Identification

Name
Dextropropoxyphene
Accession Number
DB00647  (APRD00548)
Type
Small Molecule
Groups
Approved, Illicit, Investigational, Withdrawn
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.

Structure
Thumb
Synonyms
  • d-Propoxyphene
  • Destropropossifene
  • Dextropropoxifeno
  • Dextropropoxyphen
  • Dextropropoxyphène
  • Dextropropoxyphenum
  • Propoxyphene
External IDs
IDS-ND-004(SECT.2) / J5.928E / L 16298 / SK 65 / SK-65
Product Ingredients
IngredientUNIICASInChI Key
Dextropropoxyphene hydrochlorideCB2TL9PS0T1639-60-7QMQBBUPJKANITL-MYXGOWFTSA-N
Dextropropoxyphene napsylate38M219L1OJ26570-10-5GBKONKCASNNUQD-VGHSCWAPSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
642 TabTablet65 mgOralPendopharm Division Of De Pharmascience Inc1968-12-312010-11-25Canada
DarvonCapsule65 mg/1OralXanodyne Pharmaceuticals2009-09-252010-11-19Us
Darvon-NTablet, film coated100 mg/1OralXanodyne Pharmaceuticals2009-09-252010-11-19Us
Darvon-NCapsule100 mgOralPaladin Labs Inc1973-12-312010-12-23Canada
Darvon-NTablet, film coated100 mg/1OralPhysicians Total Care, Inc.2007-01-082008-06-30Us
Darvon-NTablet, film coated100 mg/1OralStat Rx USA2009-09-25Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Novo-propoxyn Cap 65mgCapsule65 mgOralNovopharm Limited1970-12-312005-08-10Canada
PropoxypheneCapsule65 mg/1OralStat Rx USA2009-10-27Not applicableUs
PropoxypheneCapsule65 mg/1OralPd Rx Pharmaceuticals, Inc.1973-06-202015-05-08Us
PropoxypheneCapsule65 mg/1OralWest Ward Pharmaceutical1973-06-202010-11-24Us
PropoxypheneCapsule65 mg/1OralPd Rx Pharmaceuticals, Inc.2010-05-102015-05-08Us
Propoxyphene HydrochlorideCapsule65 mg/1Oralbryant ranch prepack2009-11-102010-11-15Us
Propoxyphene HydrochlorideCapsule65 mg/1OralMylan Pharmaceuticals2009-11-022014-01-31Us
Propoxyphene HydrochlorideCapsule65 mg/1OralQualitest2009-07-172010-11-23Us
Propoxyphene HydrochlorideCapsule65 mg/1OralHeritage2009-05-01Not applicableUs23155 01220180906 25352 n3d8l6
Propoxyphene HydrochlorideCapsule65 mg/1OralPar Pharmaceutical2009-04-152011-04-15Us
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
692 TabDextropropoxyphene hydrochloride (65 mg) + Acetylsalicylic acid (375 mg) + Caffeine (30 mg)TabletOralMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1986-02-131998-04-21Canada
692 TabletDextropropoxyphene hydrochloride (65 mg) + Acetylsalicylic acid (375 mg) + Caffeine (30 mg)TabletOralLioh Inc.1998-09-012006-08-25Canada
Balacet 325Dextropropoxyphene napsylate (100 mg/1) + Acetaminophen (325 mg/1)Tablet, film coatedOralCornerstone Therapeutics Inc.2004-06-282010-08-10Us
Balacet 325Dextropropoxyphene napsylate (100 mg/1) + Acetaminophen (325 mg/1)Tablet, film coatedOralCornerstone Therapeutics Inc.2004-06-282010-11-19Us
Darvocet A500Dextropropoxyphene napsylate (100 mg/1) + Acetaminophen (500 mg/1)Tablet, film coatedOralPhysicians Total Care, Inc.2004-09-022010-11-30Us
Darvocet A500Dextropropoxyphene napsylate (100 mg/1) + Acetaminophen (500 mg/1)Tablet, film coatedOralXanodyne Pharmaceuticals2009-11-302010-11-19Us
Darvocet N100Dextropropoxyphene napsylate (100 mg/1) + Acetaminophen (650 mg/1)Tablet, film coatedOralPhysicians Total Care, Inc.2003-10-302010-11-30Us
Darvocet-N 100Dextropropoxyphene napsylate (100 mg/1) + Acetaminophen (650 mg/1)Tablet, film coatedOralXanodyne Pharmaceuticals2009-09-252010-11-19Us
Darvocet-N 50Dextropropoxyphene napsylate (50 mg/1) + Acetaminophen (325 mg/1)Tablet, film coatedOralXanodyne Pharmaceuticals2009-09-252010-11-19Us
Darvon N Compound Pulvule 405Dextropropoxyphene napsylate (100 mg) + Acetylsalicylic acid (375 mg) + Caffeine (30 mg)CapsuleOralEli Lilly & Co. Ltd.1973-12-311999-08-11Canada
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Propoxyphene and AcetaminophenDextropropoxyphene napsylate (100 mg/1) + Acetaminophen (650 mg/1)Tablet, film coatedOralVintage Pharmaceuticals, LLC2007-05-092007-05-09Us
Propoxyphene and AcetaminophenDextropropoxyphene napsylate (50 mg/1) + Acetaminophen (325 mg/1)Tablet, film coatedOralVintage Pharmaceuticals, LLC2007-05-092007-05-09Us
Propoxyphene and AcetaminophenDextropropoxyphene napsylate (100 mg/1) + Acetaminophen (650 mg/1)Tablet, film coatedOralVintage Pharmaceuticals, LLC2007-05-092007-05-09Us
Propoxyphene and AcetaminophenDextropropoxyphene napsylate (100 mg/1) + Acetaminophen (650 mg/1)Tablet, film coatedOralVintage Pharmaceuticals, LLC2007-05-092007-05-09Us
Propoxyphene Hydrochloride and AcetaminophenDextropropoxyphene hydrochloride (65 mg/1) + Acetaminophen (650 mg/1)TabletOralUNSPECIFIED2006-04-07Not applicableUs
Propoxyphene Hydrochloride and AcetaminophenDextropropoxyphene hydrochloride (65 mg/1) + Acetaminophen (650 mg/1)Tablet, film coatedOralVintage Pharmaceuticals, LLC2007-07-262007-07-26Us
Propoxyphene Napsylate and AcetominophenDextropropoxyphene napsylate (100 mg/1) + Acetaminophen (500 mg/1)Tablet, film coatedOralAndrx Pharmaceuticals, Inc.2008-08-01Not applicableUs
Propoxyphene Napsylate and AcetominophenDextropropoxyphene napsylate (100 mg/1) + Acetaminophen (650 mg/1)Tablet, film coatedOralAndrx Pharmaceuticals, Inc.2008-11-18Not applicableUs
Propoxyphene Napsylate and AcetominophenDextropropoxyphene napsylate (100 mg/1) + Acetaminophen (650 mg/1)Tablet, film coatedOralAndrx Pharmaceuticals, Inc.2008-11-18Not applicableUs
Therapoxyphene 650Dextropropoxyphene napsylate (100 mg/1) + Acetaminophen (650 mg/1)TabletOralPhysician Therapeutics Llc2010-10-142010-12-03Us
International/Other Brands
Abalgin (DLF) / Dacoton (Standard) / Darvon (Eli Lilly) / Deprancol (Parke Davis) / Depronal (Pfizer) / Dolene / Doloxene (Aspen Pharmacare)
Categories
UNII
S2F83W92TK
CAS number
469-62-5
Weight
Average: 339.4712
Monoisotopic: 339.219829177
Chemical Formula
C22H29NO2
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

Pharmacology

Indication

For the relief of mild to moderate pain

Associated Conditions
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.

TargetActionsOrganism
AMu-type opioid receptor
agonist
Human
ADelta-type opioid receptor
agonist
Human
AKappa-type opioid receptor
antagonist
Human
ULiver carboxylesterase 1Not AvailableHuman
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
PathwayCategory
Propoxyphene Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
2,5-Dimethoxy-4-ethylamphetamine2,5-Dimethoxy-4-ethylamphetamine may increase the analgesic activities of Dextropropoxyphene.
2,5-Dimethoxy-4-ethylthioamphetamine2,5-Dimethoxy-4-ethylthioamphetamine may increase the analgesic activities of Dextropropoxyphene.
3,4-Methylenedioxyamphetamine3,4-Methylenedioxyamphetamine may increase the analgesic activities of Dextropropoxyphene.
4-Bromo-2,5-dimethoxyamphetamine4-Bromo-2,5-dimethoxyamphetamine may increase the analgesic activities of Dextropropoxyphene.
7-NitroindazoleThe risk or severity of adverse effects can be increased when Dextropropoxyphene is combined with 7-Nitroindazole.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinolineThe risk or severity of adverse effects can be increased when Dextropropoxyphene is combined with 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline.
AcepromazineThe risk or severity of adverse effects can be increased when Dextropropoxyphene is combined with Acepromazine.
AceprometazineThe risk or severity of adverse effects can be increased when Dextropropoxyphene is combined with Aceprometazine.
AcetazolamideThe risk or severity of adverse effects can be increased when Dextropropoxyphene is combined with Acetazolamide.
Acetyl sulfisoxazoleThe metabolism of Dextropropoxyphene can be decreased when combined with Acetyl sulfisoxazole.
Food Interactions
  • Take without regard to meals. Avoid alcohol.

References

Synthesis Reference

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

US4661625
General References
  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:12818953]
  2. 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. [PubMed:10690289]
  3. Tyers MB: A classification of opiate receptors that mediate antinociception in animals. Br J Pharmacol. 1980 Jul;69(3):503-12. [PubMed:6249436]
  4. FDA data [Link]
  5. Drug Information [Link]
  6. Drugs.com [Link]
External Links
KEGG Drug
D07809
KEGG Compound
C07406
PubChem Compound
10100
PubChem Substance
46506690
ChemSpider
9696
BindingDB
82269
ChEBI
51173
ChEMBL
CHEMBL1213351
Therapeutic Targets Database
DAP000017
PharmGKB
PA451142
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Propoxyphene
ATC Codes
N02AC54 — Dextropropoxyphene, combinations excl. psycholepticsN02AC74 — Dextropropoxyphene, combinations with psycholepticsN02AC04 — Dextropropoxyphene
MSDS
Download (46.1 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedSupportive CarePain / Unspecified Adult Solid Tumor, Protocol Specific1
4TerminatedTreatmentHealthy Volunteers1

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
FormRouteStrength
TabletOral65 mg
TabletOral
CapsuleOral
CapsuleOral100 mg
Tablet, film coatedOral100 mg/1
CapsuleOral65 mg
CapsuleOral65 mg/1
Tablet, film coatedOral
Prices
Unit descriptionCostUnit
Propoxyphene napsylate powder5.33USD g
Darvon-n 100 mg tablet2.16USD tablet
Darvon 65 mg capsule1.71USD capsule
Propoxyphene N-APAP 100-500 mg tablet1.6USD tablet
Darvon 65 mg pulvule1.49USD each
Propoxyphene N-APAP 50-325 mg tablet1.32USD tablet
Propoxyphene-APAP 65-650 mg tablet0.57USD tablet
Propoxyphene N-APAP 100-650 mg tablet0.47USD tablet
Propoxyphene hcl 65 mg capsule0.43USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)75.5 °CPhysProp
water solubility3.32 mg/L (at 25 °C)MCFARLAND,JW ET AL. (2001)
logP4.18HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.00419 mg/mLALOGPS
logP4.06ALOGPS
logP4.9ChemAxon
logS-4.9ALOGPS
pKa (Strongest Basic)9.52ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.54 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity102.88 m3·mol-1ChemAxon
Polarizability38.86 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.997
Blood Brain Barrier+0.9503
Caco-2 permeable+0.7277
P-glycoprotein substrateSubstrate0.5798
P-glycoprotein inhibitor IInhibitor0.7851
P-glycoprotein inhibitor IINon-inhibitor0.6469
Renal organic cation transporterNon-inhibitor0.6086
CYP450 2C9 substrateNon-substrate0.833
CYP450 2D6 substrateNon-substrate0.9117
CYP450 3A4 substrateSubstrate0.6032
CYP450 1A2 substrateInhibitor0.6357
CYP450 2C9 inhibitorNon-inhibitor0.7637
CYP450 2D6 inhibitorInhibitor0.6887
CYP450 2C19 inhibitorNon-inhibitor0.7628
CYP450 3A4 inhibitorNon-inhibitor0.7992
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.646
Ames testNon AMES toxic0.8896
CarcinogenicityCarcinogens 0.7164
BiodegradationNot ready biodegradable0.9714
Rat acute toxicity2.9360 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9033
hERG inhibition (predictor II)Inhibitor0.6837
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - CI-BGC-MSsplash10-067l-0393000000-d81188159d7476252fd4
GC-MS Spectrum - EI-BGC-MSsplash10-0a4i-9000000000-9c987f1baf068ed1fd6e
Mass Spectrum (Electron Ionization)MSsplash10-0a4i-9200000000-39d80ee06dde3e5036f4
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Stilbenes
Sub Class
Not Available
Direct Parent
Stilbenes
Alternative Parents
Phenylbutylamines / Benzyloxycarbonyls / Phenylpropanes / Aralkylamines / Trialkylamines / Carboxylic acid esters / Amino acids and derivatives / Monocarboxylic acids and derivatives / Organopnictogen compounds / Organic oxides
show 2 more
Substituents
Stilbene / Phenylbutylamine / Benzyloxycarbonyl / Phenylpropane / Aralkylamine / Monocyclic benzene moiety / Benzenoid / Tertiary aliphatic amine / Tertiary amine / Carboxylic acid ester
show 13 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
1-benzyl-3-(dimethylamino)-2-methyl-1-phenylpropyl propanoate (CHEBI:51173)

Targets

Kind
Protein
Organism
Human
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
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  2. 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. [PubMed:10690289]
  3. Tyers MB: A classification of opiate receptors that mediate antinociception in animals. Br J Pharmacol. 1980 Jul;69(3):503-12. [PubMed:6249436]
  4. 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. [PubMed:9399970]
  5. 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. [PubMed:7562497]
  6. 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. [PubMed:19604717]
  7. 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. [PubMed:10379623]
Kind
Protein
Organism
Human
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
  1. 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. [PubMed:6151117]
Kind
Protein
Organism
Human
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
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  2. 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. [PubMed:6151117]
Kind
Protein
Organism
Human
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
  1. 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. [PubMed:10381793]

Enzymes

Kind
Protein
Organism
Human
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
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. 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 . [PubMed:15764408]
  3. 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. [PubMed:8877250]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
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
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid 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 oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid 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 oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]

Drug created on June 13, 2005 07:24 / Updated on September 21, 2018 00:03