL, Fedgchin M, Singh J, Van Gerven J, Zuiker R, Lim KS, van der Ark P, Wajs E, Xi L, Zannikos P, Drevets WC: Effect of intranasal esketamine on cognitive functioning in healthy participants: a randomized, double-blind, placebo-controlled study. Psychopharmacology (Berl). 2018 Apr;235(4):1107-1119. doi: 10.1007/s00213-018-4828-5. Epub 2018 Feb 1. [Article]
Spravato FDA label [File]

Details2. Glutamate receptor ionotropic, NMDA 2B

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Antagonist
Curator comments: Possible target.

General Function: Zinc ion binding
Specific Function: NMDA receptor subtype of glutamate-gated ion channels with high calcium permeability and voltage-dependent sensitivity to magnesium. Mediated by glycine. In concert with DAPK1 at extrasynaptic site...
Gene Name: GRIN2B
Uniprot ID: Q13224
Uniprot Name: Glutamate receptor ionotropic, NMDA 2B
Molecular Weight: 166365.885 Da

References

Molero P, Ramos-Quiroga JA, Martin-Santos R, Calvo-Sanchez E, Gutierrez-Rojas L, Meana JJ: Antidepressant Efficacy and Tolerability of Ketamine and Esketamine: A Critical Review. CNS Drugs. 2018 May;32(5):411-420. doi: 10.1007/s40263-018-0519-3. [Article]

Details3. Elongation factor 2

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Translation elongation factor activity
Specific Function: Catalyzes the GTP-dependent ribosomal translocation step during translation elongation. During this step, the ribosome changes from the pre-translocational (PRE) to the post-translocational (POST) ...
Gene Name: EEF2
Uniprot ID: P13639
Uniprot Name: Elongation factor 2
Molecular Weight: 95337.385 Da

References

Molero P, Ramos-Quiroga JA, Martin-Santos R, Calvo-Sanchez E, Gutierrez-Rojas L, Meana JJ: Antidepressant Efficacy and Tolerability of Ketamine and Esketamine: A Critical Review. CNS Drugs. 2018 May;32(5):411-420. doi: 10.1007/s40263-018-0519-3. [Article]
Zanos P, Thompson SM, Duman RS, Zarate CA Jr, Gould TD: Convergent Mechanisms Underlying Rapid Antidepressant Action. CNS Drugs. 2018 Mar;32(3):197-227. doi: 10.1007/s40263-018-0492-x. [Article]

Details4. Brain-derived neurotrophic factor

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Agonist
Curator comments: Possible target.

General Function: Neurotrophin trkb receptor binding
Specific Function: During development, promotes the survival and differentiation of selected neuronal populations of the peripheral and central nervous systems. Participates in axonal growth, pathfinding and in the m...
Gene Name: BDNF
Uniprot ID: P23560
Uniprot Name: Brain-derived neurotrophic factor
Molecular Weight: 27817.72 Da

References

Molero P, Ramos-Quiroga JA, Martin-Santos R, Calvo-Sanchez E, Gutierrez-Rojas L, Meana JJ: Antidepressant Efficacy and Tolerability of Ketamine and Esketamine: A Critical Review. CNS Drugs. 2018 May;32(5):411-420. doi: 10.1007/s40263-018-0519-3. [Article]
Haile CN, Murrough JW, Iosifescu DV, Chang LC, Al Jurdi RK, Foulkes A, Iqbal S, Mahoney JJ 3rd, De La Garza R 2nd, Charney DS, Newton TF, Mathew SJ: Plasma brain derived neurotrophic factor (BDNF) and response to ketamine in treatment-resistant depression. Int J Neuropsychopharmacol. 2014 Feb;17(2):331-6. doi: 10.1017/S1461145713001119. Epub 2013 Oct 8. [Article]
Autry AE, Monteggia LM: Brain-derived neurotrophic factor and neuropsychiatric disorders. Pharmacol Rev. 2012 Apr;64(2):238-58. doi: 10.1124/pr.111.005108. Epub 2012 Mar 8. [Article]

Details5. BDNF/NT-3 growth factors receptor

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Curator comments: Possible target.

General Function: Protein homodimerization activity
Specific Function: Receptor tyrosine kinase involved in the development and the maturation of the central and the peripheral nervous systems through regulation of neuron survival, proliferation, migration, differenti...
Gene Name: NTRK2
Uniprot ID: Q16620
Uniprot Name: BDNF/NT-3 growth factors receptor
Molecular Weight: 91998.175 Da

References

Molero P, Ramos-Quiroga JA, Martin-Santos R, Calvo-Sanchez E, Gutierrez-Rojas L, Meana JJ: Antidepressant Efficacy and Tolerability of Ketamine and Esketamine: A Critical Review. CNS Drugs. 2018 May;32(5):411-420. doi: 10.1007/s40263-018-0519-3. [Article]
Autry AE, Monteggia LM: Brain-derived neurotrophic factor and neuropsychiatric disorders. Pharmacol Rev. 2012 Apr;64(2):238-58. doi: 10.1124/pr.111.005108. Epub 2012 Mar 8. [Article]
van de Loo AJAE, Bervoets AC, Mooren L, Bouwmeester NH, Garssen J, Zuiker R, van Amerongen G, van Gerven J, Singh J, der Ark PV, Fedgchin M, Morrison R, Wajs E, Verster JC: The effects of intranasal esketamine (84 mg) and oral mirtazapine (30 mg) on on-road driving performance: a double-blind, placebo-controlled study. Psychopharmacology (Berl). 2017 Nov;234(21):3175-3183. doi: 10.1007/s00213-017-4706-6. Epub 2017 Jul 28. [Article]

Enzymes

Details1. Cytochrome P450 2B6

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate
Inducer

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

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]
Ricardo Jorge Dinis-Oliveira (2017). Metabolism and metabolomics of ketamine: a toxicological approach. Taylor & Francis Group.
Spravato FDA label [File]

Details2. Cytochrome P450 3A4

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

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]
Ricardo Jorge Dinis-Oliveira (2017). Metabolism and metabolomics of ketamine: a toxicological approach. Taylor & Francis Group.
Spravato FDA label [File]

Details3. Cytochrome P450 2C19

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Steroid hydroxylase activity
Specific Function: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name: CYP2C19
Uniprot ID: P33261
Uniprot Name: Cytochrome P450 2C19
Molecular Weight: 55930.545 Da

References

Ricardo Jorge Dinis-Oliveira (2017). Metabolism and metabolomics of ketamine: a toxicological approach. Taylor & Francis Group.
Spravato FDA label [File]

Details4. Cytochrome P450 2C9

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: CYP2C9
Uniprot ID: P11712
Uniprot Name: Cytochrome P450 2C9
Molecular Weight: 55627.365 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]
Ricardo Jorge Dinis-Oliveira (2017). Metabolism and metabolomics of ketamine: a toxicological approach. Taylor & Francis Group.
Spravato FDA label [File]

Drug created at October 20, 2016 20:51 / Updated at December 05, 2023 12:31

Esketamine

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Structure for Esketamine (DB11823)

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