{"ATC Code":"N02AX06","Abbreviation":[],"Absorption, Distribution and Excretion":"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.  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.","Aliases":["Tapentadol","175591-23-8","CG5503","Bn 200","Cg5503","BN 200","BN-200","CG-5503","CG5503 IR","3-((1R,2R)-3-(Dimethylamino)-1-ethyl-2-methylpropyl)phenol","H8A007M585","NSC-759619","CG 5503","Dtxsid30170003","phenol, 3-[(1r,2r)-3-(dimethylamino)-1-ethyl-2-methylpropyl]-","Phenol, 3-((1R,2R)-3-(dimethylamino)-1-ethyl-2-methylpropyl)-","3-[(1r,2r)-3-(dimethylamino)-1-ethyl-2-methylpropyl]phenol","3-((2R,3R)-1-dimethylamino-2-methylpentan-3-yl)phenol","3-[(2R,3R)-1-dimethylamino-2-methylpentan-3-yl]phenol","tapentadolum","Dtxcid1092494","3-((2R,3R)-1-(dimethylamino)-2-methylpentan-3-yl)phenol","DEA No. 9780","Unii-h8a007m585","HSDB 8309","(R,R)-Tapentadol","Schembl116924","GTPL7477","Chembl1201776","Schembl29447436","Schembl29611116","Chebi:135935","CS-M0020","Bdbm50386381","Akos015951190","DB06204","NSC 759619","NS00002711","A26964","D06007","Q414463","Brd-k04283354-003-01-9","(1R,2R)-3-(3-dimethylamino-1-ethyl-2-methyl-propyl)-phenol"],"Biological Half-Life":"The terminal half-life is about four hours after oral administration.","CAS":"175591-23-8","ChemicalClasses":["phenylpropylamine"],"Chirality":"absolute","Drug Classes":["Breastfeeding","Lactation","Milk, Human","Analgesic, Opioid","Narcotics"],"Drug 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.  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. Tapentadol oral solution is used in patients aged six years and older with a body weight of at least 16 kg. 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.","Drug Warnings":"/BOXED WARNING/ WARNING: ADDICTION, ABUSE, AND MISUSE. Nucynta ER exposes patients and other users to the risks of opioid addiction, abuse, and misuse, which can lead to overdose and death. Assess each patient's risk prior to prescribing Nucynta ER, and monitor all patients regularly for the development of these behaviors or conditions.","DurationOfAction":"4 – 6 hours","EliminationHalfLife":"4 hours","Esters":[],"European Community (EC) Number":"605-757-6","FDA Pharmacological Classification":"H8A007M585","Formating":[],"HeavyAtomCount":16,"Human Drugs":"Breastfeeding; Lactation; Milk, Human; Analgesic, Opioid; Narcotics","IUPACName":"3-[(2R,3R)-1-(dimethylamino)-2-methylpentan-3-yl]phenol","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","InChIKey":"KWTWDQCKEHXFFR-SMDDNHRTSA-N","Interactions":"Potential pharmacologic interaction (potentially serious, sometimes fatal serotonin syndrome) when tapentadol is used concurrently with other serotonergic drugs (including serotonin [5-hydroxytryptamine; 5-HT] type 1 receptor agonists [\"triptans\"], selective serotonin-reuptake inhibitors (SSRIs), selective serotonin- and norepinephrine-reuptake inhibitors (SNRIs), tricyclic antidepressants), or drugs that impair the metabolism of serotonin.","MeSH Pharmacological Classification":"Compounds with activity like OPIATE ALKALOIDS, acting at OPIOID RECEPTORS. Properties include induction of ANALGESIA or NARCOSIS.","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. 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. Tapentadol also inhibits noradrenaline reuptake, thereby increasing noradrenaline levels and activating alpha-2 receptors to promote analgesia. Tapentadol is a weak serotonin reuptake inhibitor; however, this action does not contribute to its analgesic effect.","Melting Point":"202-205","Metabolism/Metabolites":"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. The major pathway of tapentadol metabolism is conjugation with glucuronic acid to produce glucuronides. 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.  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.","MolecularFormula":"C\u003csub\u003e14\u003c/sub\u003eH\u003csub\u003e23\u003c/sub\u003eNO","MolecularWeight":"221.34 g/mol","Non-Human Toxicity Values":"LD50 Rat iv 40 mg/kg","Opticalactivity":"( - )","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.  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.","PubChemId":9838022,"Record Description":["LiverTox|Analgesic|Severe pain|Opiate"],"Records":{"UNII":{"Impurities":[]}},"RefChem":"58438","RefCount":5,"RefCur":"","References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/Tapentadol","Name":"Tapentadol","Sub":false}]},{"Name":"Wikidata","Urls":[{"Link":"https://www.wikidata.org/wiki/Q414463","Name":"Tapentadol","Sub":false}]},{"Name":"DrugBank","Urls":[{"Link":"https://go.drugbank.com/drugs/DB06204","Name":"Tapentadol","Sub":false}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/9838022","Name":"Tapentadol","Sub":false}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=175591-23-8","Name":"Tapentadol","Sub":false}]},{"Name":"KEGG","Urls":[{"Link":"https://www.kegg.jp/entry/D06007","Name":"Tapentadol","Sub":false}]},{"Name":"UNII","Urls":[{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/H8A007M585","Name":"Tapentadol","Sub":false}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID30170003","Name":"Tapentadol","Sub":false}]}],"Refs":["National Center for Biotechnology Information. PubChem Compound Summary for CID 9838022, Tapentadol. Accessed January 2, 2026. \u003ca href=https://pubchem.ncbi.nlm.nih.gov/compound/9838022\u003ehttps://pubchem.ncbi.nlm.nih.gov/compound/9838022\u003c/a\u003e","U.S. Food and Drug Administration; National Center for Advancing Translational Sciences. Tapentadol. UNII: H8A007M585. Global Substance Registration System. Accessed January 2, 2026. \u003ca href=https://gsrs.ncats.nih.gov/ginas/app/beta/substances/H8A007M585\u003ehttps://gsrs.ncats.nih.gov/ginas/app/beta/substances/H8A007M585\u003c/a\u003e","Anvisa. RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial. Diário Oficial da União. March 31, 2023. Accessed January 2, 2026. \u003ca href=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992\u003ehttps://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992\u003c/a\u003e","Tapentadol. MedLine Plus. March 15, 2024. Accessed January 2, 2026. \u003ca href=https://medlineplus.gov/druginfo/meds/a610006.html\u003ehttps://medlineplus.gov/druginfo/meds/a610006.html\u003c/a\u003e"],"SMILES":"CC[C@@H](C1=CC(=CC=C1)O)[C@@H](C)CN(C)C","SaltData":[{"AcidCount":1,"Amine":"Tapentadol","AmineCount":1,"Formula":"O=C(O)C(O)C(O)C(=O)O","Name":"tartrate","Structure":"\u003csvg xmlns=\"http://www.w3.org/2000/svg\" preserveAspectRatio=\"none\" style=\"display:block\" viewBox=\"0 0 188.873 67.122\"\u003e\u003crect width=\"100%\" height=\"100%\" fill=\"#fff\"/\u003e\u003cdesc\u003eGenerated by the Chemistry Development Kit (http://github.com/cdk)\u003c/desc\u003e\u003cg fill=\"#ff0d0d\" stroke=\"#000\" stroke-linecap=\"round\" stroke-linejoin=\"round\" stroke-width=\".7\"\u003e\u003cpath fill=\"#fff\" stroke=\"none\" d=\"M0 0h189v68H0z\"/\u003e\u003cg class=\"mol\"\u003e\u003cpath d=\"m73.123 6.887-13.199 7.62\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m60.228 29.572-.607.35M60.444 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participants conducted around the world. The Web site is maintained by the National Library of Medicine (NLM) and the National Institutes of Health (NIH). Each ClinicalTrials.gov record presents summary information about a study protocol and includes the following: Disease or condition; Intervention (for example, the medical product, behavior, or procedure being studied); Title, description, and design of the study; Requirements for participation (eligibility criteria); Locations where the study is being conducted; Contact information for the study locations; and Links to relevant information on other health Web sites, such as NLM's MedlinePlus for patient health information and PubMed for citations and abstracts for scholarly articles in the field of medicine. Tapentadol is included in the database.","Title":"Tapentadol","UNII":"H8A007M585","Wikidata":"Q414463","Wikipedia":"Tapentadol","XLogP":3.5}