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Identification
NameTapentadol
Accession NumberDB06204
TypeSmall Molecule
GroupsApproved
Description

Opioid analgesic for treatment of moderate to severe pain. FDA approved on Nov 20, 2008.

Structure
Thumb
Synonyms
BN-200
CG-5503
Nucynta
Tapentadol
External Identifiers
  • R331333
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Nucyntatablet, film coated100 mg/1oralStat Rx USA2009-06-01Not applicableUs
Nucyntatablet, film coated100 mg/1oralLake Erie Medical DBA Quality Care Products LLC2009-06-01Not applicableUs
Nucyntatablet, film coated50 mg/1oralbryant ranch prepack2009-06-01Not applicableUs
Nucyntatablet, film coated100 mg/1oralJanssen Pharmaceuticals, Inc.2009-06-01Not applicableUs
Nucyntatablet, film coated75 mg/1oralLake Erie Medical Surgical & Supply DBA Quality Care Products LLC2011-07-13Not applicableUs
Nucyntatablet, film coated100 mg/1oralPhysicians Total Care, Inc.2010-03-19Not applicableUs
Nucyntatablet, film coated75 mg/1oralJanssen Pharmaceuticals, Inc.2009-06-01Not applicableUs
Nucyntatablet50 mg/1oralLake Erie Medical DBA Quality Care Products LLC2010-09-29Not applicableUs
Nucyntatablet, film coated75 mg/1oralPhysicians Total Care, Inc.2010-03-19Not applicableUs
Nucyntatablet, film coated50 mg/1oralJanssen Pharmaceuticals, Inc.2009-06-01Not applicableUs
Nucyntatablet, film coated50 mg/1oralRebel Distributors Corp2009-06-01Not applicableUs
Nucyntatablet, film coated50 mg/1oralPhysicians Total Care, Inc.2010-03-19Not applicableUs
Nucyntasolution20 mg/mLoralJanssen Pharmaceuticals, Inc.2012-10-15Not applicableUs
Nucyntatablet, film coated75 mg/1oralSTAT Rx USA LLC2009-06-01Not applicableUs
Nucyntatablet, film coated50 mg/1oralStat Rx USA2009-06-01Not applicableUs
Nucyntatablet, film coated100 mg/1oralbryant ranch prepack2009-06-01Not applicableUs
Nucynta CRtablet (extended-release)250 mgoralJanssen Inc2011-02-172015-03-25Canada
Nucynta CRtablet (extended-release)200 mgoralJanssen Inc2011-02-172014-12-04Canada
Nucynta CRtablet (extended-release)150 mgoralJanssen Inc2011-02-172014-09-30Canada
Nucynta CRtablet (extended-release)100 mgoralJanssen Inc2011-02-172014-08-19Canada
Nucynta CRtablet (extended-release)50 mgoralJanssen Inc2011-02-172014-08-19Canada
Nucynta ERtablet, film coated, extended release50 mg/1oralJanssen Pharmaceuticals, Inc.2011-08-25Not applicableUs
Nucynta ERtablet, film coated, extended release150 mg/1oralJanssen Pharmaceuticals, Inc.2011-08-25Not applicableUs
Nucynta ERtablet, film coated, extended release250 mg/1oralJanssen Pharmaceuticals, Inc.2011-08-25Not applicableUs
Nucynta ERtablet, film coated, extended release50 mg/1oralLake Erie Medical DBA Quality Care Products LLC2011-08-25Not applicableUs
Nucynta ERtablet, film coated, extended release100 mg/1oralJanssen Pharmaceuticals, Inc.2011-08-25Not applicableUs
Nucynta ERtablet, film coated, extended release200 mg/1oralJanssen Pharmaceuticals, Inc.2011-08-25Not applicableUs
Nucynta ERtablet, film coated, extended release100 mg/1oralLake Erie Medical DBA Quality Care Products LLC2011-08-25Not applicableUs
Nucynta Extended-releasetablet (extended-release)150 mgoralJanssen Inc2014-04-16Not applicableCanada
Nucynta Extended-releasetablet (extended-release)250 mgoralJanssen Inc2014-04-16Not applicableCanada
Nucynta Extended-releasetablet (extended-release)100 mgoralJanssen Inc2014-04-16Not applicableCanada
Nucynta Extended-releasetablet (extended-release)50 mgoralJanssen Inc2014-04-16Not applicableCanada
Nucynta Extended-releasetablet (extended-release)200 mgoralJanssen Inc2014-04-16Not applicableCanada
Nucynta Irtablet (immediate release)100 mgoralJanssen Inc2012-03-20Not applicableCanada
Nucynta Irtablet (immediate release)75 mgoralJanssen Inc2012-03-20Not applicableCanada
Nucynta Irtablet (immediate release)50 mgoralJanssen Inc2012-03-20Not applicableCanada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
PalexiaGrünenthal Ltd
TAPAL MSN Labs
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Tapentadol Hydrochloride
Thumb
  • InChI Key: ZELFLGGRLLOERW-YECZQDJWSA-N
  • Monoisotopic Mass: 257.154642102
  • Average Mass: 257.799
DBSALT000169
Categories
UNIIH8A007M585
CAS number175591-23-8
WeightAverage: 221.3385
Monoisotopic: 221.177964363
Chemical FormulaC14H23NO
InChI KeyInChIKey=KWTWDQCKEHXFFR-SMDDNHRTSA-N
InChI
InChI=1S/C14H23NO/c1-5-14(11(2)10-15(3)4)12-7-6-8-13(16)9-12/h6-9,11,14,16H,5,10H2,1-4H3/t11-,14+/m0/s1
IUPAC Name
3-[(2R,3R)-1-(dimethylamino)-2-methylpentan-3-yl]phenol
SMILES
CC[[email protected]]([C@@H](C)CN(C)C)C1=CC(O)=CC=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylpropylamines. These are compounds containing a phenylpropylamine moiety, which consists of a phenyl group substituted at the third carbon by an propan-1-amine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylpropylamines
Direct ParentPhenylpropylamines
Alternative Parents
Substituents
  • Phenylpropylamine
  • Phenylpropane
  • Aralkylamine
  • Phenol
  • Tertiary aliphatic amine
  • Tertiary amine
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationThe immediate-release formulation of tapentadol is indicated for the relief of moderate to severe acute pain. The long-acting formulation serves as a continuous, around-the-clock analgesic that is indicated for the relief of moderate to severe chronic pain or neuropathic pain associated with diabetic peripheral neuropathy.
PharmacodynamicsTapentadol is a centrally-acting synthetic analgesic. It is 18 times less potent than morphine in terms of binding to human mu-opioid receptors. It also increases norepinephrine concentrations in the brains of rats via inhibition of norepinephrine reuptake. Selective mu-opioid antagonists like naloxone can block analgesia from tapentadol. It also has not effect on the QT interval.
Mechanism of actionTapendadol causes large increases in levels of extracellular norepinephrine (NE) due to a dual mechanism of action involving mu opioid receptor (MOR) agonism as well as noradrenaline reuptake inhibition.
Related Articles
AbsorptionBioavailability, immediate release (IR), 86 mg: 32%; Bioavailability, extended release (ER), 86 mg: 32%; Cmax, IR: 64.2 ng/mL; Cmax, ER: 22.5 ng/mL; T max, IR: 1.5 hours; T max, ER: 5.0 hours; Tapentadol accumulates following multiple repeat doses.
Volume of distribution

Following IV administration, volume of distribution is 540 ± 98 L.

Protein binding~20%
Metabolism

97% of the dose is metabolized mostly via conjugation with glucuronic acid to produce glucuronides. Tapentadol is also metabolized into N-desmethyl tapentadol (13%) by CYP2C9 and CYP 2C19. CYP2D6 is involved in the formation of the metabolite, hydroxy tapentadol (2%). All metabolites are inactive.

SubstrateEnzymesProduct
Tapentadol
Not Available
N-desmethyl tapentadolDetails
Route of eliminationTapentadol and its metabolites are excreted almost exclusively (99%) via the kidneys. Approximately 70% (55% O-glucuronide and 15% sulfate of tapentadol) is excreted in conjugated form. A total of 3% of drug was excreted in urine as unchanged drug.
Half lifeElimination half-life, IV: 4 hours.
Clearance

Total clearance = 1530 ± 177 ml/min.

ToxicityOral, rabbit: LD50 = 3200 mg/kg; Oral, mouse: LD50 = 300 mg/kg; Oral, rat: LD50: 980 mg/kg; The most common reasons for discontinuation due to adverse events were dizziness, nausea, vomiting, somnolence, and headache.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9937
Blood Brain Barrier+0.9232
Caco-2 permeable+0.7912
P-glycoprotein substrateSubstrate0.559
P-glycoprotein inhibitor INon-inhibitor0.9304
P-glycoprotein inhibitor IINon-inhibitor0.9408
Renal organic cation transporterNon-inhibitor0.6918
CYP450 2C9 substrateNon-substrate0.8085
CYP450 2D6 substrateNon-substrate0.5219
CYP450 3A4 substrateSubstrate0.5509
CYP450 1A2 substrateInhibitor0.6665
CYP450 2C9 inhibitorNon-inhibitor0.8856
CYP450 2D6 inhibitorNon-inhibitor0.5538
CYP450 2C19 inhibitorNon-inhibitor0.921
CYP450 3A4 inhibitorNon-inhibitor0.8389
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8875
Ames testNon AMES toxic0.6862
CarcinogenicityNon-carcinogens0.5177
BiodegradationNot ready biodegradable0.9421
Rat acute toxicity2.6035 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7187
hERG inhibition (predictor II)Inhibitor0.6155
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
Solutionoral20 mg/mL
Tabletoral50 mg/1
Tablet, film coatedoral100 mg/1
Tablet, film coatedoral50 mg/1
Tablet, film coatedoral75 mg/1
Tablet, film coated, extended releaseoral100 mg/1
Tablet, film coated, extended releaseoral150 mg/1
Tablet, film coated, extended releaseoral200 mg/1
Tablet, film coated, extended releaseoral250 mg/1
Tablet, film coated, extended releaseoral50 mg/1
Tablet (extended-release)oral100 mg
Tablet (extended-release)oral150 mg
Tablet (extended-release)oral200 mg
Tablet (extended-release)oral250 mg
Tablet (extended-release)oral50 mg
Tablet (immediate release)oral100 mg
Tablet (immediate release)oral50 mg
Tablet (immediate release)oral75 mg
PricesNot Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6071970 No1997-06-062017-06-06Us
US7994364 No2005-06-272025-06-27Us
US8075872 No2003-11-202023-11-20Us
US8114383 No2004-10-102024-10-10Us
US8309060 No2003-11-202023-11-20Us
US8420056 No2003-11-202023-11-20Us
US8536130 No2008-09-222028-09-22Us
USRE39593 No2002-08-052022-08-05Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
logP2.87 FDA label
pKa9.34 - 10.45 FDA label
Predicted Properties
PropertyValueSource
Water Solubility0.78 mg/mLALOGPS
logP3.47ALOGPS
logP2.96ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)10.28ChemAxon
pKa (Strongest Basic)9.6ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area23.47 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity69.56 m3·mol-1ChemAxon
Polarizability26.58 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Giuseppe Motta, Domenico Vergani, Giorgio Bertolini, “PROCESS FOR THE PREPARATION OF TAPENTADOL AND INTERMEDIATES THEREOF.” U.S. Patent US20120232306, issued September 13, 2012.

US20120232306
General References
  1. Tzschentke TM, Christoph T, Kogel B, Schiene K, Hennies HH, Englberger W, Haurand M, Jahnel U, Cremers TI, Friderichs E, De Vry J: (-)-(1R,2R)-3-(3-dimethylamino-1-ethyl-2-methyl-propyl)-phenol hydrochloride (tapentadol HCl): a novel mu-opioid receptor agonist/norepinephrine reuptake inhibitor with broad-spectrum analgesic properties. J Pharmacol Exp Ther. 2007 Oct;323(1):265-76. Epub 2007 Jul 26. [PubMed:17656655 ]
  2. Gohler K, Brett M, Smit JW, Rengelshausen J, Terlinden R: Comparative pharmacokinetics and bioavailability of tapentadol following oral administration of immediate- and prolonged-release formulations. Int J Clin Pharmacol Ther. 2013 Apr;51(4):338-48. doi: 10.5414/CP201722. [PubMed:23357834 ]
  3. Xu XS, Smit JW, Lin R, Stuyckens K, Terlinden R, Nandy P: Population pharmacokinetics of tapentadol immediate release (IR) in healthy subjects and patients with moderate or severe pain. Clin Pharmacokinet. 2010 Oct;49(10):671-82. doi: 10.2165/11535390-000000000-00000. [PubMed:20818833 ]
External Links
ATC CodesN02AX06
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelDownload (666 KB)
MSDSDownload (481 KB)
Interactions
Drug Interactions
Drug
AcetazolamideThe risk or severity of adverse effects can be increased when Tapentadol is combined with Acetazolamide.
AlfentanilTapentadol may increase the central nervous system depressant (CNS depressant) activities of Alfentanil.
AlosetronAlosetron may decrease the analgesic activities of Tapentadol.
AlprazolamTapentadol may increase the central nervous system depressant (CNS depressant) activities of Alprazolam.
AlvimopanThe risk or severity of adverse effects can be increased when Tapentadol is combined with Alvimopan.
AmilorideThe risk or severity of adverse effects can be increased when Tapentadol is combined with Amiloride.
AmitriptylineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Amitriptyline.
Ammonium chlorideAmmonium chloride may increase the excretion rate of Tapentadol which could result in a higher serum level.
AmobarbitalTapentadol may increase the central nervous system depressant (CNS depressant) activities of Amobarbital.
AmoxapineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Amoxapine.
AmphetamineAmphetamine may increase the analgesic activities of Tapentadol.
AripiprazoleTapentadol may increase the central nervous system depressant (CNS depressant) activities of Aripiprazole.
AsenapineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Asenapine.
AzelastineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Azelastine.
BaclofenTapentadol may increase the central nervous system depressant (CNS depressant) activities of Baclofen.
BendroflumethiazideThe risk or severity of adverse effects can be increased when Tapentadol is combined with Bendroflumethiazide.
BrexpiprazoleTapentadol may increase the central nervous system depressant (CNS depressant) activities of Brexpiprazole.
BrimonidineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Brimonidine.
BromazepamTapentadol may increase the central nervous system depressant (CNS depressant) activities of Bromazepam.
BrompheniramineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Brompheniramine.
BumetanideThe risk or severity of adverse effects can be increased when Tapentadol is combined with Bumetanide.
BuspironeTapentadol may increase the central nervous system depressant (CNS depressant) activities of Buspirone.
ButabarbitalTapentadol may increase the central nervous system depressant (CNS depressant) activities of Butabarbital.
ButorphanolButorphanol may decrease the analgesic activities of Tapentadol.
CarbamazepineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Carbamazepine.
CarbinoxamineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Carbinoxamine.
CarisoprodolTapentadol may increase the central nervous system depressant (CNS depressant) activities of Carisoprodol.
CathinoneCathinone may increase the analgesic activities of Tapentadol.
CetirizineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Cetirizine.
ChlordiazepoxideTapentadol may increase the central nervous system depressant (CNS depressant) activities of Chlordiazepoxide.
ChlorothiazideThe risk or severity of adverse effects can be increased when Tapentadol is combined with Chlorothiazide.
ChlorphenamineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Chlorphenamine.
ChlorpromazineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Chlorpromazine.
ChlorthalidoneThe risk or severity of adverse effects can be increased when Tapentadol is combined with Chlorthalidone.
ChlorzoxazoneTapentadol may increase the central nervous system depressant (CNS depressant) activities of Chlorzoxazone.
ClemastineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Clemastine.
ClobazamTapentadol may increase the central nervous system depressant (CNS depressant) activities of Clobazam.
ClomipramineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Clomipramine.
ClonazepamTapentadol may increase the central nervous system depressant (CNS depressant) activities of Clonazepam.
ClonidineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Clonidine.
ClorazepateTapentadol may increase the central nervous system depressant (CNS depressant) activities of Clorazepate.
ClozapineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Clozapine.
CyclizineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Cyclizine.
CyclobenzaprineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Cyclobenzaprine.
CyclothiazideThe risk or severity of adverse effects can be increased when Tapentadol is combined with Cyclothiazide.
CyproheptadineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Cyproheptadine.
DantroleneTapentadol may increase the central nervous system depressant (CNS depressant) activities of Dantrolene.
DapoxetineThe risk or severity of adverse effects can be increased when Dapoxetine is combined with Tapentadol.
DesfluraneTapentadol may increase the central nervous system depressant (CNS depressant) activities of Desflurane.
DesipramineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Desipramine.
DesloratadineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Desloratadine.
DesmopressinThe risk or severity of adverse effects can be increased when Tapentadol is combined with Desmopressin.
Dexchlorpheniramine maleateTapentadol may increase the central nervous system depressant (CNS depressant) activities of Dexchlorpheniramine maleate.
DiazepamTapentadol may increase the central nervous system depressant (CNS depressant) activities of Diazepam.
DimenhydrinateTapentadol may increase the central nervous system depressant (CNS depressant) activities of Dimenhydrinate.
DiphenhydramineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Diphenhydramine.
DolasetronDolasetron may decrease the analgesic activities of Tapentadol.
DoxepinTapentadol may increase the central nervous system depressant (CNS depressant) activities of Doxepin.
DoxylamineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Doxylamine.
DronabinolDronabinol may increase the central nervous system depressant (CNS depressant) activities of Tapentadol.
DroperidolTapentadol may increase the central nervous system depressant (CNS depressant) activities of Droperidol.
EfavirenzTapentadol may increase the central nervous system depressant (CNS depressant) activities of Efavirenz.
EluxadolineTapentadol may increase the activities of Eluxadoline.
EntacaponeTapentadol may increase the central nervous system depressant (CNS depressant) activities of Entacapone.
EstazolamTapentadol may increase the central nervous system depressant (CNS depressant) activities of Estazolam.
EszopicloneTapentadol may increase the central nervous system depressant (CNS depressant) activities of Eszopiclone.
Etacrynic acidThe risk or severity of adverse effects can be increased when Tapentadol is combined with Ethacrynic acid.
EthanolEthanol may increase the central nervous system depressant (CNS depressant) activities of Tapentadol.
EthosuximideTapentadol may increase the central nervous system depressant (CNS depressant) activities of Ethosuximide.
EthotoinTapentadol may increase the central nervous system depressant (CNS depressant) activities of Ethotoin.
EthoxzolamideThe risk or severity of adverse effects can be increased when Tapentadol is combined with Ethoxzolamide.
EzogabineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Ezogabine.
FelbamateTapentadol may increase the central nervous system depressant (CNS depressant) activities of Felbamate.
FentanylTapentadol may increase the central nervous system depressant (CNS depressant) activities of Fentanyl.
FexofenadineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Fexofenadine.
FlibanserinTapentadol may increase the central nervous system depressant (CNS depressant) activities of Flibanserin.
FlunarizineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Flunarizine.
FlupentixolTapentadol may increase the central nervous system depressant (CNS depressant) activities of Flupentixol.
FluphenazineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Fluphenazine.
FlurazepamTapentadol may increase the central nervous system depressant (CNS depressant) activities of Flurazepam.
FluvoxamineThe risk or severity of adverse effects can be increased when Fluvoxamine is combined with Tapentadol.
FosphenytoinTapentadol may increase the central nervous system depressant (CNS depressant) activities of Fosphenytoin.
FurosemideThe risk or severity of adverse effects can be increased when Tapentadol is combined with Furosemide.
GabapentinTapentadol may increase the central nervous system depressant (CNS depressant) activities of Gabapentin.
gabapentin enacarbilTapentadol may increase the central nervous system depressant (CNS depressant) activities of gabapentin enacarbil.
Gamma Hydroxybutyric AcidTapentadol may increase the central nervous system depressant (CNS depressant) activities of Gamma Hydroxybutyric Acid.
GranisetronGranisetron may decrease the analgesic activities of Tapentadol.
GuanfacineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Guanfacine.
HaloperidolTapentadol may increase the central nervous system depressant (CNS depressant) activities of Haloperidol.
HydrochlorothiazideThe risk or severity of adverse effects can be increased when Tapentadol is combined with Hydrochlorothiazide.
HydrocodoneTapentadol may increase the central nervous system depressant (CNS depressant) activities of Hydrocodone.
HydroflumethiazideThe risk or severity of adverse effects can be increased when Tapentadol is combined with Hydroflumethiazide.
HydromorphoneTapentadol may increase the central nervous system depressant (CNS depressant) activities of Hydromorphone.
HydroxyzineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Hydroxyzine.
IloperidoneTapentadol may increase the central nervous system depressant (CNS depressant) activities of Iloperidone.
ImipramineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Imipramine.
IndapamideThe risk or severity of adverse effects can be increased when Tapentadol is combined with Indapamide.
IsocarboxazidThe risk or severity of adverse effects can be increased when Tapentadol is combined with Isocarboxazid.
IsofluraneTapentadol may increase the central nervous system depressant (CNS depressant) activities of Isoflurane.
KetamineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Ketamine.
LamotrigineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Lamotrigine.
LevetiracetamTapentadol may increase the central nervous system depressant (CNS depressant) activities of Levetiracetam.
LevocabastineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Levocabastine.
LevocetirizineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Levocetirizine.
LevorphanolTapentadol may increase the central nervous system depressant (CNS depressant) activities of Levorphanol.
LinezolidThe risk or severity of adverse effects can be increased when Tapentadol is combined with Linezolid.
LoratadineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Loratadine.
LorazepamTapentadol may increase the central nervous system depressant (CNS depressant) activities of Lorazepam.
LoxapineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Loxapine.
LurasidoneTapentadol may increase the central nervous system depressant (CNS depressant) activities of Lurasidone.
Magnesium SulfateMagnesium Sulfate may increase the central nervous system depressant (CNS depressant) activities of Tapentadol.
MaprotilineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Maprotiline.
MeclizineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Meclizine.
MeprobamateTapentadol may increase the central nervous system depressant (CNS depressant) activities of Meprobamate.
MetaxaloneTapentadol may increase the central nervous system depressant (CNS depressant) activities of Metaxalone.
MethadoneTapentadol may increase the central nervous system depressant (CNS depressant) activities of Methadone.
MethocarbamolTapentadol may increase the central nervous system depressant (CNS depressant) activities of Methocarbamol.
MethohexitalTapentadol may increase the central nervous system depressant (CNS depressant) activities of Methohexital.
MethotrimeprazineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Methotrimeprazine.
MethsuximideTapentadol may increase the central nervous system depressant (CNS depressant) activities of Methsuximide.
MetoclopramideThe risk or severity of adverse effects can be increased when Tapentadol is combined with Metoclopramide.
MetolazoneThe risk or severity of adverse effects can be increased when Tapentadol is combined with Metolazone.
MetyrosineTapentadol may increase the sedative activities of Metyrosine.
MidazolamTapentadol may increase the central nervous system depressant (CNS depressant) activities of Midazolam.
MinocyclineMinocycline may increase the central nervous system depressant (CNS depressant) activities of Tapentadol.
MirtazapineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Mirtazapine.
MoclobemideThe risk or severity of adverse effects can be increased when Tapentadol is combined with Moclobemide.
MorphineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Morphine.
NabiloneNabilone may increase the central nervous system depressant (CNS depressant) activities of Tapentadol.
NaltrexoneThe therapeutic efficacy of Tapentadol can be decreased when used in combination with Naltrexone.
NitrazepamTapentadol may increase the central nervous system depressant (CNS depressant) activities of Nitrazepam.
Nitrous oxideTapentadol may increase the central nervous system depressant (CNS depressant) activities of Nitrous oxide.
NortriptylineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Nortriptyline.
OlanzapineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Olanzapine.
OlopatadineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Olopatadine.
OndansetronOndansetron may decrease the analgesic activities of Tapentadol.
OrphenadrineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Orphenadrine.
OxazepamTapentadol may increase the central nervous system depressant (CNS depressant) activities of Oxazepam.
OxycodoneTapentadol may increase the central nervous system depressant (CNS depressant) activities of Oxycodone.
OxymorphoneTapentadol may increase the central nervous system depressant (CNS depressant) activities of Oxymorphone.
PaliperidoneTapentadol may increase the central nervous system depressant (CNS depressant) activities of Paliperidone.
PalonosetronPalonosetron may decrease the analgesic activities of Tapentadol.
ParaldehydeTapentadol may increase the central nervous system depressant (CNS depressant) activities of Paraldehyde.
PegvisomantThe therapeutic efficacy of Pegvisomant can be decreased when used in combination with Tapentadol.
PentobarbitalTapentadol may increase the central nervous system depressant (CNS depressant) activities of Pentobarbital.
PerampanelPerampanel may increase the central nervous system depressant (CNS depressant) activities of Tapentadol.
PerphenazineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Perphenazine.
PethidineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Pethidine.
PhenelzineThe risk or severity of adverse effects can be increased when Tapentadol is combined with Phenelzine.
PhenobarbitalTapentadol may increase the central nervous system depressant (CNS depressant) activities of Phenobarbital.
PhenytoinTapentadol may increase the central nervous system depressant (CNS depressant) activities of Phenytoin.
PimozideTapentadol may increase the central nervous system depressant (CNS depressant) activities of Pimozide.
PipotiazineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Pipotiazine.
PizotifenTapentadol may increase the central nervous system depressant (CNS depressant) activities of Pizotifen.
PomalidomideTapentadol may increase the central nervous system depressant (CNS depressant) activities of Pomalidomide.
PramipexoleTapentadol may increase the sedative activities of Pramipexole.
PregabalinTapentadol may increase the central nervous system depressant (CNS depressant) activities of Pregabalin.
PrimidoneTapentadol may increase the central nervous system depressant (CNS depressant) activities of Primidone.
ProcarbazineThe risk or severity of adverse effects can be increased when Tapentadol is combined with Procarbazine.
ProchlorperazineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Prochlorperazine.
ProcyclidineThe risk or severity of adverse effects can be increased when Procyclidine is combined with Tapentadol.
PromazineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Promazine.
PromethazineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Promethazine.
PropofolTapentadol may increase the central nervous system depressant (CNS depressant) activities of Propofol.
ProtriptylineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Protriptyline.
QuazepamTapentadol may increase the central nervous system depressant (CNS depressant) activities of Quazepam.
QuetiapineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Quetiapine.
RamelteonTapentadol may increase the central nervous system depressant (CNS depressant) activities of Ramelteon.
RamosetronTapentadol may increase the activities of Ramosetron.
RasagilineThe risk or severity of adverse effects can be increased when Tapentadol is combined with Rasagiline.
RemifentanilTapentadol may increase the central nervous system depressant (CNS depressant) activities of Remifentanil.
ReserpineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Reserpine.
RisperidoneTapentadol may increase the central nervous system depressant (CNS depressant) activities of Risperidone.
RopiniroleTapentadol may increase the sedative activities of Ropinirole.
RotigotineTapentadol may increase the sedative activities of Rotigotine.
RufinamideThe risk or severity of adverse effects can be increased when Rufinamide is combined with Tapentadol.
ScopolamineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Scopolamine.
Scopolamine butylbromideTapentadol may increase the central nervous system depressant (CNS depressant) activities of Scopolamine butylbromide.
SecobarbitalTapentadol may increase the central nervous system depressant (CNS depressant) activities of Secobarbital.
SelegilineThe risk or severity of adverse effects can be increased when Tapentadol is combined with Selegiline.
SevofluraneTapentadol may increase the central nervous system depressant (CNS depressant) activities of Sevoflurane.
Sodium oxybateSodium oxybate may increase the central nervous system depressant (CNS depressant) activities of Tapentadol.
SpironolactoneThe risk or severity of adverse effects can be increased when Tapentadol is combined with Spironolactone.
StiripentolTapentadol may increase the central nervous system depressant (CNS depressant) activities of Stiripentol.
SuccinylcholineSuccinylcholine may increase the bradycardic activities of Tapentadol.
SufentanilTapentadol may increase the central nervous system depressant (CNS depressant) activities of Sufentanil.
SuvorexantTapentadol may increase the central nervous system depressant (CNS depressant) activities of Suvorexant.
TasimelteonTapentadol may increase the central nervous system depressant (CNS depressant) activities of Tasimelteon.
Tedizolid PhosphateThe risk or severity of adverse effects can be increased when Tapentadol is combined with Tedizolid Phosphate.
TemazepamTapentadol may increase the central nervous system depressant (CNS depressant) activities of Temazepam.
TetrabenazineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Tetrabenazine.
ThalidomideTapentadol may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
ThioridazineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Thioridazine.
ThiothixeneTapentadol may increase the central nervous system depressant (CNS depressant) activities of Thiothixene.
TiagabineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Tiagabine.
TicrynafenThe risk or severity of adverse effects can be increased when Tapentadol is combined with Ticrynafen.
TizanidineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Tizanidine.
TolcaponeTapentadol may increase the central nervous system depressant (CNS depressant) activities of Tolcapone.
TopiramateTapentadol may increase the central nervous system depressant (CNS depressant) activities of Topiramate.
TorasemideThe risk or severity of adverse effects can be increased when Tapentadol is combined with Torasemide.
TramadolTapentadol may increase the central nervous system depressant (CNS depressant) activities of Tramadol.
TranylcypromineThe risk or severity of adverse effects can be increased when Tapentadol is combined with Tranylcypromine.
TriamtereneThe risk or severity of adverse effects can be increased when Tapentadol is combined with Triamterene.
TriazolamTapentadol may increase the central nervous system depressant (CNS depressant) activities of Triazolam.
TrichlormethiazideThe risk or severity of adverse effects can be increased when Tapentadol is combined with Trichlormethiazide.
TrifluoperazineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Trifluoperazine.
TrimipramineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Trimipramine.
TriprolidineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Triprolidine.
VigabatrinTapentadol may increase the central nervous system depressant (CNS depressant) activities of Vigabatrin.
ZaleplonTapentadol may increase the central nervous system depressant (CNS depressant) activities of Zaleplon.
ZiconotideTapentadol may increase the central nervous system depressant (CNS depressant) activities of Ziconotide.
ZiprasidoneTapentadol may increase the central nervous system depressant (CNS depressant) activities of Ziprasidone.
ZolpidemTapentadol may increase the central nervous system depressant (CNS depressant) activities of Zolpidem.
ZonisamideTapentadol may increase the central nervous system depressant (CNS depressant) activities of Zonisamide.
ZopicloneTapentadol may increase the central nervous system depressant (CNS depressant) activities of Zopiclone.
ZuclopenthixolTapentadol may increase the central nervous system depressant (CNS depressant) activities of Zuclopenthixol.
Food Interactions
  • Food increases the AUC and Cmax of tapentadol. Despite this, tapentadol can be given without regards to food.

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. Agonist binding to the receptor induces coupling to an inactive GDP-bound heterotrimeric G-protein complex and subsequent exchange of GDP for GTP in the G-protein alpha subunit leading to dissociati...
Gene Name:
OPRM1
Uniprot ID:
P35372
Molecular Weight:
44778.855 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Norepinephrine:sodium symporter activity
Specific Function:
Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:
SLC6A2
Uniprot ID:
P23975
Molecular Weight:
69331.42 Da
References
  1. Tzschentke TM, Christoph T, Kogel B, Schiene K, Hennies HH, Englberger W, Haurand M, Jahnel U, Cremers TI, Friderichs E, De Vry J: (-)-(1R,2R)-3-(3-dimethylamino-1-ethyl-2-methyl-propyl)-phenol hydrochloride (tapentadol HCl): a novel mu-opioid receptor agonist/norepinephrine reuptake inhibitor with broad-spectrum analgesic properties. J Pharmacol Exp Ther. 2007 Oct;323(1):265-76. Epub 2007 Jul 26. [PubMed:17656655 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
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 synthetic opioids and for the psychoactive diterpene salvinorin A. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates th...
Gene Name:
OPRK1
Uniprot ID:
P41145
Molecular Weight:
42644.665 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
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 nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate cyclase. Signaling leads to the inhibition of adenylate cyclase activity. Inhibits neurot...
Gene Name:
OPRD1
Uniprot ID:
P41143
Molecular Weight:
40368.235 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Voltage-gated potassium channel activity
Specific Function:
This is one of the several different receptors for 5-hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor is a ligand-gated ion channel, which when activated causes fast, depolarizing responses in neurons. It is a cation-specific, but otherwise relatively nonselective, ion channel.
Gene Name:
HTR3A
Uniprot ID:
P46098
Molecular Weight:
55279.835 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Serotonin:sodium symporter activity
Specific Function:
Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into the pre-synaptic terminal for re-utilization. Plays a key role in mediating regulation of the availability of serotonin to other receptors of serotonergic systems. Terminates the action of serotonin an...
Gene Name:
SLC6A4
Uniprot ID:
P31645
Molecular Weight:
70324.165 Da
References
  1. Raffa RB, Buschmann H, Christoph T, Eichenbaum G, Englberger W, Flores CM, Hertrampf T, Kogel B, Schiene K, Strassburger W, Terlinden R, Tzschentke TM: Mechanistic and functional differentiation of tapentadol and tramadol. Expert Opin Pharmacother. 2012 Jul;13(10):1437-49. doi: 10.1517/14656566.2012.696097. Epub 2012 Jun 15. [PubMed:22698264 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Retinoic acid binding
Specific Function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols. Isoform 2 lacks transferase activity but acts as a negative regulator of isoform 1.
Gene Name:
UGT1A9
Uniprot ID:
O60656
Molecular Weight:
59940.495 Da
References
  1. Kneip C, Terlinden R, Beier H, Chen G: Investigations into the drug-drug interaction potential of tapentadol in human liver microsomes and fresh human hepatocytes. Drug Metab Lett. 2008 Jan;2(1):67-75. [PubMed:19356073 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Glucuronosyltransferase activity
Specific Function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol...
Gene Name:
UGT2B7
Uniprot ID:
P16662
Molecular Weight:
60694.12 Da
References
  1. Kneip C, Terlinden R, Beier H, Chen G: Investigations into the drug-drug interaction potential of tapentadol in human liver microsomes and fresh human hepatocytes. Drug Metab Lett. 2008 Jan;2(1):67-75. [PubMed:19356073 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
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 antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular Weight:
55768.94 Da
References
  1. Kneip C, Terlinden R, Beier H, Chen G: Investigations into the drug-drug interaction potential of tapentadol in human liver microsomes and fresh human hepatocytes. Drug Metab Lett. 2008 Jan;2(1):67-75. [PubMed:19356073 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular Weight:
55627.365 Da
References
  1. Kneip C, Terlinden R, Beier H, Chen G: Investigations into the drug-drug interaction potential of tapentadol in human liver microsomes and fresh human hepatocytes. Drug Metab Lett. 2008 Jan;2(1):67-75. [PubMed:19356073 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular Weight:
55930.545 Da
References
  1. Kneip C, Terlinden R, Beier H, Chen G: Investigations into the drug-drug interaction potential of tapentadol in human liver microsomes and fresh human hepatocytes. Drug Metab Lett. 2008 Jan;2(1):67-75. [PubMed:19356073 ]
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Drug created on March 19, 2008 10:17 / Updated on August 24, 2016 01:52