5-bromo-N-(4,5-dihydro-1H-imidazol-2-yl)quinoxalin-6-amine

• ChemBase ID: 367
• Molecular Formular: C11H10BrN5
• Molecular Mass: 292.1346
• Monoisotopic Mass: 291.01195735
• SMILES: Brc1c(NC2=NCCN2)ccc2nccnc12
• Canonical SMILES: Brc1c(ccc2c1nccn2)NC1=NCCN1
• InChI: 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)
• InChIKey: XYLJNLCSTIOKRM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-bromo-N-(4,5-dihydro-1H-imidazol-2-yl)quinoxalin-6-amine
• IUPAC Traditional name: brimonidine
• Brand Name: Alphagan; Alphagan P
• Synonyms: Brimonidine tartrate; Bromoxidine; Brimonidine; 5-Bromo-N-(2-imidazolin-2-yl)-6-quinoxalinamine; 5-Bromo-N-(4,5-dihydro-1H-imidazol-2-yl)-6-quinoxalinamine; Brimonidine; UK 14,304; 5-Bromo-6-(2-imidazolin-2-ylamino)quinoxaline; AGN-190342; UK-14304; 5-bromo-N-(4,5-dihydro-1H-imidazol-2-yl)quinoxalin-6-amine; 5-bromo-6-(imidazolin-2-ylamino)quinoxaline

Database IDs

• CAS Number: 59803-98-4
• MDL Number: MFCD00153878
• PubChem SID: 24277812; 160963830; 46507305
• PubChem CID: 2435

CALCULATED PROPERTIES

JChem

• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -0.8992662
• LogD (pH = 7.4): 0.41908175
• Log P: 1.3715845
• Molar Refractivity: 68.4944 cm^3
• Polarizability: 26.612398 Å^3
• Polar Surface Area: 62.2 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.27
• LOG S: -3.28
• Solubility (Water): 1.54e-01 g/l

PROPERTIES

Physical Property

• Solubility: 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: <0.8 mg/mL; DMSO; DMSO: >6.5 mg/mL; ethanol: <8 mg/mL (warm); H2O: insoluble; Methanol; Soluble (1.5 mg/mL)
• Apperance: Yellow Solid
• Melting Point: 246-248°C; 258 - 260°C
• Hydrophobicity(logP): 1.486; 1.7

Safety Information

• Storage Condition: Refrigerator
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 1
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 25
• Safety Statements: 45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• RID/ADR: UN 2811 6.1/PG 3

Pharmacology Properties

• Gene Information: human ... ADRA1A(148), ADRA2A(150), ADRA2B(151), ADRA2C(152)

Product Information

• Purity: 95%; 97%

DETAILS

DrugBank - DB00484

• Drug Groups: approved
• Description: Brimonidine is a drug used to treat glaucoma. It acts via decreasing aqueous humor synthesis. [Wikipedia]
• Indication: For the lowering of intraocular pressure in patients with open-angle glaucoma or ocular hypertension.
• Pharmacology: Brimonidine significantly lowers intraocular pressure with minimal effects on cardiovascular and pulmonary parameters. It lowers intraocular pressure by reducing aqueous humor production and increasing uveoscleral outflow.
• Toxicity: Oral LD₅₀ is 50 mg/kg in mice and 100 mg/kg in rats.
• Affected Organisms: Humans and other mammals
• Biotransformation: Metabolized primarily by the liver.
• Absorption: Minimal systemic absorption occurs after ocular insertion.
• Half Life: 2 hours
• Elimination: It is metabolized primarily by the liver. Urinary excretion is the major route of elimination of the drug and its metabolites.
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - U104

Biochem/physiol Actions
UK 14,304 is an α2-adrenoceptor agonist.

Toronto Research Chemicals - B677520

α2-Adrenoceptor agonist. Antiglaucoma.

REFERENCES

• Katz, L.J., et al.: Am. J. Ophthalmol., 127, 20 (1999)
• Cantor, L. B., Expert Opin. Pharmacother., 1, 815 (2000).