Etomidate

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Etomidate are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Etomidate?

The molecule Etomidate presents a molecular formula of C14H16N2O2 and its IUPAC name is ethyl 3-[(1R)-1-phenylethyl]imidazole-4-carboxylate.

Etomidate is a short-acting, intravenous anesthetic agent. Its chemical structure is similar to that of other imidazole agents, such as midazolam and propofol. Etomidate is a highly lipophilic molecule, meaning that it easily crosses the blood-brain barrier and rapidly enters the brain. This results in a quick onset of action and a short duration of action..

Etomidate has a relatively low risk of causing hypotension (low blood pressure), and its cardiovascular effects are minimal. These properties make etomidate an ideal anesthetic agent for patients with cardiovascular disease. Etomidate also has a low risk of causing respiratory depression, and it does not stimulate the central nervous system..

The most common side effect of etomidate is pain at the injection site. Other side effects include nausea, vomiting, dizziness, and confusion..

Etomidate is contraindicated in patients with a history of hypersensitivity to the drug..

3D structure

Cartesian coordinates

Geometry of Etomidate in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Etomidate NPUKDXXFDDZOKR-LLVKDONJSA-N chemical compound 2D structure molecule svg
Etomidate

 

Molecule descriptors

 
IUPAC nameethyl 3-[(1R)-1-phenylethyl]imidazole-4-carboxylate
InChI codeInChI=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
InChI KeyNPUKDXXFDDZOKR-LLVKDONJSA-N
SMILESCCOC(=O)c1cncn1[C@H](C)c1ccccc1

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (+)-Ethyl 1-(.alpha.-methylbenzyl)imidazole-5-carboxylate
  • (+)-Ethyl 1-(alpha-methylbenzyl)imidazole-5-carboxylate
  • (+)-Etomidate
  • (R)-(+)-1-(1-Phenylethyl)-1H-imidazole-5-carboxylic Acid Ethyl Ester
  • (R)-(+)-1-(alpha-Methylbenzyl)imidazole-5-carboxylic acid ethyl ester
  • (R)-1-(1-phenylethyl)-1H-imidazole-5-carboxylic acid ethyl ester
  • (R)-1-(1-phenylethyl)-1H-imidazole-5-carboxylicacid ethyl ester
  • (R)-ETHYL 1-(1-PHENYLETHYL)-1H-IMIDAZOLE-5-CARBOXYLATE
  • (d)-Etomidate
  • 1-(1-Phenylethyl)-1H-imidazole-5-carboxylic acid ethyl ester
  • 1-(1-Phenylethyl)-imidazole-5-carboxylic acid, ethyl ester
  • 1-(alpha-Methylbenzyl)-1H-imidazole-5-carboxylic acid ethyl ester
  • 125E972
  • 1H-Imidazole-5-carboxylic acid, 1-((1R)-1-phenylethyl)-, ethyl ester
  • 1H-Imidazole-5-carboxylic acid, 1-(1-phenylethyl)-, ethyl ester, (+)-
  • 1H-Imidazole-5-carboxylic acid, 1-[(1R)-1-phenylethyl]-, ethyl ester
  • 3-((R)-1-Phenyl-ethyl)-3H-imidazole-4-carboxylic acid ethyl ester
  • 33125-97-2
  • AB00639951_06
  • AM803710
  • Amidate
  • Amidate (pharmaceutical)
  • BDBM50125935
  • BRN 0665833
  • C07522
  • CCG-101054
  • CS-1833
  • D-Etomidate
  • D00548
  • DB00292
  • E0897
  • Ethyl (R)-(+)-1-(1-Phenylethyl)-1H-imidazole-5-carboxylate
  • Etomidate
  • Etomidate (USP/INN)
  • Etomidate 0.1 mg/ml in Methanol
  • Etomidate 1.0 mg/ml in Methanol
  • Etomidato
  • Etomidatum
  • Etomidic acid
  • GS-3208
  • GTPL5463
  • HMS2051P18
  • HMS2232A08
  • HMS3267N06
  • HMS3412D11
  • HMS3676D11
  • HY-B0100
  • Hypnomidate
  • Imidazole-5-carboxylic acid, 1-(.alpha.-methylbenzyl)-, ethyl ester, (R)-(+)-
  • Imidazole-5-carboxylic acid, 1-(alpha-methylbenzyl)-, ethyl ester, (R)-(+)-
  • MFCD00869295
  • MLS000758268
  • MLS001424163
  • NC00304
  • NCGC00025176-01
  • NSC 759160
  • NSC-759160
  • Q-201102
  • Q418445
  • R 16659
  • R(+)-etomidate
  • R-(+)-Ethyl 1-(1-phenylethyl)-1H-imidazole-5-carboxylate
  • R-16659
  • R-ETOMIDATE
  • Radenarcon
  • SMR000466277
  • SR-01000597569
  • SR-01000597569-1
  • V8D
  • Z22628B598
  • ethyl (R)-1-(1-phenylethyl)-1H-imidazole-5-carboxylate
  • ethyl 1-[(1R)-1-phenylethyl]-1H-imidazole-5-carboxylate
  • ethyl 3-[(1R)-1-phenylethyl]imidazole-4-carboxylate
  • r-(+)-ethyl-1-(1-phenylethyl)-1h-imidazole-5-carboxylate

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC1408
  • UNII-Z22628B598
  • AKOS015920052
  • BRD-K55055802-001-10-2
  • DTXSID5023033
  • CHEMBL681
  • CHEBI:4910
  • EINECS 251-385-9
  • SCHEMBL39487

Physico-Chemical properties

IUPAC nameethyl 3-[(1R)-1-phenylethyl]imidazole-4-carboxylate
Molecular formulaC14H16N2O2
Molecular weight244.289
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity68.87
LogP2.7
Topological polar surface area44.1

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.