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
Structure for Tapentadol (DB06204)
- 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 ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Management of Diabetic peripheral neuropathic pain (dpn) •••••••••••• ••••• ••••••••• ••••••••• •••••• •••••••••• •••••••••• ••••••••••• ••••••••• ••••••• ••••••• •••••••• ••••••• Management of Severe pain •••••••••••• •••••••••• ••••••••••• ••••••••• •••••••• ••••••••• ••••••••• •••••• ••••••••• ••••••• •••••••• ••••••• Management of Severe pain, acute •••••••••••• ••••••••••• •••••• ••••••••• •••••••••• ••••••••••• ••••••••• •••••••• •••• •••••• •• •• ••••• •• ••• ••••••••• •••••• ••••••••• ••••••••• •••••••• Management of Severe pain, acute •••••••••••• ••••••••••• •••••• ••••••••• ••••••••• •••••• ••••••••• •••••••••• •••••• •• •• •• ••••• •••••••••• ••••••••••• ••••••••• ••••••• •••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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
Target Actions Organism UMu-type opioid receptor agonistHumans USodium-dependent noradrenaline transporter inhibitorHumans UKappa-type opioid receptor agonistHumans UDelta-type opioid receptor agonistHumans USodium-dependent serotonin transporter inhibitorHumans - 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 outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- 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 Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine Tapentadol may increase the central nervous system depressant (CNS depressant) activities of 1,2-Benzodiazepine. Acenocoumarol The risk or severity of adverse effects can be increased when Tapentadol is combined with Acenocoumarol. Acetazolamide Tapentadol may increase the central nervous system depressant (CNS depressant) activities of Acetazolamide. Acetophenazine Tapentadol may increase the central nervous system depressant (CNS depressant) activities of Acetophenazine. Aclidinium The 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 regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Tapentadol hydrochloride 71204KII53 175591-09-0 ZELFLGGRLLOERW-YECZQDJWSA-N - International/Other Brands
- Palexia (Grünenthal Ltd) / TAPAL (MSN Labs )
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Nucynta Tablet, film coated 75 mg/1 Oral Stat Rx USA 2009-06-01 Not applicable US 
Nucynta Tablet, film coated 100 mg/1 Oral Janssen Pharmaceuticals, Inc. 2009-06-01 2020-03-31 US Nucynta Tablet, film coated 50 mg/1 Oral Lake Erie Medical DBA Quality Care Products LLC 2010-09-29 2019-06-30 US Nucynta Tablet, film coated 75 mg/1 Oral Physicians Total Care, Inc. 2010-03-19 Not applicable US Nucynta Tablet, film coated 100 mg/1 Oral Stat Rx USA 2009-06-01 Not applicable US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Apo-tapentadol Tablet, multilayer, extended release 50 mg Oral Apotex Corporation Not applicable Not applicable Canada 
Apo-tapentadol Tablet, multilayer, extended release 100 mg Oral Apotex Corporation Not applicable Not applicable Canada Apo-tapentadol Tablet, multilayer, extended release 75 mg Oral Apotex Corporation Not applicable Not applicable Canada
Categories
- ATC Codes
- N02AX06 — Tapentadol
- Drug Categories
- Adrenergic Agents
- Adrenergic Uptake Inhibitors
- Analgesics
- Antidepressive Agents
- Benzene Derivatives
- Central Nervous System Agents
- Central Nervous System Depressants
- Combined Inhibitors of Serotonin/Norepinephrine Reuptake
- Cytochrome P-450 CYP2C19 Substrates
- Cytochrome P-450 CYP2C9 Substrates
- Cytochrome P-450 CYP2D6 Substrates
- Cytochrome P-450 Substrates
- Membrane Transport Modulators
- Narcotics
- Nervous System
- Neurotransmitter Agents
- Neurotransmitter Uptake Inhibitors
- Opiate Agonists
- Opioid Agonist
- Opioids
- Peripheral Nervous System Agents
- Phenols
- Sensory System Agents
- Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome
- Serotonin Agents
- Serotonin Modulators
- UGT1A9 Substrates
- UGT2B7 substrates
- 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
- 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]
- 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]
- 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]
- 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]
- FDA Approved Drug Products: NUCYNTA (tapentadol) tablets for oral use C-II Initial U.S. (July 2023) [Link]
- Johnson & Johnson: NUCYNTA® ER (Tapentadol Extended-Release Tablets) Receives FDA Approval For The Management Of Moderate To Severe Chronic Pain [Link]
- FDA Approved Drug Products: NUCYNTA ER (tapentadol) extended-release tablets for oral use C-II (March 2021) [Link]
- FDA Approved Drug Products: NUCYNTA (tapentadol) oral solution C-II (July 2023) [Link]
- Cayman Chemical: Tapentadol (hydrochloride) MSDS [Link]
- FDA Approved Drug Products: NUCYNTA® (tapentadol) oral solution C-II [Link]
- External Links
- KEGG Drug
- D06007
- PubChem Compound
- 9838022
- PubChem Substance
- 175427057
- ChemSpider
- 8013742
- BindingDB
- 50386381
- 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 Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Prevention Osteoarthritis of the Knee 1 4 Completed Supportive Care Effects of 2 Mu-opiates on Gastrointestinal Transit 1 4 Completed Treatment Acute Pain / Analgesics, Antipyretics, and Antirheumatics Causing Adverse Effects in Therapeutic Use / Opioids Use / Pain Uterus / Postoperative pain / Visceral Pain 1 4 Completed Treatment Back Pain Lower Back / Neuropathic Pain 1 4 Completed Treatment Back pain / Back Pain Lower Back / Neuropathic Pain 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet, coated Oral 50 mg Solution Oral 2 g Solution Oral 20 mg/1mL Tablet, film coated Oral 100 mg/1 Tablet, film coated Oral 50 mg/1 Tablet, film coated Oral 75 mg/1 Tablet, extended release Oral 100 mg Tablet, extended release Oral 150 mg Tablet, extended release Oral 200 mg Tablet, extended release Oral 250 mg Tablet, extended release Oral 50 mg Tablet, film coated, extended release Oral 100 mg/1 Tablet, film coated, extended release Oral 150 mg/1 Tablet, film coated, extended release Oral 200 mg/1 Tablet, film coated, extended release Oral 250 mg/1 Tablet, film coated, extended release Oral 50 mg/1 Tablet, film coated Oral 100 mg Tablet Oral 100 mg Tablet, film coated Oral 150 mg Tablet Oral 150 mg Tablet Oral 200 mg Tablet Oral 250 mg Tablet Oral 50 mg Tablet, multilayer, extended release Oral 100 mg Tablet, multilayer, extended release Oral 50 mg Tablet, multilayer, extended release Oral 75 mg Tablet, film coated Oral 50 mg Tablet, film coated Oral 75 mg Solution Oral 20 MG/ML Solution Oral 20.000 mg Solution Oral 4 MG/ML Tablet Oral 87.360 mg Tablet, extended release Oral 25 MG Solution Oral Tablet Oral 50.000 mg Tablet, extended release Oral Tablet, coated Oral 5000000 mg Solution Oral 200000 g Tablet, film coated Oral 7500000 mg Tablet, extended release Oral 10000000 mg Tablet, extended release Oral 15000000 mg Tablet, extended release Oral 2500000 mg Tablet, extended release Oral 5000000 mg Tablet, film coated Oral - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US8309060 No 2012-11-13 2023-11-20 US US8114383 No 2012-02-14 2024-10-10 US US6071970 No 2000-06-06 2017-06-06 US US7994364 No 2011-08-09 2025-06-27 US USRE39593 No 2007-04-24 2022-08-05 US US8075872 No 2011-12-13 2023-11-20 US US8536130 No 2013-09-17 2028-09-22 US US8420056 No 2013-04-16 2023-11-20 US US11007156 No 2021-05-18 2022-10-22 US US11344512 No 2008-04-21 2028-04-21 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 202-205 https://www.trc-canada.com/prod-img/MSDS/T007200MSDS.pdf logP 2.87 https://www.accessdata.fda.gov/drugsatfda_docs/label/2023/022304s024lbl.pdf pKa 9.34-10.45 https://www.accessdata.fda.gov/drugsatfda_docs/label/2023/022304s024lbl.pdf - Predicted Properties
Property Value Source Water Solubility 0.78 mg/mL ALOGPS logP 3.47 ALOGPS logP 2.96 Chemaxon logS -2.4 ALOGPS pKa (Strongest Acidic) 10.28 Chemaxon pKa (Strongest Basic) 9.6 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 23.47 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 69.56 m3·mol-1 Chemaxon Polarizability 26.58 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9937 Blood Brain Barrier + 0.9232 Caco-2 permeable + 0.7912 P-glycoprotein substrate Substrate 0.559 P-glycoprotein inhibitor I Non-inhibitor 0.9304 P-glycoprotein inhibitor II Non-inhibitor 0.9408 Renal organic cation transporter Non-inhibitor 0.6918 CYP450 2C9 substrate Non-substrate 0.8085 CYP450 2D6 substrate Non-substrate 0.5219 CYP450 3A4 substrate Substrate 0.5509 CYP450 1A2 substrate Inhibitor 0.6665 CYP450 2C9 inhibitor Non-inhibitor 0.8856 CYP450 2D6 inhibitor Non-inhibitor 0.5538 CYP450 2C19 inhibitor Non-inhibitor 0.921 CYP450 3A4 inhibitor Non-inhibitor 0.8389 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8875 Ames test Non AMES toxic 0.6862 Carcinogenicity Non-carcinogens 0.5177 Biodegradation Not ready biodegradable 0.9421 Rat acute toxicity 2.6035 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7187 hERG inhibition (predictor II) Inhibitor 0.6155
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0a4r-7910000000-b213e0bd5375a87d082f Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-007a-9520000000-e79b0e4c1b13a4735dea Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-00di-0190000000-59a2a10eb790c5f920c0 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0aor-9700000000-fb3c356f666635c31e02 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-004i-1920000000-c21bddb91338bd37cb53 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-9300000000-665439127dc2c30d384f Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-00xr-2900000000-52a98d813733e5500262 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 164.8888643 predictedDarkChem Lite v0.1.0 [M-H]- 157.6324 predictedDeepCCS 1.0 (2019) [M+H]+ 164.0210643 predictedDarkChem Lite v0.1.0 [M+H]+ 159.9904 predictedDeepCCS 1.0 (2019) [M+Na]+ 164.8670643 predictedDarkChem Lite v0.1.0 [M+Na]+ 166.08356 predictedDeepCCS 1.0 (2019)
Targets
- 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
- 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]
- 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]
- 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]
- 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]
- 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
- 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]
- 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]
- 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]
- 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]
- 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
- 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]
- 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]
- 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]
- 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
- 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]
- 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]
- 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]
- 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
- 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]
- 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
- 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]
- 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]
- FDA Approved Drug Products: NUCYNTA (tapentadol) tablets for oral use C-II Initial U.S. (July 2023) [Link]
- 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
- 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]
- 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]
- 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
- 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]
- 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
- 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]
- 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
- 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]
- 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 February 20, 2024 23:55