기본 정보
- 표준 SMILES
Brc1c(NC2=NCCN2)ccc2nccnc12- InChIKey
XYLJNLCSTIOKRM-UHFFFAOYSA-N- 분자식
- C11H10BrN5
- 평균 분자량
- 292.13 g/mol
- 단동위원소 질량
- 291.01196
이름 및 식별자
- 우선 이름
- Brimonidine
- IUPAC
- 5-bromo-N-(4,5-dihydro-1H-imidazol-2-yl)quinoxalin-6-amine
- 영어명
- Brimonidine
- 분자식
- C11H10BrN5
- 분자량
- 292.13
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- CAS
59803-98-4- PubChem CID
- 2435
- DTXSID
DTXSID3045221- ChEMBL
CHEMBL844- ChEBI
CHEBI:3175- UNII
- E6GNX3HHTE
- EC Number
- 620-306-3
- Nikkaji
- J23.694B
물성
구조 계산 물성
- XLogP
- 0.6
- 극성 표면적
- 62.2 Ų
- 수소 결합 공여자 수
- 2
- 수소 결합 수용자 수
- 3
- 회전 가능 결합 수
- 2
- 무거운 원자 수
- 17
- 형식 전하
- 0
- 복잡도
- 308
실험 및 물리화학적 성질
Solubility
34
1.54e-01 g/L
11.2 [ug/mL] (The mean of the results at pH 7.4)
Melting Point
207.5
207.5 °C
물리화학적 성질
- 녹는점
- 207.5 °C · 207.5 °C
- 끓는 점
- 432.6 · 432.6±55.0 °C(Predicted)
- 밀도
- 1.82 · 1.82±0.1 g/cm3(Predicted)
- 저장 조건
- 2 · Keep in dark place,Sealed in dry,2-8°C
- 용해도
- 45 % · 45%(w/v) 수성 2-히드록시프로필-β-시클로덱스트린: <0.8mg/mL
- 산도 계수 (pKa)
- 7.69 · 7.69±0.10(Predicted)
- 물리적 상태
- powder to crystal
- 색상
- Light yellow to Amber to Dark green
- 생물학적 소스
- mouse
- 수용성
- 45 % · 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: DMSO: >6.5mg/mLethanol: H2O: insoluble
- Merck
- 14 · 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
화학적 성질
Yellow Solid
안전 및 규제
GHS 분류
GHS Classification
Danger
H301 (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.
유해성 정보
독성 정보
Exposure Routes
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 ± 62 pg/mL and 417 ± 264 pg.hr/mL, respectively. These values were reached on Day 15 of treatment.
Toxicity Summary
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.
Effects During Pregnancy and Lactation
◉ Summary of Use during Lactation;Limited 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 Infants;A 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 Breastmilk;Relevant published information was not found as of the revision date.
안전 데이터
- wgk
- -
- rtecs
- VD1200000
- ridadr
- UN 2811 6.1/PG 3
- HS 번호
- 29332900
- risk_code
- 25-36/37/38
- hazard_code
- T
- safety_code
- 26-36-45
- 포장분류
- Ⅲ
- 위험 등급
- 6.1
- Hazard Classifications
- Acute Tox. 3 Oral
- 스토리지 클래스
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
화학 및 산업
약리 정보
ATC Code
S01EA05
S - Sensory organs;S01 - Ophthalmologicals;S01G - Decongestants and antiallergics;S01GA - Sympathomimetics used as decongestants;S01GA07 - Brimonidine
D - Dermatologicals;D11 - Other dermatological preparations;D11A - Other dermatological preparations;D11AX - Other dermatologicals;D11AX21 - Brimonidine
S - Sensory organs;S01 - Ophthalmologicals;S01E - Antiglaucoma preparations and miotics;S01EA - Sympathomimetics in glaucoma therapy;S01EA05 - Brimonidine
QS - Sensory organs;QS01 - Ophthalmologicals;QS01G - Decongestants and antiallergics;QS01GA - Sympathomimetics used as decongestants;QS01GA07 - Brimonidine
QS - Sensory organs;QS01 - Ophthalmologicals;QS01E - Antiglaucoma preparations and miotics;QS01EA - Sympathomimetics in glaucoma therapy;QS01EA05 - Brimonidine
Pharmacodynamics
Brimonidine is a highly selective alpha-2 adrenergic receptor agonist that is 1000-fold more selective for the alpha2-adrenergic receptor than the alpha1-adrenergic receptor. This characteristic gives the drug some therapeutic advantages, since it reduces the risk of systemic side effects, such as systemic hypotension, bradycardia, and sedation. In addition, there is a reduction in the risk for developing alpha-1 mediated ocular unwanted effects, such as conjunctival blanching, mydriasis, and eyelid retraction. However, despite high alpha-2 receptor specificity, brimonidine may still produce alpha-1 adrenoceptor-mediated ocular effects, such as conjunctival vasoconstriction. Brimonidine has a peak ocular hypotensive effect occurring at two hours post-dosing. In a randomized, double-blind clinical study, ocular administration of 0.2% brimonidine in healthy volunteers resulted in a 23% reduction of mean intraocular pressure from baseline at 3 hours following administration. In comparative studies consisting of patients with open-angle glaucoma or ocular hypertension, the ocular hypotensive effect of brimonidine was maintained during treatment periods of up to 1 year. Brimonidine mediates vasoconstrictive effects and it was shown to exhibit anti-inflammatory properties in _ex vivo_ human skin model and _in vivo_ inflammation models. In a clinial trials consisting of adults with moderate to severe facial erythema of rosacea, brimonidine was shown to improve the extent of redness at 3 hours after application, compared to placebo. It was shown to be a potent vasoconstrictor of human subcutaneous vessels with a diameter of less than 200 µm. In _in vivo_ mouse inflammation models, brimonidine displayed anti-inflammatory properties by inhibiting edema. In a randomized, double-blind study, brimonidine reduced erythema for the 12 hours of the study in a dose-dependent manner. When adminsitered systemically, brimonidine was shown to cause cardiovascular effects by decreasing
Mechanism of Action
In the eye, alpha-1 adrenoceptors play a role in vasoconstriction, mydriasis, eyelid retraction, and elevation of intraocular pressure (IOP) whereas alpha-2 adrenoceptors are responsible for IOP reduction via a complex Gi-coupled signaling cascade pathway. Activation of alpha-2 receptors leads to inhibition of adenylyl cyclase and reduction of cyclic AMP levels. As a result, there is a decrease in norpinephrine (NE) release at the synaptic junction, NE-induced stimulation of beta-2 adrenoceptors, and production of aqueous humor by the ciliary epithelium. An elevated IOP is the most significant risk factor for developing glaucomatous optic neuropathy, which is associated with progressive visual field loss and functional disability if left untreated. Regardless of the etiology of the disease, the aim of current therapies for glaucoma is to reduce IOP, as reduction of IOP significantly reduces the risk of progression of vision loss even when IOP is already within the normal range. When administered ophthalmically, brimonidine is rapidly absorbed into the eye, acts as an agonist at ocular alpha-2 adrenoceptors and lowers IOP via a dual mechanism of action. It is proposed that initial dosing of the drug causes a reduction in aqueous humour production and chronic dosing leads to an increase in uveoscleral outflow. Brimonidine does not affect episcleral venous pressure. By reducing IOP, brimonidine aims to reduce the likelihood of glaucomatous visual field loss in ocular hypertension, and slow the progression of visual field defect in established open-angle glaucoma. When applied topically on skin, brimonidine reduces erythema through direct vasocontriction of small arteries and veins. As brimonidine mediates a potent peripheral vasoconstrictive activity by selectively working on the alpha-2 adrenoceptors, the use of brimonidine is thought to be efficacious for the treatment of facial erythema of rosacea, which is thought to arise from vasomotor instability and abnormal va
Metabolism/Metabolites
Brimonidine is reported to be metabolized in the cornea. Brominidine that reaches the systemic circulation upon topical administration undergoes extensive hepatic metabolism mediated by hepatic aldehyde oxidases.
Metabolized primarily by the liver. Route of Elimination: Urinary excretion is the major route of elimination of the drug and its metabolites. Half Life: 2 hours [ophthalmic solution]
FDA Pharmacological Classification
E6GNX3HHTE
BRIMONIDINE
Mechanisms of Action [MoA] - Adrenergic alpha-Agonists
Established Pharmacologic Class [EPC] - alpha-Adrenergic Agonist
Brimonidine is an alpha-Adrenergic Agonist. The mechanism of action of brimonidine is as an Adrenergic alpha-Agonist.
BRIMONIDINE
MeSH Pharmacological Classification
Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS.
Compounds that bind to and activate ADRENERGIC ALPHA-2 RECEPTORS.
Absorption, Distribution and Excretion
Brimonidine readily penetrates the cornea following ocular administration to reach pharmacologically active concentrations in the aqueous humor and ciliary body, the putative sites of its IOP-lowering activity. Following ocular administration of 0.2% brimonidine solution, the peak plasma concentrations were achieved within 1 to 4 hours. In a clinical study of adult subjects with facial erythema of rosacea, brimonidine was cutaneously applied on facial skin in a repeated manner. While there was no drug accumulation in plasma, the highest peak plasma concentrations (Cmax) and AUC were 46 ± 62 pg/mL and 417 ± 264 pgxhr/mL, respectively.
Brimonidine and its metabolites are predominantly eliminated via urinary excretion, with 74% of the total dose being found in the urine.
The volume of distribution of brimonidine has not been established. In animal studies, brimonidine was shown to cross the placenta and enter into the fetal circulation to a limited extent. As its lipophilicity is relatively low, brimonidine is not reported to easily cross the blood-brain barrier.
The apparent clearance has not been studied. However, the systemic clearance of brimonidine is reported to be rapid. Approximately 87% of the total radioactive dose of brimonidine was shown to be eliminated within 120 hours following oral administration.
용도 및 제조
Uses
Use (kg; approx.) in Germany (2009): >10;Consumption (g per capita; approx.) in Germany (2009): 0.000122;Calculated removal (%): 22
The ophthalmic solution is indicated for patients with open-angle glaucoma or ocular hypertension to lower intraocular pressure. The topical gel is indicated for the treatment of persistent (nontransient) facial erythema of rosacea in adults 18 years or older.
응용 분야
개요Launched 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.
용도a2-Adrenoceptor agonist. Antiglaucoma
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