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药品详细

Oxycodone(羟考酮)

化学结构式图
中文名
羟考酮
英文名
Oxycodone
分子式
C18H21NO4
化学名
(1S,5R,13R,17S)-17-hydroxy-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10-trien-14-one
分子量
Average: 315.3636
Monoisotopic: 315.147058165
CAS号
76-42-6
ATC分类
N02A 未知
药物类型
small molecule
阶段
illicit, approved
商品名
同义名
基本介绍

Semisynthetic derivative of codeine that acts as a narcotic analgesic more potent and addicting than codeine. [PubChem]

生产厂家
  • Actavis totowa llc
  • Avanthi inc
  • Corepharma llc
  • Endo Pharmaceuticals
  • Kv pharmaceutical co
  • Mallinckrodt inc
  • Purdue pharma lp
  • Roxane laboratories inc
  • Sun pharmaceutical industries inc
  • Tyco healthcare mallinckrodt
  • Vintage pharmaceuticals inc
  • Xanodyne pharmaceuticals inc
封装厂家
参考
Synthesis Reference Not Available
General Reference
  1. Ordonez Gallego A, Gonzalez Baron M, Espinosa Arranz E: Oxycodone: a pharmacological and clinical review. Clin Transl Oncol. 2007 May;9(5):298-307. Pubmed
  2. Riley J, Eisenberg E, Muller-Schwefe G, Drewes AM, Arendt-Nielsen L: Oxycodone: a review of its use in the management of pain. Curr Med Res Opin. 2008 Jan;24(1):175-92. Pubmed
剂型
规格
化合物类型
Type small molecule
Classes
  • Morphinans
  • Benzylisoquinolines
Substructures
  • Morphinans
  • Benzofurans
  • Hydroxy Compounds
  • Naphthalenes
  • Phenols and Derivatives
  • Benzylisoquinolines
  • Ethers
  • Benzene and Derivatives
  • Phenylpiperidines
  • Aliphatic and Aryl Amines
  • Alcohols and Polyols
  • Phenanthrenes
  • Catechols
  • Phenethylamines
  • Heterocyclic compounds
  • Aromatic compounds
  • Anisoles
  • Phenylpropylamines
  • (Iso)quinolines and Derivatives
  • Cyclohexenes and Derivatives
  • Phenyl Esters
  • Amphetamines
  • Catecholamines and Derivatives
  • Piperidines
  • Ketones
适应症
药理
Indication For the treatment of diarrhoea, pulmonary oedema and for the relief of moderate to moderately severe pain.
Pharmacodynamics Oxycodone, a semisynthetic opiate agonist derived from the opioid alkaloid, thebaine, is similar to other phenanthrene derivatives such as hydrocodone and morphine. Oxycodone is available in combination with aspirin or acetaminophen to control pain and restless leg and Tourette syndromes.
Mechanism of action Oxycodone acts as a weak agonist at mu, kappa, and delta opioid receptors within the central nervous system (CNS). Oxycodone primarily affects mu-type opioid receptors, which are coupled with G-protein receptors and function as modulators, both positive and negative, of synaptic transmission via G-proteins that activate effector proteins. Binding of the opiate stimulates the exchange of GTP for GDP on the G-protein complex. As the effector system is adenylate cyclase and cAMP located at the inner surface of the plasma membrane, opioids decrease intracellular cAMP by inhibiting adenylate cyclase. Subsequently, the release of nociceptive neurotransmitters such as substance P, GABA, dopamine, acetylcholine, and noradrenaline is inhibited. Opioids such as oxycodone also inhibit the release of vasopressin, somatostatin, insulin, and glucagon. Opioids close N-type voltage-operated calcium channels (kappa-receptor agonist) and open calcium-dependent inwardly rectifying potassium channels (mu and delta receptor agonist). This results in hyperpolarization and reduced neuronal excitability.
Absorption Well absorbed with an oral bioavailability of 60% to 87%
Volume of distribution
  • 2.6 L/kg
Protein binding 45%
Metabolism
Hepatic

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

Substrate Enzymes Product
Oxycodone
oxymorphone Details
Oxycodone
noroxycodone Details
Route of elimination Oxycodone and its metabolites are excreted primarily via the kidney.
Half life 4.5 hours
Clearance
  • 0.8 L/min [adults]
Toxicity Symptoms of overdose include respiratory depression, somnolence progressing to stupor or coma, skeletal muscle flaccidity, cold and clammy skin, constricted pupils, bradycardia, hypotension, and death.
Affected organisms
  • Humans and other mammals
Pathways
Pathway Name SMPDB ID
Smp00409 Oxycodone Pathway SMP00409
理化性质
Properties
State solid
Experimental Properties
Property Value Source
melting point 219 °C PhysProp
water solubility 100 mg/ml Not Available
logP 0.3 Not Available
Predicted Properties
Property Value Source
water solubility 5.59e+00 g/l ALOGPS
logP 1.04 ALOGPS
logP 1.03 ChemAxon
logS -1.8 ALOGPS
pKa (strongest acidic) 13.56 ChemAxon
pKa (strongest basic) 8.21 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 5 ChemAxon
hydrogen donor count 1 ChemAxon
polar surface area 59 ChemAxon
rotatable bond count 1 ChemAxon
refractivity 84.04 ChemAxon
polarizability 32.8 ChemAxon
药物相互作用
Drug Interaction
Alvimopan Increases levels by receptor binding competition. Discontinue opioid administration at least 7 days prior to administrating Alvimopan.
Cimetidine Cimetidine, a moderate CYP3A4 inhibitor, may decrease the metabolism of oxycodone. Monitor for changes in the therapeutic and adverse effects of oxycodone if cimetidine is initiated, discontinued or dose changed.
Citalopram Increased risk of serotonin syndrome
Escitalopram Increased risk of serotonin syndrome
Fluoxetine Increased risk of serotonin syndrome
Fluvoxamine Increased risk of serotonin syndrome
Paroxetine Increased risk of serotonin syndrome
Sertraline Increased risk of serotonin syndrome
Triprolidine The CNS depressants, Triprolidine and Oxycodone, may increase adverse/toxic effects due to additivity. Monitor for increased CNS depressant effects during concomitant therapy.
食物相互作用
  • Take without regard to meals. Avoid alcohol.

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