Brimonidine Tartrate

• CAT Number: A000158
• CAS Number: 70359-46-5
• Molecular Formula: C15H16BrN5O6
• Molecular Weight: 442.2
• Purity: ≥95%
• Target: Adrenergic Receptor Agonist
• Storage: -20°C
• InChI: 1S/C11H10BrN5.C4H6O6/c12-9-7(17-11-15-5-6-16-11)1-2-8-10(9)14-4-3-13-8;5-1(3(7)8)2(6)4(9)10/h1-4H,5-6H2,(H2,15,16,17);1-2,5-6H,(H,7,8)(H,9,10)/t;1-,2-/m.1/s1
• InChIKey: QZHBYNSSDLTCRG-LREBCSMRSA-N
• SMILES: C1CN=C(N1)NC2=C(C3=NC=CN=C3C=C2)Br.C(C(C(=O)O)O)(C(=O)O)O

Brimonidine Tartrate(CAS: 70359-46-5) is the tartrate salt form of brimonidine, an imidazole derivative and a selective alpha-2 adrenergic receptor agonist. Upon ocular administration, brimonidine tartrate acts on the blood vessels causing them to constrict which leads to a decrease in the production of aqueous humor. Brimonidine tartrate also enhances the outflow of aqueous humor. This drug is used in the treatment of glaucoma to reduce intraocular pressure. A quinoxaline derivative and ADRENERGIC ALHPA-2 RECEPTOR AGONIST that is used to manage INTRAOCULAR PRESSURE associated with OPEN-ANGLE GLAUCOMA and OCULAR HYPERTENSION.

Overview of Clinical Research

Originator: Pfizer
Developer: AbbVie; Allergan; Senju Pharmaceutical
Class: Antiglaucomas; Antihypertensives; Eye disorder therapies; Imidazoles; Quinoxalines; Skin disorder therapies; Small molecules
Mechanism of Action: Alpha 2 adrenergic receptor agonists
Orphan Drug Status: No
New Molecular Entity: Yes

Reference

[1]. Expert Opin Pharmacother. 2019 Jan;20(1):115-122. doi: 10.1080/14656566.2018.1544241. Epub 2018 Nov 8.
Brimonidine tartrate for the treatment of glaucoma.
Oh DJ(1), Chen JL(1), Vajaranant TS(1), Dikopf MS(1).
Author information: (1)a Department of Ophthalmology and Visual Sciences, Illinois Eye and Ear Infirmary , University of Illinois at Chicago , Chicago , IL , USA.
Brimonidine tartrate is a commonly used eyedrop for short- and long-term lowering of intraocular pressure. Its use has been popularized due to its effects on aqueous suppression and uveoscleral outflow, as well as the suggestion of neuroprotection. Although available with alternative preservative vehicles, brimonidine is associated with high rates of local allergy and is contraindicated in breastfeeding women, neonates, young children, and the elderly due to risk of central nervous system depression. Other topical agents with differing advantages have challenged brimonidine's role in the treatment algorithm of ocular hypertension and glaucoma. Areas covered: The authors review the development of topical alpha-adrenergic agonists, with particular attention to the currently available formulations of brimonidine tartrate. Its mechanism of action, pharmacodynamics and safety, and clinical efficacy are analyzed. Expert opinion: Despite clinical familiarity with brimonidine after two decades of use, agents that offer daily dosing, nocturnal effect, and more favorable ocular and systemic side effect profiles have ultimately led to brimonidine's adjunctive use in patients with elevated intraocular pressure or high- or low-tension glaucomas. Still, brimonidine may be advantageous in patients undergoing laser trabeculoplasty or iridotomy, in certain forms of glaucoma, or in pregnant individuals prior to the last trimester, underscoring its clinical importance.
DOI: 10.1080/14656566.2018.1544241 PMID: 30407890

[2]. Dermatol Surg. 2018 Jan;44(1):144-147. doi: 10.1097/DSS.0000000000001389.
Topical Brimonidine Tartrate 0.33% Gel on Postlaser Erythema: Our Experience and Review of the Literature.
Lee SJ(1), Kim H, Kim HS.
Author information: (1)Yonsei Star Skin and Laser Clinic, Seoul, Korea Department of Dermatology, Incheon St. Mary's Hospital, The Catholic University of Korea, Incheon, Korea.
DOI: 10.1097/DSS.0000000000001389 PMID: 29077635

[3]. Eye (Lond). 2021 Feb;35(2):672-675. doi: 10.1038/s41433-020-1007-9. Epub 2020 Jun 9.
Effect of brimonidine tartrate 0.15% on scotopic pupil size and upper eyelid position: controlled trial.
Tuncer I(1), Bilgin S(2), Zengin MÖ(3), Mangan MS(4), Karaca A(5), Doğan C(6), Çınar E(7).
Author information: (1)Alfa Medical Center, Izmir, Turkey. . (2)Medifema Hospital, Izmir, Turkey. (3)Izmir Katip Celebi University Medical Faculty, Izmir, Turkey. (4)Haydarpasa Numune Education and Research Hospital, Istanbul, Turkey. (5)Alfa Medical Center, Izmir, Turkey. (6)Cerrahpasa School of Medicine, Istanbul University, Istanbul, Turkey. (7)Ekol Hospital, Izmir, Turkey.
BACKGROUND: To evaluate the effect of brimonidine tartrate 0.15% ophthalmic solution on pupil size under scotopic condition and upper eyelid position. METHODS: This study comprised 72 eyes of 36 healthy subjects. A single drop of brimonidine tartrate 0.15% ophthalmic solution was instilled in the right eye and artificial tear was instilled in the left eye. Pupil size was measured using an infra-red pupillometer under scotopic condition before and at 30 min, 2, 4, 6, 8 and 10 h after instillation. Measurement of margin reflex distance 1 (MRD1) was performed using a millimetre ruler before and after at 10 min after instillation. RESULTS: The mean age of the subjects was 32.19 ± 11.43 years (range 10-52 years), 17 were female and 19 were male. Before brimonidine instillation, the mean pupil size was 6.09 ± 1.03 mm in the brimonidine eyes and 6.06 ± 1.04 mm in the control eyes. There was a significant decrease in mean pupil size at 30 min (4.45 ± 1.04), 2 h (4.49 ± 1.06), 4 h (4.59 ± 1.06), 6 h (4.89 ± 1.06) and 8 h (5.38 ± 1.02) after instillation compared to before in brimonidine eyes (p < 0.001 for all). There was a significant miosis continued for at least 6 h (5.95 ± 1.03) in control eyes (p < 0.001). There was no significant change in MRD1, before and after instillation both in brimonidine and control eyes. CONCLUSIONS: Brimonidine tartrate 0.15% had a significant miosis under scotopic condition for at least 8 h after instillation and had a significant miosis on the untreated eye for at least 6 h.
DOI: 10.1038/s41433-020-1007-9 PMCID: PMC8027394 PMID: 32518394

[4]. Expert Rev Clin Pharmacol. 2014 Sep;7(5):567-77. doi: 10.1586/17512433.2014.945910. Epub 2014 Aug 4.
Brimonidine tartrate for the treatment of facial flushing and erythema in rosacea.
Tong LX(1), Moore AY.
Author information: (1)David Geffen School of Medicine at the University of California, Los Angeles, CA, USA.
Rosacea is a chronic inflammatory dermatologic condition that can often be disfiguring with significant negative impact on patients' quality of life. Sanrosa (brimonidine tartate) is a novel therapeutic agent targeting the facial flushing and erythema of rosacea through its α₂ adrenergic receptor agonist activity. The goal of this article is to discuss current treatment options for rosacea and the properties of brimonidine tartate as well as the evidence surrounding its efficacy and safety profile.
DOI: 10.1586/17512433.2014.945910 PMID: 25091290

[5]. Int Ophthalmol. 2021 Jan;41(1):293-301. doi: 10.1007/s10792-020-01581-4. Epub 2020 Nov 11.
Effect of brimonidine tartrate 0.2% ophthalmic solution on visual quality after implantable collamer lens implantation with a central hole.
Chen X(1)(2)(3), Wang X(4)(5)(6), Naidu RK(7), Qian Y(1)(2)(3), Miao H(1)(2)(3), Zhou X(1)(2)(3).
Author information: (1)Department of Ophthalmology, Eye and ENT Hospital of Fudan University, No. 19 BaoQing Road, Shanghai, 200031, People's Republic of China. (2)Myopia Key Laboratory of the Health Ministry, No. 19 BaoQing Road, Shanghai, 200031, People's Republic of China. (3)Research Center of Ophthalmology and Optometry, Shanghai, People's Republic of China. (4)Department of Ophthalmology, Eye and ENT Hospital of Fudan University, No. 19 BaoQing Road, Shanghai, 200031, People's Republic of China. . (5)Myopia Key Laboratory of the Health Ministry, No. 19 BaoQing Road, Shanghai, 200031, People's Republic of China. . (6)Research Center of Ophthalmology and Optometry, Shanghai, People's Republic of China. . (7)School of Medicine, The University of Sydney, Camperdown, NSW, Australia.
PURPOSE: To investigate the effect of brimonidine tartrate 0.2% on visual quality after implantable collamer lens with a central hole (ICL V4c). METHODS: This study comprised 59 consecutive patients implanted with an ICL V4c. Brimonidine was administered randomly into one eye of the patients with symptomatic glare or halos 1 week postoperatively and the contralateral eye with artificial tears as the control group. Visual quality (measured by a optical quality analysis system), pupil size and refraction under scotopic light conditions were measured before and 0.5, 1.5, 3 and 6 h after administration of brimonidine. A symptom questionnaire was also evaluated. RESULTS: The visual quality improved and reached its maximum value, and the scotopic pupil size reached its minimum value 1.5 h after brimonidine administration, with a statistically significant difference seen from 0.5 to 3 h compared to baseline. No changes in refraction were seen after brimonidine. The questionnaire showed that symptoms of glare or halos could be eliminated after brimonidine in 58% of patients, be alleviated in 37% of patients and be unchanged in 5% of patient. However, 10% of patients experienced conjunctival congestion and some patients experienced reduced drug efficacy 1 month after treatment. CONCLUSION: Brimonidine can be used to improve night visual quality in early postoperative period after ICL V4c implantation. It helps patients to quickly adapt to the glare or halos.
DOI: 10.1007/s10792-020-01581-4 PMID: 33175316