(2Z)-7-chloro-2-(methylimino)-5-phenyl-3,4-dihydro-2H-1,4-benzodiazepin-4-ol

• ChemBase编号: 358
• 分子式: C16H14ClN3O
• 平均质量: 299.75486
• 单一同位素质量: 299.08253976
• SMILES: Clc1cc2=C(N(O)C/C(=N/C)/N=c2cc1)c1ccccc1
• Canonical SMILES: C/N=C\1/CN(O)C(=c2c(=N1)ccc(c2)Cl)c1ccccc1
• InChI: InChI=1S/C16H14ClN3O/c1-18-15-10-20(21)16(11-5-3-2-4-6-11)13-9-12(17)7-8-14(13)19-15/h2-9,21H,10H2,1H3/b18-15-
• InChIKey: BUCORZSTKDOEKQ-SDXDJHTJSA-N

名称和登记号

名称

• IUPAC标准名: (2Z)-7-chloro-2-(methylimino)-5-phenyl-3,4-dihydro-2H-1,4-benzodiazepin-4-ol
• IUPAC传统名: chlordiazepoxide
• 商标名: Chloridiazepoxide; Chlorodiazepoxide; Chlozepid; Clopoxide; Clordiazepossido; Contol; Control; Decacil; Eden; Elenium; Helogaphen; Ifibrium; Kalmocaps; Librax; Librelease; Librinin; Libritabs; Librium; Limbitrol; Limbitrol Ds; Lygen; Menrium; Mesural; Methaminodiazepoxide; Mildmen; Multum; Napoton; Napton; Novo-Poxide; Psicosan; Radepur; Risolid; Silibrin; Tropium; Viopsicol; A-Poxide; Abboxide; Apo-Chlordiazepoxide; Balance; CD 2; CDO; CDP; Chloradiazepoxide; Chlordiazachel; Chlordiazepoxid; Chlordiazepoxide Base; Chlordiazepoxide Hcl; Chlordiazepoxidum; Chloridazepoxide; Chloridiazepide
• 别名: Chlordiazepoxide

登记号

• CAS号: 58-25-3
• PubChem SID: 160963821
• PubChem CID: 2712

理论计算性质

JChem

• Acid pKa: 14.691953
• 质子受体: 4
• 质子供体: 1
• LogD (pH = 5.5): 1.6254307
• LogD (pH = 7.4): 1.6284057
• Log P: 1.6284437
• 摩尔折射率: 87.4266 cm^3
• 极化性: 31.666967 Å^3
• 极化表面积: 48.19 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.98
• LOG S: -3.8
• 溶解度: 4.78e-02 g/l

分子性质

理化性质

• 溶解度: 2000 mg/L
• 疏水性(logP): 1.7

详细说明

DrugBank - DB00475

• Drug Groups: illicit; approved
• Description: An anxiolytic benzodiazepine derivative with anticonvulsant, sedative, and amnesic properties. It has also been used in the symptomatic treatment of alcohol withdrawal. [PubChem]
• Indication: For the management of anxiety disorders or for the short-term relief of symptoms of anxiety, withdrawal symptoms of acute alcoholism, and preoperative apprehension and anxiety.
• Pharmacology: Chlordiazepoxide has antianxiety, sedative, appetite-stimulating and weak analgesic actions. The drug seems to block EEG arousal from stimulation in the brain stem reticular formation. The drug has been studied extensively in many species of animals and these studies are suggestive of action on the limbic system of the brain, which recent evidence indicates is involved in emotional responses. Hostile monkeys were made tame by oral drug doses which did not cause sedation. Chlordiazepoxide revealed a "taming" action with the elimination of fear and aggression. The taming effect of chlordiazepoxide was further demonstrated in rats made vicious by lesions in the septal area of the brain. The drug dosage which effectively blocked the vicious reaction was well below the dose which caused sedation in these animals.
• Toxicity: LD₅₀=537 mg/kg (Orally in rats). Signs of overdose include respiratory depression, muscle weakness, somnolence (general depressed activity).
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• Half Life: 24-48 hours
• Elimination: Chlordiazepoxide is excreted in the urine, with 1% to 2% unchanged and 3% to 6% as conjugate.
• References: Skerritt JH, Johnston GA: Enhancement of GABA binding by benzodiazepines and related anxiolytics. Eur J Pharmacol. 1983 May 6;89(3-4):193-8. [Pubmed] ; Oishi R, Nishibori M, Itoh Y, Saeki K: Diazepam-induced decrease in histamine turnover in mouse brain. Eur J Pharmacol. 1986 May 27;124(3):337-42. [Pubmed] ; Earley JV, Fryer RI, Ning RY: Quinazolines and 1,4-benzodiazepines. LXXXIX: Haptens useful in benzodiazepine immunoassay development. J Pharm Sci. 1979 Jul;68(7):845-50. [Pubmed] ; Olive G, Dreux C: [Pharmacologic bases of use of benzodiazepines in pereinatal medicine] Arch Fr Pediatr. 1977 Jan;34(1):74-89. [Pubmed] ; Vozeh S: [Pharmacokinetic of benzodiazepines in old age] Schweiz Med Wochenschr. 1981 Nov 21;111(47):1789-93. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

参考文献

• Skerritt JH, Johnston GA: Enhancement of GABA binding by benzodiazepines and related anxiolytics. Eur J Pharmacol. 1983 May 6;89(3-4):193-8. Pubmed
• Oishi R, Nishibori M, Itoh Y, Saeki K: Diazepam-induced decrease in histamine turnover in mouse brain. Eur J Pharmacol. 1986 May 27;124(3):337-42. Pubmed
• Earley JV, Fryer RI, Ning RY: Quinazolines and 1,4-benzodiazepines. LXXXIX: Haptens useful in benzodiazepine immunoassay development. J Pharm Sci. 1979 Jul;68(7):845-50. Pubmed
• Olive G, Dreux C: [Pharmacologic bases of use of benzodiazepines in pereinatal medicine] Arch Fr Pediatr. 1977 Jan;34(1):74-89. Pubmed
• Vozeh S: [Pharmacokinetic of benzodiazepines in old age] Schweiz Med Wochenschr. 1981 Nov 21;111(47):1789-93. Pubmed