ethyl 1-(1-phenylethyl)-1H-imidazole-5-carboxylate

• ChemBase ID: 177
• Molecular Formular: C14H16N2O2
• Molecular Mass: 244.28904
• Monoisotopic Mass: 244.12117776
• SMILES: O(C(=O)c1n(C(c2ccccc2)C)cnc1)CC
• Canonical SMILES: CCOC(=O)c1cncn1C(c1ccccc1)C
• 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
• InChIKey: NPUKDXXFDDZOKR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 1-(1-phenylethyl)-1H-imidazole-5-carboxylate
• IUPAC Traditional name: etomidate
• Brand Name: Amidate; Hypnomidate
• Synonyms: ethyl 1-(1-phenylethyl)-1H-imidazole-5-carboxylate; Etomidic acid; Etomidate; Amidate; 1-(1-phenylethyl)-imidazole-5-carboxylic acid ethyl ester

Database IDs

• CAS Number: 33125-97-2
• MDL Number: MFCD00867535; MFCD00869295
• PubChem SID: 160963640
• PubChem CID: 36339
• ATC CODE: N01AX07
• CHEMBL: 23731
• Chemspider ID: 33418
• DrugBank ID: DB00292
• KEGG ID: D00548
• Unique Ingredient Identifier: Z22628B598
• Wikipedia Title: Etomidate

CALCULATED PROPERTIES

JChem

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.4663537
• LogD (pH = 7.4): 2.4993365
• Log P: 2.4997861
• Molar Refractivity: 69.5923 cm^3
• Polarizability: 26.606922 Å^3
• Polar Surface Area: 44.12 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.66
• LOG S: -2.71
• Solubility (Water): 4.77e-01 g/l

PROPERTIES

Physical Property

• Solubility: 63.2 mg/L
• Melting Point: 68 - 70°C
• Boiling Point: 392°C (737.6°F)
• Hydrophobicity(logP): 2.667; 2.9

Safety Information

• Storage Condition: -20°C

Pharmacology Properties

• Target: GABA transporter
• Admin Routes: Intravenous
• Excretion: Renal (85%) and biliary (15%)
• Half Life: 75 minutes
• Metabolism: Ester hydrolysis
• Protein Bound: 75%
• Legal Status: POM (UK)
• Pregnancy Category: D (United States)

Product Information

• Purity: 95%; 95+%; 98%
• Salt Data: Free Base

DETAILS

DrugBank - DB00292

• Drug Groups: approved
• Description: Imidazole derivative anesthetic and hypnotic with little effect on blood gases, ventilation, or the cardiovascular system. It has been proposed as an induction anesthetic. [PubChem]
• Indication: Used in the induction of general anesthesia.
• Pharmacology: 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.
• 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.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic. Metabolized rapidly by ester hydrolysis to inactive metabolites.
• Half Life: 75 minutes.
• Protein Binding: 76%, primarily to serum albumin.
• Elimination: Approximately 75% of the administered dose is excreted in the urine during the first day after injection.
• External Links: Wikipedia; Drugs.com

Selleck Chemicals - S1329

Research Area: Neurological Disease
Biological Activity:
Etomidate is a GABAA receptors agonist at GABAA receptors . Etomidate is a short acting intravenous anaesthetic agent used for the induction of general anaesthesia and for sedation for short procedures such as reduction of dislocated joints and cardioversion. [1]

REFERENCES

• http://en.wikipedia.org/wiki/Etomidate