基本情報
- 標準SMILES
O=C1CN=C(c2ccccc2)c2cc(Cl)ccc2N1- InChIKey
AKPLHCDWDRPJGD-UHFFFAOYSA-N- 分子式
- C15H11ClN2O
- 平均分子量
- 270.71 g/mol
- 単同位体質量
- 270.05599065
概要
Nordazepam is a 1,4-benzodiazepinone having phenyl and chloro substituents at positions 5 and 7 respectively; it has anticonvulsant, anxiolytic, muscle relaxant and sedative properties but is used primarily in the treatment of anxiety. It has a role as an anxiolytic drug, an anticonvulsant, a sedative, a GABA modulator and a human metabolite. It is a 1,4-benzodiazepinone and an organochlorine compound.
名称と識別子
- 優先名称
- Nordiazepam
- IUPAC
- 7-chloro-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one
- 現地名
- ノルダゼパム
- 英語名
- Nordazepam
- 分子式
- C15H11ClN2O
- 分子量
- 270.71
名称と別名
名称をさらに表示
データベース識別子
- CAS
1088-11-5- PubChem CID
- 2997
- DTXSID
DTXSID2049000- ChEMBL
CHEMBL523- ChEBI
CHEBI:111762- UNII
- 67220MCM01
- EC Number
- 214-123-4
- Nikkaji
- J7.250H
物性
構造計算による物性
- XLogP
- 2.9
- 極性表面積
- 41.5 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
- 1
- 重原子数
- 19
- 形式電荷
- 0
- 複雑度
- 376
実験および物理化学的性質
Drugs
DEA NFLIS-Drug Category -> Benzodiazepines
DEA Schedule IV Controlled Substance -> Depressants
Pharmaceuticals -> Benzodiazepines
Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds
Pharmaceuticals -> Listed in ZINC15
物理化学的性質
- 融点
- 208 · 208-210°C
- 沸点
- 453.1 · 453.1±45.0 °C(Predicted)
- 比重(密度)
- 1.2576 · 1.2576 (rough estimate)
- 屈折率
- 1.633 · 1.6330 (estimate)
- 闪点
- 11 °C · 11 °C
- 貯蔵温度
- 2 · 2-8°C
- 溶解性
- 10 mg/mL · DMSO:>10mg/mL
- 酸解離定数(Pka)
- 3.5 · pKa 3.5 12.0 (5%MeOH in H2O t=20 I=0.15) (Uncertain)
- 外見
- ニート&_&パウダー
- 色
- 白から薄い黄褐色
- 主な用途
- 臨床検査
- InChI
- 1S/C15H11ClN2O/c16-11-6-7-13-12(8-11)15(17-9-14(19)18-13)10-4-2-1-3-5-10/h1-8H,9H2,(H,18,19)
- InChIKey
- AKPLHCDWDRPJGD-UHFFFAOYSA-N
- SMILES
- Clc1ccc2NC(=O)CN=C(c3ccccc3)c2c1
- LogP
- 2.93 · 2.930
- NISTの化学物質情報
- Nordazepam(1088-11-5)
- EPAの化学物質情報
- 2 H-1,4-Benzodiazepin-2-one, · 2H-1,4-Benzodiazepin-2-one, 7-chloro-1,3-dihydro-5-phenyl- (1088-11-5)
化学的性質
化学的特性Off-White Solid
安全と法規制
GHS分類
GHS Classification
This chemical does not meet GHS hazard criteria for 8.3% (4 of 48) of reports.
Warning
H302 (89.6%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 48 reports by companies from 4 notifications to the ECHA C&L Inventory.
危険有害性情報
Regulatory Information
DEA schedule IV controlled substance
Status: Active Update: 04-04-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/21623
2H-1,4-Benzodiazepin-2-one, 7-chloro-1,3-dihydro-5-phenyl-: Does not have an individual approval but may be used under an appropriate group standard
毒性情報
Treatment
General supportive measures should be employed, along with intravenous fluids, and an adequate airway maintained. Hypotension may be combated by the use of norepinephrine or metaraminol. Dialysis is of limited value. Flumazenil (Anexate) is a competitive benzodiazepine receptor antagonist that can be used as an antidote for benzodiazepine overdose. In particular, flumazenil is very effective at reversing the CNS depression associated with benzodiazepines but is less effective at reversing respiratory depression. Its use, however, is controversial as it has numerous contraindications. It is contraindicated in patients who are on long-term benzodiazepines, those who have ingested a substance that lowers the seizure threshold, or in patients who have tachycardia or a history of seizures. As a general rule, medical observation and supportive care are the mainstay of treatment of benzodiazepine overdose. Although benzodiazepines are absorbed by activated charcoal, gastric decontamination with activated charcoal is not beneficial in pure benzodiazepine overdose as the risk of adverse effects often outweigh any potential benefit from the procedure. It is recommended only if benzodiazepines have been taken in combination with other drugs that may benefit from decontamination. Gastric lavage (stomach pumping) or whole bowel irrigation are also not recommended.
Toxicity Summary
Benzodiazepines bind nonspecifically to benzodiazepine receptors BNZ1, which mediates sleep, and BNZ2, which affects affects muscle relaxation, anticonvulsant activity, motor coordination, and memory. As benzodiazepine receptors are thought to be coupled to gamma-aminobutyric acid-A (GABAA) receptors, this enhances the effects of GABA by increasing GABA affinity for the GABA receptor. Binding of the inhibitory neurotransmitter GABA to the site opens the chloride channel, resulting in a hyperpolarized cell membrane that prevents further excitation of the cell.
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
Nordazepam
DILI Positive
DOI:10.1016/j.drudis.2019.09.022
USGS Health-Based Screening Levels for Evaluating Water-Quality
Nordiazepam
Pharmaceutical
Smith, C.D. and Nowell, L.H., 2024. Health-Based Screening Levels for evaluating water-quality data (3rd ed.). DOI:10.5066/F71C1TWP
安全データ
- wgk
- 3
- rtecs
- DF1750000
- ridadr
- 3249
- 毒性
- LD50 in mice (mg/kg): 2750 orally, >400 i.p. (Randall); LD50 in mice, rats (mg/kg): 1300, >5200 orally (company communication)
- hs_code
- 2933910000
- risk_code
- 22-39/23/24/25-23/24/25-11
- hazard_code
- Xn,T,F
- safety_code
- 7-16-36/37-45
- hazard_class
- 6.1(b)
- packing_group
- III
- Hazard Classifications
- Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralFlam. Liq. 2STOT SE 1
- ストレージクラス
- 3 - Flammable liquids
化学と産業
薬理情報
ATC Code
N05BA16
N - Nervous system
QN - Nervous system
MeSH Pharmacological Classification
Agents that alleviate ANXIETY, tension, and ANXIETY DISORDERS, promote sedation, and have a calming effect without affecting clarity of consciousness or neurologic conditions. ADRENERGIC BETA-ANTAGONISTS are commonly used in the symptomatic treatment of anxiety but are not included here.
Substances that do not act as agonists or antagonists but do affect the GAMMA-AMINOBUTYRIC ACID receptor-ionophore complex. GABA-A receptors (RECEPTORS, GABA-A) appear to have at least three allosteric sites at which modulators act: a site at which BENZODIAZEPINES act by increasing the opening frequency of GAMMA-AMINOBUTYRIC ACID-activated chloride channels; a site at which BARBITURATES act to prolong the duration of channel opening; and a site at which some steroids may act. GENERAL ANESTHETICS probably act at least partly by potentiating GABAergic responses, but they are not included here.
用途と製造
Use Classification
Pharmaceuticals
Pharmaceuticals -> Transformation products
上流・下流製品情報
上流原料
下流製品
補足説明
定義ChEBI: A 1,4-benzodiazepinone having phenyl and chloro substituents at positions 5 and 7 respectively; it has anticonvulsant, anxiolytic, muscle relaxant and sedative properties but is used primarily in the treatment of anxiety.
関連反応
関連ノート
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