Etomidate

Title: Etomidate
CAS Registry Number: 33125-97-2
CAS Name: 1-[(1R)-1-Phenylethyl]-1H-imidazole-5-carboxylic acid ethyl ester
Additional Names: (R)-(+)-1-(a-methylbenzyl)imidazole-5-carboxylic acid ethyl ester
Manufacturers' Codes: R-16659
Trademarks: Amidate (Abbott); Hypnomidate (Janssen)
Molecular Formula: C14H16N2O2
Molecular Weight: 244.29
Percent Composition: C 68.83%, H 6.60%, N 11.47%, O 13.10%
Literature References: Prepn of the (±)-form: BE 662474; E. F. Godefroi, C. A. M. van der Eijcken, US 3354173 (1965, 1967 both to Janssen); E. F. Godefroi et al., J. Med. Chem. 8, 220 (1965). Prepn of the (R)-(+)-form: L. F. C. Roevens et al., DE 2609573; eidem, US 3991072 (both 1976 to Janssen). Metabolism: E. Goetz, Anaesthesist 23, 331 (1974). Pharmacokinetics: M. J. Van Hamme et al., Anesthesiology 49, 274 (1978). Pharmacology: P. A. J. Janssen et al., Arch. Int. Pharmacodyn. Ther. 214, 92 (1975). Clinical study: R. J. Fragen, N. Caldwell, Anesthesiology 50, 242 (1979). Comprehensive description: Z. L. Chang, J. B. Martin, Anal. Profiles Drug Subs. 12, 191-214 (1983).
Properties: Crystals from diisopropyl ether, mp 67°. [a]D20 +66° (c = 1 in ethanol). uv max (isopropanol): 240 nm (e 12200). Soly in water at 25°: 0.0045 mg/100 ml. Sol in chloroform, methanol, ethanol, propylene glycol, acetone. LD50 in mice, rats (mg/kg): 29.5, 14.8-24.3 i.v. (Janssen).
Melting point: mp 67°
Optical Rotation: [a]D20 +66° (c = 1 in ethanol)
Absorption maximum: uv max (isopropanol): 240 nm (e 12200)
Toxicity data: LD50 in mice, rats (mg/kg): 29.5, 14.8-24.3 i.v. (Janssen)
Therap-Cat: Hypnotic.
Keywords: Sedative/Hypnotic.
Etomidoline Etonitazene Etonogestrel Etoperidone Etorphine

Etomidate
Etomidate skeletal.svg
Etomidate3d.png
Systematic (IUPAC) name
ethyl 3-[(1R)-1-phenylethyl]imidazole-
5-carboxylate
Clinical data
AHFS/Drugs.com monograph
Pregnancy cat. D (United States)
Legal status POM (UK)
Routes Intravenous
Pharmacokinetic data
Protein binding 75%
Metabolism Ester hydrolysis
Half-life 75 minutes
Excretion Renal (85%) and biliary (15%)
Identifiers
CAS number 33125-97-2 YesY
ATC code N01AX07
PubChem CID 36339
DrugBank DB00292
ChemSpider 33418 YesY
UNII Z22628B598 YesY
KEGG D00548 YesY
ChEMBL CHEMBL23731 YesY
Chemical data
Formula C14H16N2O2 
Mol. mass 244.289 g/mol
Physical data
Boiling point 392 °C (738 °F)
 YesY (what is this?)  (verify)

Etomidate (USAN, INN, BAN) (marketed as Amidate) is a short acting intravenous anaesthetic agent used for the induction of general anaesthesia and for sedation[1] for short procedures such as reduction of dislocated joints, tracheal intubation and cardioversion. It was discovered at Janssen Pharmaceutica in 1964 and it was introduced as an intravenous agent in 1972 in Europe and in 1983 in United States.[2]