Etomidate | CAS#33125-97-2 (free base) | intravenous anaesthetic

Etomidate
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 317856

CAS#: 33125-97-2 (free base)

Description: Etomidate is a short-acting intravenous anaesthetic agent used for the induction of general anaesthesia and sedation for short procedures such as reduction of dislocated joints, tracheal intubation, and cardioversion. It was discovered at Janssen Pharmaceutica in 1964 and was introduced as an intravenous agent in 1972 in Europe and in 1983 in the United States.

Chemical Structure

Etomidate

CAS# 33125-97-2 (free base)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 317856
Name: Etomidate
CAS#: 33125-97-2 (free base)
Chemical Formula: C14H16N2O2
Exact Mass: 244.12
Molecular Weight: 244.289
Elemental Analysis: C, 68.83; H, 6.60; N, 11.47; O, 13.10

Price and Availability

Size	Price	Availability
100mg	USD 300	2 weeks
500mg	USD 750	2 weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Related CAS #: 33125-97-2 (free base) 53188-20-8 (HCl)

Synonym: Etomidate, Amidate, Ethomidate, Hypnomidate, R 26490, R-26490, R26490, Radenarkon

IUPAC/Chemical Name: ethyl 3-[(1R)-1-phenylethyl]imidazole-4-carboxylate

InChi Key: NPUKDXXFDDZOKR-LLVKDONJSA-N

InChi Code: 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/t11-/m1/s1

SMILES Code: O=C(C1=CN=CN1[C@@H](C2=CC=CC=C2)C)OCC

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

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Product Data:

Product Data

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Biological target:	Etomidate (R 16659) is a potent GABAA receptor agonist.
In vitro activity:	Furthermore, AGEs inhibited the expression of SRY-related high mobility group-box gene 9 (SOX-9), promoting the expression of COL2A1 and ACAN. COL2A1, ACAN, and SOX-9 in chondrocytes were significantly elevated by treatment with Etomidate alone. Consistently, Etomidate ameliorated AGEs-induced downregulation of COL2A1, ACAN, and SOX-9 in a dose-dependent manner. Reference: Bioengineered. 2021 Dec;12(1):4191-4200. https://pubmed.ncbi.nlm.nih.gov/34308765/
In vivo activity:	Eto (etomidate) mitigated cardiac dysfunction and myocardium damage, as well as the release of CK and LDH caused by IR. Additionally, Eto reduced the expression of myocardial fibrosis-related proteins (collagen II and α-SMA) and the secretion of inflammatory factors (IL-6, IL-1β and TNF-α) in MIRI rats. Also, Eto inhibited IR-induced ferroptosis in myocardium, including reducing SOD content, GSH activity and GPX4 expression, while increasing the levels of MDA and iron and ACSL4. Moreover, the inhibition of Eto on IR-induced myocardial fibrosis and inflammation could be eliminated by erastin. The up-regulation of Nrf2 and HO-1 protein expression, and the nuclear translocation of Nrf2 induced by Eto in the myocardial tissues of MIRI rats could be prevented by erastin. Besides, ML385 eliminated the inhibition of Eto on ferroptosis induced by MIR. Reference: Shock. 2021 Jun 4. https://pubmed.ncbi.nlm.nih.gov/34091586/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	59.7	244.26
	DMF	30.0	122.81
	Ethanol	34.5	141.13

Preparing Stock Solutions

The following data is based on the product molecular weight 244.29 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:	1. Sun X, Zhang J, Li Y, Ren W, Wang L. Etomidate ameliorated advanced glycation end-products (AGEs)-induced reduction of extracellular matrix genes expression in chondrocytes. Bioengineered. 2021 Dec;12(1):4191-4200. doi: 10.1080/21655979.2021.1951926. PMID: 34308765. 2. Av Sá LGD, Silva CRD, de A Neto JB, Cândido TM, de Oliveira LC, do Nascimento FB, Barroso FD, da Silva LJ, de Mesquita JR, de Moraes MO, Cavalcanti BC, Júnior HV. Etomidate inhibits the growth of MRSA and exhibits synergism with oxacillin. Future Microbiol. 2020 Nov;15:1611-1619. doi: 10.2217/fmb-2020-0078. Epub 2020 Nov 20. PMID: 33215536. 3. Lv Z, Wang F, Zhang X, Zhang X, Zhang J, Liu R. Etomidate Attenuates the Ferroptosis in Myocardial Ischemia/Reperfusion Rat Model Via Nrf2 Pathway. Shock. 2021 Jun 4. doi: 10.1097/SHK.0000000000001751. Epub ahead of print. PMID: 34091586. 4. Jia L, Hao H, Wang C, Wei J. Etomidate attenuates hyperoxia-induced acute lung injury in mice by modulating the Nrf2/HO-1 signaling pathway. Exp Ther Med. 2021 Jul;22(1):785. doi: 10.3892/etm.2021.10217. Epub 2021 May 19. PMID: 34055084; PMCID: PMC8145798.
In vitro protocol:	1. Sun X, Zhang J, Li Y, Ren W, Wang L. Etomidate ameliorated advanced glycation end-products (AGEs)-induced reduction of extracellular matrix genes expression in chondrocytes. Bioengineered. 2021 Dec;12(1):4191-4200. doi: 10.1080/21655979.2021.1951926. PMID: 34308765. 2. Av Sá LGD, Silva CRD, de A Neto JB, Cândido TM, de Oliveira LC, do Nascimento FB, Barroso FD, da Silva LJ, de Mesquita JR, de Moraes MO, Cavalcanti BC, Júnior HV. Etomidate inhibits the growth of MRSA and exhibits synergism with oxacillin. Future Microbiol. 2020 Nov;15:1611-1619. doi: 10.2217/fmb-2020-0078. Epub 2020 Nov 20. PMID: 33215536.
In vivo protocol:	1. Lv Z, Wang F, Zhang X, Zhang X, Zhang J, Liu R. Etomidate Attenuates the Ferroptosis in Myocardial Ischemia/Reperfusion Rat Model Via Nrf2 Pathway. Shock. 2021 Jun 4. doi: 10.1097/SHK.0000000000001751. Epub ahead of print. PMID: 34091586. 2. Jia L, Hao H, Wang C, Wei J. Etomidate attenuates hyperoxia-induced acute lung injury in mice by modulating the Nrf2/HO-1 signaling pathway. Exp Ther Med. 2021 Jul;22(1):785. doi: 10.3892/etm.2021.10217. Epub 2021 May 19. PMID: 34055084; PMCID: PMC8145798.

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1: Tobias JD. Etomidate in pediatric anesthesiology: Where are we now? Saudi J Anaesth. 2015 Oct-Dec;9(4):451-6. doi: 10.4103/1658-354X.159475. Review. PubMed PMID: 26543467; PubMed Central PMCID: PMC4610094.

2: Raines DE. The pharmacology of etomidate and etomidate derivatives. Int Anesthesiol Clin. 2015 Spring;53(2):63-75. doi: 10.1097/AIA.0000000000000050. Review. PubMed PMID: 25807019.

3: Bruder EA, Ball IM, Ridi S, Pickett W, Hohl C. Single induction dose of etomidate versus other induction agents for endotracheal intubation in critically ill patients. Cochrane Database Syst Rev. 2015 Jan 8;1:CD010225. doi: 10.1002/14651858.CD010225.pub2. Review. PubMed PMID: 25568981.

4: Gu WJ, Wang F, Tang L, Liu JC. Single-dose etomidate does not increase mortality in patients with sepsis: a systematic review and meta-analysis of randomized controlled trials and observational studies. Chest. 2015 Feb;147(2):335-46. doi: 10.1378/chest.14-1012. Review. PubMed PMID: 25255427.

5: Mosier MJ, Lasinski AM, Gamelli RL. Suspected adrenal insufficiency in critically ill burned patients: etomidate-induced or critical illness-related corticosteroid insufficiency?-A review of the literature. J Burn Care Res. 2015 Mar-Apr;36(2):272-8. doi: 10.1097/BCR.0000000000000099. Review. PubMed PMID: 25055003.

6: Erdoes G, Basciani RM, Eberle B. Etomidate--a review of robust evidence for its use in various clinical scenarios. Acta Anaesthesiol Scand. 2014 Apr;58(4):380-9. doi: 10.1111/aas.12289. Epub 2014 Mar 3. Review. PubMed PMID: 24588359.

7: van den Heuvel I, Wurmb TE, Böttiger BW, Bernhard M. Pros and cons of etomidate--more discussion than evidence? Curr Opin Anaesthesiol. 2013 Aug;26(4):404-8. doi: 10.1097/ACO.0b013e328362a84c. Review. PubMed PMID: 23743556.

8: Hunter BR, Kirschner J. In patients with severe sepsis, does a single dose of etomidate to facilitate intubation increase mortality? Ann Emerg Med. 2013 May;61(5):571-2. doi: 10.1016/j.annemergmed.2012.12.024. Epub 2013 Mar 5. Review. PubMed PMID: 23465303.

9: Budde AO, Mets B. Pro: etomidate is the ideal induction agent for a cardiac anesthetic. J Cardiothorac Vasc Anesth. 2013 Feb;27(1):180-3. doi: 10.1053/j.jvca.2012.08.024. Epub 2012 Nov 3. Review. PubMed PMID: 23127694.

10: Malhotra AK. Con: etomidate--the ideal induction agent for a cardiac anesthetic? J Cardiothorac Vasc Anesth. 2013 Feb;27(1):178-9. doi: 10.1053/j.jvca.2012.08.023. Epub 2012 Nov 3. Review. PubMed PMID: 23127693.

11: Chan CM, Mitchell AL, Shorr AF. Etomidate is associated with mortality and adrenal insufficiency in sepsis: a meta-analysis*. Crit Care Med. 2012 Nov;40(11):2945-53. doi: 10.1097/CCM.0b013e31825fec26. Review. PubMed PMID: 22971586.

12: Ray DC, McKeown DW. Etomidate for critically ill patients. Pro: yes we can use it. Eur J Anaesthesiol. 2012 Nov;29(11):506-10. doi: 10.1097/EJA.0b013e32835819b0. Review. PubMed PMID: 22907611.

13: Flynn G, Shehabi Y. Pro/con debate: Is etomidate safe in hemodynamically unstable critically ill patients? Crit Care. 2012 Jul 19;16(4):227. doi: 10.1186/cc11242. Review. PubMed PMID: 22809235; PubMed Central PMCID: PMC3580672.

14: Sneyd JR. Novel etomidate derivatives. Curr Pharm Des. 2012;18(38):6253-6. Review. PubMed PMID: 22762475.

15: Forman SA. Monod-Wyman-Changeux allosteric mechanisms of action and the pharmacology of etomidate. Curr Opin Anaesthesiol. 2012 Aug;25(4):411-8. doi: 10.1097/ACO.0b013e328354feea. Review. PubMed PMID: 22614249; PubMed Central PMCID: PMC3673006.

16: Preda VA, Sen J, Karavitaki N, Grossman AB. Etomidate in the management of hypercortisolaemia in Cushing's syndrome: a review. Eur J Endocrinol. 2012 Aug;167(2):137-43. doi: 10.1530/EJE-12-0274. Epub 2012 May 10. Review. Erratum in: Eur J Endocrinol. 2013 Feb;168(2):X1. PubMed PMID: 22577107.

17: Cherfan AJ, Arabi YM, Al-Dorzi HM, Kenny LP. Advantages and disadvantages of etomidate use for intubation of patients with sepsis. Pharmacotherapy. 2012 May;32(5):475-82. doi: 10.1002/j.1875-9114.2012.01027.x. Epub 2012 Apr 9. Review. PubMed PMID: 22488264.

18: Toft P, Jensen AG. [Etomidate can not be recommended to patients with septic shock]. Ugeskr Laeger. 2011 May 16;173(20):1421-3. Review. Danish. PubMed PMID: 21586246.

19: Heyn J, Geiger C, Hinske CL, Briegel J, Weis F. Medical suppression of hypercortisolemia in Cushing's syndrome with particular consideration of etomidate. Pituitary. 2012 Jun;15(2):117-25. doi: 10.1007/s11102-011-0314-3. Review. PubMed PMID: 21556813.

20: Albert SG, Ariyan S, Rather A. The effect of etomidate on adrenal function in critical illness: a systematic review. Intensive Care Med. 2011 Jun;37(6):901-10. doi: 10.1007/s00134-011-2160-1. Epub 2011 Mar 4. Review. PubMed PMID: 21373823.

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