| Identification | Back Directory | [Name]
metomidate | [CAS]
5377-20-8 | [Synonyms]
AquacalM
Hypnodil
MethoxyMol
metomidate
Methomidate
MethoxyMol R-7315
Etomidate impurity B CRS
methyl 3-(1-phenylethyl)imidazole-4-carboxylate
Methyl 3-(1-phenylethyl)imidazole-5-carboxylate
Methyl 1-(α-Methylbenzyl)iMidazole-5-carboxylate
Methyl 1-(1-Phenylethyl)-1H-Imidazole-5-Carboxylate
Methyl 1-[(1RS)-1-phenylethyl]-1H-imidazole-5-carboxylate
3-(1-phenylethyl)imidazole-4-carboxylic acid methyl ester
1-(α-Methylbenzyl)iMidazole-5-carboxylic Acid Methyl Ester
1-(1-Phenylethyl)-1H-imidazole-5-carboxylic acid methyl ester
1H-Imidazole-5-carboxylic acid, 1-(1-phenylethyl)-, methyl ester | [EINECS(EC#)]
226-368-4 | [Molecular Formula]
C13H14N2O2 | [MDL Number]
MFCD01721714 | [MOL File]
5377-20-8.mol | [Molecular Weight]
230.26 |
| Chemical Properties | Back Directory | [Boiling point ]
372.26°C (rough estimate) | [density ]
1.13 | [refractive index ]
1.6450 (estimate) | [storage temp. ]
Refrigerator | [solubility ]
Chloroform, Methanol | [form ]
neat | [pka]
4.15±0.23(Predicted) | [color ]
Colourless to Pale Yellow | [InChI]
InChI=1S/C13H14N2O2/c1-10(11-6-4-3-5-7-11)15-9-14-8-12(15)13(16)17-2/h3-10H,1-2H3 | [InChIKey]
FHFZEKYDSVTYLL-UHFFFAOYSA-N | [SMILES]
C1N(C(C2=CC=CC=C2)C)C(C(OC)=O)=CN=1 |
| Hazard Information | Back Directory | [Chemical Properties]
Colourless Hazy Oil | [Uses]
Metomidate is a the methyl ester analogue of Etomidate (E933300), with sedative and hypnotic properties. Metomidate is mainly used as an anesthetic for veterinary use on its own or in combination with Azaperone (A802200) and other sedatives. | [Definition]
ChEBI: Methomidate is a member of imidazoles. | [Biological Functions]
Metomidate, a methyl analog of the anesthetic agent etomidate, is a potent inhibitor of CYP11B1 (11β-hydroxylase) and CYP11B2 (aldosterone synthase), the final two enzymes involved in cortisol and aldosterone synthesis, respectively. | [Mechanism of action]
Metomidate reduces plasma cortisol and glucose concentrations and increases fish pigmentation, presumably because of increased production of melanocyte-stimulating hormone on the same primary protein as adrenocorticotropic hormone (ACTH). Imidazole anesthetics (e.g., metomidate and etomidate) interrupt cortisol synthesis in mammals by suppressing the enzyme 11-beta-hydroxylase, which is necessary for cortisol production.
| [Clinical Use]
Metomidate can be 11CH3 labeled and used as a positron emission tomography (PET) radiotracer in combination with high-resolution computed tomography (CT) to detect adrenocortical tumors expressing these enzymes. |
|