Dextropropoxyphene

Identification

Summary

Dextropropoxyphene is an opioid analgesic used to treat mild to moderate pain.

Brand Names

Darvocet-N, Darvon

Generic Name

Dextropropoxyphene

DrugBank Accession Number

DB00647

Background

Dextropropoxyphene is an opioid analgesic manufactured by Eli Lilly and Company. It is used in the symptomatic treatment of mild pain. It displays antitussive and local anaesthetic actions. Due to the risk of cardiac arrhythmias and overdose, possibly leading to death, dextropropoxyphene has been withdrawn from the market in Europe and the United States. 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.

Type

Small Molecule

Groups

Approved, Illicit, Investigational, Withdrawn

Structure

Similar Structures

Weight: Average: 339.4712
Monoisotopic: 339.219829177
Chemical Formula: C₂₂H₂₉NO₂

Synonyms

d-Propoxyphene
Destropropossifene
Dextropropoxifeno
Dextropropoxyphen
Dextropropoxyphène
Dextropropoxyphene
Dextropropoxyphenum
Dextroproxifeno
Propoxyphene

External IDs

IDS-ND-004(SECT.2)
J5.928E
L 16298
SK 65
SK-65

Poor quality drug data slowing you down?

Unlock 38% more drug discovery time and eliminate decision-making doubts with this one-stop guide to quality drug data.

Download eBook

Poor quality drug data slowing you down?

Download eBook

Pharmacology

Indication

For the relief of mild to moderate pain.

Reduce drug development failure rates

Build, train, & validate machine-learning models
with evidence-based and structured datasets.

See how

Build, train, & validate predictive machine-learning models with structured datasets.

See how

Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Management of	Pain		••••••••••••

Contraindications & Blackbox Warnings

Prevent Adverse Drug Events Today

Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.

Learn more

Avoid life-threatening adverse drug events with our Clinical API

Learn more

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.

Target	Actions	Organism
AMu-type opioid receptor	agonist	Humans
ADelta-type opioid receptor	agonist	Humans
AKappa-type opioid receptor	antagonist	Humans
ULiver carboxylesterase 1	Not Available	Humans
UNMDA receptor	antagonist	Humans

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

Adverse Effects

Improve decision support & research outcomes

With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!

See the data

Improve decision support & research outcomes with our structured adverse effects data.

See a data sample

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)

Pathways

Pathway	Category
Propoxyphene Action Pathway	Drug action

Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">

Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Drug	Interaction
Integrate drug-drug interactions in your software
1,2-Benzodiazepine	The risk or severity of adverse effects can be increased when Dextropropoxyphene is combined with 1,2-Benzodiazepine.
Abametapir	The serum concentration of Dextropropoxyphene can be increased when it is combined with Abametapir.
Abatacept	The metabolism of Dextropropoxyphene can be increased when combined with Abatacept.
Abemaciclib	The serum concentration of Abemaciclib can be increased when it is combined with Dextropropoxyphene.
Abiraterone	The metabolism of Dextropropoxyphene can be decreased when combined with Abiraterone.

Food Interactions

Avoid alcohol.
Take with or without food. Food does not significantly affect absorption.

Products

Drug product information from 10+ global regions

Our datasets provide approved product information including:
dosage, form, labeller, route of administration, and marketing period.

Access now

Access drug product information from over 10 global regions.

Access now

Product Ingredients

Ingredient	UNII	CAS	InChI Key
Dextropropoxyphene hydrochloride	CB2TL9PS0T	1639-60-7	QMQBBUPJKANITL-MYXGOWFTSA-N
Dextropropoxyphene napsylate	38M219L1OJ	26570-10-5	GBKONKCASNNUQD-VGHSCWAPSA-N

Product Images

International/Other Brands

Abalgin (DLF) / Dacoton (Standard) / Deprancol (Parke Davis) / Depronal (Pfizer) / Dolene / Doloxene (Aspen Pharmacare)

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
642 Tab	Tablet	65 mg	Oral	Pendopharm Division Of Pharmascience Inc	1968-12-31	2010-11-25
Darvon	Capsule	65 mg/1	Oral	Xanodyne Pharmaceuticals	2009-09-25	2010-11-19
Darvon-N	Capsule	100 mg	Oral	Paladin Labs Inc	1973-12-31	2010-12-23
Darvon-N	Tablet, film coated	100 mg/1	Oral	Xanodyne Pharmaceuticals	2009-09-25	2010-11-19
Darvon-N	Tablet, film coated	100 mg/1	Oral	Physicians Total Care, Inc.	2007-01-08	2008-06-30

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Novo-propoxyn Cap 65mg	Capsule	65 mg	Oral	Novopharm Limited	1970-12-31	2005-08-10
Propoxyphene	Capsule	65 mg/1	Oral	Stat Rx USA	2009-10-27	Not applicable
Propoxyphene	Capsule	65 mg/1	Oral	Pd Rx Pharmaceuticals, Inc.	2010-05-10	2015-05-08
Propoxyphene	Capsule	65 mg/1	Oral	West Ward Pharmaceutical	1973-06-20	2010-11-24
Propoxyphene	Capsule	65 mg/1	Oral	Pd Rx Pharmaceuticals, Inc.	1973-06-20	2015-05-08

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
692 Tab	Dextropropoxyphene hydrochloride (65 mg) + Acetylsalicylic acid (375 mg) + Caffeine (30 mg)	Tablet	Oral	Merck Frosst Canada & Cie, Merck Frosst Canada & Co.	1986-02-13	1998-04-21
692 Tablet	Dextropropoxyphene hydrochloride (65 mg) + Acetylsalicylic acid (375 mg) + Caffeine (30 mg)	Tablet	Oral	Lioh Inc.	1998-09-01	2006-08-25
Balacet 325	Dextropropoxyphene napsylate (100 mg/1) + Acetaminophen (325 mg/1)	Tablet, film coated	Oral	Cornerstone Therapeutics Inc.	2004-06-28	2010-11-19
Balacet 325	Dextropropoxyphene napsylate (100 mg/1) + Acetaminophen (325 mg/1)	Tablet, film coated	Oral	Cornerstone Therapeutics Inc.	2004-06-28	2010-08-10
Darvocet A500	Dextropropoxyphene napsylate (100 mg/1) + Acetaminophen (500 mg/1)	Tablet, film coated	Oral	Xanodyne Pharmaceuticals	2009-11-30	2010-11-19

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Therapoxyphene 650	Dextropropoxyphene napsylate (100 mg/1) + Acetaminophen (650 mg/1)	Tablet	Oral	Physician Therapeutics Llc	2010-10-14	2010-12-03

Chemical Identifiers

UNII: S2F83W92TK
CAS number: 469-62-5
InChI Key: XLMALTXPSGQGBX-GCJKJVERSA-N
InChI: InChI=1S/C22H29NO2/c1-5-21(24)25-22(18(2)17-23(3)4,20-14-10-7-11-15-20)16-19-12-8-6-9-13-19/h6-15,18H,5,16-17H2,1-4H3/t18-,22+/m1/s1
IUPAC Name: (2S,3R)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl propanoate
SMILES: CCC(=O)O[C@@](CC1=CC=CC=C1)([C@H](C)CN(C)C)C1=CC=CC=C1

References

Synthesis Reference

Carl R. White, "Synthesis and purification of d-propoxyphene hydrochloride." U.S. Patent US4661625, issued April, 1973.

US4661625

General References

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. [Article]
Ulens C, Daenens P, Tytgat J: Norpropoxyphene-induced cardiotoxicity is associated with changes in ion-selectivity and gating of HERG currents. Cardiovasc Res. 1999 Dec;44(3):568-78. [Article]
Tyers MB: A classification of opiate receptors that mediate antinociception in animals. Br J Pharmacol. 1980 Jul;69(3):503-12. [Article]
FDA data [Link]
Drug Information [Link]
Drugs.com [Link]

External Links

KEGG Drug: D07809
KEGG Compound: C07406
PubChem Compound: 10100
PubChem Substance: 46506690
ChemSpider: 9696
BindingDB: 82269
RxNav: 8785
ChEBI: 51173
ChEMBL: CHEMBL1213351
ZINC: ZINC000001530769
Therapeutic Targets Database: DAP000017
PharmGKB: PA451142
RxList: RxList Drug Page
Drugs.com: Drugs.com Drug Page
Wikipedia: Dextropropoxyphene

MSDS

Download (46.1 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Completed	Supportive Care	Pain / Unspecified Adult Solid Tumor, Protocol Specific	1
4	Terminated	Treatment	Healthy Subjects (HS)	1
4	Terminated	Treatment	Spinal Stenosis of Lumbar Region	1

Pharmacoeconomics

Manufacturers

Xanodyne pharmaceutics inc
Heritage pharmaceuticals inc
Mk laboratories inc
Halsey drug co inc
Alra laboratories inc
Impax laboratories inc
Ivax pharmaceuticals inc sub teva pharmaceuticals usa
Mutual pharmaceutical co inc
Mylan pharmaceuticals inc
Nexgen pharma inc
Par pharmaceutical inc
Purepac pharmaceutical co
Private formulations inc
Roxane laboratories inc
Sandoz inc
Teva pharmaceuticals usa inc
Valeant pharmaceuticals international
Vintage pharmaceuticals inc
Watson laboratories inc
West ward pharmaceutical corp
Whiteworth towne paulsen inc
Warner chilcott div warner lambert co
Aaipharma llc

Packagers

AAIPharma Inc.
Aidarex Pharmacuticals LLC
Altura Pharmaceuticals Inc.
Amerisource Health Services Corp.
Apotheca Inc.
Aristos Pharmaceuticals
A-S Medication Solutions LLC
Blenheim Pharmacal
Bryant Ranch Prepack
Cardinal Health
Caremark LLC
Comprehensive Consultant Services Inc.
Corepharma LLC
Cornerstone Pharmacy
D.M. Graham Laboratories Inc.
Direct Dispensing Inc.
Dispensing Solutions
Diversified Healthcare Services Inc.
DSM Corp.
Golden State Medical Supply Inc.
H and H Laboratories
H.J. Harkins Co. Inc.
Heartland Repack Services LLC
Innoviant Pharmacy Inc.
Ivax Pharmaceuticals
Kaiser Foundation Hospital
Keltman Pharmaceuticals Inc.
Lake Erie Medical and Surgical Supply
Liberty Pharmaceuticals
Lilly Del Caribe Inc.
Major Pharmaceuticals
Mallinckrodt Inc.
Mckesson Corp.
Medvantx Inc.
Mikart Inc.
Murfreesboro Pharmaceutical Nursing Supply
Mylan
Nexgen Pharma Inc.
Nucare Pharmaceuticals Inc.
Palmetto Pharmaceuticals Inc.
Par Pharmaceuticals
PCA LLC
PD-Rx Pharmaceuticals Inc.
Pharmedix
Physicians Total Care Inc.
Pliva Inc.
Preferred Pharmaceuticals Inc.
Prepackage Specialists
Prepak Systems Inc.
Qualitest
Ranbaxy Laboratories
Rebel Distributors Corp.
Redpharm Drug
Remedy Repack
Resource Optimization and Innovation LLC
Sandhills Packaging Inc.
Smartscience Laboratories Inc.
Southwood Pharmaceuticals
St Mary's Medical Park Pharmacy
Stat Rx Usa
Talbert Medical Management Corp.
Teva Pharmaceutical Industries Ltd.
UDL Laboratories
Va Cmop Dallas
Veratex Corp.
Vintage Pharmaceuticals Inc.
Watson Pharmaceuticals
West-Ward Pharmaceuticals
Wockhardt Ltd.
Xanodyne Pharmaceuticals Inc.

Dosage Forms

Form	Route	Strength
Tablet	Oral	65 mg
Capsule	Oral
Capsule	Oral	100 mg
Tablet, film coated	Oral	100 mg/1
Pill
Suppository
Capsule	Oral	65 mg
Capsule	Oral	65 mg/1
Tablet	Oral
Tablet, film coated	Oral

Prices

Unit description	Cost	Unit
Propoxyphene napsylate powder	5.33USD	g
Darvon-n 100 mg tablet	2.16USD	tablet
Darvon 65 mg capsule	1.71USD	capsule
Propoxyphene N-APAP 100-500 mg tablet	1.6USD	tablet
Darvon 65 mg pulvule	1.49USD	each
Propoxyphene N-APAP 50-325 mg tablet	1.32USD	tablet
Propoxyphene-APAP 65-650 mg tablet	0.57USD	tablet
Propoxyphene N-APAP 100-650 mg tablet	0.47USD	tablet
Propoxyphene hcl 65 mg capsule	0.43USD	capsule

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	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	0.00419 mg/mL	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 Å²	Chemaxon
Rotatable Bond Count	9	Chemaxon
Refractivity	102.88 m³·mol^-1	Chemaxon
Polarizability	38.86 Å³	Chemaxon
Number of Rings	2	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	Yes	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.997
Blood Brain Barrier	+	0.9503
Caco-2 permeable	+	0.7277
P-glycoprotein substrate	Substrate	0.5798
P-glycoprotein inhibitor I	Inhibitor	0.7851
P-glycoprotein inhibitor II	Non-inhibitor	0.6469
Renal organic cation transporter	Non-inhibitor	0.6086
CYP450 2C9 substrate	Non-substrate	0.833
CYP450 2D6 substrate	Non-substrate	0.9117
CYP450 3A4 substrate	Substrate	0.6032
CYP450 1A2 substrate	Inhibitor	0.6357
CYP450 2C9 inhibitor	Non-inhibitor	0.7637
CYP450 2D6 inhibitor	Inhibitor	0.6887
CYP450 2C19 inhibitor	Non-inhibitor	0.7628
CYP450 3A4 inhibitor	Non-inhibitor	0.7992
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.646
Ames test	Non AMES toxic	0.8896
Carcinogenicity	Carcinogens	0.7164
Biodegradation	Not ready biodegradable	0.9714
Rat acute toxicity	2.9360 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9033
hERG inhibition (predictor II)	Inhibitor	0.6837

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-0a4i-9310000000-64090a7cc1eb41e95d27
GC-MS Spectrum - CI-B	GC-MS	splash10-067l-0393000000-d81188159d7476252fd4
GC-MS Spectrum - EI-B	GC-MS	splash10-0a4i-9000000000-9c987f1baf068ed1fd6e
Mass Spectrum (Electron Ionization)	MS	splash10-0a4i-9200000000-39d80ee06dde3e5036f4
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0a4i-3190000000-23a4e1c3e4e618c63c87
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-00di-9120000000-f76f3d90103e0de058a4
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-006x-4980000000-2aa2d32e113bce505fb7
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0a4i-9150000000-07d3369247f880b91798
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0ufv-0690000000-6be347209ba89b1056b0
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0a4i-9140000000-cdacdd2543f8eb2c60b9
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	197.6262793	predicted	DarkChem Lite v0.1.0
[M-H]-	180.2934	predicted	DeepCCS 1.0 (2019)
[M+H]+	197.9417793	predicted	DarkChem Lite v0.1.0
[M+H]+	182.6514	predicted	DeepCCS 1.0 (2019)
[M+Na]+	197.4102793	predicted	DarkChem Lite v0.1.0
[M+Na]+	189.34523	predicted	DeepCCS 1.0 (2019)

Targets

Build, predict & validate machine-learning models

Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.

Learn more

Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.

Learn more

Details1. Mu-type opioid receptor

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Agonist

General Function: Voltage-gated calcium channel activity
Specific Function: Receptor for endogenous opioids such as beta-endorphin and endomorphin. Receptor for natural and synthetic opioids including morphine, heroin, DAMGO, fentanyl, etorphine, buprenorphin and methadone...
Gene Name: OPRM1
Uniprot ID: P35372
Uniprot Name: Mu-type opioid receptor
Molecular Weight: 44778.855 Da

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Ulens C, Daenens P, Tytgat J: Norpropoxyphene-induced cardiotoxicity is associated with changes in ion-selectivity and gating of HERG currents. Cardiovasc Res. 1999 Dec;44(3):568-78. [Article]
Tyers MB: A classification of opiate receptors that mediate antinociception in animals. Br J Pharmacol. 1980 Jul;69(3):503-12. [Article]
Picker MJ: Discriminative stimulus effects of the mixed-opioid agonist/antagonist dezocine: cross-substitution by mu and delta opioid agonists. J Pharmacol Exp Ther. 1997 Dec;283(3):1009-17. [Article]
Codd EE, Shank RP, Schupsky JJ, Raffa RB: Serotonin and norepinephrine uptake inhibiting activity of centrally acting analgesics: structural determinants and role in antinociception. J Pharmacol Exp Ther. 1995 Sep;274(3):1263-70. [Article]
Bannwarth B, Richez C: The dextropropoxyphene controversy. Joint Bone Spine. 2009 Oct;76(5):449-51. doi: 10.1016/j.jbspin.2009.04.004. Epub 2009 Jul 14. [Article]
Walker EA, Tiano MJ, Benyas SI, Dykstra LA, Picker MJ: Naltrexone and beta-funaltrexamine antagonism of the antinociceptive and response rate-decreasing effects of morphine, dezocine, and d-propoxyphene. Psychopharmacology (Berl). 1999 May;144(1):45-53. [Article]

Details2. Delta-type opioid receptor

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Agonist

General Function: Opioid receptor activity
Specific Function: G-protein coupled receptor that functions as receptor for endogenous enkephalins and for a subset of other opioids. Ligand binding causes a conformation change that triggers signaling via guanine n...
Gene Name: OPRD1
Uniprot ID: P41143
Uniprot Name: Delta-type opioid receptor
Molecular Weight: 40368.235 Da

References

Neil A: Affinities of some common opioid analgesics towards four binding sites in mouse brain. Naunyn Schmiedebergs Arch Pharmacol. 1984 Nov;328(1):24-9. [Article]

Details3. Kappa-type opioid receptor

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Antagonist

General Function: Opioid receptor activity
Specific Function: G-protein coupled opioid receptor that functions as receptor for endogenous alpha-neoendorphins and dynorphins, but has low affinity for beta-endorphins. Also functions as receptor for various synt...
Gene Name: OPRK1
Uniprot ID: P41145
Uniprot Name: Kappa-type opioid receptor
Molecular Weight: 42644.665 Da

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Neil A: Affinities of some common opioid analgesics towards four binding sites in mouse brain. Naunyn Schmiedebergs Arch Pharmacol. 1984 Nov;328(1):24-9. [Article]

Details4. Liver carboxylesterase 1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown

General Function: Triglyceride lipase activity
Specific Function: Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acy...
Gene Name: CES1
Uniprot ID: P23141
Uniprot Name: Liver carboxylesterase 1
Molecular Weight: 62520.62 Da

References

Zhang J, Burnell JC, Dumaual N, Bosron WF: Binding and hydrolysis of meperidine by human liver carboxylesterase hCE-1. J Pharmacol Exp Ther. 1999 Jul;290(1):314-8. [Article]

Details5. NMDA receptor (Protein Group)

Kind: Protein group
Organism: Humans
Pharmacological action: Unknown
Actions: Antagonist

General Function: Voltage-gated cation channel activity
Specific Function: NMDA receptor subtype of glutamate-gated ion channels with high calcium permeability and voltage-dependent sensitivity to magnesium. Mediated by glycine. This protein plays a key role in synaptic p...

Components:

Name	UniProt ID
Glutamate receptor ionotropic, NMDA 1	Q05586
Glutamate receptor ionotropic, NMDA 2A	Q12879
Glutamate receptor ionotropic, NMDA 2B	Q13224
Glutamate receptor ionotropic, NMDA 2C	Q14957
Glutamate receptor ionotropic, NMDA 2D	O15399
Glutamate receptor ionotropic, NMDA 3A	Q8TCU5
Glutamate receptor ionotropic, NMDA 3B	O60391

References

Ebert B, Thorkildsen C, Andersen S, Christrup LL, Hjeds H: Opioid analgesics as noncompetitive N-methyl-D-aspartate (NMDA) antagonists. Biochem Pharmacol. 1998 Sep 1;56(5):553-9. doi: 10.1016/s0006-2952(98)00088-4. [Article]

Enzymes

Details1. Cytochrome P450 2D6

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate
Inhibitor

General Function: Steroid hydroxylase activity
Specific Function: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name: CYP2D6
Uniprot ID: P10635
Uniprot Name: Cytochrome P450 2D6
Molecular Weight: 55768.94 Da

References

Yue QY, Sawe J: Different effects of inhibitors on the O- and N-demethylation of codeine in human liver microsomes. Eur J Clin Pharmacol. 1997;52(1):41-7. [Article]
Kerry NL, Somogyi AA, Bochner F, Mikus G: The role of CYP2D6 in primary and secondary oxidative metabolism of dextromethorphan: in vitro studies using human liver microsomes. Br J Clin Pharmacol. 1994 Sep;38(3):243-8. [Article]
Sanz EJ, Bertilsson L: d-Propoxyphene is a potent inhibitor of debrisoquine, but not S-mephenytoin 4-hydroxylation in vivo. Ther Drug Monit. 1990 May;12(3):297-9. doi: 10.1097/00007691-199005000-00016. [Article]

Details2. Cytochrome P450 3A4

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate
Inhibitor

General Function: Vitamin d3 25-hydroxylase activity
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name: CYP3A4
Uniprot ID: P08684
Uniprot Name: Cytochrome P450 3A4
Molecular Weight: 57342.67 Da

References

Somogyi AA, Menelaou A, Fullston SV: CYP3A4 mediates dextropropoxyphene N-demethylation to nordextropropoxyphene: human in vitro and in vivo studies and lack of CYP2D6 involvement. Xenobiotica. 2004 Oct;34(10):875-87. doi: 10.1080/00498250400008371 . [Article]
Spina E, Pisani F, Perucca E: Clinically significant pharmacokinetic drug interactions with carbamazepine. An update. Clin Pharmacokinet. 1996 Sep;31(3):198-214. doi: 10.2165/00003088-199631030-00004. [Article]

Details3. Cytochrome P450 3A Subfamily (Protein Group)

Kind: Protein group
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Vitamin d3 25-hydroxylase activity
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...

Components:

Name	UniProt ID
Cytochrome P450 3A4	P08684
Cytochrome P450 3A43	Q9HB55
Cytochrome P450 3A5	P20815
Cytochrome P450 3A7	P24462

References

Yue QY, Sawe J: Different effects of inhibitors on the O- and N-demethylation of codeine in human liver microsomes. Eur J Clin Pharmacol. 1997;52(1):41-7. [Article]

Details4. UDP-glucuronosyltransferase 2B4

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Glucuronosyltransferase activity
Specific Function: UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as...
Gene Name: UGT2B4
Uniprot ID: P06133
Uniprot Name: UDP-glucuronosyltransferase 2B4
Molecular Weight: 60512.035 Da

References

Raungrut P, Uchaipichat V, Elliot DJ, Janchawee B, Somogyi AA, Miners JO: In vitro-in vivo extrapolation predicts drug-drug interactions arising from inhibition of codeine glucuronidation by dextropropoxyphene, fluconazole, ketoconazole, and methadone in humans. J Pharmacol Exp Ther. 2010 Aug;334(2):609-18. doi: 10.1124/jpet.110.167916. Epub 2010 May 18. [Article]

Drug created at June 13, 2005 13:24 / Updated at December 02, 2023 07:00

Dextropropoxyphene

Identification

Structure for Dextropropoxyphene (DB00647)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Collision Cross Sections (CCS)

Targets

References

References

References

References

Components:

References

Enzymes

References

References

Components:

References

References