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溴苯那敏 | 86-22-6

中文名称
溴苯那敏
中文别名
3-(4-溴苯基)-N,N-二甲基-3-吡啶-2-基-1-丙胺
英文名称
brompheniramine
英文别名
[3-(4-bromo-phenyl)-3-[2]pyridyl-propyl]-dimethyl-amine;bromopheniramine;3-(4-bromophenyl)-N,N-dimethyl-3-pyridin-2-ylpropan-1-amine
溴苯那敏化学式
CAS
86-22-6
化学式
C16H19BrN2
mdl
MFCD00865691
分子量
319.244
InChiKey
ZDIGNSYAACHWNL-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 熔点:
    25°C
  • 沸点:
    bp0.5 147-152°
  • 密度:
    1.3740 (rough estimate)
  • 溶解度:
    可溶于氯仿(少许)、甲醇(少许)
  • 物理描述:
    Solid
  • 颜色/状态:
    Oily liquid with slightly yellow color
  • 气味:
    Characteristic amine-like
  • 蒸汽压力:
    4.63X10-5 mm Hg at 25 °C (est)
  • 稳定性/保质期:
    SENSITIVE TO LIGHT /BROMPHENIIRAMINE MALEATE/
  • 保留指数:
    2095;2082;2082;2067;2100;2105;2109;2090;2096;2091;2067;2080;2115;2075;2096;2085.1

计算性质

  • 辛醇/水分配系数(LogP):
    3.5
  • 重原子数:
    19
  • 可旋转键数:
    5
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.312
  • 拓扑面积:
    16.1
  • 氢给体数:
    0
  • 氢受体数:
    2

ADMET

代谢
肝脏(细胞色素P-450系统),一些肾脏。
Hepatic (cytochrome P-450 system), some renal.
来源:DrugBank
代谢
药物的代谢和排泄命运尚未完全确定。溴苯那敏经过N-脱烷基化生成单脱甲基溴苯那敏和双脱甲基溴苯那敏,并代谢为丙酸衍生物,部分与甘氨酸结合,并生成其他未识别的代谢物。溴苯那敏及其代谢物主要通过尿液排泄。在大约72小时内,健康个体口服剂量的约40%通过尿液排泄,约2%通过粪便排泄。在健康个体中,口服剂量的约5-10%以原药形式通过尿液排泄,6-10%作为单脱甲基溴苯那敏,6-10%作为双脱甲基溴苯那敏,少量作为丙酸衍生物及其甘氨酸结合物,其余作为未识别的代谢物。
The metabolic and excretory fate of the drug has not been fully characterized. Brompheniramine undergoes N-dealkylation to form monodesmethylbrompheniramine and didesmethylbrompheniramine, and is metabolized to the propionic acid derivative, which is partially conjugated with glycine, and to other unidentified metabolites. Brompheniramine and its metabolites are excreted principally in urine. About 40% of an oral dose of brompheniramine is excreted in urine and about 2% in feces within 72 hours in healthy individuals. In healthy individuals, about 5-10% of an oral dose is excreted in urine as unchanged drug, 6-10% as monodesmethylbrompheniramine, 6-10% as didesmethylbrompheniramine, small amounts as the propionic acid derivative and its glycine conjugate, and the remainder as unidentified metabolites.
来源:Hazardous Substances Data Bank (HSDB)
代谢
肝脏(细胞色素P-450系统),一些肾脏。
Hepatic (cytochrome P-450 system), some renal.
来源:Toxin and Toxin Target Database (T3DB)
毒理性
  • 毒性总结
Brompheniramine 通过作为 H1 组胺受体的拮抗剂来发挥作用。它还作为适度有效的抗胆碱能剂,可能是一种类似于其他常见抗组胺药(如苯海拉明)的拮抗毒蕈碱受体剂。它对胆碱能系统的影响可能包括嗜睡、镇静、口干、喉咙干、视力模糊和心率增加等副作用。
Brompheniramine works by acting as an antagonist of the H1 histamine receptors. It also functions as a moderately effective anticholingeric agent, likely an antimuscarinic agent similar to other common antihistamines such as diphenhydramine. Its effects on the cholinergic system may include side-effects such as drowsiness, sedation, dry mouth, dry throat, blurred vision, and increased heart rate.
来源:Toxin and Toxin Target Database (T3DB)
毒理性
  • 药物性肝损伤
化合物:溴苯那敏
Compound:brompheniramine
来源:Drug Induced Liver Injury Rank (DILIrank) Dataset
毒理性
  • 药物性肝损伤
DILI 注释:无 DILI(药物性肝损伤)担忧
DILI Annotation:No-DILI-Concern
来源:Drug Induced Liver Injury Rank (DILIrank) Dataset
毒理性
  • 药物性肝损伤
标签部分:无匹配
Label Section:No match
来源:Drug Induced Liver Injury Rank (DILIrank) Dataset
毒理性
  • 药物性肝损伤
参考文献:M Chen, V Vijay, Q Shi, Z Liu, H Fang, W Tong. 美国食品药品监督管理局批准的药物标签用于研究药物诱导的肝损伤,《药物发现今日》,16(15-16):697-703, 2011. PMID:21624500 DOI:10.1016/j.drudis.2011.05.007 M Chen, A Suzuki, S Thakkar, K Yu, C Hu, W Tong. DILIrank:按人类发展药物诱导肝损伤风险排名的最大参考药物清单。《药物发现今日》2016, 21(4): 648-653. PMID:26948801 DOI:10.1016/j.drudis.2016.02.015
References:M Chen, V Vijay, Q Shi, Z Liu, H Fang, W Tong. FDA-Approved Drug Labeling for the Study of Drug-Induced Liver Injury, Drug Discovery Today, 16(15-16):697-703, 2011. PMID:21624500 DOI:10.1016/j.drudis.2011.05.007 M Chen, A Suzuki, S Thakkar, K Yu, C Hu, W Tong. DILIrank: the largest reference drug list ranked by the risk for developing drug-induced liver injury in humans. Drug Discov Today 2016, 21(4): 648-653. PMID:26948801 DOI:10.1016/j.drudis.2016.02.015
来源:Drug Induced Liver Injury Rank (DILIrank) Dataset
吸收、分配和排泄
  • 吸收
抗组胺药在口服给药后能很好地从胃肠道吸收。
Antihistamines are well absorbed from the gastrointestinal tract after oral administration.
来源:DrugBank
吸收、分配和排泄
溴苯那敏和右溴苯那敏顺丁烯二酸盐似乎能很好地从胃肠道吸收。
Brompheniramine and dexbrompheniramine maleates appear to be well absorbed from the GI tract.
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
溴苯那敏在人体组织和液体中的分布尚未完全表征,但药物似乎广泛分布。在健康成人单次口服给药后,报告称表观分布容积平均为11.7 L/kg。
Distribution of brompheniramine into human body tissues and fluids has not been fully characterized, but the drug appears to be widely distributed. Following oral administration of a single dose of the drug in healthy adults, the apparent volume of distribution reportedly averaged 11.7 L/kg.
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
在一项研究中,健康、禁食的成年人口服单剂量的马来酸溴苯那敏,剂量为0.13毫克/千克,血清中溴苯那敏的峰值浓度在7.7-15.7纳克/毫升之间,发生在2-5小时内;在其中的大多数个体中,还观察到了第二个较低的血药浓度峰,可能是由于肠肝循环所致。溴苯那敏的抗组胺作用,通过抑制由皮内注射组胺引起的风团和红斑反应来确定,似乎在单次口服给药后3-9小时内达到最大,但抑制红斑反应可能持续至少48小时;止痒效果似乎在9-24小时内达到最大。
Following oral administration of a single 0.13-mg/kg dose of brompheniramine maleate in healthy, fasting adults in one study, peak serum brompheniramine concentrations of 7.7-15.7 ng/mL occurred within 2-5 hours; in most of these individuals, a second lower peak, possibly secondary to enterohepatic circulation, also was observed. The antihistamine effect of brompheniramine, as determined by suppression of the wheal and flare responses induced by intradermal administration of histamine, appears to be maximal within 3-9 hours after a single oral dose of the drug, but suppression of the flare response may persist for up to at least 48 hours; the antipruritic effect appears to be maximal within 9-24 hours.
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
溴苯那敏及其代谢物主要在尿液中排泄。在大约72小时内,健康个体口服剂量的溴苯那敏约40%通过尿液排泄,约2%通过粪便排泄。在健康个体中,大约5-10%的口服剂量以未改变的药物形式通过尿液排泄……。
Brompheniramine and its metabolites are excreted principally in urine. About 40% of an oral dose of brompheniramine is excreted in urine and about 2% in feces within 72 hours in healthy individuals. In healthy individuals, about 5-10% of an oral dose is excreted in urine as unchanged drug ... .
来源:Hazardous Substances Data Bank (HSDB)

安全信息

  • 储存条件:
    2-8℃

SDS

SDS:c08bec6a1bb20e69095cb10f837d669d
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制备方法与用途

溴苯那敏(±)-溴苯那明是一种有效的口服活性烷基胺类抗组胺药。它是一种选择性组胺H1受体拮抗剂,Kd值为6.06 nM。此外,溴苯那敏能够阻断hERG通道、钙通道和钠通道,IC50分别为0.90 μM、16.12 μM和21.26 μM。这种药物具有抗胆碱能、抗抑郁和麻醉特性,常用于过敏性鼻炎的研究。

上下游信息

反应信息

  • 作为反应物:
    描述:
    溴苯那敏超重氢 、 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 作用下, 以 四氢呋喃 为溶剂, 55.0 ℃ 、79.0 kPa 条件下, 反应 19.0h, 生成 T-brompheniramine
    参考文献:
    名称:
    药物的多位点氢同位素标记
    摘要:
    摘要放射性标记是药物发现和开发的基础,因为它是临床前 ADME 研究和后期人体临床试验的强制性要求。本文提出了一种通用、有效且易于实施的方法,使用市售且空气稳定的铱预催化剂 [Ir(COD)(OMe)] 来多位点掺入氘和氚原子。2被描述。使用这种方法可以标记大量与药物相关的子结构,包括吡啶、吡嗪、吲哚、咔唑、苯胺、恶唑/噻唑、噻吩以及富电子苯基。各种复杂药物的标记突出了该反应的高官能团耐受性,特别是含有卤素或硫原子和腈基团。多位点氢同位素掺入可以通过原位形成互补的催化活性物质来解释:单金属铱络合物和铱纳米颗粒。
    DOI:
    10.1002/ange.202008519
  • 作为产物:
    描述:
    N-[2-(4-bromophenyl)-4-(dimethylamino)butylidene]hydroxylamine 在 decamethylrhenocene 二硫化碳sodium hydroxide四丁基硫酸氢铵 作用下, 以 二氯甲烷甲苯 为溶剂, 25.0~140.0 ℃ 、1.42 MPa 条件下, 反应 36.5h, 生成 溴苯那敏
    参考文献:
    名称:
    New Synthetic Route to Pheniramines via Hydroformylation of Functionalyzed Olefins
    摘要:
    DOI:
    10.1021/jo00102a044
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文献信息

  • Imidazole and benzimidazole derivatives useful as histamine H3 antagonists
    申请人:Aslanian G. Robert
    公开号:US20060166960A1
    公开(公告)日:2006-07-27
    Disclosed are compounds of the formula or a pharmaceutically acceptable salt or solvate thereof, wherein: n is 2-5; R is R 3 -aryl, R 3 -heteroaryl, R 3 -cycloalkyl, R 3 -heterocycloalkyl, alkyl, haloalkyl, —OR 4 , —SR 4 or —S(O) 1-2 R 5 ; R 1 and R 2 are H or optionally substituted phenyl or optionally substituted and X is —O— or —S—; or R 1 and R 2 , together with the carbon atoms to which they are attached form optionally substituted and X is —O—, —S— or —NR 7 —; Z is and the remaining variables are as defined in the specification; also disclosed are pharmaceutical compositions comprising the compounds of formula I; also disclosed are methods of treating allergy, allergy-induced airway responses, congestion, obesity and metabolic syndrome using the compounds of Formula I, as well as combinations with other drugs useful for treating those diseases.
    揭示了以下公式化合物或其药学上可接受的盐或溶剂,其中:n为2-5;R为R3-芳基,R3-杂环芳基,R3-环烷基,R3-杂环烷基,烷基,卤代烷基,—OR4,—SR4或—S(O)1-2R5;R1和R2为H或可选择地取代的苯基或可选择地取代的,X为—O—或—S—;或R1和R2,连同它们连接的碳原子形成可选择地取代的,X为—O—,—S—或—NR7—;Z为,其余变量如规范中所定义;还揭示了包括公式I化合物的药物组合物;还揭示了使用公式I化合物治疗过敏、过敏引起的气道反应、充血、肥胖和代谢综合征的方法,以及与其他用于治疗这些疾病的药物的组合。
  • [EN] 1-(4-PIPERIDINYL) BENZIMIDAZOLONES AS HISTAMINE H3 ANTAGONISTS<br/>[FR] 1-(4-PIPERIDINYL) BENZIMIDAZOLONES UTILISES EN TANT QU'ANTAGONISTES DU RECEPTEUR H3 DE L'HISTAMINE
    申请人:SCHERING CORP
    公开号:WO2003103669A1
    公开(公告)日:2003-12-18
    Disclosed are histamine H3 antagonists of the formula (I) wherein R1 is benzimidazolone derivative, M1 and M2 are optionally substituted carbon or nitrogen, R2 includes optionally substituted aryl or heteroaryl, and the remaining variables are as defined in the specification. Also disclosed are pharmaceutical compositions comprising the compounds of formula (I). Also disclosed are methods of treating various diseases or conditions, such as, for example, allergy, allergy-induced airway responses, and congestion (e.g., nasal congestion) using the compounds of Formula (I). Also disclosed are methods of treating various diseases or conditions, such as, for example, allergy, allergy-induced airway responses, and congestion (e.g., nasal congestion) using the compounds of formula (I) in combination with a H1 receptor antagonist.
    揭示了公式(I)中的组胺H3拮抗剂,其中R1是苯并咪唑酮衍生物,M1和M2是可选择地取代的碳或氮,R2包括可选择地取代的芳基或杂环基,其余变量如规范中所定义。还揭示了包括公式(I)化合物的药物组合物。还揭示了使用公式(I)化合物治疗各种疾病或症状的方法,例如过敏、过敏引起的气道反应和充血(例如,鼻塞)的方法。还揭示了使用公式(I)化合物与H1受体拮抗剂结合治疗各种疾病或症状的方法,例如过敏、过敏引起的气道反应和充血(例如,鼻塞)。
  • SUBSTITUTED INDOLES
    申请人:Gant Thomas G.
    公开号:US20090191183A1
    公开(公告)日:2009-07-30
    Disclosed herein are substituted indole cysteinyl leukotriene receptor modulators of Formula I, process of preparation thereof, pharmaceutical compositions thereof, and methods of use thereof.
    本文揭示了Formula I的替代吲哚半胱氨酸白三烯受体调节剂,其制备方法,药物组合物以及使用方法。
  • [EN] TRICYCLIC TRIAZOLE COMPOUNDS THAT MODULATE HSP90 ACTIVITY<br/>[FR] COMPOSÉS TRIAZOLES TRICYCLIQUES MODULANT L'ACTIVITÉ HSP90
    申请人:SYNTA PHARMACEUTICALS CORP
    公开号:WO2009139916A1
    公开(公告)日:2009-11-19
    The present invention relates to substituted tricyclic triazole compounds and compositions comprising substituted tricyclic triazole compounds. The invention further relates to methods of inhibiting the activity of Hsp90 in a subject in need thereof and methods for preventing or treating hyperproliferative disorders, such as cancer, in a subject in need thereof comprising administering to the subject a compound of the invention, or a composition comprising such a compound.
    本发明涉及替代三环三唑化合物和包含替代三环三唑化合物的组合物。该发明还涉及在需要的受体中抑制Hsp90活性的方法,以及预防或治疗高增殖性疾病(如癌症)的方法,其中包括向受体施用本发明的化合物或包含这种化合物的组合物。
  • [EN] SPIROLACTAM CGRP RECEPTOR ANTAGONISTS<br/>[FR] ANTAGONISTES DE RÉCEPTEUR DE CGRP À BASE DE SPIROLACTAME
    申请人:MERCK SHARP & DOHME
    公开号:WO2013169567A1
    公开(公告)日:2013-11-14
    The present invention is directed to spirolactam analogues which are antagonists of CGRP receptors and useful in the treatment or prevention of diseases in which CGRP is involved, such as migraine. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which CGRP is involved.
    本发明涉及螺内酰胺类似物,其为CGRP受体拮抗剂,可用于治疗或预防涉及CGRP的疾病,如偏头痛。该发明还涉及包含这些化合物的药物组合物,以及在预防或治疗涉及CGRP的这类疾病中使用这些化合物和组合物。
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表征谱图

  • 氢谱
    1HNMR
  • 质谱
    MS
  • 碳谱
    13CNMR
  • 红外
    IR
  • 拉曼
    Raman
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mass
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  • 峰位数据
  • 峰位匹配
  • 表征信息
Shift(ppm)
Intensity
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Assign
Shift(ppm)
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测试频率
样品用量
溶剂
溶剂用量
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