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60142-96-3 分子结构
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2-[1-(aminomethyl)cyclohexyl]acetic acid

ChemBase编号:869
分子式:C9H17NO2
平均质量:171.23678
单一同位素质量:171.12592879
SMILES和InChIs

SMILES:
OC(=O)CC1(CCCCC1)CN
Canonical SMILES:
NCC1(CCCCC1)CC(=O)O
InChI:
InChI=1S/C9H17NO2/c10-7-9(6-8(11)12)4-2-1-3-5-9/h1-7,10H2,(H,11,12)
InChIKey:
UGJMXCAKCUNAIE-UHFFFAOYSA-N

引用这个纪录

CBID:869 http://www.chembase.cn/molecule-869.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
2-[1-(aminomethyl)cyclohexyl]acetic acid
IUPAC传统名
gabapentin
2-[1-(aminomethyl)cyclohexyl]acetic acid
商标名
Aclonium
Neurontin
Novo-Gabapentin
别名
1-(Aminomethyl)cyclohexaneacetic Acid, Neurontin, GOE-3450
Fanatrex
Gabarone
Neurontin
1-(Aminomethyl)-cyclohexaneacetic acid
Gabapentin
Gabapentine [INN-French]
Gabapentino [INN-Spanish]
Gabapentino [Spanish]
Gabapentinum [INN-Latin]
Gabapetin
Gabapentin GR
gabapentin
Gabapentin
2-(1-(aminomethyl)cyclohexyl)acetic acid
(1-Aminomethyl-cyclohexyl)-acetic acid
Aclonium
2-[1-(aminomethyl)cyclohexyl]acetic acid
CAS号
60142-96-3
EC号
262-076-3
MDL号
MFCD00865286
Beilstein号
2359739
PubChem SID
160964332
46506529
24278159
PubChem CID
3446

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 4.6313047  质子受体
质子供体 LogD (pH = 5.5) -1.3162769 
LogD (pH = 7.4) -1.2728618  Log P -1.273033 
摩尔折射率 46.3283 cm3 极化性 18.621471 Å3
极化表面积 63.32 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P -1.88  LOG S -1.6 
溶解度 4.34e+00 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
4490 mg/L expand 查看数据来源
H2O: soluble10 mg/mL expand 查看数据来源
Methanol expand 查看数据来源
Water expand 查看数据来源
外观
off-white solid expand 查看数据来源
White to Off-White Solid expand 查看数据来源
熔点
162-166°C expand 查看数据来源
169 - 171°C expand 查看数据来源
疏水性(logP)
-0.66 expand 查看数据来源
1.4 expand 查看数据来源
保存条件
-20°C expand 查看数据来源
Refrigerator expand 查看数据来源
保存注意事项
IRRITANT expand 查看数据来源
RTECS编号
GU6496000 expand 查看数据来源
欧盟危险性物质标志
有毒(Toxic) 有毒(Toxic) (T) expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
德国WGK号
3 expand 查看数据来源
危险公开号
61-36/37/38 expand 查看数据来源
安全公开号
26-36/37/39-45 expand 查看数据来源
TSCA收录
false expand 查看数据来源
GHS危险品标识
GHS07 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
H315-H319-H335-H360 expand 查看数据来源
GHS警示性声明
P201-P261-P305 + P351 + P338-P308 + P313 expand 查看数据来源
个人保护装置
Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges expand 查看数据来源
相关基因信息
human ... ADORA1(134), CACNA2D1(781)rat ... Cacna1a(25398) expand 查看数据来源
生物活性机理
GABA-like amino acid which penetrates the blood-brain barrier expand 查看数据来源
regulator expand 查看数据来源
Voltage-gated N-type calcium ion channels expand 查看数据来源
纯度
>98. expand 查看数据来源
95% expand 查看数据来源
97% expand 查看数据来源
98% expand 查看数据来源
成盐信息
Free Base expand 查看数据来源
质检报告
下载链接 expand 查看数据来源
应用领域
Anticonvulsant expand 查看数据来源
CNS depressant expand 查看数据来源
Pharmacopeia Traceability
traceable to USP 1287303 expand 查看数据来源
Empirical Formula (Hill Notation)
C9H17NO2 expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank -  DB00996 external link
Item Information
Drug Groups approved; investigational
Description Gabapentin (brand name Neurontin) is a medication originally developed for the treatment of epilepsy. Presently, gabapentin is widely used to relieve pain, especially neuropathic pain. Gabapentin is well tolerated in most patients, has a relatively mild side-effect profile, and passes through the body unmetabolized.
Indication For the management of postherpetic neuralgia in adults and as adjunctive therapy in the treatment of partial seizures with and without secondary generalization in patients over 12 years of age with epilepsy.
Pharmacology Gabapentin, an analog of GABA, is used as an anticonvulsant to treat partial seizures, amyotrophic lateral sclerosis (ALS), and painful neuropathies. Potential uses include monotherapy of refractory partial seizure disorders, and treatment of spasticity in multiple sclerosis, tremor. mood disorders, and attenuation of disruptive behaviors in dementia. Gabapentin has high lipid solubility, is not metabolized by the liver, has no protein binding, and doesn't possess the usual drug interactions.
Toxicity Symptoms of overdose include ataxia, labored breathing, ptosis, sedation, hypoactivity, and excitation.
Affected Organisms
Humans and other mammals
Biotransformation All pharmacological actions following gabapentin administration are due to the activity of the parent compound; gabapentin is not appreciably metabolized in humans.
Absorption Rapid. Absorbed in part by the L-amino acid transport system, which is a carrier-mediated, saturable transport system; as the dose increases, bioavailability decreases. Bioavailability ranges from approximately 60% for a 900 mg dose per day to approximately 27% for a 4800 milligram dose per day. Food has a slight effect on the rate and extent of absorption of gabapentin (14% increase in AUC).
Half Life 5-7 hours
Protein Binding Less than 3% of gabapentin circulates bound to plasma protein.
Elimination Gabapentin is eliminated from the systemic circulation by renal excretion as unchanged drug.
Gabapentin is not appreciably metabolized in humans.
Distribution * 58±6 L
Clearance * 190 mL/min
References
Mathew NT, Rapoport A, Saper J, Magnus L, Klapper J, Ramadan N, Stacey B, Tepper S: Efficacy of gabapentin in migraine prophylaxis. Headache. 2001 Feb;41(2):119-28. [Pubmed]
Backonja MM, Serra J: Pharmacologic management part 1: better-studied neuropathic pain diseases. Pain Med. 2004 Mar;5 Suppl 1:S28-47. [Pubmed]
Choudhuri I, Sarvananthan N, Gottlob I: Survey of management of acquired nystagmus in the United Kingdom. Eye. 2007 Sep;21(9):1194-7. Epub 2006 May 26. [Pubmed]
Pande AC, Crockatt JG, Janney CA, Werth JL, Tsaroucha G: Gabapentin in bipolar disorder: a placebo-controlled trial of adjunctive therapy. Gabapentin Bipolar Disorder Study Group. Bipolar Disord. 2000 Sep;2(3 Pt 2):249-55. [Pubmed]
External Links
Wikipedia
RxList
PDRhealth
Drugs.com
Selleck Chemicals -  S2133 external link
Research Area: Neurological Disease
Biological Activity:
Gabapentin (Neurontin) is a pharmaceutical agent, specifically a GABA analogue. Gabapentin (Neurontin) was originally developed for the treatment of epilepsy, and currently, gabapentin is widely used to relieve pain, especially neuropathic pain. Its therapeutic action on neuropathic pain is thought to involve voltage-gated N-type calcium ion channels. It is thought to bind to the α2δ subunit (1 and 2) of the voltage-dependent calcium channel in the central nervous system. [1][2]
Sigma Aldrich -  G154 external link
Biochem/physiol Actions
Anticonvulsant with unknown mechanism of action; crosses the blood brain barrier; increases GABA concentrations in the brain and reduces excitatory amino acid neurotransmission, perhaps through its effects on voltage-gated calcium channels; exhibits antinociceptive, anxiolytic, neuroprotective and anti-epileptic effects.
Toronto Research Chemicals -  G117250 external link
Amino acid structurally related to γ-Aminobutyric Acid (GABA), designed to cross the blood brain barrier. Used as an anticonvulsant.

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Mathew NT, Rapoport A, Saper J, Magnus L, Klapper J, Ramadan N, Stacey B, Tepper S: Efficacy of gabapentin in migraine prophylaxis. Headache. 2001 Feb;41(2):119-28. Pubmed
  • Backonja MM, Serra J: Pharmacologic management part 1: better-studied neuropathic pain diseases. Pain Med. 2004 Mar;5 Suppl 1:S28-47. Pubmed
  • Choudhuri I, Sarvananthan N, Gottlob I: Survey of management of acquired nystagmus in the United Kingdom. Eye. 2007 Sep;21(9):1194-7. Epub 2006 May 26. Pubmed
  • Pande AC, Crockatt JG, Janney CA, Werth JL, Tsaroucha G: Gabapentin in bipolar disorder: a placebo-controlled trial of adjunctive therapy. Gabapentin Bipolar Disorder Study Group. Bipolar Disord. 2000 Sep;2(3 Pt 2):249-55. Pubmed
  • http://en.wikipedia.org/wiki/Gabapentin
  • Vollmer, K.-O. et al.: Arzneimittel-Forshc., 36, 830 (1986)
  • Saletu, B., et al.: Int. J. Clin. Pharmacol. Ther. Toxicol., 24, 362 (1986)
  • Ger. Pat., 1976, Goedecke, 2 460 891; CA, 85, 94679h, (synth)
  • Hengy, H. et al., J. Chromatogr., 1985, 341; 473, (hplc)
  • Vollmer, K.O. et al., Arzneim.-Forsch., 1986, 36, 830, (metab)
  • Bartoszyk, G.D. et al., Curr. Probl. Epilepsy, 1986, 4, 147, (rev, pharmacol)
  • Griffiths, G. et al., Helv. Chim. Acta, 1991, 74, 309, (synth, bibl)
  • Goa, K.L. et al., Drugs, 1993, 46, 409, (rev)
  • Antiepileptic Drugs, 4th edn., (eds., Levy, R.H. et al), Raven Press, 1995
  • Pellock, J.M., Drugs of Today (Barcelona), 1998, 34, 31-35, (rev, pharmacol)
  • Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 346
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专利

专利

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