Moxetomidate

CAS 1567838-90-7

MF C15H18N2O3 MW 274.31 g/mol

• 2-Methoxyethyl 1-[(1R)-1-phenylethyl]-1H-imidazole-5-carboxylate
• 1H-Imidazole-5-carboxylic acid, 1-[(1R)-1-phenylethyl]-, 2-methoxyethyl ester

2-methoxyethyl 3-[(1R)-1-phenylethyl]imidazole-4-carboxylate

2-methoxyethyl 1-[(1R)-1-phenylethyl]-1H-imidazole-5-carboxylate
GABAA receptor agonist, hypnotic, ET-26, ET 26, LPQ2K767W2

Moxetomidate (also known as methoxyetomidate or ET-26) is a novel, investigational short-acting intravenous anesthetic and sedative-hypnotic agent. It functions as a{GABA}_A} receptor agonist and is designed as a “soft drug” analogue of the traditional anesthetic etomidate.

The Purpose of Its Development

Traditional etomidate is highly valued in clinical settings for its exceptional cardiovascular stability, making it the agent of choice for inducing anesthesia in patients with low blood pressure, trauma, or severe heart conditions. However, its primary drawback is that it causes prolonged adrenocortical suppression by inhibiting the enzyme 11β-hydroxylase. This limits its safety for continuous infusions or repeated uses.

Moxetomidate was synthesized to overcome this exact limitation. It retains the favorable, heart-safe properties of etomidate while undergoing rapid metabolic breakdown into an inactive compound. This prevents prolonged suppression of the adrenal gland.

Key Scientific Properties

• Mechanism of Action: It acts as a positive allosteric modulator and agonist at the \(GABA}_A}) receptor site, depressing the central nervous system to induce hypnosis and sedation.
• Chemical Profile: Its chemical formula is C₁₅H₁₈N₂O₃ with a molecular weight of 274.31 g/mol. Its IUPAC name is 2-methoxyethyl (R)-1-(1-phenylethyl)-1H-imidazole-5-carboxylate.
• Clinical Trial Status: Developed by entities including Jinzhou Ahon Pharmaceutical Co., Ltd., moxetomidate hydrochloride (ET-26 HCl) has progressed into Phase 3 clinical trials as an induction anesthetic.

Methoxyetomidate is an investigational anesthetic agent being developed by Jinzhou Ahon Pharmaceutical Co., Ltd. It is a short-acting intravenous anesthetic that acts as a positive allosteric modulator of GABAA receptors.^[1][2] As of 2024, methoxyetomidate is undergoing Phase 3 clinical trials for use in anesthesia.^[3][1]

PAT

https://patentscope.wipo.int/search/en/detail.jsf;jsessionid=D2B4BB918D25AFB75D4682C639A62719.wapp2nB?docId=US189917922&_cid=P21-MR5QSJ-95402-1

EG 1

Preparation of the Formula (I) Compound Guided by the Present Invention

The compound of Formula (II) (CAS: 56649-48-0) (216 mg, 1 mmol), the compound of Formula (III) (CAS: 6482-24-2) (278 mg, 2 mmol), and anhydrous potassium carbonate (564 mg, 3 mmol) were mixed and added in 15 mL of N,N-dimethylformamide, and the mixture was stirred at 50° C. and reacted overnight. Next day, the reaction solution was poured into 100 mL of cold water to obtain a clear solution, and was then extracted with ethyl acetate for three times (50 mL for each time). The combined organic layer was dried with anhydrous sodium sulfate and filtered to give the filtrate. Evaporation of the solvent under the reduced pressure provided oily crude products. After purification by silica gel column (eluent: cyclohexane/ethyl acetate=3/2), colorless oily product (150 mg) was obtained, with a yield of 54%.

1) NMR: apparatus: Bruker, internal standard substance: TMS

1H-NMR (400 MHz CDCl 3) δ: 1.862 (3H, d, J=7.2 Hz), 3.393 (3H, s), 3.645 (3H, t, J=4.8 Hz), 4.31˜4.405 (2H, m), 6.348 (1H, q, J=7.2 Hz), 7.17˜7.359 (m, 5H), 7.742 (s, 1H), 7.827 (s, 1H).

13C-NMR (100 MHz CDCl 3) δ: 22.30, 55.48, 59.15, 63.53, 70.48, 122.39, 126.36, 128.08, 128.93, 138.63, 140.02, 141.20, 160.26.

2) MS: mass spectrometer: API3000 LC-Ms/Ms from American ABI company; ionization mode: ESI.

(M+H).HRMS: for C 15H 18N 2O 3+H, calcd 275.1396, found 275.1396.

3) Optical rotation value: The ethanol solution of the compound of Formula (I) was prepared at a concentration of 1 g/100 mL, and [α]D 20 value was measured using Polarimeter 341 polarimeter, with [α] D 20=+71.9°.

4) The ee value: The compound of Formula (I) was dissolved in methanol at a concentration of 1 mg/mL and then diluted 100 times before injection. The detection was performed by HPLC using chiral AD column, wavelength of UV detector: 254 nm, mobile phase: 20% isopropanol-n-hexane, flow rate: 1 mL/min. The optical purity of the compound of Formula (I) was determined to be 100% ( FIG. 1).

PAT

• N-substituted imidazole carboxylic ester chiral compound containing an ether side chain, its preparation and applicationPublication Number: US-9969695-B2Priority Date: 2013-12-23Grant Date: 2018-05-15
• N-substituted imidazole carboxylic ester chiral compound containing ether side chain, preparation method and applicationPublication Number: EP-3088394-A1Priority Date: 2013-12-23
• N-Substituted Imidazole Carboxylic Ester Chiral Compound Containing an Ether Side Chain, Its Preparation and ApplicationPublication Number: US-2017001963-A1Priority Date: 2013-12-23
• N-substituted imidazole carboxylic ester chiral compound containing ether side chain, preparation method and applicationPublication Number: WO-2015096551-A1Priority Date: 2013-12-23

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References

References

1.  “ET-26 Methoxyetomidate Hydrochloride Development Information”. Synapse by Patsnap. Retrieved 2024-11-23.
2.  Wang B, Chen S, Yang J, Yang L, Liu J, Zhang W (2017). “ET-26 hydrochloride (ET-26 HCl) has similar hemodynamic stability to that of etomidate in normal and uncontrolled hemorrhagic shock (UHS) rats”. PLOS ONE. 12 (8) e0183439. Bibcode:2017PLoSO..1283439W. doi:10.1371/journal.pone.0183439. PMC 5557577. PMID 28813523.
3.  “ET-26 Clinical Trials Overview”. Synapse by Patsnap. Retrieved 2024-11-23.

Clinical data
Other names	ET-26; Moxetomidate
Identifiers
IUPAC name
CAS Number	1567838-90-7
PubChem CID	74766803
ChemSpider	133326476
UNII	LPQ2K767W2
Chemical and physical data
Formula	C15H18N2O3
Molar mass	274.320 g·mol−1
3D model (JSmol)	Interactive image
SMILES
InChI

//////////moxetomidate, anax labs, GABAA receptor agonist, hypnotic, ET-26, ET 26, LPQ2K767W2