用户名： 密   码：
注册 | 忘记密码？
药品详细

Bupropion(安非他酮)

化学结构式图
中文名
安非他酮
英文名
Bupropion
分子式
C13H18ClNO
化学名
2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one
分子量
Average: 239.741
Monoisotopic: 239.10769191
CAS号
34841-39-9
ATC分类
N06A 未知
药物类型
small molecule
阶段
approved
商品名
同义名
基本介绍

A unicyclic, aminoketone antidepressant. The mechanism of its therapeutic actions is not well understood, but it does appear to block dopamine uptake. The hydrochloride is available as an aid to smoking cessation treatment. [PubChem]

生产厂家
  • Actavis southatlantic llc
  • Anchen pharmaceuticals inc
  • Apotex inc etobicoke site
  • Biovail Corporation
  • Biovail laboratories international srl
  • Glaxosmithkline
  • Impax laboratories inc
  • Mylan pharmaceuticals inc
  • Sandoz inc
  • Sun pharma global fze
  • Teva pharmaceuticals usa inc
  • Watson laboratories inc
封装厂家
参考
Synthesis Reference Not Available
General Reference
  1. Fryer JD, Lukas RJ: Noncompetitive functional inhibition at diverse, human nicotinic acetylcholine receptor subtypes by bupropion, phencyclidine, and ibogaine. J Pharmacol Exp Ther. 1999 Jan;288(1):88-92. Pubmed
  2. Fava M, Rush AJ, Thase ME, Clayton A, Stahl SM, Pradko JF, Johnston JA: 15 years of clinical experience with bupropion HCl: from bupropion to bupropion SR to bupropion XL. Prim Care Companion J Clin Psychiatry. 2005;7(3):106-13. Pubmed
  3. Thase ME, Haight BR, Richard N, Rockett CB, Mitton M, Modell JG, VanMeter S, Harriett AE, Wang Y: Remission rates following antidepressant therapy with bupropion or selective serotonin reuptake inhibitors: a meta-analysis of original data from 7 randomized controlled trials. J Clin Psychiatry. 2005 Aug;66(8):974-81. Pubmed
  4. : Annual report on the results of treatment in gynecological cancer. Twenty-first volume. Statements of results obtained in patients treated in 1982 to 1986, inclusive 3 and 5-year survival up to 1990. Int J Gynaecol Obstet. 1991 Sep;36 Suppl:1-315. Pubmed
  5. Thase ME, Clayton AH, Haight BR, Thompson AH, Modell JG, Johnston JA: A double-blind comparison between bupropion XL and venlafaxine XR: sexual functioning, antidepressant efficacy, and tolerability. J Clin Psychopharmacol. 2006 Oct;26(5):482-8. Pubmed
剂型
规格
化合物类型
Type small molecule
Classes
  • Phenethylamines
  • Acetophenones and Derivatives
  • Amphetamines
Substructures
  • Aliphatic and Aryl Amines
  • Amino Ketones
  • Benzene and Derivatives
  • Aryl Halides
  • Halobenzenes
  • Phenethylamines
  • Aromatic compounds
  • Benzoyl Derivatives
  • Acetophenones and Derivatives
  • Amphetamines
  • Ketones
适应症
药理
Indication For the treatment of depression and as aid to smoking cessation.
Pharmacodynamics Bupropion, an antidepressant of the aminoketone class and a non-nicotine aid to smoking cessation, is chemically unrelated to tricyclic, tetracyclic, selective serotonin re-uptake inhibitor, or other known antidepressant agents. Compared to classical tricyclic antidepressants, Bupropion is a relatively weak inhibitor of the neuronal uptake of norepinephrine, serotonin, and dopamine. In addition, Bupropion does not inhibit monoamine oxidase. Bupropion produces dose-related central nervous system (CNS) stimulant effects in animals, as evidenced by increased locomotor activity, increased rates of responding in various schedule-controlled operant behavior tasks, and, at high doses, induction of mild stereotyped behavior.
Mechanism of action Bupropion selectively inhibits the neuronal reuptake of dopamine, norepinephrine, and serotonin; actions on dopaminergic systems are more significant than imipramine or amitriptyline whereas the blockade of norepinephrine and serotonin reuptake at the neuronal membrane is weaker for bupropion than for tricyclic antidepressants. The increase in norepinephrine may attenuate nicotine withdrawal symptoms and the increase in dopamine at neuronal sites may reduce nicotine cravings and the urge to smoke. Bupropion exhibits moderate anticholinergic effects.
Absorption For sustained release, peak plasma concentrations are achieved within 3 hours.
Volume of distribution Not Available
Protein binding 84 %
Metabolism
Reduction of the carbonyl groupand/or hydroxylation of the tert-butyl group of bupropion.

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

Substrate Enzymes Product
Bupropion
Hydroxybupropion Details
Route of elimination Bupropion is extensively metabolized in humans. Oxidation of the bupropion side chain results in the formation of a glycine conjugate of metachlorobenzoic acid, which is then excreted as the major urinary metabolite. Following oral administration of 200 mg of 14C-bupropion in humans, 87% and 10% of the radioactive dose were recovered in the urine and feces, respectively. However, the fraction of the oral dose of bupropion excreted unchanged was only 0.5%, a finding consistent with the extensive metabolism of bupropion.
Half life 24 hours
Clearance Not Available
Toxicity Symptoms of overdose include seizures, hallucinations, loss of consciousness, tachycardia, and cardiac arrest.
Affected organisms
  • Humans and other mammals
Pathways Not Available
理化性质
Properties
State solid
Experimental Properties
Property Value Source
melting point 233-234 °C Not Available
water solubility 312 mg/ml Not Available
logP 3.6 Not Available
Predicted Properties
Property Value Source
water solubility 6.93e-02 g/l ALOGPS
logP 3.28 ALOGPS
logP 3.27 ChemAxon
logS -3.5 ALOGPS
pKa (strongest acidic) 18.29 ChemAxon
pKa (strongest basic) 8.22 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 2 ChemAxon
hydrogen donor count 1 ChemAxon
polar surface area 29.1 ChemAxon
rotatable bond count 4 ChemAxon
refractivity 67.7 ChemAxon
polarizability 25.93 ChemAxon
药物相互作用
Drug Interaction
Carbamazepine Carbamazepine, a strong CYP2B6 inducer, may increase the metabolism of bupropion. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of bupropion if carbamazepine is initiated, discontinued or dose changed.
Cyclosporine Bupropion may decrease the therapeutic effect of cyclosporine.
Isocarboxazid Possible severe adverse reaction with this combination
Phenelzine Possible severe adverse reaction with this combination
Rasagiline Possible severe adverse reaction with this combination
Rifabutin Rifampin reduces bupropion levels
Rifampin Rifampin reduces bupropion levels
Ritonavir Ritonavir increases the effect and toxicity of bupropion
Thioridazine Bupropion may increase the effect and toxicity of thioridazine.
Thiotepa Thiotepa, a strong CYP2B6 inhibitor, may decrease the metabolism and clearance of Bupropion, a CYP2B6 substrate. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of Bupropion if Thiotepa is initiated, discontinued or dose changed.
Tranylcypromine The MAO inhibitor, Tranylcypromine, may increase the central neurotoxic effects of the Bupropion. These agents should not be administered within 14 days of each other.
Triprolidine The CNS depressants, Triprolidine and Bupropion, may increase adverse/toxic effects due to additivity. Monitor for increased CNS depressant effects during concomitant therapy.
Zuclopenthixol Bupropion, a strong CYP2D6 inhibitor, may increase the serum concentration of zuclopenthixol by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of zuclopenthixol if bupropion is initiated, discontinued or dose changed.
食物相互作用
  • Avoid alcohol.
  • Avoid St.John's Wort.
  • Take without regard to meals.

返回 | 收藏