基本情報
- CAS
118-23-0- 標準SMILES
CN(C)CCOC(c1ccccc1)c1ccc(Br)cc1- InChIKey
NUNIWXHYABYXKF-UHFFFAOYSA-N- 分子式
- C17H20BrNO
- 平均分子量
- 334.2 g/mol
- 単同位体質量
- 333.07283
概要
Bromazine is a tertiary amino compound that is the 4-bromobenzhydryl ether of 2-(dimethylamino)ethanol. An antihistamine with antimicrobial properties, it is used in the control of cutaneous allergies. It has a role as an antimicrobial agent, a H1-receptor antagonist and a muscarinic antagonist. It is an organobromine compound and a tertiary amino compound. It contains a bromazine hydrochloride.
名称と識別子
- 優先名称
- Bromodiphenhydramine
- IUPAC
- 2-[(4-bromophenyl)-phenylmethoxy]-N,N-dimethylethanamine
- 現地名
- 2-[α-(4-ブロモフェニル)ベンジルオキシ]-N,N-ジメチルエタンアミン
- 英語名
- N-2-(4-bromobenzhydryloxy)ethyldimethylamine
- 分子式
- C17H20BrNO
- 分子量
- 334.25
名称と別名
bromodiphenhydramineBromazineBromdiphenhydramine118-23-0HistabromamineDeserolBromazinaNeo-BenadrylBromazinumDTXSID6022688beta-(p-Bromobenzhydryloxy)ethyldimethylamine2-(p-bromo-alpha-phenylbenzyloxy)-N,N-dimethylethylamine
名称をさらに表示
ブロマジンブロモ-ベナドリルブロモジフェンヒドラミンデセロールアンボドリル2-[4-ブロモフェニル(フェニル)メトキシ]-N,N-ジメチルエタンアミンアムボドリルヒスタブロムアミンブロマナウチン2-[(4-ブロモフェニル)フェニルメトキシ]-N,N-ジメチルエタンアミン2-[α-(4-ブロモフェニル)ベンジルオキシ]-N,N-ジメチルエタンアミン{2-[(4-ブロモフェニル)(フェニル)メトキシ]エチル}ジメチルアミン2-[(RS)-(4-Bromophenyl)phenylmethoxy]-N,N-dimethylethanamineBromanautineBromo-BenadrylDimenhydrinate EP Impurity HDiphenhydramine EP Impurity CN-2-(4-bromobenzhydryloxy)ethyldimethylamine2-benzhydryloxy-N-(bromomethyl)-N-methylethanamine
物性
構造計算による物性
- XLogP
- 4
- 極性表面積
- 12.5 Ų
- 水素結合供与体数
- 0
- 水素結合受容体数
- 2
- 回転可能結合数
- 6
- 重原子数
- 20
- 形式電荷
- 0
- 複雑度
- 258
実験および物理化学的性質
LogP4
Solubility3.45e-03 g/L
Human DrugsPharmaceuticals
Physical DescriptionSolid
物理化学的性質
- 沸点
- 151 · 151-154 °C(Press: 0.3 Torr)
- 比重(密度)
- 1.259 · 1.259±0.06 g/cm3(Predicted)
- 酸解離定数(Pka)
- 8.64 · pKa 8.64(H2O t = 25 c = 0.002 to 0.01) (Uncertain)
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
危険有害性情報
Regulatory InformationEthanamine, 2-(4-bromophenyl)phenylmethoxy-N,N-dimethyl-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
毒性情報
Exposure RoutesWell absorbed in the digestive tract.
Toxicity SummaryBromodiphenhydramine competes with free histamine for binding at HA-receptor sites. This antagonizes the effects of histamine on HA-receptors, leading to a reduction of the negative symptoms brought on by histamine HA-receptor binding.
Signs and SymptomsSigns of overdose include wheezing, tightness in the chest, fever, itching, bad cough, blue skin color, fits, swelling of face, lips, tongue, or throat.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
化学と産業
薬理情報
ATC Code
R - Respiratory system
QR - Respiratory system
Protein Binding96%
Pharmacodynamics
Bromodiphenhydramine is an antihistamine of the ethanolamine class. Ethanolamine antihistamines have significant antimuscarinic activity and produce marked sedation in most patients. In addition to the usual allergic symptoms, the drug also treats irritant cough and nausea, vomiting, and vertigo associated with motion sickness. It also is used commonly to treat drug-induced extrapyramidal symptoms as well as to treat mild cases of Parkinson's disease. Rather than preventing the release of histamine, as do cromolyn and nedocromil, Bromodiphenhydramine competes with free histamine for binding at HA-receptor sites. Bromodiphenhydramine competitively antagonizes the effects of histamine on HA-receptors in the GI tract, uterus, large blood vessels, and bronchial muscle. Ethanolamine derivatives have greater anticholinergic activity than do other antihistamines, which probably accounts for the antidyskinetic action of Bromodiphenhydramine. This anticholinergic action appears to be due to a central antimuscarinic effect, which also may be responsible for its antiemetic effects, although the exact mechanism is unknown.
Mechanism of ActionBromodiphenhydramine competes with free histamine for binding at HA-receptor sites. This antagonizes the effects of histamine on HA-receptors, leading to a reduction of the negative symptoms brought on by histamine HA-receptor binding.
Biological Half-Life1 to 4 hours
Metabolism/Metabolites
Hepatic (cytochrome P-450 system); some renal.
Hepatic (cytochrome P-450 system); some renal. Half Life: 1 to 4 hours
Absorption, Distribution and ExcretionWell absorbed in the digestive tract.
Cellular LocationsMembrane
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