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药品详细

Propoxyphene(丙氧芬)

化学结构式图
中文名
丙氧芬
英文名
Propoxyphene
分子式
C22H29NO2
化学名
(3R)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl propanoate
分子量
Average: 339.4712
Monoisotopic: 339.219829177
CAS号
469-62-5
ATC分类
N02A 未知;N02A 未知;N02A 未知
药物类型
small molecule
阶段
illicit, approved
商品名
同义名
基本介绍

A narcotic analgesic structurally related to methadone. Only the dextro-isomer has an analgesic effect; the levo-isomer appears to exert an antitussive effect. [PubChem]

生产厂家
  • Aaipharma llc
  • Alra laboratories inc
  • Halsey drug co inc
  • Heritage pharmaceuticals inc
  • Impax laboratories inc
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Mk laboratories inc
  • Mutual pharmaceutical co inc
  • Mylan pharmaceuticals inc
  • Nexgen pharma inc
  • Par pharmaceutical inc
  • Private formulations inc
  • Purepac pharmaceutical co
  • Roxane laboratories inc
  • Sandoz inc
  • Teva pharmaceuticals usa inc
  • Valeant pharmaceuticals international
  • Vintage pharmaceuticals inc
  • Warner chilcott div warner lambert co
  • Watson laboratories inc
  • West ward pharmaceutical corp
  • Whiteworth towne paulsen inc
  • Xanodyne pharmaceutics inc
封装厂家
参考
Synthesis Reference Not Available
General Reference
  1. Coda BA, Rudy AC, Archer SM, Wermeling DP: Pharmacokinetics and bioavailability of single-dose intranasal hydromorphone hydrochloride in healthy volunteers. Anesth Analg. 2003 Jul;97(1):117-23, table of contents. Pubmed
剂型
规格
化合物类型
Type small molecule
Classes Not Available
Substructures Not Available
适应症
药理
Indication For the relief of mild to moderate pain
Pharmacodynamics Propoxyphene, a synthetic opiate agonist, is structurally similar to methadone. Its general pharmacologic properties are those of the opiates as a group. The analgesic effect of propoxyphene is due to the d-isomer, dextropropoxyphene. It binds to the opiate receptors and leads to a decrease of the perception of pain stimuli. Propoxyphene possesses little to no antitussive activity and no antipyretic action.
Mechanism of action Propoxyphene acts as a weak agonist at OP1, OP2, and OP3 opiate receptors within the central nervous system (CNS). Propoxyphene primarily affects OP3 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 propoxyphene also inhibit the release of vasopressin, somatostatin, insulin, and glucagon. Opioids close N-type voltage-operated calcium channels (OP2-receptor agonist) and open calcium-dependent inwardly rectifying potassium channels (OP3 and OP1 receptor agonist). This results in hyperpolarization and reduced neuronal excitability.
Absorption Not Available
Volume of distribution
  • 16 L/kg
Protein binding Not Available
Metabolism
Hepatic
Route of elimination The major route of metabolism is cytochrome CYP3A4 mediated N-demethylation to norpropoxyphene, which is excreted by the kidneys. In 48 hours, approximately 20% to 25% of the administered dose of propoxyphene is excreted via the urine, most of which is free or conjugated norpropoxyphene.
Half life 6-12 hours
Clearance
  • 2.6 L/min
Toxicity Coma, respiratory depression, circulatory collapse, and pulmonary edema. Seizures occur more frequently in patients with propoxyphene intoxication than in those with opiate intoxication. LD50=230mg/kg (orally in rat, Emerson)
Affected organisms
  • Humans and other mammals
Pathways Not Available
理化性质
Properties
State solid
Experimental Properties
Property Value Source
melting point 75.5 °C PhysProp
water solubility 3.32 mg/L (at 25 °C) MCFARLAND,JW ET AL. (2001)
logP 4.18 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
water solubility 4.19e-03 g/l ALOGPS
logP 4.06 ALOGPS
logP 4.9 ChemAxon
logS -4.9 ALOGPS
pKa (strongest basic) 9.52 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 2 ChemAxon
hydrogen donor count 0 ChemAxon
polar surface area 29.54 ChemAxon
rotatable bond count 9 ChemAxon
refractivity 102.88 ChemAxon
polarizability 38.4 ChemAxon
药物相互作用
Drug Interaction
Acenocoumarol Propoxyphene may increase the anticoagulant effect of acenocoumarol.
Alvimopan Increases levels by receptor binding competition. Discontinue opioid administration at least 7 days prior to administrating Alvimopan.
Anisindione Propoxyphene may increase the anticoagulant effect of anisindione.
Atomoxetine The CYP2D6 inhibitor could increase the effect and toxicity of atomoxetine
Carbamazepine Propoxyphene increases the effect of carbamazepine
Cimetidine Cimetidine, a moderate CYP3A4 inhibitor, may decrease the metabolism of propoxyphene. Monitor for changes in the therapeutic and adverse effects of propoxyphene if cimetidine is intitiated, discontinued or dose changed.
Dicumarol Propoxyphene may increase the anticoagulant effect of dicumarol.
Insulin Lispro Concomitant therapy with drugs that may increase the blood-glucose-lowering effect of insulin lispro and thus the chance of hypoglycemia should be monitored closely.
Ritonavir Ritonavir increases the levels of analgesic
Tranylcypromine Increased risk of serotonin syndrome. Concomitant use should be avoided.
Triprolidine The CNS depressants, Triprolidine and Propoxyphene, may increase adverse/toxic effects due to additivity. Monitor for increased CNS depressant effects during concomitant therapy.
Warfarin Propoxyphene may increase the anticoagulant effect of warfarin.
食物相互作用
  • Take without regard to meals. Avoid alcohol.

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