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Brimonidine
UK 14 · UK 14,304 · UBC · HMG20 · RPS27A · CS-1362 · UK 14,34 · UK-11957
Identifikatoren & physikalische Daten
| CAS No. | 59803-98-4 |
|---|---|
| Summenformel | C11H10BrN5 |
| Durchschnittliche Molmasse | 292,13 g/mol |
| Monoisotopische Masse | 291,01196 g/mol |
| SMILES | Brc1c(NC2=NCCN2)ccc2nccnc12 |
| InChIKey | XYLJNLCSTIOKRM-UHFFFAOYSA-N |
| PubChem CID | 2435 |
| ChEMBL | CHEMBL844 |
| ChEBI | CHEBI:3175 |
| EC No. | 620-306-3 |
| DTXSID | DTXSID3045221 |
Chemische & physikalische Eigenschaften
| XLogP | 0,6 |
|---|---|
| Polarare Oberfläche (TPSA) | 62,2 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 17 |
| Formalladung | 0 |
| Komplexität | 308 |
| LogP (Verteilungskoeffizient) | 1.7 |
| Löslichkeit | 341.54e-01 g/L11.2 [ug/mL] (The mean of the results at pH 7.4)45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: <0.8 mg/mL45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: DMSO: >6.5mg/mLethanol: H2O: insoluble |
| Schmelzpunkt | 207.5207.5 °C |
| Physical Description | Solid |
| Dissociation Constants | 7.78 |
| Siedepunkt | 432.6±55.0 °C(Predicted) |
| Dichte | 1.82±0.1 g/cm3(Predicted) |
| Lagerbedingungen | Keep in dark place,Sealed in dry,2-8°C |
| pKa (Säurekonstante) | 7.69±0.10(Predicted) |
| Aggregatzustand | powder to crystal |
| Farbe | Light yellow to Amber to Dark green |
| Biologische Quelle | mouse |
| Merck | 14,1375 |
| 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 |
| SMILES | N1C2C(=C(Br)C(NC3NCCN=3)=CC=2)N=CC=1 |
| CAS Datenbank | 59803-98-4(CAS DataBase Reference) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 44 reports by companies from 5 notifications to the ECHA C&L Inventory.Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 3 (100%) |
| Expositionspfade | Minimal systemic absorption occurs after ocular insertion. When the topical gel was applied to adult patients with facial erythema associated with rosacea, the plasma maximum concentration (Cmax) and area under the concentration-time curve (AUC) were 46 䕢 pg/mL and 417 𫑰 pg.hr/mL, respectively. These values were reached on Day 15 of treatment. |
| Toxizitätsübersicht | Brimonidine is an alpha adrenergic receptor agonist (primarily alpha-2). It has a peak ocular hypotensive effect occurring at two hours post-dosing. Fluorophotometric studies in animals and humans suggest that Brimonidine has a dual mechanism of action by reducing aqueous humor production and increasing uveoscleral outflow. The topical gel reduces erythema through direct vasocontriction. |
| Signs and Symptoms | Oral LD<sub>50</sub> is 50 mg/kg in mice and 100 mg/kg in rats. |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| Effects During Pregnancy and Lactation | ◉ Summary of Use during LactationLimited information indicates that maternal use of brimonidine 0.2% ophthalmic drops do not adversely affect their nursing infants. However, some authors and the manufacturer warn of possible CNS depression, apnea, lethargy, bradycardia with brimonidine and recommend against its use during breastfeeding. To substantially diminish the amount of drug that reaches the breastmilk after using eye drops, place pressure over the tear duct by the corner of the eye for 1 minute or more, then remove the excess solution with an absorbent tissue. The manufacturer of Combigan states that it is not recommended for use during lactation, but there is no evidence for this statement.Topical brimonidine gel used to treat rosacea has not been studied during breastfeeding. It is unlikely that the topical gel would affect the breastfed infant, but the manufacturer states that it should not be used during nursing. Until more data are available, an alternative topical agent might be preferred◉ Effects in Breastfed InfantsA woman used brimonidine 0.2%, timolol gel-forming solution 0.5%, dipivefrin 0.2%, and dorzolamide 0.5% drops for glaucoma while nursing a newborn. The frequency of medication use, and extent of nursing were not stated. All medications were given immediately after nursing with punctal occlusion of the tear duct. The infant's vital signs were closely monitored with no signs of bradycardia or apnea.A woman was using ophthalmic drops containing 0.5% timolol and 0.2% brimonidine twice daily in the right eye for 6 months. During this time, she breastfed her infant (extent not stated) apparently without harm to her infant.◉ Effects on Lactation and BreastmilkRelevant published information was not found as of the revision date. |
| Toxicity Data | LD50: 50 mg/kg (oral, mice) LD50: 100 mg/kg (oral, rat) |
| Wassergefährdungsklasse (WGK) | - |
| UN-Transportnummer | UN 2811 6.1/PG 3 |
| Zollcode | 29332900 |
| RTECS-Nr. | VD1200000 |
| R-Sätze (R) | 25-36/37/38 |
| Gefahrensymbole | T |
| Sicherheitshinweise (S) | 26-36-45 |
| Gefahrenklasse | 6.1Acute Tox. 3 Oral |
| Verpackungsgruppe | Ⅲ |
| Lagerklasse | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
Anwendungen & Verwendung
Beschreibung
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.
Verwenden
a2-Adrenoceptor agonist. Antiglaucoma