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药品详细

Caffeine(咖啡因)

化学结构式图
中文名
咖啡因
英文名
Caffeine
分子式
C8H10N4O2
化学名
1,3,7-trimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
分子量
Average: 194.1906
Monoisotopic: 194.080375584
CAS号
58-08-2
ATC分类
N06B 未知;N02B Other Analgesics and Antipyretics
药物类型
small molecule
阶段
approved
商品名
同义名
基本介绍

A methylxanthine naturally occurring in some beverages and also used as a pharmacological agent. Caffeine's most notable pharmacological effect is as a central nervous system stimulant, increasing alertness and producing agitation. It also relaxes smooth muscle, stimulates cardiac muscle, stimulates diuresis, and appears to be useful in the treatment of some types of headache. Several cellular actions of caffeine have been observed, but it is not entirely clear how each contributes to its pharmacological profile. Among the most important are inhibition of cyclic nucleotide phosphodiesterases, antagonism of adenosine receptors, and modulation of intracellular calcium handling. [PubChem]

生产厂家
  • App pharmaceuticals llc
  • Luitpold pharmaceuticals inc
  • Mead johnson and co
  • Paddock laboratories inc
  • Sun pharmaceutical industries ltd
封装厂家
参考
Synthesis Reference Not Available
General Reference
  1. Nathanson JA: Caffeine and related methylxanthines: possible naturally occurring pesticides. Science. 1984 Oct 12;226(4671):184-7. Pubmed
  2. Haskell CF, Kennedy DO, Wesnes KA, Milne AL, Scholey AB: A double-blind, placebo-controlled, multi-dose evaluation of the acute behavioural effects of guarana in humans. J Psychopharmacol. 2007 Jan;21(1):65-70. Epub 2006 Mar 13. Pubmed
  3. Smit HJ, Gaffan EA, Rogers PJ: Methylxanthines are the psycho-pharmacologically active constituents of chocolate. Psychopharmacology (Berl). 2004 Nov;176(3-4):412-9. Epub 2004 May 5. Pubmed
  4. Benjamin LT Jr, Rogers AM, Rosenbaum A: Coca-Cola, caffeine, and mental deficiency: Harry Hollingworth and the Chattanooga trial of 1911. J Hist Behav Sci. 1991 Jan;27(1):42-55. Pubmed
  5. Nehlig A, Daval JL, Debry G: Caffeine and the central nervous system: mechanisms of action, biochemical, metabolic and psychostimulant effects. Brain Res Brain Res Rev. 1992 May-Aug;17(2):139-70. Pubmed
剂型
规格
化合物类型
Type small molecule
Classes
  • Xanthines
Substructures
  • Xanthines
  • Pyrimidines and Derivatives
  • Imidazoles
  • Heterocyclic compounds
  • Aromatic compounds
  • Purines and Purine Derivatives
  • Cyanamides
适应症
药理
Indication For management of fatigue, orthostatic hypotension, and for the short term treatment of apnea of prematurity in infants.
Pharmacodynamics Caffeine, a naturally occurring xanthine derivative like theobromine and the bronchodilator theophylline, is used as a CNS stimulant, mild diuretic, and respiratory stimulant (in neonates with apnea of prematurity). Often combined with analgesics or with ergot alkaloids, caffeine is used to treat migraine and other headache types. Over the counter, caffeine is available to treat drowsiness or mild water-weight gain.
Mechanism of action Caffeine stimulates medullary, vagal, vasomotor, and respiratory centers, promoting bradycardia, vasoconstriction, and increased respiratory rate. This action was previously believed to be due primarily to increased intracellular cyclic 3′,5′-adenosine monophosphate (cyclic AMP) following inhibition of phosphodiesterase, the enzyme that degrades cyclic AMP. It is now thought that xanthines such as caffeine act as antagonists at adenosine-receptors within the plasma membrane of virtually every cell. As adenosine acts as an autocoid, inhibiting the release of neurotransmitters from presynaptic sites but augmenting the actions of norepinephrine or angiotensin, antagonism of adenosine receptors promotes neurotransmitter release. This explains the stimulatory effects of caffeine. Blockade of the adenosine A1 receptor in the heart leads to the accelerated, pronounced "pounding" of the heart upon caffeine intake.
Absorption Readily absorbed after oral or parenteral administration. The peak plasma level for caffeine range from 6-10mg/L and the mean time to reach peak concentration ranged from 30 minutes to 2 hours.
Volume of distribution
  • 0.8 to 0.9 L/kg [infants]
  • 0.6 L/kg [adults]
Protein binding Low (25 to 36%).
Metabolism
Hepatic cytochrome P450 1A2 (CYP 1A2) is involved in caffeine biotransformation. About 80% of a dose of caffeine is metabolized to paraxanthine (1,7-dimethylxanthine), 10% to theobromine (3,7-dimethylxanthine), and 4% to theophylline (1,3-dimethylxanthine).

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

Substrate Enzymes Product
Caffeine
Theobromine Details
Caffeine
Theophylline Details
Caffeine
1,3,7-Trimethyluric acid Details
Caffeine
Paraxanthine Details
Caffeine
    		1,3-dimethyluric acid Details
    Caffeine
      		3-Methyluric acid Details
      Caffeine
        		9-Methyluric acid Details
        Caffeine
          		3,7-Dimethyluric acid Details
          Caffeine
            		7-Methylxanthine Details
            Caffeine
              		1,9-Dimethyluric acid Details
              Caffeine
                		1-Methyluric acid Details
                Caffeine
                  		7,9-Dimethyluric acid Details
                  Caffeine
                    		1-methylxanthine Details
                    Caffeine
                      		1,7-Dimethyluric acid Details
                      Caffeine
                        		5-Acetylamino-6-formylamino-3-methyluracil Details
                        Route of elimination In young infants, the elimination of caffeine is much slower than that in adults due to immature hepatic and/or renal function.
                        Half life 3 to 7 hours in adults, 65 to 130 hours in neonates
                        Clearance Not Available
                        Toxicity LD50=127 mg/kg (orally in mice)
                        Affected organisms
                        • Humans and other mammals
                        Pathways Not Available
                        理化性质
                        Properties
                        State solid
                        Experimental Properties
                        Property Value Source
                        melting point 238 °C PhysProp
                        water solubility 2.16E+004 mg/L (at 25 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992)
                        logP -0.07 HANSCH,C ET AL. (1995)
                        logS -0.97 ADME Research, USCD
                        Caco2 permeability -4.41 ADME Research, USCD
                        pKa 10.4 (at 40 °C) DEAN,JA (1985)
                        Predicted Properties
                        Property Value Source
                        water solubility 1.10e+01 g/l ALOGPS
                        logP -0.24 ALOGPS
                        logP -0.55 ChemAxon
                        logS -1.2 ALOGPS
                        pKa (strongest basic) -0.92 ChemAxon
                        physiological charge 0 ChemAxon
                        hydrogen acceptor count 3 ChemAxon
                        hydrogen donor count 0 ChemAxon
                        polar surface area 58.44 ChemAxon
                        rotatable bond count 0 ChemAxon
                        refractivity 49.83 ChemAxon
                        polarizability 18.95 ChemAxon
                        药物相互作用
                        Drug Interaction
                        Adenosine Caffeine may diminish the therapeutic effect of adenosine. Specific management recommendations vary slightly depending on specific adenosine product used (i.e., therapeutic vs. diagnostic use of adenosine). Significantly higher adenosine doses, or alternative agents, may be required. Monitor for decreased therapeutic effects of adenosine if the patient is already receiving caffeine. Discontinue caffeine in advance (5 half-lives, or approximately 24 hours, is specifically recommended) of scheduled diagnostic use of adenosine (e.g., for radionuclide imaging studies) whenever possible.
                        Ciprofloxacin Ciprofloxacin may increase the effect and toxicity of caffeine.
                        Clozapine Caffeine increases the effect and toxicity of clozapine
                        Conivaptan Conivaptan may increase the serum concentration of CYP3A4 substrates such as caffeine. Upon completion/discontinuation of conivaptan, allow at least 7 days before initiating therapy with drugs that are CYP3A4 substrates.
                        Grepafloxacin Grepafloxacin may increase the effect and toxicity of caffeine.
                        Lithium Caffeine decreases serum levels of lithium
                        Norfloxacin Norfloxacin may increase the effect and toxicity of caffeine.
                        Regadenoson Caffeine may diminish the vasodilatory effect of Regadenoson. Regadenoson prescribing information recommends avoiding using caffeine or other methylxanthine containing products (e.g., theophylline) for at least 12 hours prior the the administration of regadenoson. The impact of low doses of caffeine-containing products such as coffee, tea, and colas is unclear.
                        Tamsulosin Caffeine, a CYP3A4 inhibitor, may decrease the metabolism and clearance of Tamsulosin, a CYP3A4 substrate. Monitor for changes in therapeutic/adverse effects of Tamsulosin if Caffeine is initiated, discontinued, or dose changed.
                        Terbinafine Terbinafine may increase the plasma concentration of Caffeine.
                        Thiabendazole The strong CYP1A2 inhibitor, Thiabendazole, may increase the effects and toxicity of Caffeine by decreasing Caffeine metabolism and clearance. Monitor for changes in the therapeutic and adverse effects of Caffeine if Thiabendazole is initiated, discontinued or dose changed.
                        Tolterodine Caffeine may decrease the metabolism and clearance of Tolterodine. Adjust Tolterodine dose and monitor for efficacy and toxicity.
                        Vemurafenib Vemurafenib increases the AUC of caffeine (CYP1A2 substrate) 2.6-fold.
                        食物相互作用
                        Not Available

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