Brimonidine

Base Information

• Chemical Name: Brimonidine
• CAS No.: 59803-98-4
• Molecular Formula: C11H10BrN5
• Molecular Weight: 292.138
• Hs Code.: 29332900
• European Community (EC) Number: 620-306-3
• NSC Number: 318825
• UNII: E6GNX3HHTE
• DSSTox Substance ID: DTXSID3045221
• Nikkaji Number: J23.694B
• Wikipedia: Brimonidine
• Wikidata: Q577377
• NCI Thesaurus Code: C65269
• RXCUI: 134615
• Pharos Ligand ID: T29J7YXUKR9A
• Metabolomics Workbench ID: 42829
• ChEMBL ID: CHEMBL844
• Mol file: 59803-98-4.mol

Synonyms:5-Bromo-6-(2-imidazolin-2-ylamino)quinoxaline D-tartrate;5-bromo-6-(imidazolidinylideneamino)quinoxaline;5-bromo-6-(imidazolin-2-ylamino)quinoxaline;AGN 190342;AGN-190342;AGN190342;Alphagan;Alphagan P;brimonidine;brimonidine Purite;brimonidine tartrate;brimonidine tartrate (1:1);brimonidine tartrate (1:1), (S-(R*,R*))-isomer;brimonidine tartrate, (R-(R*,R*))-isomer;bromoxidine;mirvaso;Ratio Brimonidine;ratio-Brimonidine;Sanrosa;UK 14,304;UK 14,304 18;UK 14,304-18;UK 14,30418;UK 14,308;UK 14304;UK 14308;UK-14,304-18;UK-14,308;UK-14304;UK14,30418;UK14,308;UK14304

Chemical Property of Brimonidine

Chemical Property:

• Appearance/Colour: Yellow Solid
• Vapor Pressure: 1.1E-07mmHg at 25°C
• Melting Point: 207.5 °C
• Refractive Index: 1.798
• Boiling Point: 432.6 °C at 760 mmHg
• PKA: 7.69±0.10(Predicted)
• Flash Point: 215.4 °C
• PSA: 62.20000
• Density: 1.82 g/cm³
• LogP: 1.60080
• Storage Temp.: Store at RT
• Solubility.: 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: <0.8 m
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 291.01196
• Heavy Atom Count: 17
• Complexity: 308

Purity/Quality:

99% ^*data from raw suppliers

UK 14,304 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25-36/37/38
• Safety Statements: 26-36-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CN=C(N1)NC2=C(C3=NC=CN=C3C=C2)Br
• Recent ClinicalTrials: Phase 3 Evaluation of the Safety and Efficacy of LNZ101 for the Treatment of Presbyopia
• Recent EU Clinical Trials: Topical brimonidine to reduce post-inflammatory response after IPL- treatment and effect on IPL-efficacy in patients with facial telangiectasias
• Recent NIPH Clinical Trials: K-232 clinical pharmacology study
• Description: Launched in the US for open-angle glaucoma and ocular hypertension, brimonidine is a relatively selective and potent α2a,-adrenergic agonist with low affinity for the imidazoline l1 receptor. Topical application reduces intraocular pressure. This bypasses any central hypotensive effects at the l1 receptor (which can also give rise to a decrease in blood pressure and heart rate) if given systemically, since topical application results in low plasma levels concomitant with rapid systemic elimination. Brimonidine can be prepared in a four-step sequence from 4-nitrophenylenediamine.
• Uses: α2-Adrenoceptor agonist. Antiglaucoma. coronary vasodilator calcium ion influx inhibitor
• Therapeutic Function: Antiglaucoma

Technology Process of Brimonidine

There total 10 articles about Brimonidine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.2%

brimonidine tartrate (1400635-36-0) → 5-bromo-6-(imidazolin-2-ylamino)-quinoxaline (59803-98-4)

Guidance literature:

With sodium carbonate; In water; at 25 - 30 ℃;

Reference yield: 60.0%

5-bromo-6-(2-imidazolylamino)quinoxaline L-tartrate (1400635-36-0,79570-19-7) → 5-bromo-6-(imidazolin-2-ylamino)-quinoxaline (59803-98-4)

Guidance literature:

With sodium hydroxide; In water; at 0 - 5 ℃; for 0.25h;

Reference yield:

5-bromo-6-isothiocyanato-quinoxaline + ethylenediamine (107-15-3,85404-18-8) → 5-bromo-6-(imidazolin-2-ylamino)-quinoxaline (59803-98-4)

Guidance literature:

5-bromo-6-isothiocyanato-quinoxaline; ethylenediamine; In benzene; for 2h;

With methanol; Heating / reflux;

upstream raw materials:

ethylenediamine

3-methyl-6-aminoquinoxaline

6-amino-5-bromoquinoxaline hydrobromide

5-bromo-6-(2-imidazolylamino)quinoxaline L-tartrate

Downstream raw materials:

Brimonidine Tartrate 5-bromo-6-(2-imidazolidinylideneamino)quinoxaline L-tartrate

(5-bromoquinoxalin-6-yl)-(4,5-dihydro-1H-imidazol-2-yl)-amine L-tartrate

brimonidine diatrizoate

brimonidine hippurate

Refernces

• 1、 -. "COMPOUNDS, COMPOSITIONS AND METHODS FOR TREATMENT OF EYE DISORDERS AND SKIN DISEASES". Paragraph 00133; 00137. . Retrieved 2019/06/05.
• 2、 -. "DRUGS AND COMPOSITIONS FOR THE TREATMENT OF OCULAR DISORDERS". Page/Page column 271. . Retrieved 2018/10/19.