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U104

UK 14,304

Name: UK 14,304
Brand: SIGMA

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Synonym(s):

5-Bromo-N-(2-imidazolin-2-yl)-6-quinoxalinamine, 5-Bromo-N-(4,5-dihydro-1H-imidazol-2-yl)-6-quinoxalinamine, Brimonidine

Empirical Formula (Hill Notation):

C₁₁H₁₀BrN₅

CAS Number:

59803-98-4

Molecular Weight:

292.13

MDL number:

MFCD00153878

PubChem Substance ID:

24277812

Quality Level

100

solubility

45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: <0.8 mg/mL
DMSO: >6.5 mg/mL
ethanol: <8 mg/mL (warm)
H₂O: insoluble

SMILES string

Brc1c(NC2=NCCN2)ccc3nccnc13

InChI

1S/C11H10BrN5/c12-9-7(17-11-15-5-6-16-11)1-2-8-10(9)14-4-3-13-8/h1-4H,5-6H2,(H2,15,16,17)

InChI key

XYLJNLCSTIOKRM-UHFFFAOYSA-N

Gene Information

human ... ADRA1A(148) , ADRA2A(150) , ADRA2B(151) , ADRA2C(152)

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Application

UK 14,304 has been used for the activation of extracellular signal-regulated kinase (ERK) in epicardial coronary artery culture

UK 14,304 has been used in myenteric neurons to study the inhibition of R-type calcium currents. UK 14,304 has also been used for immunofluorescence microscopy assays.

Biochem/physiol Actions

UK 14,304 is an α2-adrenoceptor agonist. UK 14,304 inhibits hormone-sensitive lipase (HSL) activity and suppresses lipogenesis in adipose tissue.

Features and Benefits

This compound is featured on the α2-Adrenoceptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Preparation Note

UK 14,304 is soluble in 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin (<0.8 mg/mL), DMSO (>6.5 mg/ml) and ethanol (<8 mg/mL). However, it is insoluble in water.

Pictograms

GHS06

Signal Word

Danger

Hazard Statements

H301

Precautionary Statements

P264 - P270 - P301 + P310 - P405 - P501

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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The alpha2-adrenergic receptor agonist UK 14,304 inhibits secretin-stimulated ductal secretion by downregulation of the cAMP system in bile duct-ligated rats.

Francis H, et al.

American Journal of Physiology. Cell Physiology, 293(4), C1252-C1262 (2007)

Functional alpha-1B adrenergic receptors on human epicardial coronary artery endothelial cells.

Jensen BC, et al.

Naunyn-Schmiedeberg'S Archives of Pharmacology, 382(5-6), 475-482 (2010)

Alpha2 -adrenoceptor agonists inhibit form-deprivation myopia in the chick.

Brittany J Carr et al.

Clinical & experimental optometry, 102(4), 418-425 (2019-01-31)

The putative myopia-controlling receptor is thought to be muscarinic acetylcholine receptor subtype M4 , because mamba toxin-3 can inhibit form-deprivation myopia in chicks at a far lower concentration than atropine. However, mamba toxin-3 is equally potent at the human α1A

Effects of acute and chronic ethanol administration on the response of mouse adipose tissue hormone-sensitive lipase to alpha2-adrenoceptor activation by UK 14304.

Shih MF and Taberner PV

Alcohol and Alcoholism (Oxford, Oxfordshire), 36(5), 381-387 (2001)

Investigating the neuroprotective effect of Copolymer-1 in acute primary angle closure - Interim report of a randomized placebo-controlled double-masked clinical trial.

Kenric Rui-Pin Fan et al.

Acta ophthalmologica, 97(6), e827-e832 (2019-03-28)

To investigate the neuroprotective effect of Copolymer-1 (Cop-1) in patients with acute primary angle closure (APAC) in a randomized double-masked controlled trial. After initial medical management, APAC patients were randomized to receive either subcutaneous Cop-1 or placebo within 24 hr and

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