33125-97-2 Usage
Chemical Properties
Etomidate is a white crystalline powder. easily soluble in water, methanol, ethanol and propylene glycol, soluble in chloroform, insoluble in acetone, insoluble in ether. Its effects on the central nervous system is similar to barbiturates.
Originator
Hypnomidate,Janssen,W. Germany,1977
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.
Definition
ChEBI: Etomidate is the ethyl ester of 1-[(1R)-1-phenylethyl]-1H-imidazole-5-carboxylic acid. It is an intravenous general anaesthetic with no analgesic activity. It has a role as an intravenous anaesthetic and a sedative. It is a member of imidazoles and an ethyl ester. It derives from a 1-[(1R)-1-phenylethyl]-1H-imidazole-5-carboxylic acid.
Brand name
Amidate (Hospira);Hypnomidate concentrate;Hypnomidate injection;Hypromidate;Nalgol;Sibu.
Therapeutic Function
Hypnotic
World Health Organization (WHO)
Etomidate, a potent hypnotic agent, was introduced in 1977 for
use as an intravenous anaesthetic. Its prolonged use can inhibit adrenal
steroidogenesis and, following reports of reduced serum cortisol levels
unresponsive to ACTH injection, the manufacturer suspended promotion of
etomidate for sedation in intensive care in 1983. In 1985 regulatory action taken
only in the United Kingdom further restricted use of the drug to induction of
anaesthesia. Etomidate remains widely available and is currently registered for
induction of anaesthesia in 34 countries and for maintenance of anaesthesia in 17
countries. It has never been registered for sedation.
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.
General Description
Etomidate is a carboxylated imidazole intended for the inductionof general anesthesia. It is marketed as the morepotent R (+) isomer. It is believed to exert its anestheticeffect via positive modulation of the GABAA receptor. Itis not water soluble and is available in the United States as a2-mg/mL solution containing 35% v/v propylene glycol andin Europe as a soybean oil and medium-chain triglyceridesformulation. The propylene glycol has been associatedwith moderate-to-severe pain on injection and irritation ofthe vascular tissue. A high incidence of skeletal musclemovements were noted in about 32% of patients followingetomidate injection. Case reports of seizures are also foundin the literature.
Biological Activity
Etomidate is a general anesthetic with GABA modulatory and GABA-mimetic actions; selectively interacts with β 2- and β 3-subunit containing GABAA receptors. Short acting and potent hypnotic, with low toxicity.The possible neuroprotective effect of etomidate against streptozotocin-induced (STZ-induced) hyperglycaemia were investigated in the rat brain and spinal cord. Etomidate treatment demonstrated neuroprotective effect on the neuronal tissue against the diabetic oxidative damage.
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.
Side effects
Etomidate may cause pain on injection and may produce
myoclonic muscle movements in approximately
40% of patients during its use as an induction anesthetic.
In addition, etomidate can suppress the adrenocortical
response to stress, an effect that may last up to 10 hours.
Veterinary Drugs and Treatments
Etomidate may be useful as an alternative to thiopental or propofol
for anesthetic induction in small animals, particularly in patients
with preexisting cardiac dysfunction, head trauma, or that are critically
ill.
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.
Metabolism
Etomidate is hydrolyzed by hepatic esterases to the corresponding inactive carboxylic acid, with subsequent renal and biliary excretion terminating its action. Its apparent elimination half-life is approximately 5 to 6 hours, with a volume of distribution of 5 to 7 L/kg. Changes in hepatic blood flow or hepatic metabolism will have only moderate effects on etomidate disposition. Concerns regarding the ability of etomidate to precipitate myoclonic jerks and inhibit adrenal steroid synthesis have been reported.
Mode of action
The exact mechanism of action of etomidate is unknown. It is felt to induce sedation by interaction with GABA receptors. and likely enhances the activity of a-aminobutyric acid. However, it is not structurally related to benzodiazepines or to barbiturates. Of significantnote, etomidate exhibits no analgesic properties.
Check Digit Verification of cas no
The CAS Registry Mumber 33125-97-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,3,1,2 and 5 respectively; the second part has 2 digits, 9 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 33125-97:
(7*3)+(6*3)+(5*1)+(4*2)+(3*5)+(2*9)+(1*7)=92
92 % 10 = 2
So 33125-97-2 is a valid CAS Registry Number.
InChI:InChI=1/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
33125-97-2Relevant articles and documents
Synthesis of [1-11C]ethyl iodide from [11C]carbon monoxide and its application in alkylation reactions
Eriksson, Jonas,Antoni, Gunnar,Langstroem, Bengt
, p. 723 - 731 (2004)
A method is presented for preparing [1-11C]ethyl iodide from [11C]carbon monoxide. The method utilizes methyl iodide and [ 11C]carbon monoxide in a palladium-mediated carbonylation reaction to form a mixture of [1-11C]acetic acid and [1-11C]methyl acetate. The acetates are reduced to [1-11C]ethanol and subsequently converted to [1-11C]ethyl iodide. The synthesis time was 20 min and the decay-corrected radio-chemical yield of [1-11C]ethyl iodide was 55 ± 5%. The position of the label was confirmed by 13C- labelling and 13C-NMR analysis. [1-11C]Ethyl iodide was used in two model reactions, an O-alkylation and an N-alkylation. Starting with approximately 2.5 GBq of [11C]carbon monoxide, the isolated decay-corrected radiochemical yields for the ester and the amine derivatives were 45 ± 0.5% and 25 ± 2%, respectively, based on [ 11C]carbon monoxide. Starting with 10 GBq of [11C]carbon monoxide, 0.55 GBq of the labelled ester was isolated within 40 min with a specific radioactivity of 36 GBq/μmol. Copyright
Ruthenium-containing P450 inhibitors for dual enzyme inhibition and DNA damage
Zamora, Ana,Denning, Catherine A.,Heidary, David K.,Wachter, Erin,Nease, Leona A.,Ruiz, José,Glazer, Edith C.
, p. 2165 - 2173 (2017/02/26)
Cytochrome P450s are key players in drug metabolism, and overexpression in tumors is associated with significant resistance to many medicinal agents. Consequently, inhibition of P450s could serve as a strategy to restore drug efficacy. However, the widespread expression of P450s throughout the human body and the critical roles they play in various biosynthetic pathways motivates the development of P450 inhibitors capable of controlled local administration. Ruthenium complexes containing P450 inhibitors as ligands were synthesized in order to develop pro-drugs that can be triggered to release the inhibitors in a spatially and temporally controlled fashion. Upon light activation the compounds release ligands that directly bind and inhibit P450 enzymes, while the ruthenium center is able to directly damage DNA.
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