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药品详细

Nicotine(尼古丁)

化学结构式图
中文名
尼古丁
英文名
Nicotine
分子式
C10H14N2
化学名
3-(1-methylpyrrolidin-2-yl)pyridine
分子量
Average: 162.2316
Monoisotopic: 162.115698458
CAS号
54-11-5
ATC分类
N07B 未知;A11H 未知;C04A 未知;C10A 未知
药物类型
small molecule
阶段
approved
商品名
同义名
基本介绍

Nicotine is highly toxic alkaloid. It is the prototypical agonist at nicotinic cholinergic receptors where it dramatically stimulates neurons and ultimately blocks synaptic transmission. Nicotine is also important medically because of its presence in tobacco smoke. [PubChem]

生产厂家
  • Aveva drug delivery systems inc
  • Glaxosmithkline
  • Glaxosmithkline consumer healthcare
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Mcneil consumer healthcare
  • Novartis consumer health inc
  • Perrigo co
  • Perrigo r and d co
  • Pfizer inc
  • Pharmacia and upjohn co
  • Sanofi aventis us llc
  • Watson laboratories inc
封装厂家
参考
Synthesis Reference Not Available
General Reference
  1. Nolley EP, Kelley BM: Adolescent reward system perseveration due to nicotine: studies with methylphenidate. Neurotoxicol Teratol. 2007 Jan-Feb;29(1):47-56. Epub 2006 Oct 4. Pubmed
  2. de Leon J, Tracy J, McCann E, McGrory A, Diaz FJ: Schizophrenia and tobacco smoking: a replication study in another US psychiatric hospital. Schizophr Res. 2002 Jul 1;56(1-2):55-65. Pubmed
  3. de Leon J, Dadvand M, Canuso C, White AO, Stanilla JK, Simpson GM: Schizophrenia and smoking: an epidemiological survey in a state hospital. Am J Psychiatry. 1995 Mar;152(3):453-5. Pubmed
  4. Aguilar MC, Gurpegui M, Diaz FJ, de Leon J: Nicotine dependence and symptoms in schizophrenia: naturalistic study of complex interactions. Br J Psychiatry. 2005 Mar;186:215-21. Pubmed
剂型
规格
化合物类型
Type small molecule
Classes
  • Alkaloids and Alkaloid Derivatives
Substructures
  • Pyridines and Derivatives
  • Pyrrolidines
  • Aliphatic and Aryl Amines
  • Heterocyclic compounds
  • Aromatic compounds
  • Alkaloids and Alkaloid Derivatives
适应症
药理
Indication For the relief of nicotine withdrawal symptoms and as an aid to smoking cessation.
Pharmacodynamics Nicotine, the primary alkaloid in tobacco products binds stereo-selectively to nicotinic-cholinergic receptors on autonomic ganglia, the adrenal medulla, neuromuscular junctions and in the brain. Nicotine exerts two effects, a stimulant effect exerted at the locus ceruleus and a reward effect in the limbic system. Itranvenous administration of nicotine causes release of acetylcholine, norepinephrine, dopamine, serotonine, vasopressin, beta-endorphin and ACTH. Nicotine is a highly addictive substance. Nicotine also induces peripheral vasoconstriction, tachycardia and elevated blood pressure. Nicotine inhalers and patches are used to treat smoking withdrawl syndrome. Nicotine is classified as a stimulant of autonomic ganglia.
Mechanism of action Nicotine is a stimulant drug that acts as an agonist at nicotinic acetylcholine receptors. These are ionotropic receptors composed up of five homomeric or heteromeric subunits. In the brain, nicotine binds to nicotinic acetylcholine receptors on dopaminergic neurons in the cortico-limbic pathways. This causes the channel to open and allow conductance of multiple cations including sodium, calcium, and potassium. This leads to depolarization, which activates voltage-gated calcium channels and allows more calcium to enter the axon terminal. Calcium stimulates vesicle trafficking towards the plasma membrane and the release of dopamine into the synapse. Dopamine binding to its receptors is responsible the euphoric and addictive properties of nicotine. Nicotine also binds to nicotinic acetylcholine receptors on the chromaffin cells in the adrenal medulla. Binding opens the ion channel allowing influx of sodium, causing depolarization of the cell, which activates voltage-gated calcium channels. Calcium triggers the release of epinephrine from intracellular vesicles into the bloodstream, which causes vasoconstriction, increased blood pressure, increased heart rate, and increased blood sugar.
Absorption Absorption of nicotine through the buccal mucosa is relatively slow and the high and rapid rise followed by the decline in nicotine arterial plasma concentrations seen with cigarette smoking are not achieved with the inhaler. About 10% of absorbed nicotine is excreted unchanged in urine.
Volume of distribution
  • 2 to 3 L/kg
Protein binding Less than 5%
Metabolism
Primarily hepatic, cotinine is the primary metabolite.

Important The metabolism module of DrugBank is currently in beta. Questions or suggestions? Please contact us.

Substrate Enzymes Product
Nicotine
    		N-Methylnicotinium Details
    Nicotine
      		Nicotine imine Details
      Nicotine
        		Cotinine glucuronide Details
        Nicotine
          		Cotinine Details
          Nicotine
            		Nornicotine Details
            Nicotine
              		trans-3-Hydroxycotinine glucuronide Details
              Nicotine
                		Nicotine glucuronide Details
                Nicotine
                  		Norcotinine Details
                  Nicotine
                    		3'-Hydroxycotinine Details
                    Nicotine
                      		Cotinine N-oxide Details
                      Nicotine
                        		Nicotine-1'-N-oxide Details
                        Nicotine
                          		4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone Details
                          Nicotine
                            		4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol Details
                            Route of elimination About 10% of the nicotine absorbed is excreted unchanged in the urine.
                            Half life Cotinine has a half life of 15-20 hours, while nicotine has a half life of 1-3 hours
                            Clearance
                            • 1.2 L/min [healthy adult smoker]
                            Toxicity Symptoms of overdose include nausea, abdominal pain, vomiting, diarrhea, diaphoresis, flushing, dizziness, disturbed hearing and vision, confusion, weakness, palpitations, altered respiration and hypotension. LD50= 24 mg/kg (orally in mice).
                            Affected organisms
                            • Humans and other mammals
                            Pathways
                            Pathway Name SMPDB ID
                            Smp00431 Nicotine Pathway SMP00431
                            理化性质
                            Properties
                            State liquid
                            Experimental Properties
                            Property Value Source
                            melting point -79 °C PhysProp
                            boiling point 247 °C PhysProp
                            water solubility 1E+006 mg/L SEIDELL,A (1941)
                            logP 1.17 HANSCH,C ET AL. (1995)
                            logS 0.79 ADME Research, USCD
                            Caco2 permeability -4.71 ADME Research, USCD
                            pKa 3.1 TOMLIN,C (1997); pKa1
                            Predicted Properties
                            Property Value Source
                            water solubility 9.33e+01 g/l ALOGPS
                            logP 0.87 ALOGPS
                            logP 1.16 ChemAxon
                            logS -0.24 ALOGPS
                            pKa (strongest basic) 8.86 ChemAxon
                            physiological charge 1 ChemAxon
                            hydrogen acceptor count 2 ChemAxon
                            hydrogen donor count 0 ChemAxon
                            polar surface area 16.13 ChemAxon
                            rotatable bond count 1 ChemAxon
                            refractivity 49.66 ChemAxon
                            polarizability 18.62 ChemAxon
                            药物相互作用
                            食物相互作用
                            Not Available

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