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439-14-5 分子结构
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7-chloro-1-methyl-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one

ChemBase编号:708
分子式:C16H13ClN2O
平均质量:284.74022
单一同位素质量:284.07164073
SMILES和InChIs

SMILES:
Clc1cc2c(N(C(=O)CN=C2c2ccccc2)C)cc1
Canonical SMILES:
Clc1ccc2c(c1)C(=NCC(=O)N2C)c1ccccc1
InChI:
InChI=1S/C16H13ClN2O/c1-19-14-8-7-12(17)9-13(14)16(18-10-15(19)20)11-5-3-2-4-6-11/h2-9H,10H2,1H3
InChIKey:
AAOVKJBEBIDNHE-UHFFFAOYSA-N

引用这个纪录

CBID:708 http://www.chembase.cn/molecule-708.html

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
7-chloro-1-methyl-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one
IUPAC传统名
diazepam
商标名
Diastat, Valium
Alboral
Aliseum
Alupram
Amiprol
An-Ding
Ansiolin
Ansiolisina
Apaurin
Apo-Diazepam
Apozepam
Armonil
Assival
Atensine
Atilen
Bensedin
Bialzepam
Calmocitene
Calmpose
Cercine
Ceregulart
Condition
Diacepan
Dialag
Dialar
Diapam
Diastat
Diazemuls
Diazemulus
Diazepam Intensol
Diazepan
Diazetard
Dienpax
Dipam
Dipezona
Dizac
Domalium
Duksen
Duxen
E-Pam
Eridan
Eurosan
Evacalm
Faustan
Faustan,
Freudal
Frustan
Gewacalm
Gihitan
Kabivitrum
Kiatrium
LA III
La-Iii
Lamra
Lembrol
Levium
Liberetas
Mandrozep
Morosan
Neurolytril
Noan
Novazam
Novo-Dipam
Paceum
Pacitran
Paranten
Paxate
Paxel
Plidan
Pms-Diazepam
Pro-Pam
Q-Pam
Q-Pam Relanium
Quetinil
Quiatril
Quievita
Relaminal
Relanium
Renborin
Ruhsitus
Saromet
Sedapam
Sedipam
Seduksen
Seduxen
Serenack
Serenamin
Serenzin
Servizepam
Setonil
Sibazon
Sibazone
Solis
Sonacon
Stesolid
Stesolin
Tensopam
Tranimul
Tranqdyn
Tranquase
Tranquirit
Tranquo-Puren
Tranquo-Tablinen
Umbrium
Unisedil
Usempax Ap
Valaxona
Valeo
Valiquid
Valitran
Valium
Valrelease
Vatran
Velium
Vival
Vivol
Zetran
Zipan
别名
地西泮 溶液
地西泮
Diazepam solution
7-Chloro-1-methyl-5-phenyl-3H-1,4-benzodiazepin-2(1H)-one
Ro 5-2807
Diazepam
7-Chloro-1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one
1-Methyl-5-phenyl-7-chloro-1,3-dihydro-2H-1,4-benzodiazepin-2-one
Alboral
Aliseum
Alupram
Apaurin
Diacepan
Diaceplex
Dialag
Novazam
Valium
DAP
Methyldiazepinone
Diazepam
CAS号
439-14-5
EC号
207-122-5
200-659-6
MDL号
MFCD00057323
PubChem SID
160964171
24893306
24894120
46505210
PubChem CID
3016
CHEBI ID
49575
ATC码
N05BA01
CHEMBL
12
Chemspider ID
2908
DrugBank ID
DB00829
IUPHAR配体索引
3364
KEGG ID
D00293
美国药典/FDA物质标识码
Q3JTX2Q7TU
维基百科标题
Diazepam
Medline Plus
a682047

数据来源

数据来源

所有数据来源 商品来源 非商品来源

理论计算性质

理论计算性质

JChem ALOGPS 2.1
质子受体 质子供体
LogD (pH = 5.5) 3.0749424  LogD (pH = 7.4) 3.0760722 
Log P 3.0760865  摩尔折射率 79.8119 cm3
极化性 30.31823 Å3 极化表面积 32.67 Å2
可自由旋转的化学键 里宾斯基五规则 true 
Log P 2.63  LOG S -4.37 
溶解度 1.22e-02 g/l 

分子性质

分子性质

理化性质 安全信息 药理学性质 产品相关信息 生物活性(PubChem)
溶解度
45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: soluble1.6 mg/mL expand 查看数据来源
Chloroform expand 查看数据来源
DMF expand 查看数据来源
DMF: soluble expand 查看数据来源
ethanol: soluble expand 查看数据来源
H2O: slightly soluble expand 查看数据来源
Slightly soluble (50 mg/L) expand 查看数据来源
外观
White to Off-White Solid expand 查看数据来源
熔点
115-117°C expand 查看数据来源
闪点
11 °C expand 查看数据来源
51.8 °F expand 查看数据来源
疏水性(logP)
2.9 expand 查看数据来源
保存条件
Controlled Substance, -20°C Freezer expand 查看数据来源
RTECS编号
DF1575000 expand 查看数据来源
欧盟危险性物质标志
易燃性(Flammable) 易燃性(Flammable) (F) expand 查看数据来源
有毒(Toxic) 有毒(Toxic) (T) expand 查看数据来源
有害性(Harmful) 有害性(Harmful) (Xn) expand 查看数据来源
联合国危险货物编号
1230 expand 查看数据来源
2811 expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
德国WGK号
1 expand 查看数据来源
2 expand 查看数据来源
联合国危险货物等级
3 expand 查看数据来源
6.1 expand 查看数据来源
联合国危险货物包装类别(PG)
2 expand 查看数据来源
3 expand 查看数据来源
危险公开号
11-23/24/25-39/23/24/25 expand 查看数据来源
21/22 expand 查看数据来源
安全公开号
36/37 expand 查看数据来源
7-16-36/37-45 expand 查看数据来源
GHS危险品标识
GHS02 expand 查看数据来源
GHS06 expand 查看数据来源
GHS08 expand 查看数据来源
GHS警示词
Danger expand 查看数据来源
GHS危险声明
H225-H301-H311-H331-H370 expand 查看数据来源
H301 + H311 expand 查看数据来源
GHS警示性声明
P210-P260-P280-P301 + P310-P311 expand 查看数据来源
P280-P301 + P310-P312 expand 查看数据来源
个人保护装置
dust mask type N95 (US), Eyeshields, Faceshields, Gloves expand 查看数据来源
Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter expand 查看数据来源
RID/ADR
UN 1230 3/PG 2 expand 查看数据来源
UN 2811 6.1/PG 3 expand 查看数据来源
毒品管制信息
Home Office Schedule 4.1; psychotrope; kontrollierte Droge in Deutschland expand 查看数据来源
USDEA Schedule IV; Home Office Schedule 4.1; psychotrope; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada expand 查看数据来源
保存温度
2-8°C expand 查看数据来源
给药途径
Oral, IM, IV, suppository expand 查看数据来源
生物利用度
(93-100%) expand 查看数据来源
排泄
Renal expand 查看数据来源
半衰期
20–100 hours (36-200 hours for main active metabolite desmethyldiazepam) expand 查看数据来源
代谢
Hepatic - CYP2C19 expand 查看数据来源
法定药品分级
CD (UK) expand 查看数据来源
S4 (Australia) expand 查看数据来源
Schedule IV (Canada) expand 查看数据来源
Schedule IV (International) expand 查看数据来源
Schedule IV (US) expand 查看数据来源
妊娠期药物分类
C (Australia) expand 查看数据来源
D (US) expand 查看数据来源
相关基因信息
human ... GABRA1(2554), GABRA2(2555), GABRA3(2556), GABRA5(2558), GABRA6(2559), GABRG2(2566)mouse ... Gabrg2(14406)rat ... Gabra1(29705), Gabra2(29706) expand 查看数据来源
human ... GABRA1(2554), GABRA2(2555), GABRA3(2556), GABRA5(2558), GABRA6(2559)rat ... Gabra1(29705), Gabra2(29706) expand 查看数据来源
浓度
1.0 mg/mL in methanol expand 查看数据来源
1.0 mg/mL±5% in methanol expand 查看数据来源
级别
analytical standard, for drug analysis expand 查看数据来源
质检报告
下载链接 expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank -  DB00829 external link
Item Information
Drug Groups illicit; approved
Description A benzodiazepine with anticonvulsant, anxiolytic, sedative, muscle relaxant, and amnesic properties and a long duration of action. Its actions are mediated by enhancement of gamma-aminobutyric acid activity. It is used in the treatment of severe anxiety disorders, as a hypnotic in the short-term management of insomnia, as a sedative and premedicant, as an anticonvulsant, and in the management of alcohol withdrawal syndrome. (From Martindale, The Extra Pharmacopoeia, 30th ed, p589)
Indication Used in the treatment of severe anxiety disorders, as a hypnotic in the short-term management of insomnia, as a sedative and premedicant, as an anticonvulsant, and in the management of alcohol withdrawal syndrome.
Pharmacology Diazepam, a benzodiazepine, generates the same active metabolite as chlordiazepoxide and clorazepate. In animals, diazepam appears to act on parts of the limbic system, the thalamus and hypothalamus, and induces calming effects. Diazepam, unlike chlorpromazine and reserpine, has no demonstrable peripheral autonomic blocking action, nor does it produce extrapyramidal side effects; however, animals treated with diazepam do have a transient ataxia at higher doses. Diazepam was found to have transient cardiovascular depressor effects in dogs. Long-term experiments in rats revealed no disturbances of endocrine function. Injections into animals have produced localized irritation of tissue surrounding injection sites and some thickening of veins after intravenous use.
Toxicity Symptoms of overdose include somnolence, confusion, coma, and diminished reflexes. Respiration, pulse and blood pressure should be monitored.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic via the Cytochrome P450 enzyme system. The main active metabolite is desmethyldiazepam, in addition to minor active metabolites including temazepam and oxazepam.
Absorption Essentially complete, with a bioavailability of 93%.
Half Life Biphasic 1-2 days and 2-5 days, active metabolites with long half lives.
Protein Binding 98.5%
Elimination Diazepam and its metabolites are excreted mainly in the urine, predominantly as their glucuronide conjugates.
Distribution * 0.8 to 1.0 L/kg [young healthy males]
Clearance * 20-30 mL/min
References
Mant A, Whicker SD, McManus P, Birkett DJ, Edmonds D, Dumbrell D: Benzodiazepine utilisation in Australia: report from a new pharmacoepidemiological database. Aust J Public Health. 1993 Dec;17(4):345-9. [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]
Usami N, Yamamoto T, Shintani S, Ishikura S, Higaki Y, Katagiri Y, Hara A: Substrate specificity of human 3(20)alpha-hydroxysteroid dehydrogenase for neurosteroids and its inhibition by benzodiazepines. Biol Pharm Bull. 2002 Apr;25(4):441-5. [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]
McLean MJ, Macdonald RL: Benzodiazepines, but not beta carbolines, limit high frequency repetitive firing of action potentials of spinal cord neurons in cell culture. J Pharmacol Exp Ther. 1988 Feb;244(2):789-95. [Pubmed]
External Links
Wikipedia
RxList
PDRhealth
Drugs.com
Sigma Aldrich -  D0899 external link
Biochem/physiol Actions
Benzodiazepine anxiolytic; prototype ligand for the GABAA receptor benzodiazepine modulatory site.
Toronto Research Chemicals -  D416855 external link
Diazepam is an anxiolytic; muscle relaxant (skeletal); anticonvulsant.Diazepam is a controlled substance (depressant).

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Mant A, Whicker SD, McManus P, Birkett DJ, Edmonds D, Dumbrell D: Benzodiazepine utilisation in Australia: report from a new pharmacoepidemiological database. Aust J Public Health. 1993 Dec;17(4):345-9. 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
  • Usami N, Yamamoto T, Shintani S, Ishikura S, Higaki Y, Katagiri Y, Hara A: Substrate specificity of human 3(20)alpha-hydroxysteroid dehydrogenase for neurosteroids and its inhibition by benzodiazepines. Biol Pharm Bull. 2002 Apr;25(4):441-5. 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
  • McLean MJ, Macdonald RL: Benzodiazepines, but not beta carbolines, limit high frequency repetitive firing of action potentials of spinal cord neurons in cell culture. J Pharmacol Exp Ther. 1988 Feb;244(2):789-95. Pubmed
  • MacDonald, A., et al.: Anal. Profiles Drug Subs., 1, 79 (1972)
  • Mandelli, M., et al.: Clin. Pharmacokinet., 3, 72 (1972)
  • Bertilsson, L., et al.: Pharmacol. Ther., 45, 85 (1972)
  • Murray, J.B., et al.: J. Psychol., 124, 655 (1972)
  • Pellock, J.M., et al.: D
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