Overview
| Generic Names: | D-Propoxyphene; Dextropropoxyphene; Dextropropoxyphene-M; Dextroproxifeno; Propoxyphene HCl |
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| IUPAC Name: | [4-dimethylamino-3-methyl-1,2-di(phenyl)butan-2-yl] propanoate |
| Trade Names: | Algafan; Antalvic; Darvon; Darvon-N; Deprancol; Depromic; Dolene; Dolocap; Doloxen; Doloxene; Erantin; Femadol; Harmar; Kesso-Gesic; Propacet; Prophene 65; Propoxychel; Propoxyphene HCl 65; Proxagesic |
| PharmGKB Accession Id: | PA451142 |
Description
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]
Indication
For the relief of mild to moderate pain
ATC Therapeutic Category
- N02AC:Diphenylpropylamine derivatives
Pharmacology and Interactions
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.
Pharmacology
Propoxyphene, a synthetic opiate agonist, is structurally similar to methadone. 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.
Food Interactions
Take without regard to meals. Avoid alcohol.
Absorption, Distribution, Metabolism, Elimination & Toxicity
Biotransformation
Hepatic
Half Life
6-12 hours
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)
Chemical Properties
Chemical Formula:
C22H29NO2
SMILES Code:
CCC(=O)OC(Cc1ccccc1)(c2ccccc2)C(C)CN(C)C
(Format: OpenEye Isomeric)
Molecular Weight ( average / monoisotopic )
339.4712 / 339.2198
Curated Information
The following genes are in curated knowledge about this drug.
| Gene | Relationship | Evidence | |
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CYP2D6 |
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CYP3A |
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CYP3A4 |
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CYP3A5 |
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Non-Curated Information
A list of non-curated publications that mention this drug along with other genes is available.
Metabolizing Enzymes
Drug Targets
Curated Information
The following drugs are in curated knowledge about this drug.
| Drug | Relationship | Evidence | |
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warfarin |
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Non-Curated Information
A list of non-curated publications that mention this drug along with other drugs is available.
Drug Interactions
| acenocoumarol | Propoxyphene increases the anticoagulant effect |
| anisindione | Propoxyphene increases the anticoagulant effect |
| atomoxetine | The CYP2D6 inhibitor could increase the effect and toxicity of atomoxetine |
| carbamazepine | Propoxyphene increases the effect of carbamazepine |
| cimetidine | Cimetidine increases the effect of the narcotic |
| dicumarol | Propoxyphene increases the anticoagulant effect |
| naltrexone | Naltrexone may precipitate a withdrawal syndrome in opioid-dependent individuals |
| ritonavir | Ritonavir increases the levels of analgesic |
| warfarin | Propoxyphene increases the anticoagulant effect |
Curated Information
The following diseases are in curated knowledge about this drug.
| Disease | Relationship | Evidence | |
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Bradycardia |
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Non-Curated Information
A list of non-curated publications that mention this drug along with other diseases is available.
LinkOuts
Common Searches
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Non-Curated Publications
A list of non-curated publications that mention this drug is available.
