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Namespace Prefixes

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Statements

Subject Item
n2:DB00647
rdf:type
n3:Drug
n3:description
Dextropropoxyphene is an analgesic in the opioid category, patented (1955) and manufactured by Eli Lilly and Company. It is intended to treat mild pain and also has antitussive and local anaesthetic effects. The drug has been taken off the market in Europe and the US due to concerns of fatal overdoses and heart arrhythmias. An estimated 10 million patients have used these products. The drug is often referred to as the general form, "propoxyphene", however only the dextro-isomer (dextropropoxyphene) has any analgesic effect. The levo-isomer appears to exhibit a very limited antitussive effect.
n3:dosage
n11:271B60EB-363D-11E5-9242-09173F13E4C5 n11:271B60EC-363D-11E5-9242-09173F13E4C5
n3:generalReferences
# 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":http://www.ncbi.nlm.nih.gov/pubmed/12818953
n3:group
withdrawn approved illicit
n3:halfLife
6-12 hours
n3:indication
For the relief of mild to moderate pain
n3:manufacturer
n5:271B60CB-363D-11E5-9242-09173F13E4C5 n5:271B60D3-363D-11E5-9242-09173F13E4C5 n5:271B60D4-363D-11E5-9242-09173F13E4C5 n5:271B60E0-363D-11E5-9242-09173F13E4C5 n5:271B60E1-363D-11E5-9242-09173F13E4C5 n5:271B60DE-363D-11E5-9242-09173F13E4C5 n5:271B60DF-363D-11E5-9242-09173F13E4C5 n5:271B60DC-363D-11E5-9242-09173F13E4C5 n5:271B60DD-363D-11E5-9242-09173F13E4C5 n5:271B60D2-363D-11E5-9242-09173F13E4C5 n5:271B60DB-363D-11E5-9242-09173F13E4C5 n5:271B60D0-363D-11E5-9242-09173F13E4C5 n5:271B60D1-363D-11E5-9242-09173F13E4C5 n5:271B60CE-363D-11E5-9242-09173F13E4C5 n5:271B60CF-363D-11E5-9242-09173F13E4C5 n5:271B60CC-363D-11E5-9242-09173F13E4C5 n5:271B60CD-363D-11E5-9242-09173F13E4C5 n5:271B60D9-363D-11E5-9242-09173F13E4C5 n5:271B60DA-363D-11E5-9242-09173F13E4C5 n5:271B60D7-363D-11E5-9242-09173F13E4C5 n5:271B60D8-363D-11E5-9242-09173F13E4C5 n5:271B60D5-363D-11E5-9242-09173F13E4C5 n5:271B60D6-363D-11E5-9242-09173F13E4C5
owl:sameAs
n18:DB00647 n26:DB00647
dcterms:title
Dextropropoxyphene
adms:identifier
n7:PA451142 n8:C07406 n9:0378-7065-01 n10:DB00647 n19:51173 n20:D07809 n21:Propoxyphene
n3:mechanismOfAction
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.
n3:packager
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n3:routeOfElimination
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.
n3:synonym
Dextropropoxyphène Destropropossifene Dextropropoxyphen Dextropropoxyphenum Dextropropoxifeno d-Propoxyphene
n3:toxicity
Coma, respiratory depression, circulatory collapse, and pulmonary edema. Seizures occur more frequently in patients with propoxyphene intoxication than in those with opiate intoxication. LD<sub>50</sub>=230mg/kg (orally in rat, Emerson)
n3:volumeOfDistribution
* 16 L/kg
n3:foodInteraction
Take without regard to meals. Avoid alcohol.
n3:mixture
n25:271B6084-363D-11E5-9242-09173F13E4C5 n25:271B6082-363D-11E5-9242-09173F13E4C5 n25:271B6083-363D-11E5-9242-09173F13E4C5 n25:271B6080-363D-11E5-9242-09173F13E4C5 n25:271B6081-363D-11E5-9242-09173F13E4C5 n25:271B607E-363D-11E5-9242-09173F13E4C5 n25:271B607F-363D-11E5-9242-09173F13E4C5
n3:salt
n3:synthesisReference
Carl R. White, "Synthesis and purification of d-propoxyphene hydrochloride." U.S. Patent US4661625, issued April, 1973.
n22:hasConcept
n23:M0017770
foaf:page
n13:propox.htm n27:propoxyphene.html
n3:IUPAC-Name
n4:271B60F1-363D-11E5-9242-09173F13E4C5
n3:InChI
n4:271B60F7-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n4:271B60F6-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n4:271B60F3-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n4:271B60F4-363D-11E5-9242-09173F13E4C5
n3:SMILES
n4:271B60F5-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n4:271B60EF-363D-11E5-9242-09173F13E4C5 n4:271B6106-363D-11E5-9242-09173F13E4C5
n3:logP
n4:271B60F0-363D-11E5-9242-09173F13E4C5 n4:271B60ED-363D-11E5-9242-09173F13E4C5 n4:271B6108-363D-11E5-9242-09173F13E4C5
n3:logS
n4:271B60EE-363D-11E5-9242-09173F13E4C5
n15:hasATCCode
n16:N02AC04
n3:H-Bond-Acceptor-Count
n4:271B60FD-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n4:271B60FE-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n4:271B60F8-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n4:271B60F9-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n4:271B60FB-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n4:271B60FA-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n4:271B60FC-363D-11E5-9242-09173F13E4C5
n3:affectedOrganism
Humans and other mammals
n3:casRegistryNumber
469-62-5
n3:category
n3:clearance
* 2.6 L/min
n3:containedIn
n24:271B60E9-363D-11E5-9242-09173F13E4C5 n24:271B60EA-363D-11E5-9242-09173F13E4C5 n24:271B60E3-363D-11E5-9242-09173F13E4C5 n24:271B60E4-363D-11E5-9242-09173F13E4C5 n24:271B60E2-363D-11E5-9242-09173F13E4C5 n24:271B60E7-363D-11E5-9242-09173F13E4C5 n24:271B60E8-363D-11E5-9242-09173F13E4C5 n24:271B60E5-363D-11E5-9242-09173F13E4C5 n24:271B60E6-363D-11E5-9242-09173F13E4C5
n3:Bioavailability
n4:271B6102-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n4:271B6104-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n4:271B6105-363D-11E5-9242-09173F13E4C5
n3:Melting-Point
n4:271B6107-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n4:271B6101-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n4:271B6100-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n4:271B6103-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n4:271B60F2-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
n4:271B60FF-363D-11E5-9242-09173F13E4C5