Tapentadol

Identification

Summary

Tapentadol is an opioid used to manage severe pain that has not responded to non-opioid medications, and for which opioid analgesic therapy is appropriate.

Brand Names
Nucynta
Generic Name
Tapentadol
DrugBank Accession Number
DB06204
Background

Tapentadol is a centrally-acting synthetic analgesic with a dual mechanism of action. It is a mu-opioid receptor agonist that also inhibits norepinephrine reuptake.2,3

Tapentadol was first approved by the FDA on November 20, 2008. The extended-release formulation of tapentadol was also approved by the FDA on August 26, 2011.6 Used in the management of pain, tapentadol is typically reserved for patients who have limited alternative treatment options.

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 221.3385
Monoisotopic: 221.177964363
Chemical Formula
C14H23NO
Synonyms
  • 3-[(1R,2R)-3-(Dimethylamino)-1-ethyl-2-methylpropyl]phenol
  • PHENOL, 3-((1R,2R)-3-(DIMETHYLAMINO)-1-ETHYL-2-METHYLPROPYL)-
  • Tapentadol
External IDs
  • BN 200
  • BN-200
  • BN200
  • CG 5503
  • CG-5503
  • CG5503
  • CG5503 IR
  • R331333

Pharmacology

Indication

Tapentadol is indicated for the management of acute pain severe enough to require an opioid analgesic and for which alternative treatments are inadequate. Due to the risks of addiction, drug abuse, and drug misuse, tapentadol is reserved for patients for whom alternative treatment options are unavailable.5,7,8

The immediate-release tapentadol oral tablets are approved for use in patients six years and older with a body weight of at least 40 kg.5 Tapentadol oral solution is used in patients aged six years and older with a body weight of at least 16 kg.8 These formulations are not intended for long-term use unless the pain remains severe enough to require an opioid analgesic, for which alternative treatment options remain inadequate.

The extended-release tablets of tapentadol are indicated for the management of pain severe enough to require daily, around-the-clock, long-term opioid treatment and for which alternative treatment options are inadequate. They are also indicated for the management of neuropathic pain associated with diabetic peripheral neuropathy (DPN) in adults severe enough to require daily, around-the-clock, long-term opioid treatment and for which alternative treatment options are inadequate. This formulation is not indicated as an as-needed (prn) analgesic.7

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 TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Management ofDiabetic peripheral neuropathic pain (dpn)•••••••••••••••••••••••••• ••••••••• •••••• •••••••••• •••••••••• ••••••••••• ••••••••• •••••••••••••• •••••••• •••••••
Management ofSevere pain•••••••••••••••••••••• ••••••••••• ••••••••• •••••••• ••••••••• ••••••••• •••••• •••••••••••••••• •••••••• •••••••
Management ofSevere pain, acute••••••••••••••••••••••• •••••• ••••••••••••••••••• ••••••••••• ••••••••• •••••••• •••• •••••• •• •• ••••• •• ••• ••••••••• •••••• ••••••••• •••••••••••••••••
Management ofSevere pain, acute••••••••••••••••••••••• •••••• •••••••••••••••••• •••••• ••••••••• •••••••••• •••••• •• •• •• ••••• •••••••••• ••••••••••• ••••••••• •••••••••••••
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

Tapentadol is an opioid agonist that exerts physiological effects commonly caused by the opioid drug class. These effects include miosis, reduced gastrointestinal motility, and peripheral vasodilation. Tapentadol produces respiratory depression by reducing the responsiveness of the brain stem respiratory centers to both increases in carbon dioxide tension and electrical stimulation.5

Tapentadol has a high potential for misuse and abuse, which can lead to the development of substance use disorder. Abuse of tapentadol poses a risk of overdose and death, which increases with alcohol or other central nervous system depressants.5

Mechanism of action

Tapentadol is a centrally-acting synthetic analgesic. Although their clinical relevance is unclear, tapentadol is believed to have two main mechanisms of action.5 Tapentadol is a selective mu-opioid receptor (MOR) agonist: it binds to MOR with an affinity greater than or equal to ten-fold affinity compared to delta- and kappa-opioid receptors.3 Tapentadol also inhibits noradrenaline reuptake, thereby increasing noradrenaline levels and activating alpha-2 receptors to promote analgesia.3,4 Tapentadol is a weak serotonin reuptake inhibitor; however, this action does not contribute to its analgesic effect.3

TargetActionsOrganism
UMu-type opioid receptor
agonist
Humans
USodium-dependent noradrenaline transporter
inhibitor
Humans
UKappa-type opioid receptor
agonist
Humans
UDelta-type opioid receptor
agonist
Humans
USodium-dependent serotonin transporter
inhibitor
Humans
Absorption

The mean absolute bioavailability after single-dose administration of tapentadol in a fasted state is approximately 32% due to extensive first-pass metabolism. Maximum serum concentrations of tapentadol are typically observed at around 1.25 hours after dosing. Dose-proportional increases in the Cmax and AUC values of tapentadol have been observed over the 50 to 150 mg dose range. A multiple (every 6 hours) dose study with doses ranging from 75 to 175 mg tapentadol showed a mean accumulation factor of 1.6 for the parent drug and 1.8 for the major metabolite tapentadol- O-glucuronide, which are primarily determined by the dosing interval and apparent half-life of tapentadol and its metabolite.5

The AUC and Cmax increased by 25% and 16%, respectively, when tapentadol was administered after a high-fat, high-calorie breakfast. Tapentadol may be given with or without food.5

Volume of distribution

Tapentadol is widely distributed throughout the body. Following intravenous administration, the volume of distribution (Vz) for tapentadol is 540 ± 98 L.5

Protein binding

The plasma protein binding is approximately 20%.5

Metabolism

In humans, about 97% of the parent compound is metabolized. Tapentadol is mainly metabolized by Phase II pathways, and only a small amount is metabolized by Phase I oxidative pathways; thus, drug metabolism mediated by cytochrome P450 system is of less importance than phase II conjugation.5 The major pathway of tapentadol metabolism is conjugation with glucuronic acid to produce glucuronides.1,5 After oral administration, approximately 70% of the drug, of which 55% is the O-glucuronide metabolite and 15% is the sulfate metabolite, is excreted in urine. About 3% of the dose was excreted in urine as the unchanged parent drug.5

Tapentadol can also undergo CYP2C9- and CYP2C19-mediated demethylation to form N-desmethyl tapentadol, which accounts for 13% of the dose. About 2% of tapentadol can also undergo CYP2D6-mediated hydroxylation to form Hydroxy tapentadol. N-desmethyl tapentadol and Hydroxy tapentadol can further be glucuronidated. Metabolites of tapentadol do not contribute to the pharmacological activity of tapentadol.1,5

Hover over products below to view reaction partners

Route of elimination

Tapentadol and its metabolites are 99% excreted via the kidneys.5

Half-life

The terminal half-life is about four hours after oral administration.5

Clearance

The total clearance is 1530 ± 177 mL/min.5

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

Intraperitoneal lowest published toxic dose (TDLO) is 10 mg/kg in rats.9

Acute overdosage with tapentadol is characterized by respiratory depression, somnolence progressing to stupor or coma, skeletal muscle flaccidity, cold and clammy skin, constricted pupils, and, in some cases, pulmonary edema, bradycardia, hypotension, partial or complete airway obstruction, atypical snoring, and death. Marked mydriasis rather than miosis may be seen due to severe hypoxia in overdose situations.5

Tapentadol overdose is managed by reestablishing a patent and protected airway and using assisted or controlled ventilation if needed. Other supportive measures can manage circulatory shock and pulmonary edema. Cardiac arrest or arrhythmias will require advanced life-support measures.5

Opioid antagonists, such as naloxone, are specific antidotes to respiratory depression resulting from opioid overdose. They should be administered, in multiple doses, depending on patient response. As administration of the recommended usual dosage of the opioid antagonist will precipitate an acute withdrawal syndrome in individuals with physical dependence on opioids, administration of the opioid antagonist should be initiated with care and by titration with smaller than usual doses.5

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
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.
DrugInteraction
1,2-BenzodiazepineTapentadol may increase the central nervous system depressant (CNS depressant) activities of 1,2-Benzodiazepine.
AcenocoumarolThe risk or severity of adverse effects can be increased when Tapentadol is combined with Acenocoumarol.
AcetazolamideTapentadol may increase the central nervous system depressant (CNS depressant) activities of Acetazolamide.
AcetophenazineTapentadol may increase the central nervous system depressant (CNS depressant) activities of Acetophenazine.
AclidiniumThe risk or severity of urinary retention and constipation can be increased when Aclidinium is combined with Tapentadol.
Food Interactions
  • Avoid alcohol. Due to the additive pharmacological effect, the concomitant use with alcohol increases the risk for central nervous system depression, respiratory depression, profound sedation, coma, and death.
  • Take with or without food. A high-fat, high-calorie meal increases absorption, but not to a clinically significant extent.

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
IngredientUNIICASInChI Key
Tapentadol hydrochloride71204KII53175591-09-0ZELFLGGRLLOERW-YECZQDJWSA-N
International/Other Brands
Palexia (Grünenthal Ltd) / TAPAL (MSN Labs )
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
NucyntaTablet, film coated50 mg/1OralLake Erie Medical DBA Quality Care Products LLC2010-09-292019-06-30US flag
NucyntaTablet, film coated75 mg/1OralDepo Nf Sub, Llc2017-06-16Not applicableUS flag
NucyntaTablet, film coated50 mg/1OralQuality Care Products, LLC2019-09-13Not applicableUS flag
NucyntaTablet, film coated50 mg/1OralRebel Distributors2009-06-01Not applicableUS flag
NucyntaTablet, film coated100 mg/1OralLake Erie Medical DBA Quality Care Products LLC2009-06-012019-10-11US flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Apo-tapentadolTablet, multilayer, extended release50 mgOralApotex CorporationNot applicableNot applicableCanada flag
Apo-tapentadolTablet, multilayer, extended release100 mgOralApotex CorporationNot applicableNot applicableCanada flag
Apo-tapentadolTablet, multilayer, extended release75 mgOralApotex CorporationNot applicableNot applicableCanada flag

Categories

ATC Codes
N02AX06 — Tapentadol
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenylpropanes
Direct Parent
Phenylpropanes
Alternative Parents
Aralkylamines / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Trialkylamines / Organopnictogen compounds / Organooxygen compounds / Hydrocarbon derivatives
Substituents
1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Amine / Aralkylamine / Aromatic homomonocyclic compound / Hydrocarbon derivative / Organic nitrogen compound / Organic oxygen compound / Organonitrogen compound / Organooxygen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
H8A007M585
CAS number
175591-23-8
InChI Key
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[C@H]([C@@H](C)CN(C)C)C1=CC(O)=CC=C1

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. Barbosa J, Faria J, Queiros O, Moreira R, Carvalho F, Dinis-Oliveira RJ: Comparative metabolism of tramadol and tapentadol: a toxicological perspective. Drug Metab Rev. 2016 Nov;48(4):577-592. doi: 10.1080/03602532.2016.1229788. Epub 2016 Sep 15. [Article]
  2. Wade WE, Spruill WJ: Tapentadol hydrochloride: a centrally acting oral analgesic. Clin Ther. 2009 Dec;31(12):2804-18. doi: 10.1016/j.clinthera.2009.12.003. [Article]
  3. Singh DR, Nag K, Shetti AN, Krishnaveni N: Tapentadol hydrochloride: A novel analgesic. Saudi J Anaesth. 2013 Jul;7(3):322-6. doi: 10.4103/1658-354X.115319. [Article]
  4. Alshehri FS: Tapentadol: A Review of Experimental Pharmacology Studies, Clinical Trials, and Recent Findings. Drug Des Devel Ther. 2023 Mar 21;17:851-861. doi: 10.2147/DDDT.S402362. eCollection 2023. [Article]
  5. FDA Approved Drug Products: NUCYNTA (tapentadol) tablets for oral use C-II Initial U.S. (July 2023) [Link]
  6. Johnson & Johnson: NUCYNTA® ER (Tapentadol Extended-Release Tablets) Receives FDA Approval For The Management Of Moderate To Severe Chronic Pain [Link]
  7. FDA Approved Drug Products: NUCYNTA ER (tapentadol) extended-release tablets for oral use C-II (March 2021) [Link]
  8. FDA Approved Drug Products: NUCYNTA (tapentadol) oral solution C-II (July 2023) [Link]
  9. Cayman Chemical: Tapentadol (hydrochloride) MSDS [Link]
  10. FDA Approved Drug Products: NUCYNTA® (tapentadol) oral solution C-II [Link]
KEGG Drug
D06007
PubChem Compound
9838022
PubChem Substance
175427057
ChemSpider
8013742
BindingDB
50386381
RxNav
787390
ChEBI
135935
ChEMBL
CHEMBL1201776
ZINC
ZINC000000020783
PharmGKB
PA166179720
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Tapentadol
MSDS
Download (481 KB)

Clinical Trials

Clinical Trials

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Tablet, coatedOral50 mg
SolutionOral2 g
SolutionOral20 mg/1mL
Tablet, film coatedOral100 mg/1
Tablet, film coatedOral50 mg/1
Tablet, film coatedOral75 mg/1
Tablet, extended releaseOral100 mg
Tablet, extended releaseOral150 mg
Tablet, extended releaseOral200 mg
Tablet, extended releaseOral250 mg
Tablet, extended releaseOral50 mg
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, film coatedOral100 mg
TabletOral100 mg
Tablet, film coatedOral150 mg
TabletOral150 mg
TabletOral200 mg
TabletOral250 mg
TabletOral50 mg
Tablet, multilayer, extended releaseOral100 mg
Tablet, multilayer, extended releaseOral50 mg
Tablet, multilayer, extended releaseOral75 mg
Tablet, film coatedOral50 mg
Tablet, film coatedOral75 mg
SolutionOral20 MG/ML
SolutionOral20.000 mg
SolutionOral4 MG/ML
TabletOral87.360 mg
Tablet, extended releaseOral25 MG
SolutionOral
TabletOral50.000 mg
Tablet, extended releaseOral
Tablet, coatedOral5000000 mg
SolutionOral200000 g
Tablet, film coatedOral7500000 mg
Tablet, extended releaseOral10000000 mg
Tablet, extended releaseOral15000000 mg
Tablet, extended releaseOral2500000 mg
Tablet, extended releaseOral5000000 mg
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US8309060No2012-11-132023-11-20US flag
US8114383No2012-02-142024-10-10US flag
US6071970No2000-06-062017-06-06US flag
US7994364No2011-08-092025-06-27US flag
USRE39593No2007-04-242022-08-05US flag
US8075872No2011-12-132023-11-20US flag
US8536130No2013-09-172028-09-22US flag
US8420056No2013-04-162023-11-20US flag
US11007156No2021-05-182022-10-22US flag
US11344512No2008-04-212028-04-21US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)202-205https://www.trc-canada.com/prod-img/MSDS/T007200MSDS.pdf
logP2.87 https://www.accessdata.fda.gov/drugsatfda_docs/label/2023/022304s024lbl.pdf
pKa9.34-10.45 https://www.accessdata.fda.gov/drugsatfda_docs/label/2023/022304s024lbl.pdf
Predicted Properties
PropertyValueSource
Water Solubility0.78 mg/mLALOGPS
logP3.47ALOGPS
logP2.96Chemaxon
logS-2.4ALOGPS
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 RuleNoChemaxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0a4r-7910000000-b213e0bd5375a87d082f
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-007a-9520000000-e79b0e4c1b13a4735dea
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0190000000-59a2a10eb790c5f920c0
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0aor-9700000000-fb3c356f666635c31e02
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-1920000000-c21bddb91338bd37cb53
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-9300000000-665439127dc2c30d384f
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00xr-2900000000-52a98d813733e5500262
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-164.8888643
predicted
DarkChem Lite v0.1.0
[M-H]-157.6324
predicted
DeepCCS 1.0 (2019)
[M+H]+164.0210643
predicted
DarkChem Lite v0.1.0
[M+H]+159.9904
predicted
DeepCCS 1.0 (2019)
[M+Na]+164.8670643
predicted
DarkChem Lite v0.1.0
[M+Na]+166.08356
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
Details
1. Mu-type opioid receptor
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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. 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. [Article]
  2. Singh DR, Nag K, Shetti AN, Krishnaveni N: Tapentadol hydrochloride: A novel analgesic. Saudi J Anaesth. 2013 Jul;7(3):322-6. doi: 10.4103/1658-354X.115319. [Article]
  3. Chang EJ, Choi EJ, Kim KH: Tapentadol: Can It Kill Two Birds with One Stone without Breaking Windows? Korean J Pain. 2016 Jul;29(3):153-7. doi: 10.3344/kjp.2016.29.3.153. Epub 2016 Jul 1. [Article]
  4. Alshehri FS: Tapentadol: A Review of Experimental Pharmacology Studies, Clinical Trials, and Recent Findings. Drug Des Devel Ther. 2023 Mar 21;17:851-861. doi: 10.2147/DDDT.S402362. eCollection 2023. [Article]
  5. FDA Approved Drug Products: NUCYNTA (tapentadol) tablets for oral use C-II Initial U.S. (July 2023) [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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
Uniprot Name
Sodium-dependent noradrenaline transporter
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. [Article]
  2. Singh DR, Nag K, Shetti AN, Krishnaveni N: Tapentadol hydrochloride: A novel analgesic. Saudi J Anaesth. 2013 Jul;7(3):322-6. doi: 10.4103/1658-354X.115319. [Article]
  3. Chang EJ, Choi EJ, Kim KH: Tapentadol: Can It Kill Two Birds with One Stone without Breaking Windows? Korean J Pain. 2016 Jul;29(3):153-7. doi: 10.3344/kjp.2016.29.3.153. Epub 2016 Jul 1. [Article]
  4. Alshehri FS: Tapentadol: A Review of Experimental Pharmacology Studies, Clinical Trials, and Recent Findings. Drug Des Devel Ther. 2023 Mar 21;17:851-861. doi: 10.2147/DDDT.S402362. eCollection 2023. [Article]
  5. FDA Approved Drug Products: NUCYNTA (tapentadol) tablets for oral use C-II Initial U.S. (July 2023) [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
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. 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. [Article]
  2. Singh DR, Nag K, Shetti AN, Krishnaveni N: Tapentadol hydrochloride: A novel analgesic. Saudi J Anaesth. 2013 Jul;7(3):322-6. doi: 10.4103/1658-354X.115319. [Article]
  3. Chang EJ, Choi EJ, Kim KH: Tapentadol: Can It Kill Two Birds with One Stone without Breaking Windows? Korean J Pain. 2016 Jul;29(3):153-7. doi: 10.3344/kjp.2016.29.3.153. Epub 2016 Jul 1. [Article]
  4. Alshehri FS: Tapentadol: A Review of Experimental Pharmacology Studies, Clinical Trials, and Recent Findings. Drug Des Devel Ther. 2023 Mar 21;17:851-861. doi: 10.2147/DDDT.S402362. eCollection 2023. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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. 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. [Article]
  2. Singh DR, Nag K, Shetti AN, Krishnaveni N: Tapentadol hydrochloride: A novel analgesic. Saudi J Anaesth. 2013 Jul;7(3):322-6. doi: 10.4103/1658-354X.115319. [Article]
  3. Chang EJ, Choi EJ, Kim KH: Tapentadol: Can It Kill Two Birds with One Stone without Breaking Windows? Korean J Pain. 2016 Jul;29(3):153-7. doi: 10.3344/kjp.2016.29.3.153. Epub 2016 Jul 1. [Article]
  4. Alshehri FS: Tapentadol: A Review of Experimental Pharmacology Studies, Clinical Trials, and Recent Findings. Drug Des Devel Ther. 2023 Mar 21;17:851-861. doi: 10.2147/DDDT.S402362. eCollection 2023. [Article]
Kind
Protein
Organism
Humans
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 t...
Gene Name
SLC6A4
Uniprot ID
P31645
Uniprot Name
Sodium-dependent serotonin transporter
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. [Article]
  2. Alshehri FS: Tapentadol: A Review of Experimental Pharmacology Studies, Clinical Trials, and Recent Findings. Drug Des Devel Ther. 2023 Mar 21;17:851-861. doi: 10.2147/DDDT.S402362. eCollection 2023. [Article]

Enzymes

Kind
Protein
Organism
Humans
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 un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
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. [Article]
  2. Barbosa J, Faria J, Queiros O, Moreira R, Carvalho F, Dinis-Oliveira RJ: Comparative metabolism of tramadol and tapentadol: a toxicological perspective. Drug Metab Rev. 2016 Nov;48(4):577-592. doi: 10.1080/03602532.2016.1229788. Epub 2016 Sep 15. [Article]
  3. FDA Approved Drug Products: NUCYNTA (tapentadol) tablets for oral use C-II Initial U.S. (July 2023) [Link]
  4. Tapentadol FDA Label [File]
Kind
Protein
Organism
Humans
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 im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
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. [Article]
  2. Barbosa J, Faria J, Queiros O, Moreira R, Carvalho F, Dinis-Oliveira RJ: Comparative metabolism of tramadol and tapentadol: a toxicological perspective. Drug Metab Rev. 2016 Nov;48(4):577-592. doi: 10.1080/03602532.2016.1229788. Epub 2016 Sep 15. [Article]
  3. FDA Approved Drug Products: NUCYNTA (tapentadol) tablets for oral use C-II Initial U.S. (July 2023) [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
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. Barbosa J, Faria J, Queiros O, Moreira R, Carvalho F, Dinis-Oliveira RJ: Comparative metabolism of tramadol and tapentadol: a toxicological perspective. Drug Metab Rev. 2016 Nov;48(4):577-592. doi: 10.1080/03602532.2016.1229788. Epub 2016 Sep 15. [Article]
  2. FDA Approved Drug Products: NUCYNTA (tapentadol) tablets for oral use C-II Initial U.S. (July 2023) [Link]
Kind
Protein
Organism
Humans
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 su...
Gene Name
UGT2B7
Uniprot ID
P16662
Uniprot Name
UDP-glucuronosyltransferase 2B7
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. [Article]
  2. Barbosa J, Faria J, Queiros O, Moreira R, Carvalho F, Dinis-Oliveira RJ: Comparative metabolism of tramadol and tapentadol: a toxicological perspective. Drug Metab Rev. 2016 Nov;48(4):577-592. doi: 10.1080/03602532.2016.1229788. Epub 2016 Sep 15. [Article]
Kind
Protein
Organism
Humans
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 trans...
Gene Name
UGT1A9
Uniprot ID
O60656
Uniprot Name
UDP-glucuronosyltransferase 1-9
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. [Article]
  2. Barbosa J, Faria J, Queiros O, Moreira R, Carvalho F, Dinis-Oliveira RJ: Comparative metabolism of tramadol and tapentadol: a toxicological perspective. Drug Metab Rev. 2016 Nov;48(4):577-592. doi: 10.1080/03602532.2016.1229788. Epub 2016 Sep 15. [Article]

Drug created at March 19, 2008 16:17 / Updated at May 19, 2024 10:11