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Identification
- Summary
Etomidate is a short-acting intravenous anesthetic indicated for the induction of anesthesia and supplementation of subpotent anesthesia during short operative procedures.
- Brand Names
- Amidate
- Generic Name
- Etomidate
- DrugBank Accession Number
- DB00292
- Background
Imidazole derivative anesthetic and hypnotic with little effect on blood gases, ventilation, or the cardiovascular system. It has been proposed as an induction anesthetic.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Etomidate (DB00292)
- Weight
- Average: 244.289
Monoisotopic: 244.121177766 - Chemical Formula
- C14H16N2O2
- Synonyms
- (+)-ethyl 1-(α-methylbenzyl)imidazole-5-carboxylate
- (+)-etomidate
- (R)-(+)-1-(α-methylbenzyl)imidazole-5-carboxylic acid ethyl ester
- (R)-1-(1-phenylethyl)-1H-imidazole-5-carboxylic acid ethyl ester
- 3-((R)-1-Phenyl-ethyl)-3H-imidazole-4-carboxylic acid ethyl ester
- Etomidate
- Etomidato
- Etomidatum
- R-(+)-ethyl 1-(1-phenylethyl)-1H-imidazole-5-carboxylate
Pharmacology
- Indication
Used in the induction of general anesthesia.
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- Contraindications & Blackbox Warnings
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Etomidate is a non-barbiturate hypnotic that acts at the level of the reticular-activating system to produce anesthesia. Etomidate is an imidazole compound that appears to depress CNS function via GABA. Duration of action is intermediate between thiopental and methohexital, and recovery from a single dose is rapid with little residual depression. Like the barbiturates and propofol, etomidate is does not induce analgesia. Etomidate induces unconsciousness within one circulation time. Recovery is rapid as a result of extensive redistribution and rapid metabolism.
- Mechanism of action
Etomidate binds at a distinct binding site associated with a Cl- ionopore at the GABAA receptor, increasing the duration of time for which the Cl- ionopore is open. The post-synaptic inhibitory effect of GABA in the thalamus is, therefore, prolonged.
Target Actions Organism AGamma-aminobutyric acid receptor subunit gamma-3 modulatorHumans AGamma-aminobutyric acid receptor subunit alpha-1 agonistHumans AAlpha-2B adrenergic receptor agonistHumans AGABA(A) Receptor positive allosteric modulatorHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
76%, primarily to serum albumin.
- Metabolism
Hepatic. Metabolized rapidly by ester hydrolysis to inactive metabolites.
- Route of elimination
Approximately 75% of the administered dose is excreted in the urine during the first day after injection.
- Half-life
75 minutes.
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Undesirable side effects of etomidate that may limit its use include pain on injection, myoclonus and adrenocortical suppression lasting 4-6 hours following an induction dose.
- 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 Etomidate is combined with 1,2-Benzodiazepine. Abacavir Etomidate may decrease the excretion rate of Abacavir which could result in a higher serum level. Acebutolol The therapeutic efficacy of Etomidate can be decreased when used in combination with Acebutolol. Aceclofenac The risk or severity of hypertension can be increased when Etomidate is combined with Aceclofenac. Acemetacin The risk or severity of hypertension can be increased when Etomidate is combined with Acemetacin. - Food Interactions
- No interactions found.
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.- International/Other Brands
- Hypnomidate (Janssen)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Amidate Injection, solution 2 mg/1mL Intravenous Henry Schein, Inc. 2022-01-06 Not applicable US 
Amidate Injection, solution 2 mg/1mL Intravenous General Injectables & Vaccines, Inc 2010-08-01 2023-05-01 US Amidate Injection, solution 2 mg/1mL Intravenous General Injectables & Vaccines, Inc 2010-03-10 2017-06-19 US Amidate Injection, solution 2 mg/1mL Intravenous Hospira, Inc. 2005-07-26 Not applicable US Amidate Injection, solution 2 mg/1mL Intravenous Hospira, Inc. 2006-11-07 2006-11-07 US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Etomidate Injection, solution 2 mg/1mL Intravenous Mylan Institutional Inc. 2019-03-01 Not applicable US Etomidate Injection, solution 2 mg/1mL Intravenous Mylan Institutional Inc. 2013-04-26 2015-03-01 US Etomidate Injection, solution 2 mg/1mL Intravenous Fresenius Kabi Italia S.R.L. 2021-08-01 Not applicable US Etomidate Injection 2 mg/1mL Intravenous Hikma Pharmaceuticals USA Inc. 2016-02-25 Not applicable US Etomidate Injection, solution 2 mg/1mL Intravenous Caplin Steriles Limited 2021-03-15 Not applicable US
Categories
- ATC Codes
- N01AX07 — Etomidate
- Drug Categories
- Adrenergic Agonists
- Adrenergic alpha-2 Receptor Agonists
- Adrenergic alpha-Agonists
- Agents producing tachycardia
- Agents that produce hypertension
- Anesthetics
- Anesthetics, General
- Anesthetics, Intravenous
- Central Nervous System Agents
- Central Nervous System Depressants
- Drugs that are Mainly Renally Excreted
- Hypnotics and Sedatives
- Imidazoles
- Nervous System
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as carbonylimidazoles. These are substituted imidazoles in which the imidazole ring bears a carbonyl group.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Azoles
- Sub Class
- Imidazoles
- Direct Parent
- Carbonylimidazoles
- Alternative Parents
- N-substituted imidazoles / Benzene and substituted derivatives / Heteroaromatic compounds / Carboxylic acid esters / Monocarboxylic acids and derivatives / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds / Organic oxides show 1 more
- Substituents
- Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Carboxylic acid derivative / Carboxylic acid ester / Heteroaromatic compound / Hydrocarbon derivative / Imidazole-4-carbonyl group / Monocarboxylic acid or derivatives / Monocyclic benzene moiety show 7 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- ethyl ester, imidazoles (CHEBI:4910)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- Z22628B598
- CAS number
- 33125-97-2
- InChI Key
- NPUKDXXFDDZOKR-LLVKDONJSA-N
- InChI
- InChI=1S/C14H16N2O2/c1-3-18-14(17)13-9-15-10-16(13)11(2)12-7-5-4-6-8-12/h4-11H,3H2,1-2H3/t11-/m1/s1
- IUPAC Name
- ethyl 1-[(1R)-1-phenylethyl]-1H-imidazole-5-carboxylate
- SMILES
- CCOC(=O)C1=CN=CN1[C@H](C)C1=CC=CC=C1
References
- Synthesis Reference
Douglas E. Raines, "ETOMIDATE ANALOGUES THAT DO NOT INHIBIT ADRENOCORTICAL STEROID SYNTHESIS." U.S. Patent US20130079381, issued March 28, 2013.
US20130079381- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014437
- KEGG Drug
- D00548
- KEGG Compound
- C07522
- PubChem Compound
- 667484
- PubChem Substance
- 46507012
- ChemSpider
- 580864
- BindingDB
- 50125935
- 4177
- ChEBI
- 4910
- ChEMBL
- CHEMBL681
- ZINC
- ZINC000000001408
- Therapeutic Targets Database
- DAP000669
- PharmGKB
- PA164743987
- PDBe Ligand
- V8D
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Etomidate
- PDB Entries
- 6x3v / 8f6y / 8pvb
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 Completed Not Available Blood Pressures / Hypotension Drug-Induced 1 somestatus stop reason just information to hide Not Available Completed Not Available Neuromuscular Monitoring 1 somestatus stop reason just information to hide Not Available Completed Not Available Postoperative Complications 1 somestatus stop reason just information to hide Not Available Completed Basic Science Depression 1 somestatus stop reason just information to hide Not Available Completed Basic Science Obesity 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Hospira inc
- Bedford laboratories div ben venue laboratories inc
- Parenta pharmaceuticals inc
- Pharmaforce inc
- Packagers
- American Regent
- Bedford Labs
- Ben Venue Laboratories Inc.
- Ebewe Pharma
- General Injectables and Vaccines Inc.
- Hospira Inc.
- Dosage Forms
Form Route Strength Solution Intravenous 20.000 mg Solution Intravenous 20 mg Injection, emulsion Intravenous 2 mg/ml Injection Intravenous 2 mg/1mL Injection, solution Intravenous 2 mg/1mL Injection, solution Intravenous 20 mg/10mL Injection, solution Intravenous 40 mg/20mL Solution Intravenous 2 mg/1mL Emulsion 2 mg/1ml Injection, emulsion Intravenous 20 mg/10mL Injection Intravenous 20 mg/10ml Emulsion Intravenous 20 mg Emulsion Parenteral 2 mg Injection Intravenous Injection, solution Intravenous 2 mg/ml Injection Intravenous 20 mg Solution Intravenous 2 mg / mL Emulsion Intravenous 2 mg - Prices
Unit description Cost Unit Amidate 2 mg/ml vial 1.55USD ml Amidate 2 mg/ml ampul 1.19USD ml Etomidate 2 mg/ml vial 1.18USD 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) 142-142.8 Godefroi, E.F. and Van Der Eijcken, C.A.M.; U.S. Patent 3,354,173; November 21, 1967; assigned to Janssen Pharrnaceutica NV (Belgium). water solubility 63.2 mg/L Not Available logP 3.05 POMONA (1987) - Predicted Properties
Property Value Source Water Solubility 0.477 mg/mL ALOGPS logP 2.66 ALOGPS logP 2.5 Chemaxon logS -2.7 ALOGPS pKa (Strongest Basic) 4.25 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 44.12 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 69.59 m3·mol-1 Chemaxon Polarizability 26.43 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9908 Blood Brain Barrier + 0.95 Caco-2 permeable + 0.6275 P-glycoprotein substrate Non-substrate 0.7386 P-glycoprotein inhibitor I Non-inhibitor 0.8567 P-glycoprotein inhibitor II Non-inhibitor 0.8597 Renal organic cation transporter Non-inhibitor 0.7918 CYP450 2C9 substrate Non-substrate 0.7947 CYP450 2D6 substrate Non-substrate 0.9117 CYP450 3A4 substrate Non-substrate 0.7671 CYP450 1A2 substrate Inhibitor 0.9107 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Inhibitor 0.5432 CYP450 3A4 inhibitor Inhibitor 0.7959 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.8357 Ames test Non AMES toxic 0.7989 Carcinogenicity Non-carcinogens 0.8795 Biodegradation Not ready biodegradable 0.5121 Rat acute toxicity 2.5459 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9622 hERG inhibition (predictor II) Non-inhibitor 0.8553
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0a6r-2910000000-df43a9b83f023b0bb392 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0005-5910000000-e3e55142d021e58cf423 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0297-2970000000-ab1c97a95da9dcaa9899 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-052b-7900000000-49c3144b2769b573db82 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0007-6920000000-a474ce5287ce573c4d69 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4j-3910000000-ca3a936261938f9917a4 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-006w-7900000000-54ef843e8eb9687f7902 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]- 167.8104813 predictedDarkChem Lite v0.1.0 [M-H]- 157.00337 predictedDeepCCS 1.0 (2019) [M+H]+ 168.4249813 predictedDarkChem Lite v0.1.0 [M+H]+ 159.36137 predictedDeepCCS 1.0 (2019) [M+Na]+ 168.2031813 predictedDarkChem Lite v0.1.0 [M+Na]+ 165.45451 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
- Modulator
- General Function
- Gamma subunit of the heteropentameric ligand-gated chloride channel gated by gamma-aminobutyric acid (GABA), a major inhibitory neurotransmitter in the brain (By similarity). GABA-gated chloride channels, also named GABA(A) receptors (GABAAR), consist of five subunits arranged around a central pore and contain GABA active binding site(s) located at the alpha and beta subunit interface(s) (By similarity). When activated by GABA, GABAARs selectively allow the flow of chloride across the cell membrane down their electrochemical gradient (By similarity)
- Specific Function
- GABA-A receptor activity
- Gene Name
- GABRG3
- Uniprot ID
- Q99928
- Uniprot Name
- Gamma-aminobutyric acid receptor subunit gamma-3
- Molecular Weight
- 54288.16 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Alpha subunit of the heteropentameric ligand-gated chloride channel gated by Gamma-aminobutyric acid (GABA), a major inhibitory neurotransmitter in the brain (PubMed:23909897, PubMed:25489750, PubMed:29950725, PubMed:30602789). GABA-gated chloride channels, also named GABA(A) receptors (GABAAR), consist of five subunits arranged around a central pore and contain GABA active binding site(s) located at the alpha and beta subunit interface(s) (PubMed:29950725, PubMed:30602789). When activated by GABA, GABAARs selectively allow the flow of chloride anions across the cell membrane down their electrochemical gradient (PubMed:23909897, PubMed:29950725, PubMed:30602789). Alpha-1/GABRA1-containing GABAARs are largely synaptic (By similarity). Chloride influx into the postsynaptic neuron following GABAAR opening decreases the neuron ability to generate a new action potential, thereby reducing nerve transmission (By similarity). GABAARs containing alpha-1 and beta-2 or -3 subunits exhibit synaptogenic activity; the gamma-2 subunit being necessary but not sufficient to induce rapid synaptic contacts formation (PubMed:23909897, PubMed:25489750). GABAARs function also as histamine receptor where histamine binds at the interface of two neighboring beta subunits and potentiates GABA response (By similarity). GABAARs containing alpha, beta and epsilon subunits also permit spontaneous chloride channel activity while preserving the structural information required for GABA-gated openings (By similarity). Alpha-1-mediated plasticity in the orbitofrontal cortex regulates context-dependent action selection (By similarity). Together with rho subunits, may also control neuronal and glial GABAergic transmission in the cerebellum (By similarity)
- Specific Function
- GABA-A receptor activity
- Gene Name
- GABRA1
- Uniprot ID
- P14867
- Uniprot Name
- Gamma-aminobutyric acid receptor subunit alpha-1
- Molecular Weight
- 51801.395 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Martin LJ, Oh GH, Orser BA: Etomidate targets alpha5 gamma-aminobutyric acid subtype A receptors to regulate synaptic plasticity and memory blockade. Anesthesiology. 2009 Nov;111(5):1025-35. doi: 10.1097/ALN.0b013e3181bbc961. [Article]
- Desai R, Ruesch D, Forman SA: Gamma-amino butyric acid type A receptor mutations at beta2N265 alter etomidate efficacy while preserving basal and agonist-dependent activity. Anesthesiology. 2009 Oct;111(4):774-84. doi: 10.1097/ALN.0b013e3181b55fae. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine > norepinephrine > epinephrine = oxymetazoline > dopamine > p-tyramine = phenylephrine > serotonin > p-synephrine / p-octopamine. For antagonists, the rank order is yohimbine > chlorpromazine > phentolamine > mianserine > spiperone > prazosin > alprenolol > propanolol > pindolol
- Specific Function
- alpha2-adrenergic receptor activity
- Gene Name
- ADRA2B
- Uniprot ID
- P18089
- Uniprot Name
- Alpha-2B adrenergic receptor
- Molecular Weight
- 49953.145 Da
References
- Creagh O, Torres H, Rodriguez N, Gatica SR: Alpha-2B adrenergic receptor mediated hemodynamic profile of etomidate. P R Health Sci J. 2010 Jun;29(2):91-5. [Article]
- Paris A, Philipp M, Tonner PH, Steinfath M, Lohse M, Scholz J, Hein L: Activation of alpha 2B-adrenoceptors mediates the cardiovascular effects of etomidate. Anesthesiology. 2003 Oct;99(4):889-95. [Article]
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Positive allosteric modulator
- General Function
- Alpha subunit of the heteropentameric ligand-gated chloride channel gated by Gamma-aminobutyric acid (GABA), a major inhibitory neurotransmitter in the brain (PubMed:23909897, PubMed:25489750, PubMed:29950725, PubMed:30602789). GABA-gated chloride channels, also named GABA(A) receptors (GABAAR), consist of five subunits arranged around a central pore and contain GABA active binding site(s) located at the alpha and beta subunit interface(s) (PubMed:29950725, PubMed:30602789). When activated by GABA, GABAARs selectively allow the flow of chloride anions across the cell membrane down their electrochemical gradient (PubMed:23909897, PubMed:29950725, PubMed:30602789). Alpha-1/GABRA1-containing GABAARs are largely synaptic (By similarity). Chloride influx into the postsynaptic neuron following GABAAR opening decreases the neuron ability to generate a new action potential, thereby reducing nerve transmission (By similarity). GABAARs containing alpha-1 and beta-2 or -3 subunits exhibit synaptogenic activity; the gamma-2 subunit being necessary but not sufficient to induce rapid synaptic contacts formation (PubMed:23909897, PubMed:25489750). GABAARs function also as histamine receptor where histamine binds at the interface of two neighboring beta subunits and potentiates GABA response (By similarity). GABAARs containing alpha, beta and epsilon subunits also permit spontaneous chloride channel activity while preserving the structural information required for GABA-gated openings (By similarity). Alpha-1-mediated plasticity in the orbitofrontal cortex regulates context-dependent action selection (By similarity). Together with rho subunits, may also control neuronal and glial GABAergic transmission in the cerebellum (By similarity)
- Specific Function
- GABA-A receptor activity
Components:
References
- ChEMBL Compound Report Card [Link]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- A cytochrome P450 monooxygenase involved in the biosynthesis of adrenal corticoids (PubMed:12530636, PubMed:1518866, PubMed:1775135, PubMed:18215163, PubMed:23322723). Catalyzes a variety of reactions that are essential for many species, including detoxification, defense, and the formation of endogenous chemicals like steroid hormones. Steroid 11beta, 18- and 19-hydroxylase with preferred regioselectivity at 11beta, then 18, and lastly 19 (By similarity). Catalyzes the hydroxylation of 11-deoxycortisol and 11-deoxycorticosterone (21-hydroxyprogesterone) at 11beta position, yielding cortisol or corticosterone, respectively, but cannot produce aldosterone (PubMed:12530636, PubMed:1518866, PubMed:1775135, PubMed:18215163, PubMed:23322723). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate for hydroxylation and reducing the second into a water molecule. Two electrons are provided by NADPH via a two-protein mitochondrial transfer system comprising flavoprotein FDXR (adrenodoxin/ferredoxin reductase) and nonheme iron-sulfur protein FDX1 or FDX2 (adrenodoxin/ferredoxin) (PubMed:18215163). Due to its lack of 18-oxidation activity, it is incapable of generating aldosterone (PubMed:23322723). Could also be involved in the androgen metabolic pathway (Probable)
- Specific Function
- corticosterone 18-monooxygenase activity
- Gene Name
- CYP11B1
- Uniprot ID
- P15538
- Uniprot Name
- Cytochrome P450 11B1, mitochondrial
- Molecular Weight
- 57572.44 Da
References
- Weber MM, Lang J, Abedinpour F, Zeilberger K, Adelmann B, Engelhardt D: Different inhibitory effect of etomidate and ketoconazole on the human adrenal steroid biosynthesis. Clin Investig. 1993 Nov;71(11):933-8. [Article]
- Hermansson V, Asp V, Bergman A, Bergstrom U, Brandt I: Comparative CYP-dependent binding of the adrenocortical toxicants 3-methylsulfonyl-DDE and o,p'-DDD in Y-1 adrenal cells. Arch Toxicol. 2007 Nov;81(11):793-801. Epub 2007 May 9. [Article]
- Hahner S, Sturmer A, Fassnacht M, Hartmann RW, Schewe K, Cochran S, Zink M, Schirbel A, Allolio B: Etomidate unmasks intraadrenal regulation of steroidogenesis and proliferation in adrenal cortical cell lines. Horm Metab Res. 2010 Jun;42(7):528-34. doi: 10.1055/s-0030-1249629. Epub 2010 Mar 29. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- A cytochrome P450 monooxygenase that catalyzes the biosynthesis of aldosterone, the main mineralocorticoid in the human body responsible for salt and water homeostasis, thus involved in blood pressure regulation, arterial hypertension, and the development of heart failure (PubMed:11856349, PubMed:12530636, PubMed:1518866, PubMed:15356073, PubMed:1594605, PubMed:1775135, PubMed:22446688, PubMed:23322723, PubMed:9814482, PubMed:9814506). Catalyzes three sequential oxidative reactions of 11-deoxycorticosterone (21-hydroxyprogesterone), namely 11-beta hydroxylation, followed by two successive oxidations at C18 yielding 18-hydroxy and then 18-oxo intermediates (that would not leave the enzyme active site during the consecutive hydroxylation reactions), ending with the formation of aldosterone (PubMed:11856349, PubMed:12530636, PubMed:1518866, PubMed:1594605, PubMed:1775135, PubMed:22446688, PubMed:23322723, PubMed:9814506). Can also produce 18-hydroxycortisol and 18-oxocortisol, derived from successive oxidations of cortisol at C18, normally found at very low levels, but significantly increased in primary aldosteronism, the most common form of secondary hypertension (PubMed:15356073, PubMed:9814482). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate and reducing the second into a water molecule. Two electrons are provided by NADPH via a two-protein mitochondrial transfer system comprising flavoprotein FDXR (adrenodoxin/ferredoxin reductase) and nonheme iron-sulfur protein FDX1 or FDX2 (adrenodoxin/ferredoxin) (PubMed:11856349, PubMed:1594605, PubMed:23322723, PubMed:9814506). Could also be involved in the androgen metabolic pathway (Probable)
- Specific Function
- corticosterone 18-monooxygenase activity
- Gene Name
- CYP11B2
- Uniprot ID
- P19099
- Uniprot Name
- Cytochrome P450 11B2, mitochondrial
- Molecular Weight
- 57559.62 Da
References
- Hahner S, Sturmer A, Fassnacht M, Hartmann RW, Schewe K, Cochran S, Zink M, Schirbel A, Allolio B: Etomidate unmasks intraadrenal regulation of steroidogenesis and proliferation in adrenal cortical cell lines. Horm Metab Res. 2010 Jun;42(7):528-34. doi: 10.1055/s-0030-1249629. Epub 2010 Mar 29. [Article]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Facilitative glucose transporter, which is responsible for constitutive or basal glucose uptake (PubMed:10227690, PubMed:10954735, PubMed:18245775, PubMed:19449892, PubMed:25982116, PubMed:27078104, PubMed:32860739). Has a very broad substrate specificity; can transport a wide range of aldoses including both pentoses and hexoses (PubMed:18245775, PubMed:19449892). Most important energy carrier of the brain: present at the blood-brain barrier and assures the energy-independent, facilitative transport of glucose into the brain (PubMed:10227690). In association with BSG and NXNL1, promotes retinal cone survival by increasing glucose uptake into photoreceptors (By similarity). Required for mesendoderm differentiation (By similarity)
- Specific Function
- D-glucose transmembrane transporter activity
- Gene Name
- SLC2A1
- Uniprot ID
- P11166
- Uniprot Name
- Solute carrier family 2, facilitated glucose transporter member 1
- Molecular Weight
- 54083.325 Da
References
- Stephenson KN, Croxen RL, El-Barbary A, Fenstermacher JD, Haspel HC: Inhibition of glucose transport and direct interactions with type 1 facilitative glucose transporter (GLUT-1) by etomidate, ketamine, and propofol: a comparison with barbiturates. Biochem Pharmacol. 2000 Sep 1;60(5):651-9. [Article]
Drug created at June 13, 2005 13:24 / Updated at October 21, 2024 12:33