Lormetazepam

HCID 13314CAS 848-75-9

기본 정보

표준 SMILES
CN1C(=O)C(O)N=C(c2ccccc2Cl)c2cc(Cl)ccc21
InChIKey
FJIKWRGCXUCUIG-UHFFFAOYSA-N
분자식
C16H12Cl2N2O2
평균 분자량
335.2 g/mol
단동위원소 질량
334.02758298

개요

Lormetazepam is a 1,4-benzodiazepinone compound having a methyl substituent at the 1-position, a hydroxy substituent at the 3-position, a 2-chlorophenyl group at the 5-position and a chloro substituent at the 7-position. It has a role as a sedative. It is a 1,4-benzodiazepinone and an organochlorine compound.

이름 및 식별자

우선 이름
Lormetazepam
IUPAC
7-chloro-5-(2-chlorophenyl)-3-hydroxy-1-methyl-3H-1,4-benzodiazepin-2-one
영어명
LORMETAZEPAM
분자식
C16H12Cl2N2O2
분자량
335.18

이름 및 동의어

LormetazepamMethyllorazepamN-MethyllorazepamLoramet848-75-9LormetazepamumChlorotemazepamWY-40827-Chloro-5-(2-chlorophenyl)-1,3-dihydro-3-hydroxy-1-methyl-2H-1,4-benzodiazepin-2-one7-Chloro-5-(o-chlorophenyl)-1,3-dihydro-3-hydroxy-1-methyl-2H-1,4-benzodiazepin-2-one7-Chloro-5-(2-chlorophenyl)-3-hydroxy-1-methyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one7-chloro-5-(2-chlorophenyl)-3-hydroxy-1-methyl-3H-1,4-benzodiazepin-2-one
이름 더 보기
ErgocalmNoctamidRO 5-5516lormethazepam(RS)-Lormetazepam
GU56C842ZA2H-1,4-Benzodiazepin-2-one, 7-chloro-5-(2-chlorophenyl)-1,3-dihydro-3-hydroxy-1-methyl-DTXSID408624422H-1,4-Benzodiazepin-2-one, 1,3-dihydro-7-chloro-5-(o-chlorophenyl)-3-hydroxy-1-methyl-CHEBI:529937-Chloro-5-(2-chlorophenyl)-3-hydroxy-1-methyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one(+-)-LormetazepamRefChem:800047

데이터베이스 식별자

CAS
848-75-9
PubChem CID
13314
DTXSID
DTXSID40862442
ChEMBL
CHEMBL22097
ChEBI
CHEBI:52993
UNII
GU56C842ZA
EC Number
212-700-5
Nikkaji
J7.142K

물성

구조 계산 물성

XLogP
2.4
극성 표면적
52.9 Ų
수소 결합 공여자 수
1
수소 결합 수용자 수
3
회전 가능 결합 수
1
무거운 원자 수
22

실험 및 물리화학적 성질

Drugs · 5건

DEA NFLIS-Drug Category -> Benzodiazepines

DEA Schedule IV Controlled Substance -> Depressants

Pharmaceuticals -> Benzodiazepines

Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds

Pharmaceuticals

LogP2.5
Human Drugs · 2건

Breast Feeding; Lactation; Milk, Human; Hypnotics and Sedatives; Anti-Anxiety Agents; Benzodiazepines

Pharmaceuticals

Melting Point206 °C
Physical DescriptionSolid
Collision Cross Section169.5 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]

물리화학적 성질

녹는점
163 · 163-168°C
끓는 점
575.8 · 575.8±50.0 °C(Predicted)
밀도
1.4463 · 1.4463 (rough estimate)
굴절률
1.61 · 1.6100 (estimate)
인화점
9 ℃ · 9℃
저장 조건
-20 °C · Controlled Substance, -20°C Freezer

화학적 성질

Pale Green Solid

안전 및 규제

GHS 분류

GHS Classification · 4건

Danger

H319 (33.3%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

P203, P260, P261, P263, P264, P264+P265, P270, P271, P280, P304+P340, P305+P351+P338, P318, P319, P337+P317, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 3 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

유해성 정보

Regulatory Information · 2건

DEA schedule IV controlled substance

Lormetazepam: Does not have an individual approval but may be used under an appropriate group standard

Hazard Classes and CategoriesEye Irrit. 2 (33.3%)

독성 정보

Treatment · 1건

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 · 1건

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.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver Injury · 4건

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

Lormetazepam

DILI Positive

DOI:10.1016/j.drudis.2019.09.022

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

안전 데이터

wgk
1
ridadr
3249
risk_code
11-23/24/25-39/23/24/25-22
hazard_code
F,T
safety_code
7-16-36/37-45-36
포장분류
III

화학 및 산업

약리 정보

ATC Code · 3건

N05CD06

N - Nervous system

QN - Nervous system

Pharmacodynamics · 1건

Lormetazepam is a benzodiazepine which reduces central nervous system (CNS) activity. It produces anxiolytic, muscle relaxant, sedative and hypnotic effects. Because it is a short-acting benzodiapine, it does not produce significant sedation after waking.

Mechanism of Action · 1건

Lormetazepam, as a benzodiazepine, binds to the regulatory site between the α and γ subunits of γ-aminobutryic acid (GABA) A receptors with γ2 and α1, α2, α3, or α5 subunits. This facilitates the opening of the chloride channel allowing chloride ions to flow into the neuron resulting in hyperpolarization. Hyperpolarized neurons require greater simulation to reach their action potential threshold. The general inhibitory effect on neuronal depolarization produces the effects of lormetazepam.

Biological Half-LifeThe terminal phase half life is 11 h.
Metabolism/MetabolitesMetabolised to an inactive metabolite via glucuronide conjugation
MeSH Pharmacological ClassificationDrugs used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.

용도 및 제조

Uses · 2건

Use (kg; approx.) in Germany (2009): >25

Lormetazepam is a short-acting benzodiazepine and is sometimes used in patients who have difficulty in maintaining sleep or falling asleep.

Use ClassificationPharmaceuticals

응용 분야

용도An analog of Lorazepam (L469850). Sedative, hypnotic. Controlled substance (depressant).

상·하류 제품 정보

상류 원료

관련 반응

1건

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