キシロメタゾリン
Xylometazoline
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基本情報
- CAS
526-36-3- 標準SMILES
Cc1cc(C(C)(C)C)cc(C)c1CC1=NCCN1- InChIKey
HUCJFAOMUPXHDK-UHFFFAOYSA-N- 分子式
- C16H24N2
- 平均分子量
- 244.37 g/mol
- 単同位体質量
- 244.19394877
概要
Xylometazoline is an alkylbenzene.
名称と識別子
- 優先名称
- Xylometazoline
- IUPAC
- 2-[(4-tert-butyl-2,6-dimethylphenyl)methyl]-4,5-dihydro-1H-imidazole
- 現地名
- キシロメタゾリン
- 英語名
- 2-(4-TERT-BUTYL-2,6-DIMETHYL-BENZYL)-4,5-DIHYDRO-1H-IMIDAZOLE
- 分子式
- C16H24N2
- 分子量
- 244.38
名称と別名
xylometazoline526-36-3XylomethazolineOtrivenXilometazolina2-[(4-tert-butyl-2,6-dimethylphenyl)methyl]-4,5-dihydro-1H-imidazoleXylometazolinumBalminilWPY40FTH8K2-(4-tert-Butyl-2,6-dimethylbenzyl)-2-imidazoline1H-Imidazole, 2-((4-(1,1-dimethylethyl)-2,6-dimethylphenyl)methyl)-4,5-dihydro-DTXSID8046957
名称をさらに表示
2-[[4-(1,1-ジメチルエチル)-2,6-ジメチルフェニル]メチル]-4,5-ジヒドロ-1H-イミダゾールキシロメタゾリン2-[(4-tert-ブチル-2,6-ジメチルフェニル)メチル]-4,5-ジヒドロ-1H-イミダゾールOtrixOtrivinBa-11391OtrivineRhinoxilinAKOS BBS-00000259XYLOMETAZOLINEANDITSHYDROCHLORIDE
1H-Imidazole, 2-[[4-(1,1-dimethylethyl)-2,6-dimethylphenyl]methyl]-4,5-dihydro-stasNasanOtrivin MentolNasentropfen ALNasenspray AL2-((4-tert-butyl-2,6-dimethylphenyl)methyl)-4,5-dihydro-1H-imidazoleNasenSpray ratiopharm
データベース識別子
- CAS
526-36-3- PubChem CID
- 5709
- DTXSID
DTXSID8046957- ChEMBL
CHEMBL312448- ChEBI
CHEBI:10082- UNII
- WPY40FTH8K
- EC Number
- 208-390-6
- Nikkaji
- J6.660E
物性
構造計算による物性補完中
- XLogP
- 3.2
- 極性表面積
- 24.4 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 1
- 回転可能結合数
- 3
- 重原子数
- 18
- 形式電荷
- 0
- 複雑度
- 302
実験および物理化学的性質
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceutical
Pharmaceuticals
LogP3.2
Human Drugs
Breast Feeding; Lactation; Milk, Human; Adrenergic alpha-Agonists; Sympathomimetics; Nasal Decongestants
Pharmaceuticals
Ear, nose and throat medicines [c]
Melting Point
317-329
131 - 133 °C
Physical DescriptionSolid
Collision Cross Section
161.58 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
170.4 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]
物理化学的性質
- 融点
- 131 · 131-133°
- 沸点
- 394.2 · 394.2±21.0 °C(Predicted)
- 比重(密度)
- 1 · 1.00±0.1 g/cm3(Predicted)
- 貯蔵温度
- -20 °C · Store at -20°C
- 溶解性
- 49 mg/mL · DMSO: 49 mg/mL (200.51 mM);Ethanol: 49 mg/mL (200.51 mM)
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 InformationChemical: 1H-Imidazole, 2-[[4-(1,1-dimethylethyl)-2,6-dimethylphenyl]methyl]-4,5-dihydro-
Other Safety InformationIMAP assessments - 1H-Imidazole, 2-[[4-(1,1-dimethylethyl)-2,6-dimethylphenyl]methyl]-4,5-dihydro-: Environment tier I assessment
毒性情報
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
Xylometazoline
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
- LD50 oral in mouse: 215mg/kg
化学と産業
薬理情報
ATC Code
R01AA07
R - Respiratory system
R - Respiratory system
S - Sensory organs
QR - Respiratory system
QR - Respiratory system
Protein BindingNo information is available on xylometazoline pharmacokinetics.
Pharmacodynamics
Xylometazoline is a sympathomimetic agent that causes vasoconstriction of the nasal mucosa. In one study comprising subjects with nasal congestion associated with the common cold, the median time of onset of subjective relief of nasal congestion was about 1.7 minutes and the time of subjective peak relief of nasal congestion was 30 minutes. Previous studies reported rebound swelling, rebound nasal congestion, rhinitis medicamentosa, and shorter duration of decongestant effect from the long-term use of xylometazoline in healthy volunteers, suggesting that the drug is most effective if used temporarily. An early _in vitro_ study demonstrated xylometazoline to exert anti-oxidant actions, where it inhibited microsomal lipid peroxidation and mediated hydroxyl radical scavenging activity. This suggests that xylometazoline has a beneficial effect against oxidants, which play a role in tissue damage in inflammation.
Mechanism of Action
Nasal congestion is caused by various etiologies, such as rhinosinusitis and allergic or non-allergic rhinitis, leading to congestion of the venous sinusoids lining the nasal mucosa. Activation of α-adrenergic receptors leads to vasoconstriction of the blood vessels of the nasal mucosa and resumption of nasal airflow. As the most abundantly expressed in the human nasal mucosa, α<sub>1A</sub>- and α<sub>2B</sub>-adrenoceptors may play the most important role in vasoconstriction of the human nasal mucosa. Xylometazoline is a more selective agonist at α<sub>2B</sub>-adrenoceptors, with affinity at α<sub>1A</sub>-, α<sub>2A</sub>-, α<sub>2C</sub>-, α<sub>1B</sub>-, and α<sub>1D</sub>-adrenoceptors. Xylometazoline decreases nasal resistance during inspiration and expiration and increases the volume of nasal airflow. Compared to [oxymetazoline], another imidazoline nasal decongestant, xylometazoline had a slightly faster onset of action although they had a similar duration of action. In one study, subjects with nasal congestion reported relief of earache and sore throat in addition to nasal decongestion: it is speculated that oxymetazoline mediates this effect by causing vasoconstriction of the nasal mucosa that contains the venous sinuses and nasal decongestion allows breathing through the nose, providing relief from sore throat caused by mouth breathing that dries and irritates the throat.
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