基本情報
- CAS
3572-43-8- 標準SMILES
CN(Cc1cc(Br)cc(Br)c1N)C1CCCCC1- InChIKey
OJGDCBLYJGHCIH-UHFFFAOYSA-N- 分子式
- C14H20Br2N2
- 平均分子量
- 376.13 g/mol
- 単同位体質量
- 373.99932
概要
Bromhexine is a substituted aniline that is 2,4-dibromoaniline which is substituted at position 6 by a [cyclohexyl(methyl)amino]methyl group. It is used (as the monohydrochloride salt) as a mucolytic for the treatment of respiratory disorders associated with productive cough (i.e. a cough characterised by the production of sputum). It has a role as a mucolytic. It is an organobromine compound, a substituted aniline and a tertiary amino compound. It is a conjugate base of a bromhexine(1+).
名称と識別子
- 優先名称
- Bromhexine
- IUPAC
- 2,4-dibromo-6-[[cyclohexyl(methyl)amino]methyl]aniline
- 現地名
- ブロムヘキシン
- 英語名
- BROMOHEXINE
- 分子式
- C14H20Br2N2
- 分子量
- 376.13
名称と別名
bromhexine3572-43-8Benzenemethanamine, 2-amino-3,5-dibromo-N-cyclohexyl-N-methyl-BromhexinaBromhexinumFluibron2,4-dibromo-6-[[cyclohexyl(methyl)amino]methyl]aniline2,4-Dibromo-6-((cyclohexyl(methyl)amino)methyl)anilineQ1J152VB1PCHEBI:770322,4-dibromo-6-{[cyclohexyl(methyl)amino]methyl}anilineDTXSID6022686
名称をさらに表示
N-シクロヘキシル-N-メチル-(2-アミノ-3,5-ジブロムベンジル)-アンモニウム塩ブロメキシン2-アミノ-3,5-ジブロモ-N-シクロヘキシル-N-メチルベンゼンメタンアミンブロムヘキシンアウキシト2,4-ジブロモ-6-{[シクロヘキシル(メチル)アミノ]メチル}アニリン6-[(N-メチルシクロヘキシルアミノ)メチル]-2,4-ジブロモアニリンBroMhexine IMpurity EBromexineAuxitNa 274Aids001646Aids-001646BROMOHEXINEAKOS B015997AURORA KA-7546
NA274N-cyclohexyl-N-methyl-(2-amino-3,5-dibrombenzyl)amine3,5-dibromo-N(alpha)-cyclohexyl-N(alpha)-methyltoluene-alpha-2-diamineBromexinaDurElixbromhexin von ctDur ElixBC, Bromhexin
物性
構造計算による物性
- XLogP
- 4.3
- 極性表面積
- 29.3 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 2
- 回転可能結合数
- 3
- 重原子数
- 18
- 形式電荷
- 0
- 複雑度
- 256
実験および物理化学的性質
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals
Solubility<1 mg/mL
Human Drugs
Breast Feeding; Lactation; Milk, Human; Expectorants
Pharmaceuticals
Melting Point232-235
Dissociation Constants8.69
Collision Cross Section167.85 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
物理化学的性質
- 融点
- 238 ℃ · 238℃
- 沸点
- 413.8 · 413.8±40.0 °C(Predicted)
- 比重(密度)
- 1.57 · 1.57
- 貯蔵温度
- 2 · 2-8°C(protect from light)
- 溶解性
- 75 mg/mL · DMSO: 75 mg/mL (199.40 mM);Ethanol: 75 mg/mL (199.40 mM)
- 酸解離定数(Pka)
- 8.34 · 8.34±0.20(Predicted)
- 水溶解度
- Water: Insoluble
- InChI
- InChI=1S/C14H20Br2N2/c1-18(12-5-3-2-4-6-12)9-10-7-11(15)8-13(16)14(10)17/h7-8,12H,2-6,9,17H2,1H3
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。
GHS分類
GHS Classification
Warning
H400 (100%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]
P273, P391, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
危険有害性情報
Regulatory Information
Chemical: Benzenemethanamine, 2-amino-3,5-dibromo-N-cyclohexyl-N-methyl-
REACH registered substance: Bromhexine (EC: 222-684-1)
Bromhexine: 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.
Other Safety InformationIMAP assessments - Benzenemethanamine, 2-amino-3,5-dibromo-N-cyclohexyl-N-methyl-: Environment tier I assessment
Hazard Classes and CategoriesAquatic Acute 1 (100%)
毒性情報
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
Bromhexine
DILI Positive
DOI:10.1016/j.drudis.2019.09.022
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
安全データ
- 毒性
- Approx LD50 orally in rabbits: >10 g/kg (Boyd, Sheppard)
化学と産業
薬理情報
ATC Code
R05CB02
R - Respiratory system
QR - Respiratory system
Protein BindingBromhexine is approximately 95% bound to plasma proteins.
PharmacodynamicsBromhexine thins airway secretions, improving breathing and discomfort associated with thick mucus in airways associated with a variety of respiratory conditions.
Mechanism of Action
Inflammation of the airways, increased mucus secretion, and altered mucociliary clearance are the hallmarks of various diseases of the respiratory tract. Mucus clearance is necessary for lung health; bromhexine aids in mucus clearance by reducing the viscosity of mucus and activating the ciliary epithelium, allowing secretions to be expelled from the respiratory tract. Recent have studies have demonstrated that bromhexine inhibits the transmembrane serine protease 2 receptor (TMPRSS2) in humans. Activation of TMPRSS2 plays an important role in viral respiratory diseases such as influenza A and Middle East Respiratory Syndrome (MERS). Inhibition of receptor activation and viral entry by bromhexine may be effective in preventing or treating various respiratory illnesses, including COVID-19. In vitro studies have suggested the action of ambroxol (a metabolite of bromhexine) on the angiogensin-converting enzyme receptor 2 (ACE2), prevents entry of the viral envelope-anchored spike glycoprotein of SARS-Cov-2 into alveolar cells or increases the secretion of surfactant, preventing viral entry.
Biological Half-LifeFollowing single oral doses ranging from 8 and 32 mg, the terminal half-life of bromhexine has been measured between 6.6 and 31.4 hours.
Metabolism/Metabolites
Bromhexine is almost completely metabolized to a variety of hydroxylated metabolites in addition to dibromanthranilic acid. Ambroxol is a known metabolite of bromhexine. In one study of human plasma, (E)-4-hydroxydemethylbromhexine (E-4-HDMB) and (E)-3-hydroxydemethylbromhexine (E-3-HDMB) were quantified as major metabolites of ambroxol, and (Z)-4-hydroxydemethylbromhexine and (Z)-3-hydroxydemethylbromhexine were quantified as minor metabolites.
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