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4205-90-7 分子结构
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N-(2,6-dichlorophenyl)-4,5-dihydro-1H-imidazol-2-amine

ChemBase编号:457
分子式:C9H9Cl2N3
平均质量:230.09386
单一同位素质量:229.01735266
SMILES和InChIs

SMILES:
Clc1c(NC2=NCCN2)c(Cl)ccc1
Canonical SMILES:
Clc1cccc(c1NC1=NCCN1)Cl
InChI:
InChI=1S/C9H9Cl2N3/c10-6-2-1-3-7(11)8(6)14-9-12-4-5-13-9/h1-3H,4-5H2,(H2,12,13,14)
InChIKey:
GJSURZIOUXUGAL-UHFFFAOYSA-N

引用这个纪录

CBID:457 http://www.chembase.cn/molecule-457.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
N-(2,6-dichlorophenyl)-4,5-dihydro-1H-imidazol-2-amine
IUPAC传统名
clonidine
商标名
Adesipress
Catapres
Catapres-TTS
Catapresan
Catapressan
Catarpres
Catarpresan
Clonistada
Dixarit
Duraclon
Duraclont
Ipotensium
Isoglaucon
Tenso-Timelets
别名
Clonidinum [INN-Latin]
Clonidinhydrochlorid
Clonidine HCl
Clonidin
Chlornidinum
ST 155BS
Clonidine
CAS号
4205-90-7
PubChem SID
46508119
160963920
PubChem CID
2803
CHEBI ID
3757
ATC码
S01EA04
C02AC01
N02CX02
CHEMBL
134
Chemspider ID
2701
DrugBank ID
DB00575
IUPHAR配体索引
516
KEGG ID
D00281
美国药典/FDA物质标识码
MN3L5RMN02
维基百科标题
Clonidine
Medline Plus
a682243

数据来源

数据来源

所有数据来源 商品来源 非商品来源
数据来源 数据ID 价格

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) 0.26298487  LogD (pH = 7.4) 1.6616611 
Log P 2.4850886  摩尔折射率 59.0888 cm3
极化性 21.926537 Å3 极化表面积 36.42 Å2
可自由旋转的化学键 里宾斯基五规则 true 
Log P 2.55  LOG S -2.68 
溶解度 4.80e-01 g/l 

分子性质

分子性质

理化性质 药理学性质 生物活性(PubChem)
溶解度
Appreciable expand 查看数据来源
疏水性(logP)
2.7 expand 查看数据来源
给药途径
oral, transdermal expand 查看数据来源
生物利用度
75-95% expand 查看数据来源
排泄
urine (40-50%) expand 查看数据来源
半衰期
12-33 hours expand 查看数据来源
代谢
Hepatic to inactive metabolites expand 查看数据来源
蛋白结合率
20-40% expand 查看数据来源
法定药品分级
Rx-only expand 查看数据来源
妊娠期药物分类
C (US) expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank Wikipedia Wikipedia
DrugBank -  DB00575 external link
Item Information
Drug Groups approved
Description Clonidine, an imidazoline-derivative hypotensive agent is a centrally-acting α2-adrenergic agonist. It crosses the blood-brain barrier and acts in the hypothalamus to induce a decrease in blood pressure. It may also be administered as an epidural infusion as an adjunct treatment in the management of severe cancer pain that is not relieved by opiate analgesics alone. Clonidine may be used for differential diagnosis of pheochromocytoma in hypertensive patients. Other uses for clonidine include prophylaxis of vascular migraine headaches, treatment of severe dysmenorrhea, management of vasomotor symptoms associated with menopause, rapid detoxification in the management of opiate withdrawal, treatment of alcohol withdrawal used in conjunction with benzodiazepines, management of nicotine dependence, topical use to reduce intraocular pressure in the treatment of open-angle and secondary glaucoma and hemorrhagic glaucoma associated with hypertension, and in the treatment of attention-deficit hyperactivity disorder (ADHD). Clonidine also exhibits some peripheral activity.
Indication May be used as an adjunct in the treatment of hypertension, as an epidural infusion as an adjunct treatment in the management of severe cancer pain that is not relieved by opiate analgesics alone, for differential diagnosis of pheochromocytoma in hypertensive patients, prophylaxis of vascular migraine headaches, treatment of severe dysmenorrhea, management of vasomotor symptoms associated with menopause, rapid detoxification in the management of opiate withdrawal, treatment of alcohol withdrawal used in conjunction with benzodiazepines, management of nicotine dependence, topical use to reduce intraocular pressure in the treatment of open-angle and secondary glaucoma and hemorrhagic glaucoma associated with hypertension, and in the treatment of attention-deficit hyperactivity disorder (ADHD).
Pharmacology Clonidine is an α-adrenergic agent that acts specifically on α2-receptors. α2-receptors regulate a number of signaling pathways mediated by multiple Gi proteins, Gαi1, Gαi2, and G&alphai3. Stimulation of α2-receptors mediates effects such as inhibition of adenylyl cyclase, stimulation fo phospholipase D, stimulation of mitogen-activated protein kinases, stimulation of K+ currents and inhibition of Ca2+ currents. Three G-protein coupled α2-receptor subtypes have been identified: α2A, α2B, and α2C. Each subtype has a unique pattern of tissue distribution in the central nervous system and peripheral tissues. The α2A-receptor is widely distributed throughout the central nervous system; it is found in the locus coeruleus, brain stem nuclei, cerebral cortex, septum, hypothalamus, and hippocampus. α2A-receptors are also expressed in the kidneys, spleen, thymus, lung and salivary glands. The α2C-receptor is primarily expressed in the central nervous system, including the striatum, olfactory tubercle, hippocampus and cerebral cortex. Low levels of the α2C-subtype are also found in the kidneys. The α2B-receptor is located primarily in the periphery (kidney, liver, lung and heart) with low levels of expression in the thalamic nuclei of the central nervous system. The α2A- and α2C-receptors are located presynaptically and inhibit the released of noradrenaline from sympathetic nerves. Stimulation of these receptors decreases sympathetic tone, resulting in decreases in blood pressure and heart rate. Sedation and analgesia is mediated by centrally located α2A-receptors, while peripheral α2B-receptors mediate constriction of vascular smooth muscle. α2A-Receptors also mediate essential components of the analgesic effect of nitrous oxide in the spinal cord. Clonidine stimulates all three α2-receptor subtypes with similar potency. Its actions in the nervous system decreases blood pressure in patients with hypertension and decreases sympathetic overactivity in patients undergoing opioid withdrawal. Clonidine is also a potent sedative and analgesic and can prevent post-operative shivering in intensive and post-operative care. Its use in differential diagnosis of pheochromocytoma owes to the fact that hypertension in patients with pheochromocytoma is refractory to antihypertensive treatment with clonidine.
Toxicity Oral LD50 is 150 mg/kg in rat and 30 mg/kg in dog. Symptoms of overdose include constriction of pupils of the eye, drowsiness, high blood pressure followed by a drop in pressure, irritability, low body temperature, slowed breathing, slowed heartbeat, slowed reflexes, and weakness.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic. Metabolized via minor pathways. The major metabolite, p-hydroxyclonidine, is present in concentrations less than 10% of those of unchanged clonidine in urine. Four metabolites have been detected, but only p-hydroxyclonidine has been identified.
Absorption Well absorbed following oral administration. Bioavailability following chronic administration is approximately 65%.
Half Life 6-20 hours; 40-60% is excreted in urine unchanged, 20% is excreted in feces. Less than 10% is excreted by p-hydroxyclonidine.
Protein Binding 20-40%, primarily to albumin
References
Schapiro NA: "Dude, you don't have Tourette's:" Tourette's syndrome, beyond the tics. Pediatr Nurs. 2002 May-Jun;28(3):243-6, 249-53. [Pubmed]
Hossmann V, Maling TJ, Hamilton CA, Reid JL, Dollery CT: Sedative and cardiovascular effects of clonidine and nitrazepam. Clin Pharmacol Ther. 1980 Aug;28(2):167-76. [Pubmed]
External Links
Wikipedia
RxList
PDRhealth
Drugs.com

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Schapiro NA: "Dude, you don't have Tourette's:" Tourette's syndrome, beyond the tics. Pediatr Nurs. 2002 May-Jun;28(3):243-6, 249-53. Pubmed
  • Hossmann V, Maling TJ, Hamilton CA, Reid JL, Dollery CT: Sedative and cardiovascular effects of clonidine and nitrazepam. Clin Pharmacol Ther. 1980 Aug;28(2):167-76. Pubmed
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专利

专利

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