Etomidate

Base Information

• Chemical Name: Etomidate
• CAS No.: 33125-97-2
• Molecular Formula: C14H16N2O2
• Molecular Weight: 244.293
• Hs Code.: 29332900
• European Community (EC) Number: 251-385-9
• UNII: Z22628B598
• DSSTox Substance ID: DTXSID5023033
• Nikkaji Number: J17.549H
• Wikipedia: Etomidate
• Wikidata: Q418445
• NCI Thesaurus Code: C47527
• RXCUI: 4177
• Pharos Ligand ID: VQGGC11AF8PL
• Metabolomics Workbench ID: 42681
• ChEMBL ID: CHEMBL681
• Mol file: 33125-97-2.mol

Synonyms:Ethomidate;Etomidate;Hypnomidate;R 26490;R-26490;R26490;Radenarkon

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Chemical Property of Etomidate

Chemical Property:

• Appearance/Colour: Colourless solid
• Vapor Pressure: 2.46E-06mmHg at 25°C
• Melting Point: 72-74 °C
• Refractive Index: 1.561
• Boiling Point: 391.485 °C at 760 mmHg
• PKA: pKa 4.24(H2O t=25.0) (Uncertain)
• Flash Point: 190.563 °C
• PSA: 44.12000
• Density: 1.118 g/cm³
• LogP: 2.66910
• Storage Temp.: 2-8°C
• Solubility.: DMSO: >10 mg/mL
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 244.121177757
• Heavy Atom Count: 18
• Complexity: 277

Purity/Quality:

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)C1=CN=CN1C(C)C2=CC=CC=C2
• Isomeric SMILES: CCOC(=O)C1=CN=CN1[C@H](C)C2=CC=CC=C2
• Recent ClinicalTrials: Prospective Study of Induction Medications Used in the Trauma RSI
• Recent EU Clinical Trials: Propofol and etomidate.
• Uses: Etomidate is a GABAA receptors agonist with short-acting sedative, hypnotic, and general anesthetic properties. It is a unique drug used for induction of general anesthesia and sedation. It is also a hypnotic. Hypnotic effect of Etomidate is strong , and its efficacy is about 12 times higher than thiopental, it has no analgesic effect.
• Therapeutic Function: Hypnotic
• Biological Functions: The pharmacological properties of etomidate (Amidate) are similar to those of the barbiturates, although its use may provide a greater margin of safety because of its limited effects on the cardiovascular and respiratory systems. Since it has a relatively short elimination halflife (t1/2β = 2.9 hours), in addition to its use as an induction agent, etomidate has been used as a supplement to maintain anesthesia in some critically ill patients. Etomidate is rapidly hydrolyzed in the liver.
• Clinical Use: Etomidate should only beused for induction of anesthesia when the cardiac benefitsoutweigh the risks associated with adrenal insufficiency.Etomidate is quickly distributed throughout most organsin the body after intravenous administration and the tissueconcentrations equal and sometimes exceed the plasmaconcentrations. The lipid solubility of the drug allows it torapidly penetrate into the brain with peak concentrationsoccurring within 1 minute of administration. Etomidate israpidly metabolized in the plasma and liver via esterases.About 75% of the drug is eliminated in the urine as the inactiveester hydrolyzed carboxylic acid.
• Drug interactions: Potentially hazardous interactions with other drugsAdrenergic neurone blockers: enhanced hypotensive effect.Antihypertensives: enhanced hypotensive effect.Antidepressants: avoid MAOIs for 2 weeks before surgery; increased risk of arrhythmias and hypotension with tricyclics.Antipsychotics: enhanced hypotensive effect.

Technology Process of Etomidate

There total 6 articles about Etomidate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

ethanol (64-17-5) + 1-[(1R)-1-phenylethyl]-5-hydroxymethylimidazole → etomidate (33125-97-2,56649-47-9)

Guidance literature:

With sodium cyanide; manganese(IV) oxide; acetic acid; at 80 ℃; for 12h;

DOI:10.1002/ejoc.201700833

Reference yield: 70.0%

(S)-1-phenylethanol (1445-91-6) + 1H-imidazole-5-carboxylic acid ethyl ester (23785-21-9) → etomidate (33125-97-2,56649-47-9)

Guidance literature:

With di-tert-butyl-diazodicarboxylate; triphenylphosphine; In tetrahydrofuran; at -40 ℃; Inert atmosphere;

DOI:10.1021/jo201237h

Reference yield:

[1-11C]ethyl iodide (97849-55-3) + (R)-(+)-1-(1-phenylethyl)-1H-imidazole-5-carboxylic acid (56649-48-0) → etomidate (33125-97-2,56649-47-9)

Guidance literature:

With tetra(n-butyl)ammonium hydroxide; In N,N-dimethyl-formamide; at 120 ℃; for 0.0833333h;

DOI:10.1002/jlcr.855

upstream raw materials:

[1-11C]ethyl iodide

(R)-(+)-1-(1-phenylethyl)-1H-imidazole-5-carboxylic acid

(S)-1-phenylethanol

1H-imidazole-5-carboxylic acid ethyl ester

Downstream raw materials:

(R)-(+)-1-(1-phenylethyl)-1H-imidazole-5-carboxylic acid

Refernces

• 1、 Zamora, Ana,Denning, Catherine A.,Heidary, David K.,Wachter, Erin,Nease, Leona A.,Ruiz, José,Glazer, Edith C.. "Ruthenium-containing P450 inhibitors for dual enzyme inhibition and DNA damage". . p. 2165 - 2173. Retrieved 2017/02/26.
• 2、 Laha, Joydev K.,Cuny, Gregory D.. "Synthesis of fused imidazoles, pyrroles, and indoles with a defined stereocenter α to nitrogen utilizing mitsunobu alkylation followed by palladium-catalyzed cyclization". experimental part. p. 8477 - 8482. Retrieved 2011/12/04.