기본 정보
- 표준 SMILES
O=C1CN=C(c2ccccc2)c2cc(Cl)ccc2N1- InChIKey
AKPLHCDWDRPJGD-UHFFFAOYSA-N- 분자식
- C15H11ClN2O
- 평균 분자량
- 270.71 g/mol
- 단동위원소 질량
- 270.05599065
개요
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.
이름 및 식별자
- 우선 이름
- Nordiazepam
- IUPAC
- 7-chloro-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one
- 영어명
- Nordazepam
- 분자식
- C15H11ClN2O
- 분자량
- 270.71
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- CAS
1088-11-5- PubChem CID
- 2997
- DTXSID
DTXSID2049000- ChEMBL
CHEMBL523- ChEBI
CHEBI:111762- UNII
- 67220MCM01
- EC Number
- 214-123-4
- Nikkaji
- J7.250H
물성
구조 계산 물성
- XLogP
- 2.9
- 극성 표면적
- 41.5 Ų
- 수소 결합 공여자 수
- 1
- 수소 결합 수용자 수
- 2
- 회전 가능 결합 수
- 1
- 무거운 원자 수
- 19
- 형식 전하
- 0
- 복잡도
- 376
실험 및 물리화학적 성질
Drugs
DEA NFLIS-Drug Category -> Benzodiazepines
DEA Schedule IV Controlled Substance -> Depressants
Pharmaceuticals -> Benzodiazepines
Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds
Pharmaceuticals -> Listed in ZINC15
물리화학적 성질
- 녹는점
- 208 · 208-210°C
- 끓는 점
- 453.1 · 453.1±45.0 °C(Predicted)
- 밀도
- 1.2576 · 1.2576 (rough estimate)
- 굴절률
- 1.633 · 1.6330 (estimate)
- 인화점
- 11 °C · 11 °C
- 저장 조건
- 2 · 2-8°C
- 용해도
- 10 mg/mL · DMSO: >10mg/mL
- 산도 계수 (pKa)
- 3.5 · pKa 3.5 12.0 (5%MeOH in H2O t=20 I=0.15) (Uncertain)
- 물리적 상태
- 깔끔한 &_& 파우더
- 색상
- 흰색에서 밝은 황갈색
- 주요 응용
- 임상 시험
- 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
- Nordazepam(1088-11-5)
- EPA
- 2 H-1,4-Benzodiazepin-2-one, · 2H-1,4-Benzodiazepin-2-one, 7-chloro-1,3-dihydro-5-phenyl- (1088-11-5)
화학적 성질
Off-White Solid
안전 및 규제
GHS 분류
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.
유해성 정보
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
독성 정보
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
안전 데이터
- wgk
- 3
- rtecs
- DF1750000
- ridadr
- 3249
- 독성
- LD50 in mice (mg/kg): 2750 orally, >400 i.p. (Randall); LD50 in mice, rats (mg/kg): 1300, >5200 orally (company communication)
- HS 번호
- 2933910000
- risk_code
- 22-39/23/24/25-23/24/25-11
- hazard_code
- Xn,T,F
- safety_code
- 7-16-36/37-45
- 포장분류
- III
- 위험 등급
- 6.1(b)
- Hazard Classifications
- Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralFlam. Liq. 2STOT SE 1
- 스토리지 클래스
- 3 - Flammable liquids
화학 및 산업
약리 정보
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.
용도 및 제조
Use Classification
Pharmaceuticals
Pharmaceuticals -> Transformation products
상·하류 제품 정보
상류 원료
하류 제품
추가 설명
정의ChEBI: 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.
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